Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1c(-c2ccc(OCCCl)cc2)ccc2c1ncn2C(c1ccccc1)(c1ccccc1)c1ccccc1
InChiKey
QOBQOGKSFDONBC-UHFFFAOYSA-N
Route Signature
7f3883555b8add28fc72b3057d746aece2a311ddf6852ed32f685fe1a3ae549d
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_c1b0922ea7e92477a442611c",
"signature": "7f3883555b8add28fc72b3057d746aece2a311ddf6852ed32f685fe1a3ae549d",
"contentHash": "c1498d529ab177b480febdc3ba5fe024abd1af7b445181d26297180c8e8264af",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_458086807b7a2e31993c52dd",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00293",
"moleculeId": "sa_e4dd93b21be28ec3d3b9c3e1",
"smiles": "Cc1c(-c2ccc(OCCCl)cc2)ccc2c1ncn2C(c1ccccc1)(c1ccccc1)c1ccccc1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_e4dd93b21be28ec3d3b9c3e1",
"inchikey": "QOBQOGKSFDONBC-UHFFFAOYSA-N",
"smiles": "Cc1c(-c2ccc(OCCCl)cc2)ccc2c1ncn2C(c1ccccc1)(c1ccccc1)c1ccccc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 4
},
"rootNode": {
"id": "3878",
"routeId": "sa_c1b0922ea7e92477a442611c",
"moleculeId": "sa_e4dd93b21be28ec3d3b9c3e1",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_e4dd93b21be28ec3d3b9c3e1",
"inchikey": "QOBQOGKSFDONBC-UHFFFAOYSA-N",
"smiles": "Cc1c(-c2ccc(OCCCl)cc2)ccc2c1ncn2C(c1ccccc1)(c1ccccc1)c1ccccc1"
},
"smiles": "Cc1c(-c2ccc(OCCCl)cc2)ccc2c1ncn2C(c1ccccc1)(c1ccccc1)c1ccccc1",
"reactionStepId": "sa_21e1d696f2496c14f9b6cb17",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100222345A1;0251;937370\",\"rsmi\":\"Cc1ccc(S(=O)(=O)O[CH2:9][CH2:10][Cl:11])cc1.[CH3:1][c:2]1[c:3](-[c:4]2[cH:5][cH:6][c:7]([OH:8])[cH:12][cH:13]2)[cH:14][cH:15][c:16]2[c:17]1[n:18][cH:19][n:20]2[C:21]([c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)([c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1)[c:34]1[cH:35][cH:36][cH:37][cH:38][cH:39]1>CC#N.O=C(O)O.[K+].[K+]>[CH3:1][c:2]1[c:3](-[c:4]2[cH:5][cH:6][c:7]([O:8][CH2:9][CH2:10][Cl:11])[cH:12][cH:13]2)[cH:14][cH:15][c:16]2[c:17]1[n:18][cH:19][n:20]2[C:21]([c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)([c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1)[c:34]1[cH:35][cH:36][cH:37][cH:38][cH:39]1\"},\"mapped_reaction_smiles\":\"Cc1ccc(S(=O)(=O)O[CH2:9][CH2:10][Cl:11])cc1.[CH3:1][c:2]1[c:3](-[c:4]2[cH:5][cH:6][c:7]([OH:8])[cH:12][cH:13]2)[cH:14][cH:15][c:16]2[c:17]1[n:18][cH:19][n:20]2[C:21]([c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)([c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1)[c:34]1[cH:35][cH:36][cH:37][cH:38][cH:39]1>CC#N.O=C(O)O.[K+].[K+]>[CH3:1][c:2]1[c:3](-[c:4]2[cH:5][cH:6][c:7]([O:8][CH2:9][CH2:10][Cl:11])[cH:12][cH:13]2)[cH:14][cH:15][c:16]2[c:17]1[n:18][cH:19][n:20]2[C:21]([c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)([c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1)[c:34]1[cH:35][cH:36][cH:37][cH:38][cH:39]1\"}",
"reactionStep": {
"id": "sa_21e1d696f2496c14f9b6cb17",
"reactionHash": "31cb9a35bcec5521f79cd3d4a0bbefe2e06161d8d87123866159f439b6612cb8"
},
"children": [
{
"id": "3879",
"routeId": "sa_c1b0922ea7e92477a442611c",
"moleculeId": "sa_54417340f4df7ad87c474009",
"parentId": "3878",
"isLeaf": false,
"molecule": {
"id": "sa_54417340f4df7ad87c474009",
"inchikey": "WNZBMPRSKRKZQF-UHFFFAOYSA-N",
"smiles": "Cc1c(-c2ccc(O)cc2)ccc2c1ncn2C(c1ccccc1)(c1ccccc1)c1ccccc1"
},
"smiles": "Cc1c(-c2ccc(O)cc2)ccc2c1ncn2C(c1ccccc1)(c1ccccc1)c1ccccc1",
"reactionStepId": "sa_c078e84c0b621ff691b43582",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100222345A1;0248;937369\",\"rsmi\":\"Br[c:3]1[c:2]([CH3:1])[c:14]2[c:13]([cH:12][cH:11]1)[n:17]([C:18]([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)([c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)[c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1)[cH:16][n:15]2.OB(O)[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][cH:10]1>COCCOC.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][c:2]1[c:3](-[c:4]2[cH:5][cH:6][c:7]([OH:8])[cH:9][cH:10]2)[cH:11][cH:12][c:13]2[c:14]1[n:15][cH:16][n:17]2[C:18]([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)([c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)[c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1\"},\"mapped_reaction_smiles\":\"Br[c:3]1[c:2]([CH3:1])[c:14]2[c:13]([cH:12][cH:11]1)[n:17]([C:18]([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)([c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)[c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1)[cH:16][n:15]2.OB(O)[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:9][cH:10]1>COCCOC.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][c:2]1[c:3](-[c:4]2[cH:5][cH:6][c:7]([OH:8])[cH:9][cH:10]2)[cH:11][cH:12][c:13]2[c:14]1[n:15][cH:16][n:17]2[C:18]([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)([c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)[c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1\"}",
"reactionStep": {
"id": "sa_c078e84c0b621ff691b43582",
"reactionHash": "14248541e94fca33008e6e019273bc5236fc9ae6a74a5739b6ed85d1f8eda68f"
},
"children": [
{
"id": "3880",
"routeId": "sa_c1b0922ea7e92477a442611c",
"moleculeId": "sa_c61789bba57fadeea1a75725",
"parentId": "3879",
"isLeaf": true,
"molecule": {
"id": "sa_c61789bba57fadeea1a75725",
"inchikey": "COIQUVGFTILYGA-UHFFFAOYSA-N",
"smiles": "OB(O)c1ccc(O)cc1"
},
"smiles": "OB(O)c1ccc(O)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3881",
"routeId": "sa_c1b0922ea7e92477a442611c",
"moleculeId": "sa_105270b67d0629c71740fc28",
"parentId": "3879",
"isLeaf": false,
"molecule": {
"id": "sa_105270b67d0629c71740fc28",
"inchikey": "DTWPIOAUEMRNHD-UHFFFAOYSA-N",
"smiles": "Cc1c(Br)ccc2c1ncn2C(c1ccccc1)(c1ccccc1)c1ccccc1"
},
"smiles": "Cc1c(Br)ccc2c1ncn2C(c1ccccc1)(c1ccccc1)c1ccccc1",
"reactionStepId": "sa_af99762da205a798cf8c419f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100222345A1;0264;937374\",\"rsmi\":\"Cl[C:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1.[CH3:1][c:2]1[c:3]([Br:4])[cH:5][cH:6][c:7]2[c:8]1[n:9][cH:10][nH:11]2>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.[HH].I.[Na+]>[CH3:1][c:2]1[c:3]([Br:4])[cH:5][cH:6][c:7]2[c:8]1[n:9][cH:10][n:11]2[C:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"Cl[C:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1.[CH3:1][c:2]1[c:3]([Br:4])[cH:5][cH:6][c:7]2[c:8]1[n:9][cH:10][nH:11]2>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.[HH].I.[Na+]>[CH3:1][c:2]1[c:3]([Br:4])[cH:5][cH:6][c:7]2[c:8]1[n:9][cH:10][n:11]2[C:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1\"}",
"reactionStep": {
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"reactionHash": "622f3cdd4a24b4c0c2562e5d0b6c8dc1aa9e1bd6d82d8589b68b903a2002e77a"
},
"children": [
{
"id": "3882",
"routeId": "sa_c1b0922ea7e92477a442611c",
"moleculeId": "sa_966de284747392e3a06c0765",
"parentId": "3881",
"isLeaf": true,
"molecule": {
"id": "sa_966de284747392e3a06c0765",
"inchikey": "JBWKIWSBJXDJDT-UHFFFAOYSA-N",
"smiles": "ClC(c1ccccc1)(c1ccccc1)c1ccccc1"
},
"smiles": "ClC(c1ccccc1)(c1ccccc1)c1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3883",
"routeId": "sa_c1b0922ea7e92477a442611c",
"moleculeId": "sa_69e8dfcfebc87bd810cc4674",
"parentId": "3881",
"isLeaf": false,
"molecule": {
"id": "sa_69e8dfcfebc87bd810cc4674",
"inchikey": "JNXOUOKRAGYUNE-UHFFFAOYSA-N",
"smiles": "Cc1c(Br)ccc2[nH]cnc12"
},
"smiles": "Cc1c(Br)ccc2[nH]cnc12",
"reactionStepId": "sa_33f3cbc0fdd664ab3cbcf6a9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100222345A1;0261;937373\",\"rsmi\":\"O=[CH:10]O.[CH3:1][c:2]1[c:3]([Br:4])[cH:5][cH:6][c:7]([NH2:11])[c:8]1[NH2:9]>Cl.N>[CH3:1][c:2]1[c:3]([Br:4])[cH:5][cH:6][c:7]2[c:8]1[n:9][cH:10][nH:11]2\"},\"mapped_reaction_smiles\":\"O=[CH:10]O.[CH3:1][c:2]1[c:3]([Br:4])[cH:5][cH:6][c:7]([NH2:11])[c:8]1[NH2:9]>Cl.N>[CH3:1][c:2]1[c:3]([Br:4])[cH:5][cH:6][c:7]2[c:8]1[n:9][cH:10][nH:11]2\"}",
"reactionStep": {
"id": "sa_33f3cbc0fdd664ab3cbcf6a9",
"reactionHash": "923af15f4a6e6e4732da9cc0661249c18a849847ee96541d97bddbd0232de5f6"
},
"children": [
{
"id": "3884",
"routeId": "sa_c1b0922ea7e92477a442611c",
"moleculeId": "sa_3bff5ea8042027b95a7e61c6",
"parentId": "3883",
"isLeaf": true,
"molecule": {
"id": "sa_3bff5ea8042027b95a7e61c6",
"inchikey": "BDAGIHXWWSANSR-UHFFFAOYSA-N",
"smiles": "O=CO"
},
"smiles": "O=CO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3885",
"routeId": "sa_c1b0922ea7e92477a442611c",
"moleculeId": "sa_02b62f29482fb8684e7296a3",
"parentId": "3883",
"isLeaf": false,
"molecule": {
"id": "sa_02b62f29482fb8684e7296a3",
"inchikey": "JBZQNBSYFRCDRA-UHFFFAOYSA-N",
"smiles": "Cc1c(Br)ccc(N)c1N"
},
"smiles": "Cc1c(Br)ccc(N)c1N",
"reactionStepId": "sa_98061e96df90273c8656ee2f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100222345A1;0258;937372\",\"rsmi\":\"O=[N+:4]([O-])[c:3]1[c:2]([CH3:1])[c:9]([Br:10])[cH:8][cH:7][c:5]1[N+:6](=O)[O-]>CCO.CCOC(C)=O.Cl[Sn]Cl.O.O=C(O)O.[Na+]>[CH3:1][c:2]1[c:3]([NH2:4])[c:5]([NH2:6])[cH:7][cH:8][c:9]1[Br:10]\"},\"mapped_reaction_smiles\":\"O=[N+:4]([O-])[c:3]1[c:2]([CH3:1])[c:9]([Br:10])[cH:8][cH:7][c:5]1[N+:6](=O)[O-]>CCO.CCOC(C)=O.Cl[Sn]Cl.O.O=C(O)O.[Na+]>[CH3:1][c:2]1[c:3]([NH2:4])[c:5]([NH2:6])[cH:7][cH:8][c:9]1[Br:10]\"}",
"reactionStep": {
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"reactionHash": "55872979026c0d1f33497f4df1be1f90a3f68990fd6a26665e2605a2fb3d1536"
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"children": [
{
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"moleculeId": "sa_81e98fa960f8115653e56dae",
"parentId": "3885",
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"molecule": {
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"inchikey": "OXYXHHOXCIPFBY-UHFFFAOYSA-N",
"smiles": "Cc1c(Br)ccc([N+](=O)[O-])c1[N+](=O)[O-]"
},
"smiles": "Cc1c(Br)ccc([N+](=O)[O-])c1[N+](=O)[O-]",
"reactionStepId": "sa_8b8af71ead228172c7c6fe68",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100222345A1;0255;937371\",\"rsmi\":\"O[N+:8](=[O:9])[O-:10].[CH3:1][c:2]1[c:3]([Br:4])[cH:5][cH:6][cH:7][c:11]1[N+:12](=[O:13])[O-:14]>NC(N)=O.O=S(=O)(O)O>[CH3:1][c:2]1[c:3]([Br:4])[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]1[N+:12](=[O:13])[O-:14]\"},\"mapped_reaction_smiles\":\"O[N+:8](=[O:9])[O-:10].[CH3:1][c:2]1[c:3]([Br:4])[cH:5][cH:6][cH:7][c:11]1[N+:12](=[O:13])[O-:14]>NC(N)=O.O=S(=O)(O)O>[CH3:1][c:2]1[c:3]([Br:4])[cH:5][cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]1[N+:12](=[O:13])[O-:14]\"}",
"reactionStep": {
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"reactionHash": "2be85ac4262e7eb0653d9263aff91a6f838361a52a5157339a9cba2a1104ddbe"
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"children": [
{
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"molecule": {
"id": "sa_edac0a7fd043198784a28dd9",
"inchikey": "GRYLNZFGIOXLOG-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])O"
},
"smiles": "O=[N+]([O-])O",
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},
{
"id": "3888",
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"molecule": {
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"inchikey": "LYTNSGFSAXWBCA-UHFFFAOYSA-N",
"smiles": "Cc1c(Br)cccc1[N+](=O)[O-]"
},
"smiles": "Cc1c(Br)cccc1[N+](=O)[O-]",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
]
}
]
}
]
},
{
"id": "3889",
"routeId": "sa_c1b0922ea7e92477a442611c",
"moleculeId": "sa_bf8953522263b3720f2f873b",
"parentId": "3878",
"isLeaf": true,
"molecule": {
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"inchikey": "ZXNMIUJDTOMBPV-UHFFFAOYSA-N",
"smiles": "Cc1ccc(S(=O)(=O)OCCCl)cc1"
},
"smiles": "Cc1ccc(S(=O)(=O)OCCCl)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}