create_descriptors_for_smiles.ipynb

{
 "cells": [
  {
   "cell_type": "markdown",
   "metadata": {},
   "source": [
    "# Create Descriptors for Molecules"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 1,
   "metadata": {},
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "Populating the interactive namespace from numpy and matplotlib\n"
     ]
    }
   ],
   "source": [
    "%pylab inline\n",
    "%load_ext autoreload\n",
    "%autoreload 2"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 2,
   "metadata": {},
   "outputs": [],
   "source": [
    "tmp_smile = 'CC1CC(C(C(C=C(C(C(C=CC=C(C(=O)NC2=CC(=O)C(=C(C1)C2=O)NCC=C)C)OC)OC(=O)N)C)C)O)OC'"
   ]
  },
  {
   "cell_type": "markdown",
   "metadata": {},
   "source": [
    "### 2D RDKIT"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 3,
   "metadata": {},
   "outputs": [],
   "source": [
    "from rdkit import Chem\n",
    "from rdkit.Chem import Descriptors\n",
    "from rdkit.ML.Descriptors import MoleculeDescriptors\n",
    "\n",
    "def get_rdkit_descriptors(input_smile):\n",
    "    calc = MoleculeDescriptors.MolecularDescriptorCalculator([x[0] for x in Descriptors._descList])\n",
    "    mol = Chem.MolFromSmiles(input_smile)\n",
    "    ds = calc.CalcDescriptors(mol)\n",
    "    features = list(ds)\n",
    "    feature_names = list(calc.GetDescriptorNames())\n",
    "    return np.array(features,dtype=np.float32), feature_names    "
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 4,
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
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       "         2.30000000e+02,  0.00000000e+00,  4.04704005e-01, -4.38726693e-01,\n",
       "         4.38726693e-01,  4.04704005e-01,  1.21428573e+00,  1.90476191e+00,\n",
       "         2.50000000e+00,  1.65777874e+01,  9.84752178e+00,  2.32994890e+00,\n",
       "        -2.29647946e+00,  2.28428364e+00, -2.37488079e+00,  6.23184729e+00,\n",
       "        -1.19791485e-01,  2.62030768e+00,  1.21242590e+03,  3.15597496e+01,\n",
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       "         1.37708559e+01,  1.06005707e+01,  1.06005707e+01,  7.21674061e+00,\n",
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       "         1.67471447e+01,  6.41948938e+00, -2.14388061e+00,  0.00000000e+00,\n",
       "         5.33546925e+00,  1.08966589e+01,  2.91860890e+00,  4.83870953e-01,\n",
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       "         0.00000000e+00,  0.00000000e+00,  0.00000000e+00,  2.00000000e+00,\n",
       "         1.00000000e+00,  0.00000000e+00,  0.00000000e+00,  0.00000000e+00,\n",
       "         0.00000000e+00,  0.00000000e+00,  0.00000000e+00,  0.00000000e+00,\n",
       "         0.00000000e+00,  4.00000000e+00,  2.00000000e+00,  0.00000000e+00,\n",
       "         0.00000000e+00,  0.00000000e+00,  0.00000000e+00,  0.00000000e+00,\n",
       "         0.00000000e+00,  0.00000000e+00,  0.00000000e+00,  2.00000000e+00,\n",
       "         0.00000000e+00,  0.00000000e+00,  0.00000000e+00,  0.00000000e+00,\n",
       "         3.00000000e+00,  0.00000000e+00,  0.00000000e+00,  0.00000000e+00,\n",
       "         0.00000000e+00,  0.00000000e+00,  0.00000000e+00,  0.00000000e+00,\n",
       "         0.00000000e+00,  0.00000000e+00,  2.00000000e+00,  1.00000000e+00,\n",
       "         0.00000000e+00,  0.00000000e+00,  2.00000000e+00,  0.00000000e+00,\n",
       "         0.00000000e+00,  0.00000000e+00,  0.00000000e+00,  0.00000000e+00,\n",
       "         0.00000000e+00,  0.00000000e+00,  0.00000000e+00,  0.00000000e+00,\n",
       "         0.00000000e+00,  0.00000000e+00,  0.00000000e+00,  0.00000000e+00,\n",
       "         0.00000000e+00,  0.00000000e+00,  1.00000000e+00,  0.00000000e+00,\n",
       "         0.00000000e+00,  0.00000000e+00,  0.00000000e+00,  0.00000000e+00,\n",
       "         0.00000000e+00,  0.00000000e+00,  0.00000000e+00,  0.00000000e+00,\n",
       "         0.00000000e+00,  0.00000000e+00,  0.00000000e+00,  0.00000000e+00],\n",
       "       dtype=float32),\n",
       " ['MaxEStateIndex',\n",
       "  'MinEStateIndex',\n",
       "  'MaxAbsEStateIndex',\n",
       "  'MinAbsEStateIndex',\n",
       "  'qed',\n",
       "  'MolWt',\n",
       "  'HeavyAtomMolWt',\n",
       "  'ExactMolWt',\n",
       "  'NumValenceElectrons',\n",
       "  'NumRadicalElectrons',\n",
       "  'MaxPartialCharge',\n",
       "  'MinPartialCharge',\n",
       "  'MaxAbsPartialCharge',\n",
       "  'MinAbsPartialCharge',\n",
       "  'FpDensityMorgan1',\n",
       "  'FpDensityMorgan2',\n",
       "  'FpDensityMorgan3',\n",
       "  'BCUT2D_MWHI',\n",
       "  'BCUT2D_MWLOW',\n",
       "  'BCUT2D_CHGHI',\n",
       "  'BCUT2D_CHGLO',\n",
       "  'BCUT2D_LOGPHI',\n",
       "  'BCUT2D_LOGPLOW',\n",
       "  'BCUT2D_MRHI',\n",
       "  'BCUT2D_MRLOW',\n",
       "  'BalabanJ',\n",
       "  'BertzCT',\n",
       "  'Chi0',\n",
       "  'Chi0n',\n",
       "  'Chi0v',\n",
       "  'Chi1',\n",
       "  'Chi1n',\n",
       "  'Chi1v',\n",
       "  'Chi2n',\n",
       "  'Chi2v',\n",
       "  'Chi3n',\n",
       "  'Chi3v',\n",
       "  'Chi4n',\n",
       "  'Chi4v',\n",
       "  'HallKierAlpha',\n",
       "  'Ipc',\n",
       "  'Kappa1',\n",
       "  'Kappa2',\n",
       "  'Kappa3',\n",
       "  'LabuteASA',\n",
       "  'PEOE_VSA1',\n",
       "  'PEOE_VSA10',\n",
       "  'PEOE_VSA11',\n",
       "  'PEOE_VSA12',\n",
       "  'PEOE_VSA13',\n",
       "  'PEOE_VSA14',\n",
       "  'PEOE_VSA2',\n",
       "  'PEOE_VSA3',\n",
       "  'PEOE_VSA4',\n",
       "  'PEOE_VSA5',\n",
       "  'PEOE_VSA6',\n",
       "  'PEOE_VSA7',\n",
       "  'PEOE_VSA8',\n",
       "  'PEOE_VSA9',\n",
       "  'SMR_VSA1',\n",
       "  'SMR_VSA10',\n",
       "  'SMR_VSA2',\n",
       "  'SMR_VSA3',\n",
       "  'SMR_VSA4',\n",
       "  'SMR_VSA5',\n",
       "  'SMR_VSA6',\n",
       "  'SMR_VSA7',\n",
       "  'SMR_VSA8',\n",
       "  'SMR_VSA9',\n",
       "  'SlogP_VSA1',\n",
       "  'SlogP_VSA10',\n",
       "  'SlogP_VSA11',\n",
       "  'SlogP_VSA12',\n",
       "  'SlogP_VSA2',\n",
       "  'SlogP_VSA3',\n",
       "  'SlogP_VSA4',\n",
       "  'SlogP_VSA5',\n",
       "  'SlogP_VSA6',\n",
       "  'SlogP_VSA7',\n",
       "  'SlogP_VSA8',\n",
       "  'SlogP_VSA9',\n",
       "  'TPSA',\n",
       "  'EState_VSA1',\n",
       "  'EState_VSA10',\n",
       "  'EState_VSA11',\n",
       "  'EState_VSA2',\n",
       "  'EState_VSA3',\n",
       "  'EState_VSA4',\n",
       "  'EState_VSA5',\n",
       "  'EState_VSA6',\n",
       "  'EState_VSA7',\n",
       "  'EState_VSA8',\n",
       "  'EState_VSA9',\n",
       "  'VSA_EState1',\n",
       "  'VSA_EState10',\n",
       "  'VSA_EState2',\n",
       "  'VSA_EState3',\n",
       "  'VSA_EState4',\n",
       "  'VSA_EState5',\n",
       "  'VSA_EState6',\n",
       "  'VSA_EState7',\n",
       "  'VSA_EState8',\n",
       "  'VSA_EState9',\n",
       "  'FractionCSP3',\n",
       "  'HeavyAtomCount',\n",
       "  'NHOHCount',\n",
       "  'NOCount',\n",
       "  'NumAliphaticCarbocycles',\n",
       "  'NumAliphaticHeterocycles',\n",
       "  'NumAliphaticRings',\n",
       "  'NumAromaticCarbocycles',\n",
       "  'NumAromaticHeterocycles',\n",
       "  'NumAromaticRings',\n",
       "  'NumHAcceptors',\n",
       "  'NumHDonors',\n",
       "  'NumHeteroatoms',\n",
       "  'NumRotatableBonds',\n",
       "  'NumSaturatedCarbocycles',\n",
       "  'NumSaturatedHeterocycles',\n",
       "  'NumSaturatedRings',\n",
       "  'RingCount',\n",
       "  'MolLogP',\n",
       "  'MolMR',\n",
       "  'fr_Al_COO',\n",
       "  'fr_Al_OH',\n",
       "  'fr_Al_OH_noTert',\n",
       "  'fr_ArN',\n",
       "  'fr_Ar_COO',\n",
       "  'fr_Ar_N',\n",
       "  'fr_Ar_NH',\n",
       "  'fr_Ar_OH',\n",
       "  'fr_COO',\n",
       "  'fr_COO2',\n",
       "  'fr_C_O',\n",
       "  'fr_C_O_noCOO',\n",
       "  'fr_C_S',\n",
       "  'fr_HOCCN',\n",
       "  'fr_Imine',\n",
       "  'fr_NH0',\n",
       "  'fr_NH1',\n",
       "  'fr_NH2',\n",
       "  'fr_N_O',\n",
       "  'fr_Ndealkylation1',\n",
       "  'fr_Ndealkylation2',\n",
       "  'fr_Nhpyrrole',\n",
       "  'fr_SH',\n",
       "  'fr_aldehyde',\n",
       "  'fr_alkyl_carbamate',\n",
       "  'fr_alkyl_halide',\n",
       "  'fr_allylic_oxid',\n",
       "  'fr_amide',\n",
       "  'fr_amidine',\n",
       "  'fr_aniline',\n",
       "  'fr_aryl_methyl',\n",
       "  'fr_azide',\n",
       "  'fr_azo',\n",
       "  'fr_barbitur',\n",
       "  'fr_benzene',\n",
       "  'fr_benzodiazepine',\n",
       "  'fr_bicyclic',\n",
       "  'fr_diazo',\n",
       "  'fr_dihydropyridine',\n",
       "  'fr_epoxide',\n",
       "  'fr_ester',\n",
       "  'fr_ether',\n",
       "  'fr_furan',\n",
       "  'fr_guanido',\n",
       "  'fr_halogen',\n",
       "  'fr_hdrzine',\n",
       "  'fr_hdrzone',\n",
       "  'fr_imidazole',\n",
       "  'fr_imide',\n",
       "  'fr_isocyan',\n",
       "  'fr_isothiocyan',\n",
       "  'fr_ketone',\n",
       "  'fr_ketone_Topliss',\n",
       "  'fr_lactam',\n",
       "  'fr_lactone',\n",
       "  'fr_methoxy',\n",
       "  'fr_morpholine',\n",
       "  'fr_nitrile',\n",
       "  'fr_nitro',\n",
       "  'fr_nitro_arom',\n",
       "  'fr_nitro_arom_nonortho',\n",
       "  'fr_nitroso',\n",
       "  'fr_oxazole',\n",
       "  'fr_oxime',\n",
       "  'fr_para_hydroxylation',\n",
       "  'fr_phenol',\n",
       "  'fr_phenol_noOrthoHbond',\n",
       "  'fr_phos_acid',\n",
       "  'fr_phos_ester',\n",
       "  'fr_piperdine',\n",
       "  'fr_piperzine',\n",
       "  'fr_priamide',\n",
       "  'fr_prisulfonamd',\n",
       "  'fr_pyridine',\n",
       "  'fr_quatN',\n",
       "  'fr_sulfide',\n",
       "  'fr_sulfonamd',\n",
       "  'fr_sulfone',\n",
       "  'fr_term_acetylene',\n",
       "  'fr_tetrazole',\n",
       "  'fr_thiazole',\n",
       "  'fr_thiocyan',\n",
       "  'fr_thiophene',\n",
       "  'fr_unbrch_alkane',\n",
       "  'fr_urea'])"
      ]
     },
     "execution_count": 4,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "get_rdkit_descriptors(tmp_smile)"
   ]
  },
  {
   "cell_type": "markdown",
   "metadata": {},
   "source": [
    "### MACCS"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 5,
   "metadata": {},
   "outputs": [],
   "source": [
    "from rdkit import Chem\n",
    "from rdkit.Chem import MACCSkeys\n",
    "\n",
    "def get_maccs(input_smile):\n",
    "    MACCS_list = []\n",
    "    mol = Chem.MolFromSmiles(input_smile)\n",
    "    header = ['maccs_bit' + str(i) for i in range(167)]\n",
    "    MACCS_list = list(MACCSkeys.GenMACCSKeys(mol).ToBitString())       \n",
    "    return np.array(MACCS_list,dtype=np.float32), header"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 6,
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "(array([0., 0., 0., 0., 0., 0., 0., 0., 0., 0., 0., 0., 0., 0., 0., 0., 0.,\n",
       "        0., 0., 0., 0., 0., 0., 1., 0., 0., 1., 0., 0., 0., 0., 0., 0., 0.,\n",
       "        1., 0., 0., 0., 0., 0., 0., 0., 0., 0., 0., 1., 0., 0., 0., 0., 1.,\n",
       "        0., 0., 0., 0., 0., 0., 0., 0., 0., 0., 0., 0., 0., 0., 0., 0., 0.,\n",
       "        0., 0., 0., 0., 1., 0., 0., 0., 1., 0., 0., 0., 0., 0., 1., 0., 1.,\n",
       "        0., 0., 0., 0., 0., 1., 1., 1., 1., 0., 1., 0., 1., 0., 1., 1., 0.,\n",
       "        0., 0., 0., 1., 1., 0., 1., 0., 1., 0., 0., 0., 0., 1., 1., 1., 0.,\n",
       "        0., 0., 1., 0., 1., 0., 0., 1., 1., 1., 0., 0., 1., 1., 1., 0., 0.,\n",
       "        1., 1., 0., 1., 1., 1., 1., 1., 0., 0., 1., 0., 0., 1., 1., 1., 1.,\n",
       "        1., 1., 1., 1., 1., 1., 1., 1., 1., 0., 1., 1., 1., 0.],\n",
       "       dtype=float32),\n",
       " ['maccs_bit0',\n",
       "  'maccs_bit1',\n",
       "  'maccs_bit2',\n",
       "  'maccs_bit3',\n",
       "  'maccs_bit4',\n",
       "  'maccs_bit5',\n",
       "  'maccs_bit6',\n",
       "  'maccs_bit7',\n",
       "  'maccs_bit8',\n",
       "  'maccs_bit9',\n",
       "  'maccs_bit10',\n",
       "  'maccs_bit11',\n",
       "  'maccs_bit12',\n",
       "  'maccs_bit13',\n",
       "  'maccs_bit14',\n",
       "  'maccs_bit15',\n",
       "  'maccs_bit16',\n",
       "  'maccs_bit17',\n",
       "  'maccs_bit18',\n",
       "  'maccs_bit19',\n",
       "  'maccs_bit20',\n",
       "  'maccs_bit21',\n",
       "  'maccs_bit22',\n",
       "  'maccs_bit23',\n",
       "  'maccs_bit24',\n",
       "  'maccs_bit25',\n",
       "  'maccs_bit26',\n",
       "  'maccs_bit27',\n",
       "  'maccs_bit28',\n",
       "  'maccs_bit29',\n",
       "  'maccs_bit30',\n",
       "  'maccs_bit31',\n",
       "  'maccs_bit32',\n",
       "  'maccs_bit33',\n",
       "  'maccs_bit34',\n",
       "  'maccs_bit35',\n",
       "  'maccs_bit36',\n",
       "  'maccs_bit37',\n",
       "  'maccs_bit38',\n",
       "  'maccs_bit39',\n",
       "  'maccs_bit40',\n",
       "  'maccs_bit41',\n",
       "  'maccs_bit42',\n",
       "  'maccs_bit43',\n",
       "  'maccs_bit44',\n",
       "  'maccs_bit45',\n",
       "  'maccs_bit46',\n",
       "  'maccs_bit47',\n",
       "  'maccs_bit48',\n",
       "  'maccs_bit49',\n",
       "  'maccs_bit50',\n",
       "  'maccs_bit51',\n",
       "  'maccs_bit52',\n",
       "  'maccs_bit53',\n",
       "  'maccs_bit54',\n",
       "  'maccs_bit55',\n",
       "  'maccs_bit56',\n",
       "  'maccs_bit57',\n",
       "  'maccs_bit58',\n",
       "  'maccs_bit59',\n",
       "  'maccs_bit60',\n",
       "  'maccs_bit61',\n",
       "  'maccs_bit62',\n",
       "  'maccs_bit63',\n",
       "  'maccs_bit64',\n",
       "  'maccs_bit65',\n",
       "  'maccs_bit66',\n",
       "  'maccs_bit67',\n",
       "  'maccs_bit68',\n",
       "  'maccs_bit69',\n",
       "  'maccs_bit70',\n",
       "  'maccs_bit71',\n",
       "  'maccs_bit72',\n",
       "  'maccs_bit73',\n",
       "  'maccs_bit74',\n",
       "  'maccs_bit75',\n",
       "  'maccs_bit76',\n",
       "  'maccs_bit77',\n",
       "  'maccs_bit78',\n",
       "  'maccs_bit79',\n",
       "  'maccs_bit80',\n",
       "  'maccs_bit81',\n",
       "  'maccs_bit82',\n",
       "  'maccs_bit83',\n",
       "  'maccs_bit84',\n",
       "  'maccs_bit85',\n",
       "  'maccs_bit86',\n",
       "  'maccs_bit87',\n",
       "  'maccs_bit88',\n",
       "  'maccs_bit89',\n",
       "  'maccs_bit90',\n",
       "  'maccs_bit91',\n",
       "  'maccs_bit92',\n",
       "  'maccs_bit93',\n",
       "  'maccs_bit94',\n",
       "  'maccs_bit95',\n",
       "  'maccs_bit96',\n",
       "  'maccs_bit97',\n",
       "  'maccs_bit98',\n",
       "  'maccs_bit99',\n",
       "  'maccs_bit100',\n",
       "  'maccs_bit101',\n",
       "  'maccs_bit102',\n",
       "  'maccs_bit103',\n",
       "  'maccs_bit104',\n",
       "  'maccs_bit105',\n",
       "  'maccs_bit106',\n",
       "  'maccs_bit107',\n",
       "  'maccs_bit108',\n",
       "  'maccs_bit109',\n",
       "  'maccs_bit110',\n",
       "  'maccs_bit111',\n",
       "  'maccs_bit112',\n",
       "  'maccs_bit113',\n",
       "  'maccs_bit114',\n",
       "  'maccs_bit115',\n",
       "  'maccs_bit116',\n",
       "  'maccs_bit117',\n",
       "  'maccs_bit118',\n",
       "  'maccs_bit119',\n",
       "  'maccs_bit120',\n",
       "  'maccs_bit121',\n",
       "  'maccs_bit122',\n",
       "  'maccs_bit123',\n",
       "  'maccs_bit124',\n",
       "  'maccs_bit125',\n",
       "  'maccs_bit126',\n",
       "  'maccs_bit127',\n",
       "  'maccs_bit128',\n",
       "  'maccs_bit129',\n",
       "  'maccs_bit130',\n",
       "  'maccs_bit131',\n",
       "  'maccs_bit132',\n",
       "  'maccs_bit133',\n",
       "  'maccs_bit134',\n",
       "  'maccs_bit135',\n",
       "  'maccs_bit136',\n",
       "  'maccs_bit137',\n",
       "  'maccs_bit138',\n",
       "  'maccs_bit139',\n",
       "  'maccs_bit140',\n",
       "  'maccs_bit141',\n",
       "  'maccs_bit142',\n",
       "  'maccs_bit143',\n",
       "  'maccs_bit144',\n",
       "  'maccs_bit145',\n",
       "  'maccs_bit146',\n",
       "  'maccs_bit147',\n",
       "  'maccs_bit148',\n",
       "  'maccs_bit149',\n",
       "  'maccs_bit150',\n",
       "  'maccs_bit151',\n",
       "  'maccs_bit152',\n",
       "  'maccs_bit153',\n",
       "  'maccs_bit154',\n",
       "  'maccs_bit155',\n",
       "  'maccs_bit156',\n",
       "  'maccs_bit157',\n",
       "  'maccs_bit158',\n",
       "  'maccs_bit159',\n",
       "  'maccs_bit160',\n",
       "  'maccs_bit161',\n",
       "  'maccs_bit162',\n",
       "  'maccs_bit163',\n",
       "  'maccs_bit164',\n",
       "  'maccs_bit165',\n",
       "  'maccs_bit166'])"
      ]
     },
     "execution_count": 6,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "get_maccs(tmp_smile)"
   ]
  },
  {
   "cell_type": "markdown",
   "metadata": {},
   "source": [
    "### ECFP6"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 7,
   "metadata": {},
   "outputs": [],
   "source": [
    "from rdkit.Chem import AllChem\n",
    "from rdkit import Chem, DataStructs\n",
    "\n",
    "def mol2fp(mol, radius = 3):\n",
    "    fp = AllChem.GetMorganFingerprintAsBitVect(mol, radius = radius)\n",
    "    array = np.zeros((1,))\n",
    "    DataStructs.ConvertToNumpyArray(fp, array)\n",
    "    return array\n",
    "\n",
    "def get_ECFP6(input_smile):\n",
    "    bit_headers = ['ecfp6_bit' + str(i) for i in range(2048)]\n",
    "    arr = np.empty((0,2048), int).astype(int)\n",
    "    mol = Chem.MolFromSmiles(input_smile)\n",
    "    fp = mol2fp(mol)\n",
    "    return np.array(list(fp),np.float32), bit_headers"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 8,
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "(array([0., 0., 0., ..., 0., 0., 0.], dtype=float32),\n",
       " ['ecfp6_bit0',\n",
       "  'ecfp6_bit1',\n",
       "  'ecfp6_bit2',\n",
       "  'ecfp6_bit3',\n",
       "  'ecfp6_bit4',\n",
       "  'ecfp6_bit5',\n",
       "  'ecfp6_bit6',\n",
       "  'ecfp6_bit7',\n",
       "  'ecfp6_bit8',\n",
       "  'ecfp6_bit9',\n",
       "  'ecfp6_bit10',\n",
       "  'ecfp6_bit11',\n",
       "  'ecfp6_bit12',\n",
       "  'ecfp6_bit13',\n",
       "  'ecfp6_bit14',\n",
       "  'ecfp6_bit15',\n",
       "  'ecfp6_bit16',\n",
       "  'ecfp6_bit17',\n",
       "  'ecfp6_bit18',\n",
       "  'ecfp6_bit19',\n",
       "  'ecfp6_bit20',\n",
       "  'ecfp6_bit21',\n",
       "  'ecfp6_bit22',\n",
       "  'ecfp6_bit23',\n",
       "  'ecfp6_bit24',\n",
       "  'ecfp6_bit25',\n",
       "  'ecfp6_bit26',\n",
       "  'ecfp6_bit27',\n",
       "  'ecfp6_bit28',\n",
       "  'ecfp6_bit29',\n",
       "  'ecfp6_bit30',\n",
       "  'ecfp6_bit31',\n",
       "  'ecfp6_bit32',\n",
       "  'ecfp6_bit33',\n",
       "  'ecfp6_bit34',\n",
       "  'ecfp6_bit35',\n",
       "  'ecfp6_bit36',\n",
       "  'ecfp6_bit37',\n",
       "  'ecfp6_bit38',\n",
       "  'ecfp6_bit39',\n",
       "  'ecfp6_bit40',\n",
       "  'ecfp6_bit41',\n",
       "  'ecfp6_bit42',\n",
       "  'ecfp6_bit43',\n",
       "  'ecfp6_bit44',\n",
       "  'ecfp6_bit45',\n",
       "  'ecfp6_bit46',\n",
       "  'ecfp6_bit47',\n",
       "  'ecfp6_bit48',\n",
       "  'ecfp6_bit49',\n",
       "  'ecfp6_bit50',\n",
       "  'ecfp6_bit51',\n",
       "  'ecfp6_bit52',\n",
       "  'ecfp6_bit53',\n",
       "  'ecfp6_bit54',\n",
       "  'ecfp6_bit55',\n",
       "  'ecfp6_bit56',\n",
       "  'ecfp6_bit57',\n",
       "  'ecfp6_bit58',\n",
       "  'ecfp6_bit59',\n",
       "  'ecfp6_bit60',\n",
       "  'ecfp6_bit61',\n",
       "  'ecfp6_bit62',\n",
       "  'ecfp6_bit63',\n",
       "  'ecfp6_bit64',\n",
       "  'ecfp6_bit65',\n",
       "  'ecfp6_bit66',\n",
       "  'ecfp6_bit67',\n",
       "  'ecfp6_bit68',\n",
       "  'ecfp6_bit69',\n",
       "  'ecfp6_bit70',\n",
       "  'ecfp6_bit71',\n",
       "  'ecfp6_bit72',\n",
       "  'ecfp6_bit73',\n",
       "  'ecfp6_bit74',\n",
       "  'ecfp6_bit75',\n",
       "  'ecfp6_bit76',\n",
       "  'ecfp6_bit77',\n",
       "  'ecfp6_bit78',\n",
       "  'ecfp6_bit79',\n",
       "  'ecfp6_bit80',\n",
       "  'ecfp6_bit81',\n",
       "  'ecfp6_bit82',\n",
       "  'ecfp6_bit83',\n",
       "  'ecfp6_bit84',\n",
       "  'ecfp6_bit85',\n",
       "  'ecfp6_bit86',\n",
       "  'ecfp6_bit87',\n",
       "  'ecfp6_bit88',\n",
       "  'ecfp6_bit89',\n",
       "  'ecfp6_bit90',\n",
       "  'ecfp6_bit91',\n",
       "  'ecfp6_bit92',\n",
       "  'ecfp6_bit93',\n",
       "  'ecfp6_bit94',\n",
       "  'ecfp6_bit95',\n",
       "  'ecfp6_bit96',\n",
       "  'ecfp6_bit97',\n",
       "  'ecfp6_bit98',\n",
       "  'ecfp6_bit99',\n",
       "  'ecfp6_bit100',\n",
       "  'ecfp6_bit101',\n",
       "  'ecfp6_bit102',\n",
       "  'ecfp6_bit103',\n",
       "  'ecfp6_bit104',\n",
       "  'ecfp6_bit105',\n",
       "  'ecfp6_bit106',\n",
       "  'ecfp6_bit107',\n",
       "  'ecfp6_bit108',\n",
       "  'ecfp6_bit109',\n",
       "  'ecfp6_bit110',\n",
       "  'ecfp6_bit111',\n",
       "  'ecfp6_bit112',\n",
       "  'ecfp6_bit113',\n",
       "  'ecfp6_bit114',\n",
       "  'ecfp6_bit115',\n",
       "  'ecfp6_bit116',\n",
       "  'ecfp6_bit117',\n",
       "  'ecfp6_bit118',\n",
       "  'ecfp6_bit119',\n",
       "  'ecfp6_bit120',\n",
       "  'ecfp6_bit121',\n",
       "  'ecfp6_bit122',\n",
       "  'ecfp6_bit123',\n",
       "  'ecfp6_bit124',\n",
       "  'ecfp6_bit125',\n",
       "  'ecfp6_bit126',\n",
       "  'ecfp6_bit127',\n",
       "  'ecfp6_bit128',\n",
       "  'ecfp6_bit129',\n",
       "  'ecfp6_bit130',\n",
       "  'ecfp6_bit131',\n",
       "  'ecfp6_bit132',\n",
       "  'ecfp6_bit133',\n",
       "  'ecfp6_bit134',\n",
       "  'ecfp6_bit135',\n",
       "  'ecfp6_bit136',\n",
       "  'ecfp6_bit137',\n",
       "  'ecfp6_bit138',\n",
       "  'ecfp6_bit139',\n",
       "  'ecfp6_bit140',\n",
       "  'ecfp6_bit141',\n",
       "  'ecfp6_bit142',\n",
       "  'ecfp6_bit143',\n",
       "  'ecfp6_bit144',\n",
       "  'ecfp6_bit145',\n",
       "  'ecfp6_bit146',\n",
       "  'ecfp6_bit147',\n",
       "  'ecfp6_bit148',\n",
       "  'ecfp6_bit149',\n",
       "  'ecfp6_bit150',\n",
       "  'ecfp6_bit151',\n",
       "  'ecfp6_bit152',\n",
       "  'ecfp6_bit153',\n",
       "  'ecfp6_bit154',\n",
       "  'ecfp6_bit155',\n",
       "  'ecfp6_bit156',\n",
       "  'ecfp6_bit157',\n",
       "  'ecfp6_bit158',\n",
       "  'ecfp6_bit159',\n",
       "  'ecfp6_bit160',\n",
       "  'ecfp6_bit161',\n",
       "  'ecfp6_bit162',\n",
       "  'ecfp6_bit163',\n",
       "  'ecfp6_bit164',\n",
       "  'ecfp6_bit165',\n",
       "  'ecfp6_bit166',\n",
       "  'ecfp6_bit167',\n",
       "  'ecfp6_bit168',\n",
       "  'ecfp6_bit169',\n",
       "  'ecfp6_bit170',\n",
       "  'ecfp6_bit171',\n",
       "  'ecfp6_bit172',\n",
       "  'ecfp6_bit173',\n",
       "  'ecfp6_bit174',\n",
       "  'ecfp6_bit175',\n",
       "  'ecfp6_bit176',\n",
       "  'ecfp6_bit177',\n",
       "  'ecfp6_bit178',\n",
       "  'ecfp6_bit179',\n",
       "  'ecfp6_bit180',\n",
       "  'ecfp6_bit181',\n",
       "  'ecfp6_bit182',\n",
       "  'ecfp6_bit183',\n",
       "  'ecfp6_bit184',\n",
       "  'ecfp6_bit185',\n",
       "  'ecfp6_bit186',\n",
       "  'ecfp6_bit187',\n",
       "  'ecfp6_bit188',\n",
       "  'ecfp6_bit189',\n",
       "  'ecfp6_bit190',\n",
       "  'ecfp6_bit191',\n",
       "  'ecfp6_bit192',\n",
       "  'ecfp6_bit193',\n",
       "  'ecfp6_bit194',\n",
       "  'ecfp6_bit195',\n",
       "  'ecfp6_bit196',\n",
       "  'ecfp6_bit197',\n",
       "  'ecfp6_bit198',\n",
       "  'ecfp6_bit199',\n",
       "  'ecfp6_bit200',\n",
       "  'ecfp6_bit201',\n",
       "  'ecfp6_bit202',\n",
       "  'ecfp6_bit203',\n",
       "  'ecfp6_bit204',\n",
       "  'ecfp6_bit205',\n",
       "  'ecfp6_bit206',\n",
       "  'ecfp6_bit207',\n",
       "  'ecfp6_bit208',\n",
       "  'ecfp6_bit209',\n",
       "  'ecfp6_bit210',\n",
       "  'ecfp6_bit211',\n",
       "  'ecfp6_bit212',\n",
       "  'ecfp6_bit213',\n",
       "  'ecfp6_bit214',\n",
       "  'ecfp6_bit215',\n",
       "  'ecfp6_bit216',\n",
       "  'ecfp6_bit217',\n",
       "  'ecfp6_bit218',\n",
       "  'ecfp6_bit219',\n",
       "  'ecfp6_bit220',\n",
       "  'ecfp6_bit221',\n",
       "  'ecfp6_bit222',\n",
       "  'ecfp6_bit223',\n",
       "  'ecfp6_bit224',\n",
       "  'ecfp6_bit225',\n",
       "  'ecfp6_bit226',\n",
       "  'ecfp6_bit227',\n",
       "  'ecfp6_bit228',\n",
       "  'ecfp6_bit229',\n",
       "  'ecfp6_bit230',\n",
       "  'ecfp6_bit231',\n",
       "  'ecfp6_bit232',\n",
       "  'ecfp6_bit233',\n",
       "  'ecfp6_bit234',\n",
       "  'ecfp6_bit235',\n",
       "  'ecfp6_bit236',\n",
       "  'ecfp6_bit237',\n",
       "  'ecfp6_bit238',\n",
       "  'ecfp6_bit239',\n",
       "  'ecfp6_bit240',\n",
       "  'ecfp6_bit241',\n",
       "  'ecfp6_bit242',\n",
       "  'ecfp6_bit243',\n",
       "  'ecfp6_bit244',\n",
       "  'ecfp6_bit245',\n",
       "  'ecfp6_bit246',\n",
       "  'ecfp6_bit247',\n",
       "  'ecfp6_bit248',\n",
       "  'ecfp6_bit249',\n",
       "  'ecfp6_bit250',\n",
       "  'ecfp6_bit251',\n",
       "  'ecfp6_bit252',\n",
       "  'ecfp6_bit253',\n",
       "  'ecfp6_bit254',\n",
       "  'ecfp6_bit255',\n",
       "  'ecfp6_bit256',\n",
       "  'ecfp6_bit257',\n",
       "  'ecfp6_bit258',\n",
       "  'ecfp6_bit259',\n",
       "  'ecfp6_bit260',\n",
       "  'ecfp6_bit261',\n",
       "  'ecfp6_bit262',\n",
       "  'ecfp6_bit263',\n",
       "  'ecfp6_bit264',\n",
       "  'ecfp6_bit265',\n",
       "  'ecfp6_bit266',\n",
       "  'ecfp6_bit267',\n",
       "  'ecfp6_bit268',\n",
       "  'ecfp6_bit269',\n",
       "  'ecfp6_bit270',\n",
       "  'ecfp6_bit271',\n",
       "  'ecfp6_bit272',\n",
       "  'ecfp6_bit273',\n",
       "  'ecfp6_bit274',\n",
       "  'ecfp6_bit275',\n",
       "  'ecfp6_bit276',\n",
       "  'ecfp6_bit277',\n",
       "  'ecfp6_bit278',\n",
       "  'ecfp6_bit279',\n",
       "  'ecfp6_bit280',\n",
       "  'ecfp6_bit281',\n",
       "  'ecfp6_bit282',\n",
       "  'ecfp6_bit283',\n",
       "  'ecfp6_bit284',\n",
       "  'ecfp6_bit285',\n",
       "  'ecfp6_bit286',\n",
       "  'ecfp6_bit287',\n",
       "  'ecfp6_bit288',\n",
       "  'ecfp6_bit289',\n",
       "  'ecfp6_bit290',\n",
       "  'ecfp6_bit291',\n",
       "  'ecfp6_bit292',\n",
       "  'ecfp6_bit293',\n",
       "  'ecfp6_bit294',\n",
       "  'ecfp6_bit295',\n",
       "  'ecfp6_bit296',\n",
       "  'ecfp6_bit297',\n",
       "  'ecfp6_bit298',\n",
       "  'ecfp6_bit299',\n",
       "  'ecfp6_bit300',\n",
       "  'ecfp6_bit301',\n",
       "  'ecfp6_bit302',\n",
       "  'ecfp6_bit303',\n",
       "  'ecfp6_bit304',\n",
       "  'ecfp6_bit305',\n",
       "  'ecfp6_bit306',\n",
       "  'ecfp6_bit307',\n",
       "  'ecfp6_bit308',\n",
       "  'ecfp6_bit309',\n",
       "  'ecfp6_bit310',\n",
       "  'ecfp6_bit311',\n",
       "  'ecfp6_bit312',\n",
       "  'ecfp6_bit313',\n",
       "  'ecfp6_bit314',\n",
       "  'ecfp6_bit315',\n",
       "  'ecfp6_bit316',\n",
       "  'ecfp6_bit317',\n",
       "  'ecfp6_bit318',\n",
       "  'ecfp6_bit319',\n",
       "  'ecfp6_bit320',\n",
       "  'ecfp6_bit321',\n",
       "  'ecfp6_bit322',\n",
       "  'ecfp6_bit323',\n",
       "  'ecfp6_bit324',\n",
       "  'ecfp6_bit325',\n",
       "  'ecfp6_bit326',\n",
       "  'ecfp6_bit327',\n",
       "  'ecfp6_bit328',\n",
       "  'ecfp6_bit329',\n",
       "  'ecfp6_bit330',\n",
       "  'ecfp6_bit331',\n",
       "  'ecfp6_bit332',\n",
       "  'ecfp6_bit333',\n",
       "  'ecfp6_bit334',\n",
       "  'ecfp6_bit335',\n",
       "  'ecfp6_bit336',\n",
       "  'ecfp6_bit337',\n",
       "  'ecfp6_bit338',\n",
       "  'ecfp6_bit339',\n",
       "  'ecfp6_bit340',\n",
       "  'ecfp6_bit341',\n",
       "  'ecfp6_bit342',\n",
       "  'ecfp6_bit343',\n",
       "  'ecfp6_bit344',\n",
       "  'ecfp6_bit345',\n",
       "  'ecfp6_bit346',\n",
       "  'ecfp6_bit347',\n",
       "  'ecfp6_bit348',\n",
       "  'ecfp6_bit349',\n",
       "  'ecfp6_bit350',\n",
       "  'ecfp6_bit351',\n",
       "  'ecfp6_bit352',\n",
       "  'ecfp6_bit353',\n",
       "  'ecfp6_bit354',\n",
       "  'ecfp6_bit355',\n",
       "  'ecfp6_bit356',\n",
       "  'ecfp6_bit357',\n",
       "  'ecfp6_bit358',\n",
       "  'ecfp6_bit359',\n",
       "  'ecfp6_bit360',\n",
       "  'ecfp6_bit361',\n",
       "  'ecfp6_bit362',\n",
       "  'ecfp6_bit363',\n",
       "  'ecfp6_bit364',\n",
       "  'ecfp6_bit365',\n",
       "  'ecfp6_bit366',\n",
       "  'ecfp6_bit367',\n",
       "  'ecfp6_bit368',\n",
       "  'ecfp6_bit369',\n",
       "  'ecfp6_bit370',\n",
       "  'ecfp6_bit371',\n",
       "  'ecfp6_bit372',\n",
       "  'ecfp6_bit373',\n",
       "  'ecfp6_bit374',\n",
       "  'ecfp6_bit375',\n",
       "  'ecfp6_bit376',\n",
       "  'ecfp6_bit377',\n",
       "  'ecfp6_bit378',\n",
       "  'ecfp6_bit379',\n",
       "  'ecfp6_bit380',\n",
       "  'ecfp6_bit381',\n",
       "  'ecfp6_bit382',\n",
       "  'ecfp6_bit383',\n",
       "  'ecfp6_bit384',\n",
       "  'ecfp6_bit385',\n",
       "  'ecfp6_bit386',\n",
       "  'ecfp6_bit387',\n",
       "  'ecfp6_bit388',\n",
       "  'ecfp6_bit389',\n",
       "  'ecfp6_bit390',\n",
       "  'ecfp6_bit391',\n",
       "  'ecfp6_bit392',\n",
       "  'ecfp6_bit393',\n",
       "  'ecfp6_bit394',\n",
       "  'ecfp6_bit395',\n",
       "  'ecfp6_bit396',\n",
       "  'ecfp6_bit397',\n",
       "  'ecfp6_bit398',\n",
       "  'ecfp6_bit399',\n",
       "  'ecfp6_bit400',\n",
       "  'ecfp6_bit401',\n",
       "  'ecfp6_bit402',\n",
       "  'ecfp6_bit403',\n",
       "  'ecfp6_bit404',\n",
       "  'ecfp6_bit405',\n",
       "  'ecfp6_bit406',\n",
       "  'ecfp6_bit407',\n",
       "  'ecfp6_bit408',\n",
       "  'ecfp6_bit409',\n",
       "  'ecfp6_bit410',\n",
       "  'ecfp6_bit411',\n",
       "  'ecfp6_bit412',\n",
       "  'ecfp6_bit413',\n",
       "  'ecfp6_bit414',\n",
       "  'ecfp6_bit415',\n",
       "  'ecfp6_bit416',\n",
       "  'ecfp6_bit417',\n",
       "  'ecfp6_bit418',\n",
       "  'ecfp6_bit419',\n",
       "  'ecfp6_bit420',\n",
       "  'ecfp6_bit421',\n",
       "  'ecfp6_bit422',\n",
       "  'ecfp6_bit423',\n",
       "  'ecfp6_bit424',\n",
       "  'ecfp6_bit425',\n",
       "  'ecfp6_bit426',\n",
       "  'ecfp6_bit427',\n",
       "  'ecfp6_bit428',\n",
       "  'ecfp6_bit429',\n",
       "  'ecfp6_bit430',\n",
       "  'ecfp6_bit431',\n",
       "  'ecfp6_bit432',\n",
       "  'ecfp6_bit433',\n",
       "  'ecfp6_bit434',\n",
       "  'ecfp6_bit435',\n",
       "  'ecfp6_bit436',\n",
       "  'ecfp6_bit437',\n",
       "  'ecfp6_bit438',\n",
       "  'ecfp6_bit439',\n",
       "  'ecfp6_bit440',\n",
       "  'ecfp6_bit441',\n",
       "  'ecfp6_bit442',\n",
       "  'ecfp6_bit443',\n",
       "  'ecfp6_bit444',\n",
       "  'ecfp6_bit445',\n",
       "  'ecfp6_bit446',\n",
       "  'ecfp6_bit447',\n",
       "  'ecfp6_bit448',\n",
       "  'ecfp6_bit449',\n",
       "  'ecfp6_bit450',\n",
       "  'ecfp6_bit451',\n",
       "  'ecfp6_bit452',\n",
       "  'ecfp6_bit453',\n",
       "  'ecfp6_bit454',\n",
       "  'ecfp6_bit455',\n",
       "  'ecfp6_bit456',\n",
       "  'ecfp6_bit457',\n",
       "  'ecfp6_bit458',\n",
       "  'ecfp6_bit459',\n",
       "  'ecfp6_bit460',\n",
       "  'ecfp6_bit461',\n",
       "  'ecfp6_bit462',\n",
       "  'ecfp6_bit463',\n",
       "  'ecfp6_bit464',\n",
       "  'ecfp6_bit465',\n",
       "  'ecfp6_bit466',\n",
       "  'ecfp6_bit467',\n",
       "  'ecfp6_bit468',\n",
       "  'ecfp6_bit469',\n",
       "  'ecfp6_bit470',\n",
       "  'ecfp6_bit471',\n",
       "  'ecfp6_bit472',\n",
       "  'ecfp6_bit473',\n",
       "  'ecfp6_bit474',\n",
       "  'ecfp6_bit475',\n",
       "  'ecfp6_bit476',\n",
       "  'ecfp6_bit477',\n",
       "  'ecfp6_bit478',\n",
       "  'ecfp6_bit479',\n",
       "  'ecfp6_bit480',\n",
       "  'ecfp6_bit481',\n",
       "  'ecfp6_bit482',\n",
       "  'ecfp6_bit483',\n",
       "  'ecfp6_bit484',\n",
       "  'ecfp6_bit485',\n",
       "  'ecfp6_bit486',\n",
       "  'ecfp6_bit487',\n",
       "  'ecfp6_bit488',\n",
       "  'ecfp6_bit489',\n",
       "  'ecfp6_bit490',\n",
       "  'ecfp6_bit491',\n",
       "  'ecfp6_bit492',\n",
       "  'ecfp6_bit493',\n",
       "  'ecfp6_bit494',\n",
       "  'ecfp6_bit495',\n",
       "  'ecfp6_bit496',\n",
       "  'ecfp6_bit497',\n",
       "  'ecfp6_bit498',\n",
       "  'ecfp6_bit499',\n",
       "  'ecfp6_bit500',\n",
       "  'ecfp6_bit501',\n",
       "  'ecfp6_bit502',\n",
       "  'ecfp6_bit503',\n",
       "  'ecfp6_bit504',\n",
       "  'ecfp6_bit505',\n",
       "  'ecfp6_bit506',\n",
       "  'ecfp6_bit507',\n",
       "  'ecfp6_bit508',\n",
       "  'ecfp6_bit509',\n",
       "  'ecfp6_bit510',\n",
       "  'ecfp6_bit511',\n",
       "  'ecfp6_bit512',\n",
       "  'ecfp6_bit513',\n",
       "  'ecfp6_bit514',\n",
       "  'ecfp6_bit515',\n",
       "  'ecfp6_bit516',\n",
       "  'ecfp6_bit517',\n",
       "  'ecfp6_bit518',\n",
       "  'ecfp6_bit519',\n",
       "  'ecfp6_bit520',\n",
       "  'ecfp6_bit521',\n",
       "  'ecfp6_bit522',\n",
       "  'ecfp6_bit523',\n",
       "  'ecfp6_bit524',\n",
       "  'ecfp6_bit525',\n",
       "  'ecfp6_bit526',\n",
       "  'ecfp6_bit527',\n",
       "  'ecfp6_bit528',\n",
       "  'ecfp6_bit529',\n",
       "  'ecfp6_bit530',\n",
       "  'ecfp6_bit531',\n",
       "  'ecfp6_bit532',\n",
       "  'ecfp6_bit533',\n",
       "  'ecfp6_bit534',\n",
       "  'ecfp6_bit535',\n",
       "  'ecfp6_bit536',\n",
       "  'ecfp6_bit537',\n",
       "  'ecfp6_bit538',\n",
       "  'ecfp6_bit539',\n",
       "  'ecfp6_bit540',\n",
       "  'ecfp6_bit541',\n",
       "  'ecfp6_bit542',\n",
       "  'ecfp6_bit543',\n",
       "  'ecfp6_bit544',\n",
       "  'ecfp6_bit545',\n",
       "  'ecfp6_bit546',\n",
       "  'ecfp6_bit547',\n",
       "  'ecfp6_bit548',\n",
       "  'ecfp6_bit549',\n",
       "  'ecfp6_bit550',\n",
       "  'ecfp6_bit551',\n",
       "  'ecfp6_bit552',\n",
       "  'ecfp6_bit553',\n",
       "  'ecfp6_bit554',\n",
       "  'ecfp6_bit555',\n",
       "  'ecfp6_bit556',\n",
       "  'ecfp6_bit557',\n",
       "  'ecfp6_bit558',\n",
       "  'ecfp6_bit559',\n",
       "  'ecfp6_bit560',\n",
       "  'ecfp6_bit561',\n",
       "  'ecfp6_bit562',\n",
       "  'ecfp6_bit563',\n",
       "  'ecfp6_bit564',\n",
       "  'ecfp6_bit565',\n",
       "  'ecfp6_bit566',\n",
       "  'ecfp6_bit567',\n",
       "  'ecfp6_bit568',\n",
       "  'ecfp6_bit569',\n",
       "  'ecfp6_bit570',\n",
       "  'ecfp6_bit571',\n",
       "  'ecfp6_bit572',\n",
       "  'ecfp6_bit573',\n",
       "  'ecfp6_bit574',\n",
       "  'ecfp6_bit575',\n",
       "  'ecfp6_bit576',\n",
       "  'ecfp6_bit577',\n",
       "  'ecfp6_bit578',\n",
       "  'ecfp6_bit579',\n",
       "  'ecfp6_bit580',\n",
       "  'ecfp6_bit581',\n",
       "  'ecfp6_bit582',\n",
       "  'ecfp6_bit583',\n",
       "  'ecfp6_bit584',\n",
       "  'ecfp6_bit585',\n",
       "  'ecfp6_bit586',\n",
       "  'ecfp6_bit587',\n",
       "  'ecfp6_bit588',\n",
       "  'ecfp6_bit589',\n",
       "  'ecfp6_bit590',\n",
       "  'ecfp6_bit591',\n",
       "  'ecfp6_bit592',\n",
       "  'ecfp6_bit593',\n",
       "  'ecfp6_bit594',\n",
       "  'ecfp6_bit595',\n",
       "  'ecfp6_bit596',\n",
       "  'ecfp6_bit597',\n",
       "  'ecfp6_bit598',\n",
       "  'ecfp6_bit599',\n",
       "  'ecfp6_bit600',\n",
       "  'ecfp6_bit601',\n",
       "  'ecfp6_bit602',\n",
       "  'ecfp6_bit603',\n",
       "  'ecfp6_bit604',\n",
       "  'ecfp6_bit605',\n",
       "  'ecfp6_bit606',\n",
       "  'ecfp6_bit607',\n",
       "  'ecfp6_bit608',\n",
       "  'ecfp6_bit609',\n",
       "  'ecfp6_bit610',\n",
       "  'ecfp6_bit611',\n",
       "  'ecfp6_bit612',\n",
       "  'ecfp6_bit613',\n",
       "  'ecfp6_bit614',\n",
       "  'ecfp6_bit615',\n",
       "  'ecfp6_bit616',\n",
       "  'ecfp6_bit617',\n",
       "  'ecfp6_bit618',\n",
       "  'ecfp6_bit619',\n",
       "  'ecfp6_bit620',\n",
       "  'ecfp6_bit621',\n",
       "  'ecfp6_bit622',\n",
       "  'ecfp6_bit623',\n",
       "  'ecfp6_bit624',\n",
       "  'ecfp6_bit625',\n",
       "  'ecfp6_bit626',\n",
       "  'ecfp6_bit627',\n",
       "  'ecfp6_bit628',\n",
       "  'ecfp6_bit629',\n",
       "  'ecfp6_bit630',\n",
       "  'ecfp6_bit631',\n",
       "  'ecfp6_bit632',\n",
       "  'ecfp6_bit633',\n",
       "  'ecfp6_bit634',\n",
       "  'ecfp6_bit635',\n",
       "  'ecfp6_bit636',\n",
       "  'ecfp6_bit637',\n",
       "  'ecfp6_bit638',\n",
       "  'ecfp6_bit639',\n",
       "  'ecfp6_bit640',\n",
       "  'ecfp6_bit641',\n",
       "  'ecfp6_bit642',\n",
       "  'ecfp6_bit643',\n",
       "  'ecfp6_bit644',\n",
       "  'ecfp6_bit645',\n",
       "  'ecfp6_bit646',\n",
       "  'ecfp6_bit647',\n",
       "  'ecfp6_bit648',\n",
       "  'ecfp6_bit649',\n",
       "  'ecfp6_bit650',\n",
       "  'ecfp6_bit651',\n",
       "  'ecfp6_bit652',\n",
       "  'ecfp6_bit653',\n",
       "  'ecfp6_bit654',\n",
       "  'ecfp6_bit655',\n",
       "  'ecfp6_bit656',\n",
       "  'ecfp6_bit657',\n",
       "  'ecfp6_bit658',\n",
       "  'ecfp6_bit659',\n",
       "  'ecfp6_bit660',\n",
       "  'ecfp6_bit661',\n",
       "  'ecfp6_bit662',\n",
       "  'ecfp6_bit663',\n",
       "  'ecfp6_bit664',\n",
       "  'ecfp6_bit665',\n",
       "  'ecfp6_bit666',\n",
       "  'ecfp6_bit667',\n",
       "  'ecfp6_bit668',\n",
       "  'ecfp6_bit669',\n",
       "  'ecfp6_bit670',\n",
       "  'ecfp6_bit671',\n",
       "  'ecfp6_bit672',\n",
       "  'ecfp6_bit673',\n",
       "  'ecfp6_bit674',\n",
       "  'ecfp6_bit675',\n",
       "  'ecfp6_bit676',\n",
       "  'ecfp6_bit677',\n",
       "  'ecfp6_bit678',\n",
       "  'ecfp6_bit679',\n",
       "  'ecfp6_bit680',\n",
       "  'ecfp6_bit681',\n",
       "  'ecfp6_bit682',\n",
       "  'ecfp6_bit683',\n",
       "  'ecfp6_bit684',\n",
       "  'ecfp6_bit685',\n",
       "  'ecfp6_bit686',\n",
       "  'ecfp6_bit687',\n",
       "  'ecfp6_bit688',\n",
       "  'ecfp6_bit689',\n",
       "  'ecfp6_bit690',\n",
       "  'ecfp6_bit691',\n",
       "  'ecfp6_bit692',\n",
       "  'ecfp6_bit693',\n",
       "  'ecfp6_bit694',\n",
       "  'ecfp6_bit695',\n",
       "  'ecfp6_bit696',\n",
       "  'ecfp6_bit697',\n",
       "  'ecfp6_bit698',\n",
       "  'ecfp6_bit699',\n",
       "  'ecfp6_bit700',\n",
       "  'ecfp6_bit701',\n",
       "  'ecfp6_bit702',\n",
       "  'ecfp6_bit703',\n",
       "  'ecfp6_bit704',\n",
       "  'ecfp6_bit705',\n",
       "  'ecfp6_bit706',\n",
       "  'ecfp6_bit707',\n",
       "  'ecfp6_bit708',\n",
       "  'ecfp6_bit709',\n",
       "  'ecfp6_bit710',\n",
       "  'ecfp6_bit711',\n",
       "  'ecfp6_bit712',\n",
       "  'ecfp6_bit713',\n",
       "  'ecfp6_bit714',\n",
       "  'ecfp6_bit715',\n",
       "  'ecfp6_bit716',\n",
       "  'ecfp6_bit717',\n",
       "  'ecfp6_bit718',\n",
       "  'ecfp6_bit719',\n",
       "  'ecfp6_bit720',\n",
       "  'ecfp6_bit721',\n",
       "  'ecfp6_bit722',\n",
       "  'ecfp6_bit723',\n",
       "  'ecfp6_bit724',\n",
       "  'ecfp6_bit725',\n",
       "  'ecfp6_bit726',\n",
       "  'ecfp6_bit727',\n",
       "  'ecfp6_bit728',\n",
       "  'ecfp6_bit729',\n",
       "  'ecfp6_bit730',\n",
       "  'ecfp6_bit731',\n",
       "  'ecfp6_bit732',\n",
       "  'ecfp6_bit733',\n",
       "  'ecfp6_bit734',\n",
       "  'ecfp6_bit735',\n",
       "  'ecfp6_bit736',\n",
       "  'ecfp6_bit737',\n",
       "  'ecfp6_bit738',\n",
       "  'ecfp6_bit739',\n",
       "  'ecfp6_bit740',\n",
       "  'ecfp6_bit741',\n",
       "  'ecfp6_bit742',\n",
       "  'ecfp6_bit743',\n",
       "  'ecfp6_bit744',\n",
       "  'ecfp6_bit745',\n",
       "  'ecfp6_bit746',\n",
       "  'ecfp6_bit747',\n",
       "  'ecfp6_bit748',\n",
       "  'ecfp6_bit749',\n",
       "  'ecfp6_bit750',\n",
       "  'ecfp6_bit751',\n",
       "  'ecfp6_bit752',\n",
       "  'ecfp6_bit753',\n",
       "  'ecfp6_bit754',\n",
       "  'ecfp6_bit755',\n",
       "  'ecfp6_bit756',\n",
       "  'ecfp6_bit757',\n",
       "  'ecfp6_bit758',\n",
       "  'ecfp6_bit759',\n",
       "  'ecfp6_bit760',\n",
       "  'ecfp6_bit761',\n",
       "  'ecfp6_bit762',\n",
       "  'ecfp6_bit763',\n",
       "  'ecfp6_bit764',\n",
       "  'ecfp6_bit765',\n",
       "  'ecfp6_bit766',\n",
       "  'ecfp6_bit767',\n",
       "  'ecfp6_bit768',\n",
       "  'ecfp6_bit769',\n",
       "  'ecfp6_bit770',\n",
       "  'ecfp6_bit771',\n",
       "  'ecfp6_bit772',\n",
       "  'ecfp6_bit773',\n",
       "  'ecfp6_bit774',\n",
       "  'ecfp6_bit775',\n",
       "  'ecfp6_bit776',\n",
       "  'ecfp6_bit777',\n",
       "  'ecfp6_bit778',\n",
       "  'ecfp6_bit779',\n",
       "  'ecfp6_bit780',\n",
       "  'ecfp6_bit781',\n",
       "  'ecfp6_bit782',\n",
       "  'ecfp6_bit783',\n",
       "  'ecfp6_bit784',\n",
       "  'ecfp6_bit785',\n",
       "  'ecfp6_bit786',\n",
       "  'ecfp6_bit787',\n",
       "  'ecfp6_bit788',\n",
       "  'ecfp6_bit789',\n",
       "  'ecfp6_bit790',\n",
       "  'ecfp6_bit791',\n",
       "  'ecfp6_bit792',\n",
       "  'ecfp6_bit793',\n",
       "  'ecfp6_bit794',\n",
       "  'ecfp6_bit795',\n",
       "  'ecfp6_bit796',\n",
       "  'ecfp6_bit797',\n",
       "  'ecfp6_bit798',\n",
       "  'ecfp6_bit799',\n",
       "  'ecfp6_bit800',\n",
       "  'ecfp6_bit801',\n",
       "  'ecfp6_bit802',\n",
       "  'ecfp6_bit803',\n",
       "  'ecfp6_bit804',\n",
       "  'ecfp6_bit805',\n",
       "  'ecfp6_bit806',\n",
       "  'ecfp6_bit807',\n",
       "  'ecfp6_bit808',\n",
       "  'ecfp6_bit809',\n",
       "  'ecfp6_bit810',\n",
       "  'ecfp6_bit811',\n",
       "  'ecfp6_bit812',\n",
       "  'ecfp6_bit813',\n",
       "  'ecfp6_bit814',\n",
       "  'ecfp6_bit815',\n",
       "  'ecfp6_bit816',\n",
       "  'ecfp6_bit817',\n",
       "  'ecfp6_bit818',\n",
       "  'ecfp6_bit819',\n",
       "  'ecfp6_bit820',\n",
       "  'ecfp6_bit821',\n",
       "  'ecfp6_bit822',\n",
       "  'ecfp6_bit823',\n",
       "  'ecfp6_bit824',\n",
       "  'ecfp6_bit825',\n",
       "  'ecfp6_bit826',\n",
       "  'ecfp6_bit827',\n",
       "  'ecfp6_bit828',\n",
       "  'ecfp6_bit829',\n",
       "  'ecfp6_bit830',\n",
       "  'ecfp6_bit831',\n",
       "  'ecfp6_bit832',\n",
       "  'ecfp6_bit833',\n",
       "  'ecfp6_bit834',\n",
       "  'ecfp6_bit835',\n",
       "  'ecfp6_bit836',\n",
       "  'ecfp6_bit837',\n",
       "  'ecfp6_bit838',\n",
       "  'ecfp6_bit839',\n",
       "  'ecfp6_bit840',\n",
       "  'ecfp6_bit841',\n",
       "  'ecfp6_bit842',\n",
       "  'ecfp6_bit843',\n",
       "  'ecfp6_bit844',\n",
       "  'ecfp6_bit845',\n",
       "  'ecfp6_bit846',\n",
       "  'ecfp6_bit847',\n",
       "  'ecfp6_bit848',\n",
       "  'ecfp6_bit849',\n",
       "  'ecfp6_bit850',\n",
       "  'ecfp6_bit851',\n",
       "  'ecfp6_bit852',\n",
       "  'ecfp6_bit853',\n",
       "  'ecfp6_bit854',\n",
       "  'ecfp6_bit855',\n",
       "  'ecfp6_bit856',\n",
       "  'ecfp6_bit857',\n",
       "  'ecfp6_bit858',\n",
       "  'ecfp6_bit859',\n",
       "  'ecfp6_bit860',\n",
       "  'ecfp6_bit861',\n",
       "  'ecfp6_bit862',\n",
       "  'ecfp6_bit863',\n",
       "  'ecfp6_bit864',\n",
       "  'ecfp6_bit865',\n",
       "  'ecfp6_bit866',\n",
       "  'ecfp6_bit867',\n",
       "  'ecfp6_bit868',\n",
       "  'ecfp6_bit869',\n",
       "  'ecfp6_bit870',\n",
       "  'ecfp6_bit871',\n",
       "  'ecfp6_bit872',\n",
       "  'ecfp6_bit873',\n",
       "  'ecfp6_bit874',\n",
       "  'ecfp6_bit875',\n",
       "  'ecfp6_bit876',\n",
       "  'ecfp6_bit877',\n",
       "  'ecfp6_bit878',\n",
       "  'ecfp6_bit879',\n",
       "  'ecfp6_bit880',\n",
       "  'ecfp6_bit881',\n",
       "  'ecfp6_bit882',\n",
       "  'ecfp6_bit883',\n",
       "  'ecfp6_bit884',\n",
       "  'ecfp6_bit885',\n",
       "  'ecfp6_bit886',\n",
       "  'ecfp6_bit887',\n",
       "  'ecfp6_bit888',\n",
       "  'ecfp6_bit889',\n",
       "  'ecfp6_bit890',\n",
       "  'ecfp6_bit891',\n",
       "  'ecfp6_bit892',\n",
       "  'ecfp6_bit893',\n",
       "  'ecfp6_bit894',\n",
       "  'ecfp6_bit895',\n",
       "  'ecfp6_bit896',\n",
       "  'ecfp6_bit897',\n",
       "  'ecfp6_bit898',\n",
       "  'ecfp6_bit899',\n",
       "  'ecfp6_bit900',\n",
       "  'ecfp6_bit901',\n",
       "  'ecfp6_bit902',\n",
       "  'ecfp6_bit903',\n",
       "  'ecfp6_bit904',\n",
       "  'ecfp6_bit905',\n",
       "  'ecfp6_bit906',\n",
       "  'ecfp6_bit907',\n",
       "  'ecfp6_bit908',\n",
       "  'ecfp6_bit909',\n",
       "  'ecfp6_bit910',\n",
       "  'ecfp6_bit911',\n",
       "  'ecfp6_bit912',\n",
       "  'ecfp6_bit913',\n",
       "  'ecfp6_bit914',\n",
       "  'ecfp6_bit915',\n",
       "  'ecfp6_bit916',\n",
       "  'ecfp6_bit917',\n",
       "  'ecfp6_bit918',\n",
       "  'ecfp6_bit919',\n",
       "  'ecfp6_bit920',\n",
       "  'ecfp6_bit921',\n",
       "  'ecfp6_bit922',\n",
       "  'ecfp6_bit923',\n",
       "  'ecfp6_bit924',\n",
       "  'ecfp6_bit925',\n",
       "  'ecfp6_bit926',\n",
       "  'ecfp6_bit927',\n",
       "  'ecfp6_bit928',\n",
       "  'ecfp6_bit929',\n",
       "  'ecfp6_bit930',\n",
       "  'ecfp6_bit931',\n",
       "  'ecfp6_bit932',\n",
       "  'ecfp6_bit933',\n",
       "  'ecfp6_bit934',\n",
       "  'ecfp6_bit935',\n",
       "  'ecfp6_bit936',\n",
       "  'ecfp6_bit937',\n",
       "  'ecfp6_bit938',\n",
       "  'ecfp6_bit939',\n",
       "  'ecfp6_bit940',\n",
       "  'ecfp6_bit941',\n",
       "  'ecfp6_bit942',\n",
       "  'ecfp6_bit943',\n",
       "  'ecfp6_bit944',\n",
       "  'ecfp6_bit945',\n",
       "  'ecfp6_bit946',\n",
       "  'ecfp6_bit947',\n",
       "  'ecfp6_bit948',\n",
       "  'ecfp6_bit949',\n",
       "  'ecfp6_bit950',\n",
       "  'ecfp6_bit951',\n",
       "  'ecfp6_bit952',\n",
       "  'ecfp6_bit953',\n",
       "  'ecfp6_bit954',\n",
       "  'ecfp6_bit955',\n",
       "  'ecfp6_bit956',\n",
       "  'ecfp6_bit957',\n",
       "  'ecfp6_bit958',\n",
       "  'ecfp6_bit959',\n",
       "  'ecfp6_bit960',\n",
       "  'ecfp6_bit961',\n",
       "  'ecfp6_bit962',\n",
       "  'ecfp6_bit963',\n",
       "  'ecfp6_bit964',\n",
       "  'ecfp6_bit965',\n",
       "  'ecfp6_bit966',\n",
       "  'ecfp6_bit967',\n",
       "  'ecfp6_bit968',\n",
       "  'ecfp6_bit969',\n",
       "  'ecfp6_bit970',\n",
       "  'ecfp6_bit971',\n",
       "  'ecfp6_bit972',\n",
       "  'ecfp6_bit973',\n",
       "  'ecfp6_bit974',\n",
       "  'ecfp6_bit975',\n",
       "  'ecfp6_bit976',\n",
       "  'ecfp6_bit977',\n",
       "  'ecfp6_bit978',\n",
       "  'ecfp6_bit979',\n",
       "  'ecfp6_bit980',\n",
       "  'ecfp6_bit981',\n",
       "  'ecfp6_bit982',\n",
       "  'ecfp6_bit983',\n",
       "  'ecfp6_bit984',\n",
       "  'ecfp6_bit985',\n",
       "  'ecfp6_bit986',\n",
       "  'ecfp6_bit987',\n",
       "  'ecfp6_bit988',\n",
       "  'ecfp6_bit989',\n",
       "  'ecfp6_bit990',\n",
       "  'ecfp6_bit991',\n",
       "  'ecfp6_bit992',\n",
       "  'ecfp6_bit993',\n",
       "  'ecfp6_bit994',\n",
       "  'ecfp6_bit995',\n",
       "  'ecfp6_bit996',\n",
       "  'ecfp6_bit997',\n",
       "  'ecfp6_bit998',\n",
       "  'ecfp6_bit999',\n",
       "  ...])"
      ]
     },
     "execution_count": 8,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "get_ECFP6(tmp_smile)"
   ]
  },
  {
   "cell_type": "markdown",
   "metadata": {},
   "source": [
    "### Mordred MRC desriptors"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 9,
   "metadata": {},
   "outputs": [],
   "source": [
    "from rdkit import Chem\n",
    "from mordred import Calculator, descriptors\n",
    "from mordred.RingCount import RingCount\n",
    "import itertools\n",
    "\n",
    "def compute_ringsize(mol):\n",
    "    '''\n",
    "    check for macrolides of RS 3 to 100, return a  list of ring counts.\n",
    "    [RS3,RS4,.....,RS100]\n",
    "    [0,0,0,...,1,...,0]\n",
    "    '''\n",
    "    RS_3_100 = [i+3 for i in range(97)]\n",
    "    RS_count = []\n",
    "    for j in RS_3_100:\n",
    "        RS = RingCount(order=j)(mol)\n",
    "        RS_count.append(RS)\n",
    "    return RS_count\n",
    "\n",
    "def macrolide_ring_info(mol):\n",
    "    headers = ['n'+str(i+13)+'Ring' for i in range(87)]+['SmallestRS','LargestRS']\n",
    "    # up to nR12 is already with mordred, start with nR13 to nR100\n",
    "    ring_size = []\n",
    "    RS = compute_ringsize(mol)  # nR3 to nR100\n",
    "    RS_12_100 = RS[9:]    # start with nR12 up to nR100\n",
    "    ring_indices = [i for i,x in enumerate(RS_12_100) if x!=0]  # get index if item isn't equal to 0\n",
    "    if ring_indices:\n",
    "        # find 1, locate the last index\n",
    "        # largest_RS is based on RS 3 to 100.\n",
    "        # Add 3 (starting ring count) to get up to the actual ring size\n",
    "        smallest_RS = ring_indices[0]+12\n",
    "        largest_RS = ring_indices[-1]+12\n",
    "        RS_12_100.append(smallest_RS)  # Smallest RS\n",
    "        RS_12_100.append(largest_RS)  # Largest RS\n",
    "    else:\n",
    "        RS_12_100.extend([0,0])\n",
    "    ring_size = (RS_12_100[1:]) # up to nR12 is already with mordred, start with nR13 to nR100\n",
    "    return np.array(ring_size, dtype=np.float32), headers\n",
    "\n",
    "\n",
    "def sugar_count(mol):\n",
    "    sugar_patterns = [\n",
    "    '[OX2;$([r5]1@C@C@C(O)@C1),$([r6]1@C@C@C(O)@C(O)@C1)]',\n",
    "    '[OX2;$([r5]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C1),$([r6]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C@C1)]',\n",
    "    '[OX2;$([r5]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C(O)@C1),$([r6]1@C(!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C(O)@C(O)@C1)]',\n",
    "    '[OX2;$([r5]1@C(!@[OX2H1])@C@C@C1),$([r6]1@C(!@[OX2H1])@C@C@C@C1)]',\n",
    "    '[OX2;$([r5]1@[C@@](!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C1),$([r6]1@[C@@](!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C@C1)]',\n",
    "    '[OX2;$([r5]1@[C@](!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C1),$([r6]1@[C@](!@[OX2,NX3,SX2,FX1,ClX1,BrX1,IX1])@C@C@C@C1)]',\n",
    "    ]\n",
    "    sugar_mols = [Chem.MolFromSmarts(i) for i in sugar_patterns]\n",
    "    sugar_counts = []\n",
    "    matches_total = []\n",
    "    for s_mol in sugar_mols:\n",
    "        raw_matches = mol.GetSubstructMatches(s_mol)\n",
    "        matches = np.sum(raw_matches)\n",
    "        if matches not in matches_total and matches > 0:\n",
    "            matches_total.append([matches])\n",
    "    sugar_indices = set((list(itertools.chain(*matches_total))))\n",
    "    count = len(sugar_indices)\n",
    "    sugar_counts = count\n",
    "    \n",
    "    \n",
    "    \n",
    "    return np.array([sugar_counts],dtype=np.float32), ['nSugars']\n",
    "\n",
    "\n",
    "def core_ester_count(mol):\n",
    "    '''\n",
    "    Returns pandas frame containing the count of esters in core rings of >=12 membered macrocycles.\n",
    "    '''\n",
    "    ester_smarts = '[CX3](=[OX1])O@[r;!r3;!r4;!r5;!r6;!r7;!r8;!r9;!r10;!r11]'\n",
    "    core_ester = []\n",
    "    ester_mol = Chem.MolFromSmarts(ester_smarts)\n",
    "    ester_count = len(mol.GetSubstructMatches(ester_mol))\n",
    "    core_ester = ester_count\n",
    "    return np.array([core_ester],dtype=np.float32), ['core_ester']\n",
    "\n",
    "def mordred_compute(mol):\n",
    "    calc = Calculator(descriptors, ignore_3D=True)\n",
    "    ds = calc.pandas([mol],quiet=True) \n",
    "    features = list(ds.values)\n",
    "    feature_names = list(ds.keys())\n",
    "    return np.array(features,dtype=np.float32).flatten(), feature_names\n",
    "\n",
    "def get_mordred(input_smile):\n",
    "    mol = Chem.MolFromSmiles(input_smile)\n",
    "    features, feature_names = macrolide_ring_info(mol)\n",
    "    \n",
    "    tmp_features, tmp_feature_names = mordred_compute(mol)\n",
    "    features = np.concatenate([features,tmp_features])\n",
    "    feature_names += tmp_feature_names\n",
    "    \n",
    "    tmp_features, tmp_feature_names = sugar_count(mol)\n",
    "    features = np.concatenate([features,tmp_features])\n",
    "    feature_names += tmp_feature_names\n",
    "    \n",
    "    tmp_features, tmp_feature_names = core_ester_count(mol)\n",
    "    features = np.concatenate([features,tmp_features])\n",
    "    feature_names += tmp_feature_names\n",
    "    return features, feature_names    "
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 10,
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "(array([0.      , 0.      , 0.      , ..., 9.666667, 0.      , 0.      ],\n",
       "       dtype=float32),\n",
       " ['n13Ring',\n",
       "  'n14Ring',\n",
       "  'n15Ring',\n",
       "  'n16Ring',\n",
       "  'n17Ring',\n",
       "  'n18Ring',\n",
       "  'n19Ring',\n",
       "  'n20Ring',\n",
       "  'n21Ring',\n",
       "  'n22Ring',\n",
       "  'n23Ring',\n",
       "  'n24Ring',\n",
       "  'n25Ring',\n",
       "  'n26Ring',\n",
       "  'n27Ring',\n",
       "  'n28Ring',\n",
       "  'n29Ring',\n",
       "  'n30Ring',\n",
       "  'n31Ring',\n",
       "  'n32Ring',\n",
       "  'n33Ring',\n",
       "  'n34Ring',\n",
       "  'n35Ring',\n",
       "  'n36Ring',\n",
       "  'n37Ring',\n",
       "  'n38Ring',\n",
       "  'n39Ring',\n",
       "  'n40Ring',\n",
       "  'n41Ring',\n",
       "  'n42Ring',\n",
       "  'n43Ring',\n",
       "  'n44Ring',\n",
       "  'n45Ring',\n",
       "  'n46Ring',\n",
       "  'n47Ring',\n",
       "  'n48Ring',\n",
       "  'n49Ring',\n",
       "  'n50Ring',\n",
       "  'n51Ring',\n",
       "  'n52Ring',\n",
       "  'n53Ring',\n",
       "  'n54Ring',\n",
       "  'n55Ring',\n",
       "  'n56Ring',\n",
       "  'n57Ring',\n",
       "  'n58Ring',\n",
       "  'n59Ring',\n",
       "  'n60Ring',\n",
       "  'n61Ring',\n",
       "  'n62Ring',\n",
       "  'n63Ring',\n",
       "  'n64Ring',\n",
       "  'n65Ring',\n",
       "  'n66Ring',\n",
       "  'n67Ring',\n",
       "  'n68Ring',\n",
       "  'n69Ring',\n",
       "  'n70Ring',\n",
       "  'n71Ring',\n",
       "  'n72Ring',\n",
       "  'n73Ring',\n",
       "  'n74Ring',\n",
       "  'n75Ring',\n",
       "  'n76Ring',\n",
       "  'n77Ring',\n",
       "  'n78Ring',\n",
       "  'n79Ring',\n",
       "  'n80Ring',\n",
       "  'n81Ring',\n",
       "  'n82Ring',\n",
       "  'n83Ring',\n",
       "  'n84Ring',\n",
       "  'n85Ring',\n",
       "  'n86Ring',\n",
       "  'n87Ring',\n",
       "  'n88Ring',\n",
       "  'n89Ring',\n",
       "  'n90Ring',\n",
       "  'n91Ring',\n",
       "  'n92Ring',\n",
       "  'n93Ring',\n",
       "  'n94Ring',\n",
       "  'n95Ring',\n",
       "  'n96Ring',\n",
       "  'n97Ring',\n",
       "  'n98Ring',\n",
       "  'n99Ring',\n",
       "  'SmallestRS',\n",
       "  'LargestRS',\n",
       "  'ABC',\n",
       "  'ABCGG',\n",
       "  'nAcid',\n",
       "  'nBase',\n",
       "  'SpAbs_A',\n",
       "  'SpMax_A',\n",
       "  'SpDiam_A',\n",
       "  'SpAD_A',\n",
       "  'SpMAD_A',\n",
       "  'LogEE_A',\n",
       "  'VE1_A',\n",
       "  'VE2_A',\n",
       "  'VE3_A',\n",
       "  'VR1_A',\n",
       "  'VR2_A',\n",
       "  'VR3_A',\n",
       "  'nAromAtom',\n",
       "  'nAromBond',\n",
       "  'nAtom',\n",
       "  'nHeavyAtom',\n",
       "  'nSpiro',\n",
       "  'nBridgehead',\n",
       "  'nHetero',\n",
       "  'nH',\n",
       "  'nB',\n",
       "  'nC',\n",
       "  'nN',\n",
       "  'nO',\n",
       "  'nS',\n",
       "  'nP',\n",
       "  'nF',\n",
       "  'nCl',\n",
       "  'nBr',\n",
       "  'nI',\n",
       "  'nX',\n",
       "  'ATS0dv',\n",
       "  'ATS1dv',\n",
       "  'ATS2dv',\n",
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       "  'AATS7s',\n",
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       "  'AATS1Z',\n",
       "  'AATS2Z',\n",
       "  'AATS3Z',\n",
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       "  'AATS6Z',\n",
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       "  'ATSC3s',\n",
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       "  'ATSC2se',\n",
       "  'ATSC3se',\n",
       "  'ATSC4se',\n",
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       "  'ATSC2pe',\n",
       "  'ATSC3pe',\n",
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       "  'ATSC7pe',\n",
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       "  'ATSC0are',\n",
       "  'ATSC1are',\n",
       "  'ATSC2are',\n",
       "  'ATSC3are',\n",
       "  'ATSC4are',\n",
       "  'ATSC5are',\n",
       "  'ATSC6are',\n",
       "  'ATSC7are',\n",
       "  'ATSC8are',\n",
       "  'ATSC0p',\n",
       "  'ATSC1p',\n",
       "  'ATSC2p',\n",
       "  'ATSC3p',\n",
       "  'ATSC4p',\n",
       "  'ATSC5p',\n",
       "  'ATSC6p',\n",
       "  'ATSC7p',\n",
       "  'ATSC8p',\n",
       "  'ATSC0i',\n",
       "  'ATSC1i',\n",
       "  'ATSC2i',\n",
       "  'ATSC3i',\n",
       "  'ATSC4i',\n",
       "  'ATSC5i',\n",
       "  'ATSC6i',\n",
       "  'ATSC7i',\n",
       "  'ATSC8i',\n",
       "  'AATSC0c',\n",
       "  'AATSC1c',\n",
       "  'AATSC2c',\n",
       "  'AATSC3c',\n",
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       "  'AATSC1dv',\n",
       "  'AATSC2dv',\n",
       "  'AATSC3dv',\n",
       "  'AATSC4dv',\n",
       "  'AATSC5dv',\n",
       "  'AATSC6dv',\n",
       "  'AATSC7dv',\n",
       "  'AATSC8dv',\n",
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       "  'AATSC1d',\n",
       "  'AATSC2d',\n",
       "  'AATSC3d',\n",
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       "  'AATSC2s',\n",
       "  'AATSC3s',\n",
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       "  'AATSC5s',\n",
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       "  'AATSC2Z',\n",
       "  'AATSC3Z',\n",
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       "  'AATSC5Z',\n",
       "  'AATSC6Z',\n",
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       "  'AATSC8Z',\n",
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       "  'AATSC1m',\n",
       "  'AATSC2m',\n",
       "  'AATSC3m',\n",
       "  'AATSC4m',\n",
       "  'AATSC5m',\n",
       "  'AATSC6m',\n",
       "  'AATSC7m',\n",
       "  'AATSC8m',\n",
       "  'AATSC0v',\n",
       "  'AATSC1v',\n",
       "  'AATSC2v',\n",
       "  'AATSC3v',\n",
       "  'AATSC4v',\n",
       "  'AATSC5v',\n",
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       "  'AATSC8v',\n",
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       "  'AATSC2se',\n",
       "  'AATSC3se',\n",
       "  'AATSC4se',\n",
       "  'AATSC5se',\n",
       "  'AATSC6se',\n",
       "  'AATSC7se',\n",
       "  'AATSC8se',\n",
       "  'AATSC0pe',\n",
       "  'AATSC1pe',\n",
       "  'AATSC2pe',\n",
       "  'AATSC3pe',\n",
       "  'AATSC4pe',\n",
       "  'AATSC5pe',\n",
       "  'AATSC6pe',\n",
       "  'AATSC7pe',\n",
       "  'AATSC8pe',\n",
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       "  'AATSC1are',\n",
       "  'AATSC2are',\n",
       "  'AATSC3are',\n",
       "  'AATSC4are',\n",
       "  'AATSC5are',\n",
       "  'AATSC6are',\n",
       "  'AATSC7are',\n",
       "  'AATSC8are',\n",
       "  'AATSC0p',\n",
       "  'AATSC1p',\n",
       "  'AATSC2p',\n",
       "  'AATSC3p',\n",
       "  'AATSC4p',\n",
       "  'AATSC5p',\n",
       "  'AATSC6p',\n",
       "  'AATSC7p',\n",
       "  'AATSC8p',\n",
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       "  'AATSC1i',\n",
       "  'AATSC2i',\n",
       "  'AATSC3i',\n",
       "  'AATSC4i',\n",
       "  'AATSC5i',\n",
       "  'AATSC6i',\n",
       "  'AATSC7i',\n",
       "  'AATSC8i',\n",
       "  'MATS1c',\n",
       "  'MATS2c',\n",
       "  'MATS3c',\n",
       "  'MATS4c',\n",
       "  'MATS5c',\n",
       "  'MATS6c',\n",
       "  'MATS7c',\n",
       "  'MATS8c',\n",
       "  'MATS1dv',\n",
       "  'MATS2dv',\n",
       "  'MATS3dv',\n",
       "  'MATS4dv',\n",
       "  'MATS5dv',\n",
       "  'MATS6dv',\n",
       "  'MATS7dv',\n",
       "  'MATS8dv',\n",
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       "  'MATS2d',\n",
       "  'MATS3d',\n",
       "  'MATS4d',\n",
       "  'MATS5d',\n",
       "  'MATS6d',\n",
       "  'MATS7d',\n",
       "  'MATS8d',\n",
       "  'MATS1s',\n",
       "  'MATS2s',\n",
       "  'MATS3s',\n",
       "  'MATS4s',\n",
       "  'MATS5s',\n",
       "  'MATS6s',\n",
       "  'MATS7s',\n",
       "  'MATS8s',\n",
       "  'MATS1Z',\n",
       "  'MATS2Z',\n",
       "  'MATS3Z',\n",
       "  'MATS4Z',\n",
       "  'MATS5Z',\n",
       "  'MATS6Z',\n",
       "  'MATS7Z',\n",
       "  'MATS8Z',\n",
       "  'MATS1m',\n",
       "  'MATS2m',\n",
       "  'MATS3m',\n",
       "  'MATS4m',\n",
       "  'MATS5m',\n",
       "  'MATS6m',\n",
       "  'MATS7m',\n",
       "  'MATS8m',\n",
       "  'MATS1v',\n",
       "  'MATS2v',\n",
       "  'MATS3v',\n",
       "  'MATS4v',\n",
       "  'MATS5v',\n",
       "  'MATS6v',\n",
       "  'MATS7v',\n",
       "  'MATS8v',\n",
       "  'MATS1se',\n",
       "  'MATS2se',\n",
       "  'MATS3se',\n",
       "  'MATS4se',\n",
       "  'MATS5se',\n",
       "  'MATS6se',\n",
       "  'MATS7se',\n",
       "  'MATS8se',\n",
       "  'MATS1pe',\n",
       "  'MATS2pe',\n",
       "  'MATS3pe',\n",
       "  'MATS4pe',\n",
       "  'MATS5pe',\n",
       "  'MATS6pe',\n",
       "  'MATS7pe',\n",
       "  'MATS8pe',\n",
       "  'MATS1are',\n",
       "  'MATS2are',\n",
       "  'MATS3are',\n",
       "  'MATS4are',\n",
       "  'MATS5are',\n",
       "  'MATS6are',\n",
       "  'MATS7are',\n",
       "  'MATS8are',\n",
       "  'MATS1p',\n",
       "  'MATS2p',\n",
       "  'MATS3p',\n",
       "  'MATS4p',\n",
       "  'MATS5p',\n",
       "  'MATS6p',\n",
       "  'MATS7p',\n",
       "  'MATS8p',\n",
       "  'MATS1i',\n",
       "  'MATS2i',\n",
       "  'MATS3i',\n",
       "  'MATS4i',\n",
       "  'MATS5i',\n",
       "  'MATS6i',\n",
       "  'MATS7i',\n",
       "  'MATS8i',\n",
       "  'GATS1c',\n",
       "  'GATS2c',\n",
       "  'GATS3c',\n",
       "  'GATS4c',\n",
       "  'GATS5c',\n",
       "  'GATS6c',\n",
       "  'GATS7c',\n",
       "  'GATS8c',\n",
       "  'GATS1dv',\n",
       "  'GATS2dv',\n",
       "  'GATS3dv',\n",
       "  'GATS4dv',\n",
       "  'GATS5dv',\n",
       "  'GATS6dv',\n",
       "  'GATS7dv',\n",
       "  'GATS8dv',\n",
       "  'GATS1d',\n",
       "  'GATS2d',\n",
       "  'GATS3d',\n",
       "  'GATS4d',\n",
       "  'GATS5d',\n",
       "  'GATS6d',\n",
       "  'GATS7d',\n",
       "  'GATS8d',\n",
       "  'GATS1s',\n",
       "  'GATS2s',\n",
       "  'GATS3s',\n",
       "  'GATS4s',\n",
       "  'GATS5s',\n",
       "  'GATS6s',\n",
       "  'GATS7s',\n",
       "  'GATS8s',\n",
       "  'GATS1Z',\n",
       "  'GATS2Z',\n",
       "  'GATS3Z',\n",
       "  'GATS4Z',\n",
       "  'GATS5Z',\n",
       "  'GATS6Z',\n",
       "  'GATS7Z',\n",
       "  'GATS8Z',\n",
       "  'GATS1m',\n",
       "  'GATS2m',\n",
       "  'GATS3m',\n",
       "  'GATS4m',\n",
       "  'GATS5m',\n",
       "  'GATS6m',\n",
       "  'GATS7m',\n",
       "  'GATS8m',\n",
       "  'GATS1v',\n",
       "  'GATS2v',\n",
       "  'GATS3v',\n",
       "  'GATS4v',\n",
       "  'GATS5v',\n",
       "  'GATS6v',\n",
       "  'GATS7v',\n",
       "  'GATS8v',\n",
       "  'GATS1se',\n",
       "  'GATS2se',\n",
       "  'GATS3se',\n",
       "  'GATS4se',\n",
       "  'GATS5se',\n",
       "  'GATS6se',\n",
       "  'GATS7se',\n",
       "  'GATS8se',\n",
       "  'GATS1pe',\n",
       "  'GATS2pe',\n",
       "  'GATS3pe',\n",
       "  'GATS4pe',\n",
       "  'GATS5pe',\n",
       "  'GATS6pe',\n",
       "  'GATS7pe',\n",
       "  'GATS8pe',\n",
       "  'GATS1are',\n",
       "  'GATS2are',\n",
       "  'GATS3are',\n",
       "  'GATS4are',\n",
       "  'GATS5are',\n",
       "  'GATS6are',\n",
       "  'GATS7are',\n",
       "  'GATS8are',\n",
       "  'GATS1p',\n",
       "  'GATS2p',\n",
       "  'GATS3p',\n",
       "  'GATS4p',\n",
       "  'GATS5p',\n",
       "  'GATS6p',\n",
       "  'GATS7p',\n",
       "  'GATS8p',\n",
       "  'GATS1i',\n",
       "  'GATS2i',\n",
       "  'GATS3i',\n",
       "  'GATS4i',\n",
       "  'GATS5i',\n",
       "  'GATS6i',\n",
       "  'GATS7i',\n",
       "  'GATS8i',\n",
       "  'BCUTc-1h',\n",
       "  'BCUTc-1l',\n",
       "  'BCUTdv-1h',\n",
       "  'BCUTdv-1l',\n",
       "  'BCUTd-1h',\n",
       "  'BCUTd-1l',\n",
       "  'BCUTs-1h',\n",
       "  'BCUTs-1l',\n",
       "  'BCUTZ-1h',\n",
       "  'BCUTZ-1l',\n",
       "  'BCUTm-1h',\n",
       "  'BCUTm-1l',\n",
       "  'BCUTv-1h',\n",
       "  'BCUTv-1l',\n",
       "  'BCUTse-1h',\n",
       "  'BCUTse-1l',\n",
       "  'BCUTpe-1h',\n",
       "  'BCUTpe-1l',\n",
       "  'BCUTare-1h',\n",
       "  'BCUTare-1l',\n",
       "  'BCUTp-1h',\n",
       "  'BCUTp-1l',\n",
       "  'BCUTi-1h',\n",
       "  'BCUTi-1l',\n",
       "  'BalabanJ',\n",
       "  'SpAbs_DzZ',\n",
       "  'SpMax_DzZ',\n",
       "  'SpDiam_DzZ',\n",
       "  'SpAD_DzZ',\n",
       "  'SpMAD_DzZ',\n",
       "  'LogEE_DzZ',\n",
       "  'SM1_DzZ',\n",
       "  'VE1_DzZ',\n",
       "  'VE2_DzZ',\n",
       "  'VE3_DzZ',\n",
       "  'VR1_DzZ',\n",
       "  'VR2_DzZ',\n",
       "  'VR3_DzZ',\n",
       "  'SpAbs_Dzm',\n",
       "  'SpMax_Dzm',\n",
       "  'SpDiam_Dzm',\n",
       "  'SpAD_Dzm',\n",
       "  'SpMAD_Dzm',\n",
       "  'LogEE_Dzm',\n",
       "  'SM1_Dzm',\n",
       "  'VE1_Dzm',\n",
       "  'VE2_Dzm',\n",
       "  'VE3_Dzm',\n",
       "  'VR1_Dzm',\n",
       "  'VR2_Dzm',\n",
       "  'VR3_Dzm',\n",
       "  'SpAbs_Dzv',\n",
       "  'SpMax_Dzv',\n",
       "  'SpDiam_Dzv',\n",
       "  'SpAD_Dzv',\n",
       "  'SpMAD_Dzv',\n",
       "  'LogEE_Dzv',\n",
       "  'SM1_Dzv',\n",
       "  'VE1_Dzv',\n",
       "  'VE2_Dzv',\n",
       "  'VE3_Dzv',\n",
       "  'VR1_Dzv',\n",
       "  'VR2_Dzv',\n",
       "  'VR3_Dzv',\n",
       "  'SpAbs_Dzse',\n",
       "  'SpMax_Dzse',\n",
       "  'SpDiam_Dzse',\n",
       "  'SpAD_Dzse',\n",
       "  'SpMAD_Dzse',\n",
       "  'LogEE_Dzse',\n",
       "  'SM1_Dzse',\n",
       "  'VE1_Dzse',\n",
       "  'VE2_Dzse',\n",
       "  'VE3_Dzse',\n",
       "  'VR1_Dzse',\n",
       "  'VR2_Dzse',\n",
       "  'VR3_Dzse',\n",
       "  'SpAbs_Dzpe',\n",
       "  'SpMax_Dzpe',\n",
       "  'SpDiam_Dzpe',\n",
       "  'SpAD_Dzpe',\n",
       "  'SpMAD_Dzpe',\n",
       "  'LogEE_Dzpe',\n",
       "  'SM1_Dzpe',\n",
       "  'VE1_Dzpe',\n",
       "  'VE2_Dzpe',\n",
       "  'VE3_Dzpe',\n",
       "  'VR1_Dzpe',\n",
       "  'VR2_Dzpe',\n",
       "  'VR3_Dzpe',\n",
       "  'SpAbs_Dzare',\n",
       "  'SpMax_Dzare',\n",
       "  'SpDiam_Dzare',\n",
       "  'SpAD_Dzare',\n",
       "  'SpMAD_Dzare',\n",
       "  'LogEE_Dzare',\n",
       "  'SM1_Dzare',\n",
       "  'VE1_Dzare',\n",
       "  'VE2_Dzare',\n",
       "  'VE3_Dzare',\n",
       "  'VR1_Dzare',\n",
       "  'VR2_Dzare',\n",
       "  'VR3_Dzare',\n",
       "  'SpAbs_Dzp',\n",
       "  'SpMax_Dzp',\n",
       "  'SpDiam_Dzp',\n",
       "  'SpAD_Dzp',\n",
       "  'SpMAD_Dzp',\n",
       "  'LogEE_Dzp',\n",
       "  'SM1_Dzp',\n",
       "  'VE1_Dzp',\n",
       "  'VE2_Dzp',\n",
       "  'VE3_Dzp',\n",
       "  'VR1_Dzp',\n",
       "  'VR2_Dzp',\n",
       "  'VR3_Dzp',\n",
       "  'SpAbs_Dzi',\n",
       "  'SpMax_Dzi',\n",
       "  'SpDiam_Dzi',\n",
       "  'SpAD_Dzi',\n",
       "  'SpMAD_Dzi',\n",
       "  'LogEE_Dzi',\n",
       "  'SM1_Dzi',\n",
       "  'VE1_Dzi',\n",
       "  'VE2_Dzi',\n",
       "  'VE3_Dzi',\n",
       "  'VR1_Dzi',\n",
       "  'VR2_Dzi',\n",
       "  'VR3_Dzi',\n",
       "  'BertzCT',\n",
       "  'nBonds',\n",
       "  'nBondsO',\n",
       "  'nBondsS',\n",
       "  'nBondsD',\n",
       "  'nBondsT',\n",
       "  'nBondsA',\n",
       "  'nBondsM',\n",
       "  'nBondsKS',\n",
       "  'nBondsKD',\n",
       "  'RNCG',\n",
       "  'RPCG',\n",
       "  'C1SP1',\n",
       "  'C2SP1',\n",
       "  'C1SP2',\n",
       "  'C2SP2',\n",
       "  'C3SP2',\n",
       "  'C1SP3',\n",
       "  'C2SP3',\n",
       "  'C3SP3',\n",
       "  'C4SP3',\n",
       "  'HybRatio',\n",
       "  'FCSP3',\n",
       "  'Xch-3d',\n",
       "  'Xch-4d',\n",
       "  'Xch-5d',\n",
       "  'Xch-6d',\n",
       "  'Xch-7d',\n",
       "  'Xch-3dv',\n",
       "  'Xch-4dv',\n",
       "  'Xch-5dv',\n",
       "  'Xch-6dv',\n",
       "  'Xch-7dv',\n",
       "  'Xc-3d',\n",
       "  'Xc-4d',\n",
       "  'Xc-5d',\n",
       "  'Xc-6d',\n",
       "  'Xc-3dv',\n",
       "  'Xc-4dv',\n",
       "  'Xc-5dv',\n",
       "  'Xc-6dv',\n",
       "  'Xpc-4d',\n",
       "  'Xpc-5d',\n",
       "  'Xpc-6d',\n",
       "  'Xpc-4dv',\n",
       "  'Xpc-5dv',\n",
       "  'Xpc-6dv',\n",
       "  'Xp-0d',\n",
       "  'Xp-1d',\n",
       "  'Xp-2d',\n",
       "  'Xp-3d',\n",
       "  'Xp-4d',\n",
       "  'Xp-5d',\n",
       "  'Xp-6d',\n",
       "  'Xp-7d',\n",
       "  'AXp-0d',\n",
       "  'AXp-1d',\n",
       "  'AXp-2d',\n",
       "  'AXp-3d',\n",
       "  'AXp-4d',\n",
       "  'AXp-5d',\n",
       "  'AXp-6d',\n",
       "  'AXp-7d',\n",
       "  'Xp-0dv',\n",
       "  'Xp-1dv',\n",
       "  'Xp-2dv',\n",
       "  'Xp-3dv',\n",
       "  'Xp-4dv',\n",
       "  'Xp-5dv',\n",
       "  'Xp-6dv',\n",
       "  'Xp-7dv',\n",
       "  'AXp-0dv',\n",
       "  'AXp-1dv',\n",
       "  'AXp-2dv',\n",
       "  'AXp-3dv',\n",
       "  'AXp-4dv',\n",
       "  'AXp-5dv',\n",
       "  'AXp-6dv',\n",
       "  'AXp-7dv',\n",
       "  'SZ',\n",
       "  'Sm',\n",
       "  'Sv',\n",
       "  'Sse',\n",
       "  'Spe',\n",
       "  'Sare',\n",
       "  'Sp',\n",
       "  'Si',\n",
       "  'MZ',\n",
       "  'Mm',\n",
       "  'Mv',\n",
       "  'Mse',\n",
       "  'Mpe',\n",
       "  'Mare',\n",
       "  'Mp',\n",
       "  'Mi',\n",
       "  'SpAbs_Dt',\n",
       "  'SpMax_Dt',\n",
       "  'SpDiam_Dt',\n",
       "  'SpAD_Dt',\n",
       "  'SpMAD_Dt',\n",
       "  'LogEE_Dt',\n",
       "  'SM1_Dt',\n",
       "  'VE1_Dt',\n",
       "  'VE2_Dt',\n",
       "  'VE3_Dt',\n",
       "  'VR1_Dt',\n",
       "  'VR2_Dt',\n",
       "  'VR3_Dt',\n",
       "  'DetourIndex',\n",
       "  'SpAbs_D',\n",
       "  'SpMax_D',\n",
       "  'SpDiam_D',\n",
       "  'SpAD_D',\n",
       "  'SpMAD_D',\n",
       "  'LogEE_D',\n",
       "  'VE1_D',\n",
       "  'VE2_D',\n",
       "  'VE3_D',\n",
       "  'VR1_D',\n",
       "  'VR2_D',\n",
       "  'VR3_D',\n",
       "  'NsLi',\n",
       "  'NssBe',\n",
       "  'NssssBe',\n",
       "  'NssBH',\n",
       "  'NsssB',\n",
       "  'NssssB',\n",
       "  'NsCH3',\n",
       "  'NdCH2',\n",
       "  'NssCH2',\n",
       "  'NtCH',\n",
       "  'NdsCH',\n",
       "  'NaaCH',\n",
       "  'NsssCH',\n",
       "  'NddC',\n",
       "  'NtsC',\n",
       "  'NdssC',\n",
       "  'NaasC',\n",
       "  'NaaaC',\n",
       "  'NssssC',\n",
       "  'NsNH3',\n",
       "  ...])"
      ]
     },
     "execution_count": 10,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "get_mordred(tmp_smile)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 11,
   "metadata": {},
   "outputs": [],
   "source": [
    "def get_all_descriptors(input_smile):\n",
    "    # rdkit\n",
    "    f,f_n = get_rdkit_descriptors(input_smile)\n",
    "    \n",
    "    #MACCS\n",
    "    t_f,t_f_n = get_maccs(input_smile)\n",
    "    f = np.concatenate([f,t_f])\n",
    "    f_n += t_f_n\n",
    "    \n",
    "    #ECFP6\n",
    "    t_f,t_f_n = get_ECFP6(input_smile)\n",
    "    f = np.concatenate([f,t_f])\n",
    "    f_n += t_f_n\n",
    "    \n",
    "    # MORDRED\n",
    "    t_f,t_f_n = get_mordred(input_smile)\n",
    "    f = np.concatenate([f,t_f])\n",
    "    f_n += t_f_n\n",
    "    \n",
    "    return f, f_n"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 12,
   "metadata": {},
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "(4127,)\n",
      "4127\n"
     ]
    }
   ],
   "source": [
    "(a,b) = get_all_descriptors(tmp_smile)\n",
    "print(a.shape)\n",
    "print(len(b))"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 13,
   "metadata": {},
   "outputs": [],
   "source": [
    "param_json_path = 'data/params.json'\n",
    "import json\n",
    "with open(param_json_path) as json_file:\n",
    "    param_dict = json.load(json_file)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 14,
   "metadata": {},
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "gdsc_inchi_path: data/gdsc_compound_inchi_smiles.csv\n",
      "beat_inchi_path: data/beat_aml/beat_aml_inhibitor_inchi_smiles.csv\n",
      "xenografts_inchi_path: data/lung_cancer_xenografts/xenografts_inhibitor_inchi_smiles.csv\n",
      "ccle_inchi_path: data/ccle/ccle_inhibitor_inchi_smiles.csv\n",
      "pancreas_inchi_path: data/organoid_pancreas/pancreas_inhibitor_inchi_smiles.csv\n",
      "(528, 5)\n"
     ]
    }
   ],
   "source": [
    "### get all inchi paths and combine\n",
    "import pandas as pd\n",
    "all_data = None\n",
    "for key in param_dict.keys():\n",
    "    if 'inchi' in key:\n",
    "        print(key + ': ' + param_dict[key])\n",
    "        cur_data = pd.read_csv(param_dict[key])\n",
    "        if all_data is None:\n",
    "            all_data = cur_data.copy()\n",
    "        else:\n",
    "            all_data = pd.concat([all_data,cur_data]) \n",
    "print(all_data.shape)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 15,
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/html": [
       "<div>\n",
       "<style scoped>\n",
       "    .dataframe tbody tr th:only-of-type {\n",
       "        vertical-align: middle;\n",
       "    }\n",
       "\n",
       "    .dataframe tbody tr th {\n",
       "        vertical-align: top;\n",
       "    }\n",
       "\n",
       "    .dataframe thead th {\n",
       "        text-align: right;\n",
       "    }\n",
       "</style>\n",
       "<table border=\"1\" class=\"dataframe\">\n",
       "  <thead>\n",
       "    <tr style=\"text-align: right;\">\n",
       "      <th></th>\n",
       "      <th>Unnamed: 0</th>\n",
       "      <th>inhibitor</th>\n",
       "      <th>inchi</th>\n",
       "      <th>inchikey</th>\n",
       "      <th>canonical_smiles</th>\n",
       "    </tr>\n",
       "  </thead>\n",
       "  <tbody>\n",
       "    <tr>\n",
       "      <th>0</th>\n",
       "      <td>0</td>\n",
       "      <td>(5Z)-7-Oxozeaenol</td>\n",
       "      <td>InChI=1S/C19H22O7/c1-11-5-3-7-14(20)18(23)15(2...</td>\n",
       "      <td>NEQZWEXWOFPKOT-BYRRXHGESA-N</td>\n",
       "      <td>CC1CC=CC(=O)C(C(CC=CC2=C(C(=CC(=C2)OC)O)C(=O)O...</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>1</th>\n",
       "      <td>1</td>\n",
       "      <td>5-Fluorouracil</td>\n",
       "      <td>InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H...</td>\n",
       "      <td>GHASVSINZRGABV-UHFFFAOYSA-N</td>\n",
       "      <td>C1=C(C(=O)NC(=O)N1)F</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>2</th>\n",
       "      <td>2</td>\n",
       "      <td>A-443654</td>\n",
       "      <td>InChI=1S/C24H23N5O/c1-15-22-10-16(6-7-24(22)29...</td>\n",
       "      <td>YWTBGJGMTBHQTM-IBGZPJMESA-N</td>\n",
       "      <td>CC1=C2C=C(C=CC2=NN1)C3=CC(=CN=C3)OCC(CC4=CNC5=...</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>3</th>\n",
       "      <td>3</td>\n",
       "      <td>A-770041</td>\n",
       "      <td>InChI=1S/C34H39N9O3/c1-21(44)41-14-16-42(17-15...</td>\n",
       "      <td>ZMNWFTYYYCSSTF-UHFFFAOYSA-N</td>\n",
       "      <td>CC(=O)N1CCN(CC1)C2CCC(CC2)N3C4=NC=NC(=C4C(=N3)...</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>4</th>\n",
       "      <td>4</td>\n",
       "      <td>A-83-01</td>\n",
       "      <td>InChI=1S/C25H19N5S/c1-17-8-7-13-23(27-17)24-21...</td>\n",
       "      <td>HIJMSZGHKQPPJS-UHFFFAOYSA-N</td>\n",
       "      <td>CC1=NC(=CC=C1)C2=NN(C=C2C3=CC=NC4=CC=CC=C34)C(...</td>\n",
       "    </tr>\n",
       "  </tbody>\n",
       "</table>\n",
       "</div>"
      ],
      "text/plain": [
       "   Unnamed: 0          inhibitor  \\\n",
       "0           0  (5Z)-7-Oxozeaenol   \n",
       "1           1     5-Fluorouracil   \n",
       "2           2           A-443654   \n",
       "3           3           A-770041   \n",
       "4           4            A-83-01   \n",
       "\n",
       "                                               inchi  \\\n",
       "0  InChI=1S/C19H22O7/c1-11-5-3-7-14(20)18(23)15(2...   \n",
       "1  InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H...   \n",
       "2  InChI=1S/C24H23N5O/c1-15-22-10-16(6-7-24(22)29...   \n",
       "3  InChI=1S/C34H39N9O3/c1-21(44)41-14-16-42(17-15...   \n",
       "4  InChI=1S/C25H19N5S/c1-17-8-7-13-23(27-17)24-21...   \n",
       "\n",
       "                      inchikey  \\\n",
       "0  NEQZWEXWOFPKOT-BYRRXHGESA-N   \n",
       "1  GHASVSINZRGABV-UHFFFAOYSA-N   \n",
       "2  YWTBGJGMTBHQTM-IBGZPJMESA-N   \n",
       "3  ZMNWFTYYYCSSTF-UHFFFAOYSA-N   \n",
       "4  HIJMSZGHKQPPJS-UHFFFAOYSA-N   \n",
       "\n",
       "                                    canonical_smiles  \n",
       "0  CC1CC=CC(=O)C(C(CC=CC2=C(C(=CC(=C2)OC)O)C(=O)O...  \n",
       "1                               C1=C(C(=O)NC(=O)N1)F  \n",
       "2  CC1=C2C=C(C=CC2=NN1)C3=CC(=CN=C3)OCC(CC4=CNC5=...  \n",
       "3  CC(=O)N1CCN(CC1)C2CCC(CC2)N3C4=NC=NC(=C4C(=N3)...  \n",
       "4  CC1=NC(=CC=C1)C2=NN(C=C2C3=CC=NC4=CC=CC=C34)C(...  "
      ]
     },
     "execution_count": 15,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "all_data.head()"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 16,
   "metadata": {},
   "outputs": [
    {
     "data": {
      "application/vnd.jupyter.widget-view+json": {
       "model_id": "5c36ca3236704295ba1692399295e08a",
       "version_major": 2,
       "version_minor": 0
      },
      "text/plain": [
       "HBox(children=(FloatProgress(value=0.0, max=528.0), HTML(value='')))"
      ]
     },
     "metadata": {},
     "output_type": "display_data"
    },
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "/usr/local/apps/tensorflow_anaconda3/lib/python3.7/site-packages/numpy/core/fromnumeric.py:87: RuntimeWarning: overflow encountered in reduce\n",
      "  return ufunc.reduce(obj, axis, dtype, out, **passkwargs)\n",
      "/usr/local/apps/tensorflow_anaconda3/lib/python3.7/site-packages/numpy/core/fromnumeric.py:87: RuntimeWarning: overflow encountered in reduce\n",
      "  return ufunc.reduce(obj, axis, dtype, out, **passkwargs)\n",
      "/usr/local/apps/tensorflow_anaconda3/lib/python3.7/site-packages/numpy/core/fromnumeric.py:87: RuntimeWarning: overflow encountered in reduce\n",
      "  return ufunc.reduce(obj, axis, dtype, out, **passkwargs)\n",
      "/usr/local/apps/tensorflow_anaconda3/lib/python3.7/site-packages/numpy/core/fromnumeric.py:87: RuntimeWarning: overflow encountered in reduce\n",
      "  return ufunc.reduce(obj, axis, dtype, out, **passkwargs)\n",
      "/usr/local/apps/tensorflow_anaconda3/lib/python3.7/site-packages/numpy/core/fromnumeric.py:87: RuntimeWarning: overflow encountered in reduce\n",
      "  return ufunc.reduce(obj, axis, dtype, out, **passkwargs)\n",
      "/usr/local/apps/tensorflow_anaconda3/lib/python3.7/site-packages/numpy/core/fromnumeric.py:87: RuntimeWarning: overflow encountered in reduce\n",
      "  return ufunc.reduce(obj, axis, dtype, out, **passkwargs)\n",
      "/usr/local/apps/tensorflow_anaconda3/lib/python3.7/site-packages/numpy/core/fromnumeric.py:87: RuntimeWarning: overflow encountered in reduce\n",
      "  return ufunc.reduce(obj, axis, dtype, out, **passkwargs)\n",
      "/usr/local/apps/tensorflow_anaconda3/lib/python3.7/site-packages/numpy/core/fromnumeric.py:87: RuntimeWarning: overflow encountered in reduce\n",
      "  return ufunc.reduce(obj, axis, dtype, out, **passkwargs)\n",
      "/usr/local/apps/tensorflow_anaconda3/lib/python3.7/site-packages/numpy/core/fromnumeric.py:87: RuntimeWarning: overflow encountered in reduce\n",
      "  return ufunc.reduce(obj, axis, dtype, out, **passkwargs)\n",
      "/usr/local/apps/tensorflow_anaconda3/lib/python3.7/site-packages/numpy/core/fromnumeric.py:87: RuntimeWarning: overflow encountered in reduce\n",
      "  return ufunc.reduce(obj, axis, dtype, out, **passkwargs)\n",
      "\n"
     ]
    }
   ],
   "source": [
    "from tqdm.notebook import tqdm\n",
    "smiles = list(all_data['canonical_smiles'])\n",
    "names = list(all_data['inhibitor'])\n",
    "use_names_set = set()\n",
    "use_smiles = []\n",
    "use_names = []\n",
    "features   = []\n",
    "error_smiles = []\n",
    "error_names = []\n",
    "use_ids = []\n",
    "for i in tqdm(np.arange(len(smiles))):\n",
    "    try:\n",
    "        cur_smiles = smiles[i]\n",
    "        cur_name = names[i]\n",
    "        if cur_name in use_names_set:\n",
    "            continue\n",
    "        (a,b) = get_all_descriptors(cur_smiles)\n",
    "        use_names_set.add(cur_name)\n",
    "        use_smiles.append(cur_smiles)\n",
    "        use_names.append(cur_name)\n",
    "        features.append(a)\n",
    "        use_ids.append(i)\n",
    "    except:\n",
    "        error_smiles.append(cur_smiles)\n",
    "        error_names.append(cur_name)\n",
    "feature_names = b"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": null,
   "metadata": {},
   "outputs": [],
   "source": []
  },
  {
   "cell_type": "code",
   "execution_count": 23,
   "metadata": {},
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "[345]\n"
     ]
    }
   ],
   "source": [
    "cur_id = np.where(np.array(list(all_data['inhibitor'])) == '17-AAG (Tanespimycin)')[0]\n",
    "get_all_descriptors(smiles[cur_id[0]])\n",
    "print(cur_id)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 24,
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "True"
      ]
     },
     "execution_count": 24,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "'17-AAG (Tanespimycin)' in use_names#list(all_data['inhibitor'])"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 25,
   "metadata": {},
   "outputs": [],
   "source": [
    "feature_matrix = np.array(features,dtype=np.float32)\n",
    "out_df = pd.DataFrame({'canonical_smiles':use_smiles,\n",
    "                       'inhibitor':use_names})\n",
    "for i in range(len(feature_names)):\n",
    "    feat = feature_names[i]\n",
    "    out_df[feat] = feature_matrix[:,i]"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 26,
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/html": [
       "<div>\n",
       "<style scoped>\n",
       "    .dataframe tbody tr th:only-of-type {\n",
       "        vertical-align: middle;\n",
       "    }\n",
       "\n",
       "    .dataframe tbody tr th {\n",
       "        vertical-align: top;\n",
       "    }\n",
       "\n",
       "    .dataframe thead th {\n",
       "        text-align: right;\n",
       "    }\n",
       "</style>\n",
       "<table border=\"1\" class=\"dataframe\">\n",
       "  <thead>\n",
       "    <tr style=\"text-align: right;\">\n",
       "      <th></th>\n",
       "      <th>canonical_smiles</th>\n",
       "      <th>inhibitor</th>\n",
       "      <th>MaxEStateIndex</th>\n",
       "      <th>MinEStateIndex</th>\n",
       "      <th>MaxAbsEStateIndex</th>\n",
       "      <th>MinAbsEStateIndex</th>\n",
       "      <th>qed</th>\n",
       "      <th>MolWt</th>\n",
       "      <th>HeavyAtomMolWt</th>\n",
       "      <th>ExactMolWt</th>\n",
       "      <th>...</th>\n",
       "      <th>MW</th>\n",
       "      <th>AMW</th>\n",
       "      <th>WPath</th>\n",
       "      <th>WPol</th>\n",
       "      <th>Zagreb1</th>\n",
       "      <th>Zagreb2</th>\n",
       "      <th>mZagreb1</th>\n",
       "      <th>mZagreb2</th>\n",
       "      <th>nSugars</th>\n",
       "      <th>core_ester</th>\n",
       "    </tr>\n",
       "  </thead>\n",
       "  <tbody>\n",
       "    <tr>\n",
       "      <th>0</th>\n",
       "      <td>CC1CC=CC(=O)C(C(CC=CC2=C(C(=CC(=C2)OC)O)C(=O)O...</td>\n",
       "      <td>(5Z)-7-Oxozeaenol</td>\n",
       "      <td>12.449593</td>\n",
       "      <td>-1.546408</td>\n",
       "      <td>12.449593</td>\n",
       "      <td>0.024198</td>\n",
       "      <td>0.650373</td>\n",
       "      <td>362.377991</td>\n",
       "      <td>340.201996</td>\n",
       "      <td>362.136566</td>\n",
       "      <td>...</td>\n",
       "      <td>362.136566</td>\n",
       "      <td>7.544511</td>\n",
       "      <td>1581.0</td>\n",
       "      <td>43.0</td>\n",
       "      <td>128.0</td>\n",
       "      <td>147.0</td>\n",
       "      <td>10.500000</td>\n",
       "      <td>5.888889</td>\n",
       "      <td>0.0</td>\n",
       "      <td>1.0</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>1</th>\n",
       "      <td>C1=C(C(=O)NC(=O)N1)F</td>\n",
       "      <td>5-Fluorouracil</td>\n",
       "      <td>11.984815</td>\n",
       "      <td>-1.001157</td>\n",
       "      <td>11.984815</td>\n",
       "      <td>0.707037</td>\n",
       "      <td>0.482565</td>\n",
       "      <td>130.078003</td>\n",
       "      <td>127.054001</td>\n",
       "      <td>130.017853</td>\n",
       "      <td>...</td>\n",
       "      <td>130.017853</td>\n",
       "      <td>10.834822</td>\n",
       "      <td>84.0</td>\n",
       "      <td>10.0</td>\n",
       "      <td>42.0</td>\n",
       "      <td>46.0</td>\n",
       "      <td>4.083333</td>\n",
       "      <td>2.027778</td>\n",
       "      <td>0.0</td>\n",
       "      <td>0.0</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>2</th>\n",
       "      <td>CC1=C2C=C(C=CC2=NN1)C3=CC(=CN=C3)OCC(CC4=CNC5=...</td>\n",
       "      <td>A-443654</td>\n",
       "      <td>6.350272</td>\n",
       "      <td>-0.113155</td>\n",
       "      <td>6.350272</td>\n",
       "      <td>0.113155</td>\n",
       "      <td>0.396777</td>\n",
       "      <td>397.481995</td>\n",
       "      <td>374.298004</td>\n",
       "      <td>397.190247</td>\n",
       "      <td>...</td>\n",
       "      <td>397.190247</td>\n",
       "      <td>7.494156</td>\n",
       "      <td>2845.0</td>\n",
       "      <td>46.0</td>\n",
       "      <td>164.0</td>\n",
       "      <td>195.0</td>\n",
       "      <td>7.611111</td>\n",
       "      <td>6.472222</td>\n",
       "      <td>0.0</td>\n",
       "      <td>0.0</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>3</th>\n",
       "      <td>CC(=O)N1CCN(CC1)C2CCC(CC2)N3C4=NC=NC(=C4C(=N3)...</td>\n",
       "      <td>A-770041</td>\n",
       "      <td>13.336040</td>\n",
       "      <td>-0.228281</td>\n",
       "      <td>13.336040</td>\n",
       "      <td>0.156382</td>\n",
       "      <td>0.283438</td>\n",
       "      <td>621.745972</td>\n",
       "      <td>582.434021</td>\n",
       "      <td>621.317566</td>\n",
       "      <td>...</td>\n",
       "      <td>621.317566</td>\n",
       "      <td>7.309618</td>\n",
       "      <td>8753.0</td>\n",
       "      <td>83.0</td>\n",
       "      <td>256.0</td>\n",
       "      <td>312.0</td>\n",
       "      <td>13.500000</td>\n",
       "      <td>9.944445</td>\n",
       "      <td>0.0</td>\n",
       "      <td>0.0</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>4</th>\n",
       "      <td>CC1=NC(=CC=C1)C2=NN(C=C2C3=CC=NC4=CC=CC=C34)C(...</td>\n",
       "      <td>A-83-01</td>\n",
       "      <td>5.653641</td>\n",
       "      <td>0.490477</td>\n",
       "      <td>5.653641</td>\n",
       "      <td>0.490477</td>\n",
       "      <td>0.378026</td>\n",
       "      <td>421.528992</td>\n",
       "      <td>402.377014</td>\n",
       "      <td>421.136108</td>\n",
       "      <td>...</td>\n",
       "      <td>421.136108</td>\n",
       "      <td>8.422722</td>\n",
       "      <td>2603.0</td>\n",
       "      <td>50.0</td>\n",
       "      <td>168.0</td>\n",
       "      <td>200.0</td>\n",
       "      <td>7.861111</td>\n",
       "      <td>6.750000</td>\n",
       "      <td>0.0</td>\n",
       "      <td>0.0</td>\n",
       "    </tr>\n",
       "  </tbody>\n",
       "</table>\n",
       "<p>5 rows × 4074 columns</p>\n",
       "</div>"
      ],
      "text/plain": [
       "                                    canonical_smiles          inhibitor  \\\n",
       "0  CC1CC=CC(=O)C(C(CC=CC2=C(C(=CC(=C2)OC)O)C(=O)O...  (5Z)-7-Oxozeaenol   \n",
       "1                               C1=C(C(=O)NC(=O)N1)F     5-Fluorouracil   \n",
       "2  CC1=C2C=C(C=CC2=NN1)C3=CC(=CN=C3)OCC(CC4=CNC5=...           A-443654   \n",
       "3  CC(=O)N1CCN(CC1)C2CCC(CC2)N3C4=NC=NC(=C4C(=N3)...           A-770041   \n",
       "4  CC1=NC(=CC=C1)C2=NN(C=C2C3=CC=NC4=CC=CC=C34)C(...            A-83-01   \n",
       "\n",
       "   MaxEStateIndex  MinEStateIndex  MaxAbsEStateIndex  MinAbsEStateIndex  \\\n",
       "0       12.449593       -1.546408          12.449593           0.024198   \n",
       "1       11.984815       -1.001157          11.984815           0.707037   \n",
       "2        6.350272       -0.113155           6.350272           0.113155   \n",
       "3       13.336040       -0.228281          13.336040           0.156382   \n",
       "4        5.653641        0.490477           5.653641           0.490477   \n",
       "\n",
       "        qed       MolWt  HeavyAtomMolWt  ExactMolWt  ...          MW  \\\n",
       "0  0.650373  362.377991      340.201996  362.136566  ...  362.136566   \n",
       "1  0.482565  130.078003      127.054001  130.017853  ...  130.017853   \n",
       "2  0.396777  397.481995      374.298004  397.190247  ...  397.190247   \n",
       "3  0.283438  621.745972      582.434021  621.317566  ...  621.317566   \n",
       "4  0.378026  421.528992      402.377014  421.136108  ...  421.136108   \n",
       "\n",
       "         AMW   WPath  WPol  Zagreb1  Zagreb2   mZagreb1  mZagreb2  nSugars  \\\n",
       "0   7.544511  1581.0  43.0    128.0    147.0  10.500000  5.888889      0.0   \n",
       "1  10.834822    84.0  10.0     42.0     46.0   4.083333  2.027778      0.0   \n",
       "2   7.494156  2845.0  46.0    164.0    195.0   7.611111  6.472222      0.0   \n",
       "3   7.309618  8753.0  83.0    256.0    312.0  13.500000  9.944445      0.0   \n",
       "4   8.422722  2603.0  50.0    168.0    200.0   7.861111  6.750000      0.0   \n",
       "\n",
       "   core_ester  \n",
       "0         1.0  \n",
       "1         0.0  \n",
       "2         0.0  \n",
       "3         0.0  \n",
       "4         0.0  \n",
       "\n",
       "[5 rows x 4074 columns]"
      ]
     },
     "execution_count": 26,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "out_df.head()"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 27,
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "(389, 4074)"
      ]
     },
     "execution_count": 27,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "out_df.shape"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 28,
   "metadata": {},
   "outputs": [],
   "source": [
    "out_df.to_csv('data/molecure_descriptors.tsv',sep='\\t',index=None)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": null,
   "metadata": {},
   "outputs": [],
   "source": []
  }
 ],
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