Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1cccc(C)c1C(=O)c1ncc(Cl)cc1NS(=O)(=O)c1ccc(Cl)c(C)c1
InChiKey
LPMCAZOLVBREKD-UHFFFAOYSA-N
Route Signature
707f1604d0f4df0ab1bff324560d4f4bd2a8b1eef7cbf2b1907d1db489b0a2d8
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_40e8847085cf24ef64965882",
"signature": "707f1604d0f4df0ab1bff324560d4f4bd2a8b1eef7cbf2b1907d1db489b0a2d8",
"contentHash": "a26a943745d0146d9906ebe620e92cc7dc4dc7eba6a025a64747c5ad371d0538",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_80f519dd22111b61e8c7e33d",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00174",
"moleculeId": "sa_566c8404c715bbf408d91749",
"smiles": "COc1cccc(C)c1C(=O)c1ncc(Cl)cc1NS(=O)(=O)c1ccc(Cl)c(C)c1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_566c8404c715bbf408d91749",
"inchikey": "LPMCAZOLVBREKD-UHFFFAOYSA-N",
"smiles": "COc1cccc(C)c1C(=O)c1ncc(Cl)cc1NS(=O)(=O)c1ccc(Cl)c(C)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9230",
"routeId": "sa_40e8847085cf24ef64965882",
"moleculeId": "sa_566c8404c715bbf408d91749",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_566c8404c715bbf408d91749",
"inchikey": "LPMCAZOLVBREKD-UHFFFAOYSA-N",
"smiles": "COc1cccc(C)c1C(=O)c1ncc(Cl)cc1NS(=O)(=O)c1ccc(Cl)c(C)c1"
},
"smiles": "COc1cccc(C)c1C(=O)c1ncc(Cl)cc1NS(=O)(=O)c1ccc(Cl)c(C)c1",
"reactionStepId": "sa_86061fbf6ac63d39f46b6cd4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140031348A1;0771;1480720\",\"rsmi\":\"COC[N:14]([c:13]1[c:7]([C:5]([c:4]2[c:3]([O:2][CH3:1])[cH:30][cH:29][cH:28][c:26]2[CH3:27])=[O:6])[n:8][cH:9][c:10]([Cl:11])[cH:12]1)[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][c:20]([CH3:21])[c:22]([Cl:23])[cH:24][cH:25]1>C1COCCO1.Cl.O>[CH3:1][O:2][c:3]1[c:4]([C:5](=[O:6])[c:7]2[n:8][cH:9][c:10]([Cl:11])[cH:12][c:13]2[NH:14][S:15](=[O:16])(=[O:17])[c:18]2[cH:19][c:20]([CH3:21])[c:22]([Cl:23])[cH:24][cH:25]2)[c:26]([CH3:27])[cH:28][cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"COC[N:14]([c:13]1[c:7]([C:5]([c:4]2[c:3]([O:2][CH3:1])[cH:30][cH:29][cH:28][c:26]2[CH3:27])=[O:6])[n:8][cH:9][c:10]([Cl:11])[cH:12]1)[S:15](=[O:16])(=[O:17])[c:18]1[cH:19][c:20]([CH3:21])[c:22]([Cl:23])[cH:24][cH:25]1>C1COCCO1.Cl.O>[CH3:1][O:2][c:3]1[c:4]([C:5](=[O:6])[c:7]2[n:8][cH:9][c:10]([Cl:11])[cH:12][c:13]2[NH:14][S:15](=[O:16])(=[O:17])[c:18]2[cH:19][c:20]([CH3:21])[c:22]([Cl:23])[cH:24][cH:25]2)[c:26]([CH3:27])[cH:28][cH:29][cH:30]1\"}",
"reactionStep": {
"id": "sa_86061fbf6ac63d39f46b6cd4",
"reactionHash": "8ab048389250ecaa3f302c98291d5f1481a3863b8d381d5af787706e73782507"
},
"children": [
{
"id": "9231",
"routeId": "sa_40e8847085cf24ef64965882",
"moleculeId": "sa_e17b7cce785bf916df357f96",
"parentId": "9230",
"isLeaf": false,
"molecule": {
"id": "sa_e17b7cce785bf916df357f96",
"inchikey": "KEBCHNFBBLJBDC-UHFFFAOYSA-N",
"smiles": "COCN(c1cc(Cl)cnc1C(=O)c1c(C)cccc1OC)S(=O)(=O)c1ccc(Cl)c(C)c1"
},
"smiles": "COCN(c1cc(Cl)cnc1C(=O)c1c(C)cccc1OC)S(=O)(=O)c1ccc(Cl)c(C)c1",
"reactionStepId": "sa_a8b6d8b2e50be7653601f896",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140031348A1;0769;1480719\",\"rsmi\":\"Br[c:11]1[c:5]([N:4]([CH2:3][O:2][CH3:1])[S:23](=[O:24])(=[O:25])[c:26]2[cH:27][c:28]([CH3:29])[c:30]([Cl:31])[cH:32][cH:33]2)[cH:6][c:7]([Cl:8])[cH:9][n:10]1.CON(C)[C:12](=[O:13])[c:14]1[c:15]([O:16][CH3:17])[cH:18][cH:19][cH:20][c:21]1[CH3:22]>>[CH3:1][O:2][CH2:3][N:4]([c:5]1[cH:6][c:7]([Cl:8])[cH:9][n:10][c:11]1[C:12](=[O:13])[c:14]1[c:15]([O:16][CH3:17])[cH:18][cH:19][cH:20][c:21]1[CH3:22])[S:23](=[O:24])(=[O:25])[c:26]1[cH:27][c:28]([CH3:29])[c:30]([Cl:31])[cH:32][cH:33]1\"},\"mapped_reaction_smiles\":\"Br[c:11]1[c:5]([N:4]([CH2:3][O:2][CH3:1])[S:23](=[O:24])(=[O:25])[c:26]2[cH:27][c:28]([CH3:29])[c:30]([Cl:31])[cH:32][cH:33]2)[cH:6][c:7]([Cl:8])[cH:9][n:10]1.CON(C)[C:12](=[O:13])[c:14]1[c:15]([O:16][CH3:17])[cH:18][cH:19][cH:20][c:21]1[CH3:22]>>[CH3:1][O:2][CH2:3][N:4]([c:5]1[cH:6][c:7]([Cl:8])[cH:9][n:10][c:11]1[C:12](=[O:13])[c:14]1[c:15]([O:16][CH3:17])[cH:18][cH:19][cH:20][c:21]1[CH3:22])[S:23](=[O:24])(=[O:25])[c:26]1[cH:27][c:28]([CH3:29])[c:30]([Cl:31])[cH:32][cH:33]1\"}",
"reactionStep": {
"id": "sa_a8b6d8b2e50be7653601f896",
"reactionHash": "2dec870210695c83edf4b7468b1259ccff553ee06479c4e634eb318d4d86b4ea"
},
"children": [
{
"id": "9232",
"routeId": "sa_40e8847085cf24ef64965882",
"moleculeId": "sa_00ce952ee5b7dd95ed40c4ea",
"parentId": "9231",
"isLeaf": true,
"molecule": {
"id": "sa_00ce952ee5b7dd95ed40c4ea",
"inchikey": "JIIREUSLZQCQQM-UHFFFAOYSA-N",
"smiles": "COc1cccc(C)c1C(=O)N(C)OC"
},
"smiles": "COc1cccc(C)c1C(=O)N(C)OC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9233",
"routeId": "sa_40e8847085cf24ef64965882",
"moleculeId": "sa_835a1a77d98135e71ca6ed60",
"parentId": "9231",
"isLeaf": false,
"molecule": {
"id": "sa_835a1a77d98135e71ca6ed60",
"inchikey": "QKDCHBUFECEIKU-UHFFFAOYSA-N",
"smiles": "COCN(c1cc(Cl)cnc1Br)S(=O)(=O)c1ccc(Cl)c(C)c1"
},
"smiles": "COCN(c1cc(Cl)cnc1Br)S(=O)(=O)c1ccc(Cl)c(C)c1",
"reactionStepId": "sa_90903e6ace8b5d5cd1a53f42",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140031348A1;0763;1480716\",\"rsmi\":\"Cl[CH2:3][O:2][CH3:1].[NH:4]([c:5]1[cH:6][c:7]([Cl:8])[cH:9][n:10][c:11]1[Br:12])[S:13](=[O:14])(=[O:15])[c:16]1[cH:17][c:18]([CH3:19])[c:20]([Cl:21])[cH:22][cH:23]1>C1CCOC1.O=C(O)O.[K+].[K+]>[CH3:1][O:2][CH2:3][N:4]([c:5]1[cH:6][c:7]([Cl:8])[cH:9][n:10][c:11]1[Br:12])[S:13](=[O:14])(=[O:15])[c:16]1[cH:17][c:18]([CH3:19])[c:20]([Cl:21])[cH:22][cH:23]1\"},\"mapped_reaction_smiles\":\"Cl[CH2:3][O:2][CH3:1].[NH:4]([c:5]1[cH:6][c:7]([Cl:8])[cH:9][n:10][c:11]1[Br:12])[S:13](=[O:14])(=[O:15])[c:16]1[cH:17][c:18]([CH3:19])[c:20]([Cl:21])[cH:22][cH:23]1>C1CCOC1.O=C(O)O.[K+].[K+]>[CH3:1][O:2][CH2:3][N:4]([c:5]1[cH:6][c:7]([Cl:8])[cH:9][n:10][c:11]1[Br:12])[S:13](=[O:14])(=[O:15])[c:16]1[cH:17][c:18]([CH3:19])[c:20]([Cl:21])[cH:22][cH:23]1\"}",
"reactionStep": {
"id": "sa_90903e6ace8b5d5cd1a53f42",
"reactionHash": "e25bb09d532aa970aba2a6ae8cc756a8f6bb955319d6f191d67f508ac795d0b4"
},
"children": [
{
"id": "9234",
"routeId": "sa_40e8847085cf24ef64965882",
"moleculeId": "sa_3c0b3646df93451ef6d06e53",
"parentId": "9233",
"isLeaf": false,
"molecule": {
"id": "sa_3c0b3646df93451ef6d06e53",
"inchikey": "HEVJZMXKCYPFDD-UHFFFAOYSA-N",
"smiles": "Cc1cc(S(=O)(=O)Nc2cc(Cl)cnc2Br)ccc1Cl"
},
"smiles": "Cc1cc(S(=O)(=O)Nc2cc(Cl)cnc2Br)ccc1Cl",
"reactionStepId": "sa_21987bff1dee9aa240dd1fe1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140031348A1;0762;1480715\",\"rsmi\":\"Cl[S:8]([c:7]1[cH:6][cH:5][c:3]([Cl:4])[c:2]([CH3:1])[cH:20]1)(=[O:9])=[O:10].[NH2:11][c:12]1[cH:13][c:14]([Cl:15])[cH:16][n:17][c:18]1[Br:19]>c1ccncc1>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[NH:11][c:12]2[cH:13][c:14]([Cl:15])[cH:16][n:17][c:18]2[Br:19])[cH:20]1\"},\"mapped_reaction_smiles\":\"Cl[S:8]([c:7]1[cH:6][cH:5][c:3]([Cl:4])[c:2]([CH3:1])[cH:20]1)(=[O:9])=[O:10].[NH2:11][c:12]1[cH:13][c:14]([Cl:15])[cH:16][n:17][c:18]1[Br:19]>c1ccncc1>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[NH:11][c:12]2[cH:13][c:14]([Cl:15])[cH:16][n:17][c:18]2[Br:19])[cH:20]1\"}",
"reactionStep": {
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"reactionHash": "93d5f44de72ef2a45ccaa4e97f981327db8e4df90b9891255a3d565f46d93711"
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"children": [
{
"id": "9235",
"routeId": "sa_40e8847085cf24ef64965882",
"moleculeId": "sa_2f69f70f2f71501383f90b16",
"parentId": "9234",
"isLeaf": false,
"molecule": {
"id": "sa_2f69f70f2f71501383f90b16",
"inchikey": "AZOXQBMBDRLSCQ-UHFFFAOYSA-N",
"smiles": "Nc1cc(Cl)cnc1Br"
},
"smiles": "Nc1cc(Cl)cnc1Br",
"reactionStepId": "sa_aef2512b21ede91a74e35351",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140031348A1;0611;1480668\",\"rsmi\":\"O=[N+:1]([O-])[c:2]1[cH:3][c:4]([Cl:5])[cH:6][n:7][c:8]1[Br:9]>CCOCC.Cl.Cl[Sn]Cl.O.O>[NH2:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][n:7][c:8]1[Br:9]\"},\"mapped_reaction_smiles\":\"O=[N+:1]([O-])[c:2]1[cH:3][c:4]([Cl:5])[cH:6][n:7][c:8]1[Br:9]>CCOCC.Cl.Cl[Sn]Cl.O.O>[NH2:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][n:7][c:8]1[Br:9]\"}",
"reactionStep": {
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"reactionHash": "12dfd17f308f4aee819c78b4d343342bade45a91c0cc292fe060a1fb67ff0e83"
},
"children": [
{
"id": "9236",
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"moleculeId": "sa_32880846d9f843807b95b4d2",
"parentId": "9235",
"isLeaf": true,
"molecule": {
"id": "sa_32880846d9f843807b95b4d2",
"inchikey": "VFMIDVIAQMFGGP-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cc(Cl)cnc1Br"
},
"smiles": "O=[N+]([O-])c1cc(Cl)cnc1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
},
{
"id": "9237",
"routeId": "sa_40e8847085cf24ef64965882",
"moleculeId": "sa_c9607262896698fe38c5b4a8",
"parentId": "9234",
"isLeaf": false,
"molecule": {
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"inchikey": "WEPYREBDJIVOHD-UHFFFAOYSA-N",
"smiles": "Cc1cc(S(=O)(=O)Cl)ccc1Cl"
},
"smiles": "Cc1cc(S(=O)(=O)Cl)ccc1Cl",
"reactionStepId": "sa_ef696b76c9960aa218262792",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140031348A1;0757;1480712\",\"rsmi\":\"N[c:7]1[cH:6][cH:5][c:3]([Cl:4])[c:2]([CH3:1])[cH:12]1.[ClH:11].[S:8](=[O:9])=[O:10]>CC(=O)O.Cl.O=NO.[Na+]>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[Cl:11])[cH:12]1\"},\"mapped_reaction_smiles\":\"N[c:7]1[cH:6][cH:5][c:3]([Cl:4])[c:2]([CH3:1])[cH:12]1.[ClH:11].[S:8](=[O:9])=[O:10]>CC(=O)O.Cl.O=NO.[Na+]>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[Cl:11])[cH:12]1\"}",
"reactionStep": {
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"reactionHash": "0f43c777ae6dc640f26feed2921920a64e9d1157aaf02372bec794e86c26ff13"
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"children": [
{
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"moleculeId": "sa_a8c65e42beb863b563d58798",
"parentId": "9237",
"isLeaf": true,
"molecule": {
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"inchikey": "HIHCTGNZNHSZPP-UHFFFAOYSA-N",
"smiles": "Cc1cc(N)ccc1Cl"
},
"smiles": "Cc1cc(N)ccc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "9239",
"routeId": "sa_40e8847085cf24ef64965882",
"moleculeId": "sa_3a2c4fd75dc377c54a2f812a",
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"molecule": {
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"inchikey": "RAHZWNYVWXNFOC-UHFFFAOYSA-N",
"smiles": "O=S=O"
},
"smiles": "O=S=O",
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"metadata": null,
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},
{
"id": "9240",
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"molecule": {
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"inchikey": "VEXZGXHMUGYJMC-UHFFFAOYSA-N",
"smiles": "Cl"
},
"smiles": "Cl",
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}
]
}
]
},
{
"id": "9241",
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"molecule": {
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"inchikey": "XJUZRXYOEPSWMB-UHFFFAOYSA-N",
"smiles": "COCCl"
},
"smiles": "COCCl",
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}
]
}
]
}
]
}
}