ro2_qooh_7memring.ipynb

{
 "cells": [
  {
   "cell_type": "code",
   "execution_count": 1,
   "metadata": {},
   "outputs": [],
   "source": [
    "from rdkit.Chem import AllChem\n",
    "from rdkit.Chem import rdChemReactions\n",
    "from rdkit import Chem\n",
    "from rdkit.Chem import Draw, AllChem\n",
    "from rdkit.Chem.Descriptors import NumRadicalElectrons\n",
    "from IPython.display import Image, display\n",
    "from enum_rxns import *"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 2,
   "metadata": {
    "scrolled": true
   },
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "30\n"
     ]
    }
   ],
   "source": [
    "import pandas as pd\n",
    "rxn_sma = '[O:1]-[O:2]-[C:3]-[*:6]-[*:7]-[C:4]-[H:5]>>[H:5]-[O:1]-[O:2]-[C:3]-[*:6]-[*:7]-[C:4]'\n",
    "\n",
    "#R carbon - OC - Q carbon\n",
    "reactants = '[O]OCOCC.[O]OC(C)OCC.[O]OCOCCC.[O]OC(C)OCCC.[O]OCOCC(C)C.[O]OC(C)(C)OCC.[O]OC(C)(C)OCCC.[O]OC(C)OCC(C)C.[O]OC(C)(C)OCC(C)C'.split('.')\n",
    "#R carbon - CO - Q carbon\n",
    "reactants += '[O]OCCOC.[O]OC(C)COC.[O]OCCOCC.[O]OC(C)COCC.[O]OCCOC(C)C.[O]OC(C)(C)COC.[O]OC(C)(C)COCC.[O]OC(C)COC(C)C.[O]OC(C)(C)COC(C)C'.split('.')\n",
    "\n",
    "#ether oxygen not between R carbon and Q carbon, methoxy at 'Q' carbon\n",
    "reactants += '[O]OCCCCOC.[O]OC(C)CCCOC.[O]OCCCC(C)OC.[O]OC(C)CCC(C)OC.[O]OC(C)(C)CCCOC.[O]OC(C)(C)CCC(C)OC'.split('.')\n",
    "#ether oxygen not between R carbon and Q carbon, methoxy at 'R' carbon\n",
    "reactants += '[O]OC(OC)CCC.[O]OC(OC)CCCC.[O]OC(OC)(C)CCC.[O]OC(OC)(C)CCCC.[O]OC(OC)CCC(C)C.[O]OC(OC)(C)CCC(C)C'.split('.')\n",
    "reactants = [[x] for x in reactants] \n",
    "print(len(reactants))\n",
    "\n",
    "Images = []\n",
    "rxn_smiles_all = []\n",
    "rxn_types_all = []\n",
    "for i, reactant in enumerate(reactants):\n",
    "    possible_products = run_rxn(rxn_sma, reactant)\n",
    "    #print(possible_products)\n",
    "\n",
    "    for j, prod in enumerate(possible_products):\n",
    "        rxn_smiles = '.'.join(reactant)+'>>'+'.'.join(prod)\n",
    "        rxn_type = get_rxn_type(rxn_smiles)\n",
    "        #print(rxn_smiles, rxn_type)\n",
    "        rxn_smiles_all.append(rxn_smiles)\n",
    "        rxn_types_all.append(rxn_type)\n",
    "        #png = visualize_rxn(rxn_smiles, 'test'+str(i)+str(j)+'.png')\n",
    "        #Images.append(Image(filename = 'test'+str(i)+str(j)+'.png'))\n",
    "        #IPython.display.Image(png)\n",
    "rxn_types_all = [x + '_7mem' for x in rxn_types_all]\n",
    "        \n",
    "df = pd.DataFrame(list(map(list, zip(*[rxn_smiles_all, rxn_types_all]))), columns = ['rxn_smiles', 'rxn_type'])\n",
    "df['R'] = [ x.split('>>')[0] for x in df.rxn_smiles]\n",
    "df['P'] = [ x.split('>>')[1] for x in df.rxn_smiles]"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 3,
   "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>rxn_smiles</th>\n",
       "      <th>rxn_type</th>\n",
       "      <th>R</th>\n",
       "      <th>P</th>\n",
       "    </tr>\n",
       "  </thead>\n",
       "  <tbody>\n",
       "    <tr>\n",
       "      <th>0</th>\n",
       "      <td>[O]OCOCC&gt;&gt;[CH2]COCOO</td>\n",
       "      <td>1a-1_7mem</td>\n",
       "      <td>[O]OCOCC</td>\n",
       "      <td>[CH2]COCOO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>1</th>\n",
       "      <td>[O]OC(C)OCC&gt;&gt;[CH2]COC(C)OO</td>\n",
       "      <td>2a-1_7mem</td>\n",
       "      <td>[O]OC(C)OCC</td>\n",
       "      <td>[CH2]COC(C)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>2</th>\n",
       "      <td>[O]OCOCCC&gt;&gt;C[CH]COCOO</td>\n",
       "      <td>1a-2_7mem</td>\n",
       "      <td>[O]OCOCCC</td>\n",
       "      <td>C[CH]COCOO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>3</th>\n",
       "      <td>[O]OC(C)OCCC&gt;&gt;C[CH]COC(C)OO</td>\n",
       "      <td>2a-2_7mem</td>\n",
       "      <td>[O]OC(C)OCCC</td>\n",
       "      <td>C[CH]COC(C)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>4</th>\n",
       "      <td>[O]OCOCC(C)C&gt;&gt;C[C](C)COCOO</td>\n",
       "      <td>1a-3_7mem</td>\n",
       "      <td>[O]OCOCC(C)C</td>\n",
       "      <td>C[C](C)COCOO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>5</th>\n",
       "      <td>[O]OC(C)(C)OCC&gt;&gt;[CH2]COC(C)(C)OO</td>\n",
       "      <td>3a-1_7mem</td>\n",
       "      <td>[O]OC(C)(C)OCC</td>\n",
       "      <td>[CH2]COC(C)(C)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>6</th>\n",
       "      <td>[O]OC(C)(C)OCCC&gt;&gt;C[CH]COC(C)(C)OO</td>\n",
       "      <td>3a-2_7mem</td>\n",
       "      <td>[O]OC(C)(C)OCCC</td>\n",
       "      <td>C[CH]COC(C)(C)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>7</th>\n",
       "      <td>[O]OC(C)OCC(C)C&gt;&gt;C[C](C)COC(C)OO</td>\n",
       "      <td>2a-3_7mem</td>\n",
       "      <td>[O]OC(C)OCC(C)C</td>\n",
       "      <td>C[C](C)COC(C)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>8</th>\n",
       "      <td>[O]OC(C)(C)OCC(C)C&gt;&gt;C[C](C)COC(C)(C)OO</td>\n",
       "      <td>3a-3_7mem</td>\n",
       "      <td>[O]OC(C)(C)OCC(C)C</td>\n",
       "      <td>C[C](C)COC(C)(C)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>9</th>\n",
       "      <td>[O]OCCOC&gt;&gt;[CH2]OCCOO</td>\n",
       "      <td>1-1a_7mem</td>\n",
       "      <td>[O]OCCOC</td>\n",
       "      <td>[CH2]OCCOO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>10</th>\n",
       "      <td>[O]OC(C)COC&gt;&gt;[CH2]OCC(C)OO</td>\n",
       "      <td>2-1a_7mem</td>\n",
       "      <td>[O]OC(C)COC</td>\n",
       "      <td>[CH2]OCC(C)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>11</th>\n",
       "      <td>[O]OCCOCC&gt;&gt;C[CH]OCCOO</td>\n",
       "      <td>1-2a_7mem</td>\n",
       "      <td>[O]OCCOCC</td>\n",
       "      <td>C[CH]OCCOO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>12</th>\n",
       "      <td>[O]OC(C)COCC&gt;&gt;C[CH]OCC(C)OO</td>\n",
       "      <td>2-2a_7mem</td>\n",
       "      <td>[O]OC(C)COCC</td>\n",
       "      <td>C[CH]OCC(C)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>13</th>\n",
       "      <td>[O]OCCOC(C)C&gt;&gt;C[C](C)OCCOO</td>\n",
       "      <td>1-3a_7mem</td>\n",
       "      <td>[O]OCCOC(C)C</td>\n",
       "      <td>C[C](C)OCCOO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>14</th>\n",
       "      <td>[O]OC(C)(C)COC&gt;&gt;[CH2]OCC(C)(C)OO</td>\n",
       "      <td>3-1a_7mem</td>\n",
       "      <td>[O]OC(C)(C)COC</td>\n",
       "      <td>[CH2]OCC(C)(C)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>15</th>\n",
       "      <td>[O]OC(C)(C)COCC&gt;&gt;C[CH]OCC(C)(C)OO</td>\n",
       "      <td>3-2a_7mem</td>\n",
       "      <td>[O]OC(C)(C)COCC</td>\n",
       "      <td>C[CH]OCC(C)(C)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>16</th>\n",
       "      <td>[O]OC(C)COC(C)C&gt;&gt;C[C](C)OCC(C)OO</td>\n",
       "      <td>2-3a_7mem</td>\n",
       "      <td>[O]OC(C)COC(C)C</td>\n",
       "      <td>C[C](C)OCC(C)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>17</th>\n",
       "      <td>[O]OC(C)(C)COC(C)C&gt;&gt;C[C](C)OCC(C)(C)OO</td>\n",
       "      <td>3-3a_7mem</td>\n",
       "      <td>[O]OC(C)(C)COC(C)C</td>\n",
       "      <td>C[C](C)OCC(C)(C)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>18</th>\n",
       "      <td>[O]OCCCCOC&gt;&gt;CO[CH]CCCOO</td>\n",
       "      <td>1-2a_7mem</td>\n",
       "      <td>[O]OCCCCOC</td>\n",
       "      <td>CO[CH]CCCOO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>19</th>\n",
       "      <td>[O]OC(C)CCCOC&gt;&gt;CO[CH]CCC(C)OO</td>\n",
       "      <td>2-2a_7mem</td>\n",
       "      <td>[O]OC(C)CCCOC</td>\n",
       "      <td>CO[CH]CCC(C)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>20</th>\n",
       "      <td>[O]OCCCC(C)OC&gt;&gt;CO[C](C)CCCOO</td>\n",
       "      <td>1-3a_7mem</td>\n",
       "      <td>[O]OCCCC(C)OC</td>\n",
       "      <td>CO[C](C)CCCOO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>21</th>\n",
       "      <td>[O]OC(C)CCC(C)OC&gt;&gt;CO[C](C)CCC(C)OO</td>\n",
       "      <td>2-3a_7mem</td>\n",
       "      <td>[O]OC(C)CCC(C)OC</td>\n",
       "      <td>CO[C](C)CCC(C)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>22</th>\n",
       "      <td>[O]OC(C)(C)CCCOC&gt;&gt;CO[CH]CCC(C)(C)OO</td>\n",
       "      <td>3-2a_7mem</td>\n",
       "      <td>[O]OC(C)(C)CCCOC</td>\n",
       "      <td>CO[CH]CCC(C)(C)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>23</th>\n",
       "      <td>[O]OC(C)(C)CCC(C)OC&gt;&gt;CO[C](C)CCC(C)(C)OO</td>\n",
       "      <td>3-3a_7mem</td>\n",
       "      <td>[O]OC(C)(C)CCC(C)OC</td>\n",
       "      <td>CO[C](C)CCC(C)(C)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>24</th>\n",
       "      <td>[O]OC(OC)CCC&gt;&gt;[CH2]CCC(OC)OO</td>\n",
       "      <td>2a-1_7mem</td>\n",
       "      <td>[O]OC(OC)CCC</td>\n",
       "      <td>[CH2]CCC(OC)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>25</th>\n",
       "      <td>[O]OC(OC)CCCC&gt;&gt;C[CH]CCC(OC)OO</td>\n",
       "      <td>2a-2_7mem</td>\n",
       "      <td>[O]OC(OC)CCCC</td>\n",
       "      <td>C[CH]CCC(OC)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>26</th>\n",
       "      <td>[O]OC(OC)(C)CCC&gt;&gt;[CH2]CCC(C)(OC)OO</td>\n",
       "      <td>3a-1_7mem</td>\n",
       "      <td>[O]OC(OC)(C)CCC</td>\n",
       "      <td>[CH2]CCC(C)(OC)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>27</th>\n",
       "      <td>[O]OC(OC)(C)CCCC&gt;&gt;C[CH]CCC(C)(OC)OO</td>\n",
       "      <td>3a-2_7mem</td>\n",
       "      <td>[O]OC(OC)(C)CCCC</td>\n",
       "      <td>C[CH]CCC(C)(OC)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>28</th>\n",
       "      <td>[O]OC(OC)CCC(C)C&gt;&gt;COC(CC[C](C)C)OO</td>\n",
       "      <td>2a-3_7mem</td>\n",
       "      <td>[O]OC(OC)CCC(C)C</td>\n",
       "      <td>COC(CC[C](C)C)OO</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>29</th>\n",
       "      <td>[O]OC(OC)(C)CCC(C)C&gt;&gt;COC(C)(CC[C](C)C)OO</td>\n",
       "      <td>3a-3_7mem</td>\n",
       "      <td>[O]OC(OC)(C)CCC(C)C</td>\n",
       "      <td>COC(C)(CC[C](C)C)OO</td>\n",
       "    </tr>\n",
       "  </tbody>\n",
       "</table>\n",
       "</div>"
      ],
      "text/plain": [
       "                                  rxn_smiles   rxn_type                    R  \\\n",
       "0                       [O]OCOCC>>[CH2]COCOO  1a-1_7mem             [O]OCOCC   \n",
       "1                 [O]OC(C)OCC>>[CH2]COC(C)OO  2a-1_7mem          [O]OC(C)OCC   \n",
       "2                      [O]OCOCCC>>C[CH]COCOO  1a-2_7mem            [O]OCOCCC   \n",
       "3                [O]OC(C)OCCC>>C[CH]COC(C)OO  2a-2_7mem         [O]OC(C)OCCC   \n",
       "4                 [O]OCOCC(C)C>>C[C](C)COCOO  1a-3_7mem         [O]OCOCC(C)C   \n",
       "5           [O]OC(C)(C)OCC>>[CH2]COC(C)(C)OO  3a-1_7mem       [O]OC(C)(C)OCC   \n",
       "6          [O]OC(C)(C)OCCC>>C[CH]COC(C)(C)OO  3a-2_7mem      [O]OC(C)(C)OCCC   \n",
       "7           [O]OC(C)OCC(C)C>>C[C](C)COC(C)OO  2a-3_7mem      [O]OC(C)OCC(C)C   \n",
       "8     [O]OC(C)(C)OCC(C)C>>C[C](C)COC(C)(C)OO  3a-3_7mem   [O]OC(C)(C)OCC(C)C   \n",
       "9                       [O]OCCOC>>[CH2]OCCOO  1-1a_7mem             [O]OCCOC   \n",
       "10                [O]OC(C)COC>>[CH2]OCC(C)OO  2-1a_7mem          [O]OC(C)COC   \n",
       "11                     [O]OCCOCC>>C[CH]OCCOO  1-2a_7mem            [O]OCCOCC   \n",
       "12               [O]OC(C)COCC>>C[CH]OCC(C)OO  2-2a_7mem         [O]OC(C)COCC   \n",
       "13                [O]OCCOC(C)C>>C[C](C)OCCOO  1-3a_7mem         [O]OCCOC(C)C   \n",
       "14          [O]OC(C)(C)COC>>[CH2]OCC(C)(C)OO  3-1a_7mem       [O]OC(C)(C)COC   \n",
       "15         [O]OC(C)(C)COCC>>C[CH]OCC(C)(C)OO  3-2a_7mem      [O]OC(C)(C)COCC   \n",
       "16          [O]OC(C)COC(C)C>>C[C](C)OCC(C)OO  2-3a_7mem      [O]OC(C)COC(C)C   \n",
       "17    [O]OC(C)(C)COC(C)C>>C[C](C)OCC(C)(C)OO  3-3a_7mem   [O]OC(C)(C)COC(C)C   \n",
       "18                   [O]OCCCCOC>>CO[CH]CCCOO  1-2a_7mem           [O]OCCCCOC   \n",
       "19             [O]OC(C)CCCOC>>CO[CH]CCC(C)OO  2-2a_7mem        [O]OC(C)CCCOC   \n",
       "20              [O]OCCCC(C)OC>>CO[C](C)CCCOO  1-3a_7mem        [O]OCCCC(C)OC   \n",
       "21        [O]OC(C)CCC(C)OC>>CO[C](C)CCC(C)OO  2-3a_7mem     [O]OC(C)CCC(C)OC   \n",
       "22       [O]OC(C)(C)CCCOC>>CO[CH]CCC(C)(C)OO  3-2a_7mem     [O]OC(C)(C)CCCOC   \n",
       "23  [O]OC(C)(C)CCC(C)OC>>CO[C](C)CCC(C)(C)OO  3-3a_7mem  [O]OC(C)(C)CCC(C)OC   \n",
       "24              [O]OC(OC)CCC>>[CH2]CCC(OC)OO  2a-1_7mem         [O]OC(OC)CCC   \n",
       "25             [O]OC(OC)CCCC>>C[CH]CCC(OC)OO  2a-2_7mem        [O]OC(OC)CCCC   \n",
       "26        [O]OC(OC)(C)CCC>>[CH2]CCC(C)(OC)OO  3a-1_7mem      [O]OC(OC)(C)CCC   \n",
       "27       [O]OC(OC)(C)CCCC>>C[CH]CCC(C)(OC)OO  3a-2_7mem     [O]OC(OC)(C)CCCC   \n",
       "28        [O]OC(OC)CCC(C)C>>COC(CC[C](C)C)OO  2a-3_7mem     [O]OC(OC)CCC(C)C   \n",
       "29  [O]OC(OC)(C)CCC(C)C>>COC(C)(CC[C](C)C)OO  3a-3_7mem  [O]OC(OC)(C)CCC(C)C   \n",
       "\n",
       "                      P  \n",
       "0            [CH2]COCOO  \n",
       "1         [CH2]COC(C)OO  \n",
       "2            C[CH]COCOO  \n",
       "3         C[CH]COC(C)OO  \n",
       "4          C[C](C)COCOO  \n",
       "5      [CH2]COC(C)(C)OO  \n",
       "6      C[CH]COC(C)(C)OO  \n",
       "7       C[C](C)COC(C)OO  \n",
       "8    C[C](C)COC(C)(C)OO  \n",
       "9            [CH2]OCCOO  \n",
       "10        [CH2]OCC(C)OO  \n",
       "11           C[CH]OCCOO  \n",
       "12        C[CH]OCC(C)OO  \n",
       "13         C[C](C)OCCOO  \n",
       "14     [CH2]OCC(C)(C)OO  \n",
       "15     C[CH]OCC(C)(C)OO  \n",
       "16      C[C](C)OCC(C)OO  \n",
       "17   C[C](C)OCC(C)(C)OO  \n",
       "18          CO[CH]CCCOO  \n",
       "19       CO[CH]CCC(C)OO  \n",
       "20        CO[C](C)CCCOO  \n",
       "21     CO[C](C)CCC(C)OO  \n",
       "22    CO[CH]CCC(C)(C)OO  \n",
       "23  CO[C](C)CCC(C)(C)OO  \n",
       "24       [CH2]CCC(OC)OO  \n",
       "25       C[CH]CCC(OC)OO  \n",
       "26    [CH2]CCC(C)(OC)OO  \n",
       "27    C[CH]CCC(C)(OC)OO  \n",
       "28     COC(CC[C](C)C)OO  \n",
       "29  COC(C)(CC[C](C)C)OO  "
      ]
     },
     "execution_count": 3,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "df"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 4,
   "metadata": {},
   "outputs": [
    {
     "name": "stdout",
     "output_type": "stream",
     "text": [
      "Counter({'2a-1_7mem': 2, '2a-2_7mem': 2, '3a-1_7mem': 2, '3a-2_7mem': 2, '2a-3_7mem': 2, '3a-3_7mem': 2, '1-2a_7mem': 2, '2-2a_7mem': 2, '1-3a_7mem': 2, '3-2a_7mem': 2, '2-3a_7mem': 2, '3-3a_7mem': 2, '1a-1_7mem': 1, '1a-2_7mem': 1, '1a-3_7mem': 1, '1-1a_7mem': 1, '2-1a_7mem': 1, '3-1a_7mem': 1})\n",
      "Counter({'[O]OCOCC': 1, '[O]OC(C)OCC': 1, '[O]OCOCCC': 1, '[O]OC(C)OCCC': 1, '[O]OCOCC(C)C': 1, '[O]OC(C)(C)OCC': 1, '[O]OC(C)(C)OCCC': 1, '[O]OC(C)OCC(C)C': 1, '[O]OC(C)(C)OCC(C)C': 1, '[O]OCCOC': 1, '[O]OC(C)COC': 1, '[O]OCCOCC': 1, '[O]OC(C)COCC': 1, '[O]OCCOC(C)C': 1, '[O]OC(C)(C)COC': 1, '[O]OC(C)(C)COCC': 1, '[O]OC(C)COC(C)C': 1, '[O]OC(C)(C)COC(C)C': 1, '[O]OCCCCOC': 1, '[O]OC(C)CCCOC': 1, '[O]OCCCC(C)OC': 1, '[O]OC(C)CCC(C)OC': 1, '[O]OC(C)(C)CCCOC': 1, '[O]OC(C)(C)CCC(C)OC': 1, '[O]OC(OC)CCC': 1, '[O]OC(OC)CCCC': 1, '[O]OC(OC)(C)CCC': 1, '[O]OC(OC)(C)CCCC': 1, '[O]OC(OC)CCC(C)C': 1, '[O]OC(OC)(C)CCC(C)C': 1})\n",
      "18\n",
      "30\n",
      "0\n"
     ]
    }
   ],
   "source": [
    "from collections import Counter\n",
    "rxn_type_counter = Counter(rxn_types_all)\n",
    "reactant_counter = Counter([x.split('>>')[0] for x in rxn_smiles_all])\n",
    "print(rxn_type_counter)\n",
    "print(reactant_counter)\n",
    "print(len(Counter(rxn_types_all).keys()))\n",
    "print(len(rxn_smiles_all))\n",
    "# Sometimes >1 reactions are generated per each rxn_type from run_rxn \n",
    "#due to some unexpected hydrogen transfers from methyl substituents\n",
    "isDel = []\n",
    "for _, row in df.iterrows():\n",
    "    if rxn_type_counter[row['rxn_type']] > 1 and reactant_counter[row['rxn_smiles'].split('>>')[0]] > 1:\n",
    "        isDel.append(True)\n",
    "    else:\n",
    "        isDel.append(False)\n",
    "print(isDel.count(True))\n",
    "df['isDel'] = isDel"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 5,
   "metadata": {},
   "outputs": [],
   "source": [
    "#display(*Images)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 6,
   "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>rxn_smiles</th>\n",
       "      <th>rxn_type</th>\n",
       "      <th>R</th>\n",
       "      <th>P</th>\n",
       "      <th>isDel</th>\n",
       "    </tr>\n",
       "  </thead>\n",
       "  <tbody>\n",
       "    <tr>\n",
       "      <th>0</th>\n",
       "      <td>[O]OCOCC&gt;&gt;[CH2]COCOO</td>\n",
       "      <td>1a-1_7mem</td>\n",
       "      <td>[O]OCOCC</td>\n",
       "      <td>[CH2]COCOO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>1</th>\n",
       "      <td>[O]OC(C)OCC&gt;&gt;[CH2]COC(C)OO</td>\n",
       "      <td>2a-1_7mem</td>\n",
       "      <td>[O]OC(C)OCC</td>\n",
       "      <td>[CH2]COC(C)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>2</th>\n",
       "      <td>[O]OCOCCC&gt;&gt;C[CH]COCOO</td>\n",
       "      <td>1a-2_7mem</td>\n",
       "      <td>[O]OCOCCC</td>\n",
       "      <td>C[CH]COCOO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>3</th>\n",
       "      <td>[O]OC(C)OCCC&gt;&gt;C[CH]COC(C)OO</td>\n",
       "      <td>2a-2_7mem</td>\n",
       "      <td>[O]OC(C)OCCC</td>\n",
       "      <td>C[CH]COC(C)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>4</th>\n",
       "      <td>[O]OCOCC(C)C&gt;&gt;C[C](C)COCOO</td>\n",
       "      <td>1a-3_7mem</td>\n",
       "      <td>[O]OCOCC(C)C</td>\n",
       "      <td>C[C](C)COCOO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>5</th>\n",
       "      <td>[O]OC(C)(C)OCC&gt;&gt;[CH2]COC(C)(C)OO</td>\n",
       "      <td>3a-1_7mem</td>\n",
       "      <td>[O]OC(C)(C)OCC</td>\n",
       "      <td>[CH2]COC(C)(C)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>6</th>\n",
       "      <td>[O]OC(C)(C)OCCC&gt;&gt;C[CH]COC(C)(C)OO</td>\n",
       "      <td>3a-2_7mem</td>\n",
       "      <td>[O]OC(C)(C)OCCC</td>\n",
       "      <td>C[CH]COC(C)(C)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>7</th>\n",
       "      <td>[O]OC(C)OCC(C)C&gt;&gt;C[C](C)COC(C)OO</td>\n",
       "      <td>2a-3_7mem</td>\n",
       "      <td>[O]OC(C)OCC(C)C</td>\n",
       "      <td>C[C](C)COC(C)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>8</th>\n",
       "      <td>[O]OC(C)(C)OCC(C)C&gt;&gt;C[C](C)COC(C)(C)OO</td>\n",
       "      <td>3a-3_7mem</td>\n",
       "      <td>[O]OC(C)(C)OCC(C)C</td>\n",
       "      <td>C[C](C)COC(C)(C)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>9</th>\n",
       "      <td>[O]OCCOC&gt;&gt;[CH2]OCCOO</td>\n",
       "      <td>1-1a_7mem</td>\n",
       "      <td>[O]OCCOC</td>\n",
       "      <td>[CH2]OCCOO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>10</th>\n",
       "      <td>[O]OC(C)COC&gt;&gt;[CH2]OCC(C)OO</td>\n",
       "      <td>2-1a_7mem</td>\n",
       "      <td>[O]OC(C)COC</td>\n",
       "      <td>[CH2]OCC(C)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>11</th>\n",
       "      <td>[O]OCCOCC&gt;&gt;C[CH]OCCOO</td>\n",
       "      <td>1-2a_7mem</td>\n",
       "      <td>[O]OCCOCC</td>\n",
       "      <td>C[CH]OCCOO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>12</th>\n",
       "      <td>[O]OC(C)COCC&gt;&gt;C[CH]OCC(C)OO</td>\n",
       "      <td>2-2a_7mem</td>\n",
       "      <td>[O]OC(C)COCC</td>\n",
       "      <td>C[CH]OCC(C)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>13</th>\n",
       "      <td>[O]OCCOC(C)C&gt;&gt;C[C](C)OCCOO</td>\n",
       "      <td>1-3a_7mem</td>\n",
       "      <td>[O]OCCOC(C)C</td>\n",
       "      <td>C[C](C)OCCOO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>14</th>\n",
       "      <td>[O]OC(C)(C)COC&gt;&gt;[CH2]OCC(C)(C)OO</td>\n",
       "      <td>3-1a_7mem</td>\n",
       "      <td>[O]OC(C)(C)COC</td>\n",
       "      <td>[CH2]OCC(C)(C)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>15</th>\n",
       "      <td>[O]OC(C)(C)COCC&gt;&gt;C[CH]OCC(C)(C)OO</td>\n",
       "      <td>3-2a_7mem</td>\n",
       "      <td>[O]OC(C)(C)COCC</td>\n",
       "      <td>C[CH]OCC(C)(C)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>16</th>\n",
       "      <td>[O]OC(C)COC(C)C&gt;&gt;C[C](C)OCC(C)OO</td>\n",
       "      <td>2-3a_7mem</td>\n",
       "      <td>[O]OC(C)COC(C)C</td>\n",
       "      <td>C[C](C)OCC(C)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>17</th>\n",
       "      <td>[O]OC(C)(C)COC(C)C&gt;&gt;C[C](C)OCC(C)(C)OO</td>\n",
       "      <td>3-3a_7mem</td>\n",
       "      <td>[O]OC(C)(C)COC(C)C</td>\n",
       "      <td>C[C](C)OCC(C)(C)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>18</th>\n",
       "      <td>[O]OCCCCOC&gt;&gt;CO[CH]CCCOO</td>\n",
       "      <td>1-2a_7mem</td>\n",
       "      <td>[O]OCCCCOC</td>\n",
       "      <td>CO[CH]CCCOO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>19</th>\n",
       "      <td>[O]OC(C)CCCOC&gt;&gt;CO[CH]CCC(C)OO</td>\n",
       "      <td>2-2a_7mem</td>\n",
       "      <td>[O]OC(C)CCCOC</td>\n",
       "      <td>CO[CH]CCC(C)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>20</th>\n",
       "      <td>[O]OCCCC(C)OC&gt;&gt;CO[C](C)CCCOO</td>\n",
       "      <td>1-3a_7mem</td>\n",
       "      <td>[O]OCCCC(C)OC</td>\n",
       "      <td>CO[C](C)CCCOO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>21</th>\n",
       "      <td>[O]OC(C)CCC(C)OC&gt;&gt;CO[C](C)CCC(C)OO</td>\n",
       "      <td>2-3a_7mem</td>\n",
       "      <td>[O]OC(C)CCC(C)OC</td>\n",
       "      <td>CO[C](C)CCC(C)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>22</th>\n",
       "      <td>[O]OC(C)(C)CCCOC&gt;&gt;CO[CH]CCC(C)(C)OO</td>\n",
       "      <td>3-2a_7mem</td>\n",
       "      <td>[O]OC(C)(C)CCCOC</td>\n",
       "      <td>CO[CH]CCC(C)(C)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>23</th>\n",
       "      <td>[O]OC(C)(C)CCC(C)OC&gt;&gt;CO[C](C)CCC(C)(C)OO</td>\n",
       "      <td>3-3a_7mem</td>\n",
       "      <td>[O]OC(C)(C)CCC(C)OC</td>\n",
       "      <td>CO[C](C)CCC(C)(C)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>24</th>\n",
       "      <td>[O]OC(OC)CCC&gt;&gt;[CH2]CCC(OC)OO</td>\n",
       "      <td>2a-1_7mem</td>\n",
       "      <td>[O]OC(OC)CCC</td>\n",
       "      <td>[CH2]CCC(OC)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>25</th>\n",
       "      <td>[O]OC(OC)CCCC&gt;&gt;C[CH]CCC(OC)OO</td>\n",
       "      <td>2a-2_7mem</td>\n",
       "      <td>[O]OC(OC)CCCC</td>\n",
       "      <td>C[CH]CCC(OC)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>26</th>\n",
       "      <td>[O]OC(OC)(C)CCC&gt;&gt;[CH2]CCC(C)(OC)OO</td>\n",
       "      <td>3a-1_7mem</td>\n",
       "      <td>[O]OC(OC)(C)CCC</td>\n",
       "      <td>[CH2]CCC(C)(OC)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>27</th>\n",
       "      <td>[O]OC(OC)(C)CCCC&gt;&gt;C[CH]CCC(C)(OC)OO</td>\n",
       "      <td>3a-2_7mem</td>\n",
       "      <td>[O]OC(OC)(C)CCCC</td>\n",
       "      <td>C[CH]CCC(C)(OC)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>28</th>\n",
       "      <td>[O]OC(OC)CCC(C)C&gt;&gt;COC(CC[C](C)C)OO</td>\n",
       "      <td>2a-3_7mem</td>\n",
       "      <td>[O]OC(OC)CCC(C)C</td>\n",
       "      <td>COC(CC[C](C)C)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "    <tr>\n",
       "      <th>29</th>\n",
       "      <td>[O]OC(OC)(C)CCC(C)C&gt;&gt;COC(C)(CC[C](C)C)OO</td>\n",
       "      <td>3a-3_7mem</td>\n",
       "      <td>[O]OC(OC)(C)CCC(C)C</td>\n",
       "      <td>COC(C)(CC[C](C)C)OO</td>\n",
       "      <td>False</td>\n",
       "    </tr>\n",
       "  </tbody>\n",
       "</table>\n",
       "</div>"
      ],
      "text/plain": [
       "                                  rxn_smiles   rxn_type                    R  \\\n",
       "0                       [O]OCOCC>>[CH2]COCOO  1a-1_7mem             [O]OCOCC   \n",
       "1                 [O]OC(C)OCC>>[CH2]COC(C)OO  2a-1_7mem          [O]OC(C)OCC   \n",
       "2                      [O]OCOCCC>>C[CH]COCOO  1a-2_7mem            [O]OCOCCC   \n",
       "3                [O]OC(C)OCCC>>C[CH]COC(C)OO  2a-2_7mem         [O]OC(C)OCCC   \n",
       "4                 [O]OCOCC(C)C>>C[C](C)COCOO  1a-3_7mem         [O]OCOCC(C)C   \n",
       "5           [O]OC(C)(C)OCC>>[CH2]COC(C)(C)OO  3a-1_7mem       [O]OC(C)(C)OCC   \n",
       "6          [O]OC(C)(C)OCCC>>C[CH]COC(C)(C)OO  3a-2_7mem      [O]OC(C)(C)OCCC   \n",
       "7           [O]OC(C)OCC(C)C>>C[C](C)COC(C)OO  2a-3_7mem      [O]OC(C)OCC(C)C   \n",
       "8     [O]OC(C)(C)OCC(C)C>>C[C](C)COC(C)(C)OO  3a-3_7mem   [O]OC(C)(C)OCC(C)C   \n",
       "9                       [O]OCCOC>>[CH2]OCCOO  1-1a_7mem             [O]OCCOC   \n",
       "10                [O]OC(C)COC>>[CH2]OCC(C)OO  2-1a_7mem          [O]OC(C)COC   \n",
       "11                     [O]OCCOCC>>C[CH]OCCOO  1-2a_7mem            [O]OCCOCC   \n",
       "12               [O]OC(C)COCC>>C[CH]OCC(C)OO  2-2a_7mem         [O]OC(C)COCC   \n",
       "13                [O]OCCOC(C)C>>C[C](C)OCCOO  1-3a_7mem         [O]OCCOC(C)C   \n",
       "14          [O]OC(C)(C)COC>>[CH2]OCC(C)(C)OO  3-1a_7mem       [O]OC(C)(C)COC   \n",
       "15         [O]OC(C)(C)COCC>>C[CH]OCC(C)(C)OO  3-2a_7mem      [O]OC(C)(C)COCC   \n",
       "16          [O]OC(C)COC(C)C>>C[C](C)OCC(C)OO  2-3a_7mem      [O]OC(C)COC(C)C   \n",
       "17    [O]OC(C)(C)COC(C)C>>C[C](C)OCC(C)(C)OO  3-3a_7mem   [O]OC(C)(C)COC(C)C   \n",
       "18                   [O]OCCCCOC>>CO[CH]CCCOO  1-2a_7mem           [O]OCCCCOC   \n",
       "19             [O]OC(C)CCCOC>>CO[CH]CCC(C)OO  2-2a_7mem        [O]OC(C)CCCOC   \n",
       "20              [O]OCCCC(C)OC>>CO[C](C)CCCOO  1-3a_7mem        [O]OCCCC(C)OC   \n",
       "21        [O]OC(C)CCC(C)OC>>CO[C](C)CCC(C)OO  2-3a_7mem     [O]OC(C)CCC(C)OC   \n",
       "22       [O]OC(C)(C)CCCOC>>CO[CH]CCC(C)(C)OO  3-2a_7mem     [O]OC(C)(C)CCCOC   \n",
       "23  [O]OC(C)(C)CCC(C)OC>>CO[C](C)CCC(C)(C)OO  3-3a_7mem  [O]OC(C)(C)CCC(C)OC   \n",
       "24              [O]OC(OC)CCC>>[CH2]CCC(OC)OO  2a-1_7mem         [O]OC(OC)CCC   \n",
       "25             [O]OC(OC)CCCC>>C[CH]CCC(OC)OO  2a-2_7mem        [O]OC(OC)CCCC   \n",
       "26        [O]OC(OC)(C)CCC>>[CH2]CCC(C)(OC)OO  3a-1_7mem      [O]OC(OC)(C)CCC   \n",
       "27       [O]OC(OC)(C)CCCC>>C[CH]CCC(C)(OC)OO  3a-2_7mem     [O]OC(OC)(C)CCCC   \n",
       "28        [O]OC(OC)CCC(C)C>>COC(CC[C](C)C)OO  2a-3_7mem     [O]OC(OC)CCC(C)C   \n",
       "29  [O]OC(OC)(C)CCC(C)C>>COC(C)(CC[C](C)C)OO  3a-3_7mem  [O]OC(OC)(C)CCC(C)C   \n",
       "\n",
       "                      P  isDel  \n",
       "0            [CH2]COCOO  False  \n",
       "1         [CH2]COC(C)OO  False  \n",
       "2            C[CH]COCOO  False  \n",
       "3         C[CH]COC(C)OO  False  \n",
       "4          C[C](C)COCOO  False  \n",
       "5      [CH2]COC(C)(C)OO  False  \n",
       "6      C[CH]COC(C)(C)OO  False  \n",
       "7       C[C](C)COC(C)OO  False  \n",
       "8    C[C](C)COC(C)(C)OO  False  \n",
       "9            [CH2]OCCOO  False  \n",
       "10        [CH2]OCC(C)OO  False  \n",
       "11           C[CH]OCCOO  False  \n",
       "12        C[CH]OCC(C)OO  False  \n",
       "13         C[C](C)OCCOO  False  \n",
       "14     [CH2]OCC(C)(C)OO  False  \n",
       "15     C[CH]OCC(C)(C)OO  False  \n",
       "16      C[C](C)OCC(C)OO  False  \n",
       "17   C[C](C)OCC(C)(C)OO  False  \n",
       "18          CO[CH]CCCOO  False  \n",
       "19       CO[CH]CCC(C)OO  False  \n",
       "20        CO[C](C)CCCOO  False  \n",
       "21     CO[C](C)CCC(C)OO  False  \n",
       "22    CO[CH]CCC(C)(C)OO  False  \n",
       "23  CO[C](C)CCC(C)(C)OO  False  \n",
       "24       [CH2]CCC(OC)OO  False  \n",
       "25       C[CH]CCC(OC)OO  False  \n",
       "26    [CH2]CCC(C)(OC)OO  False  \n",
       "27    C[CH]CCC(C)(OC)OO  False  \n",
       "28     COC(CC[C](C)C)OO  False  \n",
       "29  COC(C)(CC[C](C)C)OO  False  "
      ]
     },
     "execution_count": 6,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "df[~df.isDel]"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 7,
   "metadata": {},
   "outputs": [
    {
     "data": {
      "text/plain": [
       "18"
      ]
     },
     "execution_count": 7,
     "metadata": {},
     "output_type": "execute_result"
    }
   ],
   "source": [
    "len(df[~df.isDel].rxn_type.unique())"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": 8,
   "metadata": {},
   "outputs": [],
   "source": [
    "df[~df.isDel].to_csv('ro2_qooh_7mem.csv', index = False)"
   ]
  },
  {
   "cell_type": "code",
   "execution_count": null,
   "metadata": {},
   "outputs": [],
   "source": []
  },
  {
   "cell_type": "code",
   "execution_count": null,
   "metadata": {},
   "outputs": [],
   "source": []
  }
 ],
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