Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCCN1CCC(C(=O)N(C)c2ccc(-n3nc(C4CC4)c4c3-c3sc(NC(C)=O)nc3CC4)c(Cl)c2)CC1
InChiKey
UYTVEXOHJIQEMK-UHFFFAOYSA-N
Route Signature
ebc049119eb37842b155e80771cfb99e266d4a8dc3b53e333c5919bb2290b256
Synthesis route with 4 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_8ea97d8b7f8b4d43d95a4e29",
"signature": "ebc049119eb37842b155e80771cfb99e266d4a8dc3b53e333c5919bb2290b256",
"contentHash": "668ab870b950dd44c009bed9cf10be1bf077efd7dcc78c7226a05a08c6057133",
"length": 4,
"isConvergent": false
},
"target": {
"id": "sa_6ce1150e7715785bffa8a385",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-02127",
"moleculeId": "sa_b1fc5fa59cac8b92f43c76da",
"smiles": "CCCN1CCC(C(=O)N(C)c2ccc(-n3nc(C4CC4)c4c3-c3sc(NC(C)=O)nc3CC4)c(Cl)c2)CC1",
"routeLength": 4,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_b1fc5fa59cac8b92f43c76da",
"inchikey": "UYTVEXOHJIQEMK-UHFFFAOYSA-N",
"smiles": "CCCN1CCC(C(=O)N(C)c2ccc(-n3nc(C4CC4)c4c3-c3sc(NC(C)=O)nc3CC4)c(Cl)c2)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "14659",
"routeId": "sa_8ea97d8b7f8b4d43d95a4e29",
"moleculeId": "sa_b1fc5fa59cac8b92f43c76da",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_b1fc5fa59cac8b92f43c76da",
"inchikey": "UYTVEXOHJIQEMK-UHFFFAOYSA-N",
"smiles": "CCCN1CCC(C(=O)N(C)c2ccc(-n3nc(C4CC4)c4c3-c3sc(NC(C)=O)nc3CC4)c(Cl)c2)CC1"
},
"smiles": "CCCN1CCC(C(=O)N(C)c2ccc(-n3nc(C4CC4)c4c3-c3sc(NC(C)=O)nc3CC4)c(Cl)c2)CC1",
"reactionStepId": "sa_499afb2c4ef604a1bb6690ce",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070238718A1;0354;505357\",\"rsmi\":\"Cl[C:8]([CH:7]1[CH2:6][CH2:5][N:4]([CH2:3][CH2:2][CH3:1])[CH2:39][CH2:38]1)=[O:9].[NH:10]([CH3:11])[c:12]1[cH:13][c:14]([Cl:15])[c:16](-[n:17]2[n:18][c:19]([CH:20]3[CH2:21][CH2:22]3)[c:23]3[c:24]2-[c:25]2[c:26]([n:29][c:30]([NH:31][C:32]([CH3:33])=[O:34])[s:35]2)[CH2:27][CH2:28]3)[cH:36][cH:37]1>c1ccncc1>[CH3:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([C:8](=[O:9])[N:10]([CH3:11])[c:12]2[cH:13][c:14]([Cl:15])[c:16](-[n:17]3[n:18][c:19]([CH:20]4[CH2:21][CH2:22]4)[c:23]4[c:24]3-[c:25]3[c:26]([n:29][c:30]([NH:31][C:32]([CH3:33])=[O:34])[s:35]3)[CH2:27][CH2:28]4)[cH:36][cH:37]2)[CH2:38][CH2:39]1\"},\"mapped_reaction_smiles\":\"Cl[C:8]([CH:7]1[CH2:6][CH2:5][N:4]([CH2:3][CH2:2][CH3:1])[CH2:39][CH2:38]1)=[O:9].[NH:10]([CH3:11])[c:12]1[cH:13][c:14]([Cl:15])[c:16](-[n:17]2[n:18][c:19]([CH:20]3[CH2:21][CH2:22]3)[c:23]3[c:24]2-[c:25]2[c:26]([n:29][c:30]([NH:31][C:32]([CH3:33])=[O:34])[s:35]2)[CH2:27][CH2:28]3)[cH:36][cH:37]1>c1ccncc1>[CH3:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([C:8](=[O:9])[N:10]([CH3:11])[c:12]2[cH:13][c:14]([Cl:15])[c:16](-[n:17]3[n:18][c:19]([CH:20]4[CH2:21][CH2:22]4)[c:23]4[c:24]3-[c:25]3[c:26]([n:29][c:30]([NH:31][C:32]([CH3:33])=[O:34])[s:35]3)[CH2:27][CH2:28]4)[cH:36][cH:37]2)[CH2:38][CH2:39]1\"}",
"reactionStep": {
"id": "sa_499afb2c4ef604a1bb6690ce",
"reactionHash": "5211fe07340c479e69c63f13863041b045ac3a31c04420097ff80d2a1430cd2e"
},
"children": [
{
"id": "14660",
"routeId": "sa_8ea97d8b7f8b4d43d95a4e29",
"moleculeId": "sa_3c0f1daf9918b03519a4b240",
"parentId": "14659",
"isLeaf": false,
"molecule": {
"id": "sa_3c0f1daf9918b03519a4b240",
"inchikey": "JSQCHPSHYKNQGF-UHFFFAOYSA-N",
"smiles": "CNc1ccc(-n2nc(C3CC3)c3c2-c2sc(NC(C)=O)nc2CC3)c(Cl)c1"
},
"smiles": "CNc1ccc(-n2nc(C3CC3)c3c2-c2sc(NC(C)=O)nc2CC3)c(Cl)c1",
"reactionStepId": "sa_e06f90b1ff34db9624437d0d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070238718A1;0330;505352\",\"rsmi\":\"O=[CH2:1].[NH2:2][c:3]1[cH:4][c:5]([Cl:6])[c:7](-[n:8]2[n:9][c:10]([CH:11]3[CH2:12][CH2:13]3)[c:14]3[c:15]2-[c:16]2[c:17]([n:20][c:21]([NH:22][C:23]([CH3:24])=[O:25])[s:26]2)[CH2:18][CH2:19]3)[cH:27][cH:28]1>C1CCOC1.CC(=O)O.O=C(O)O.BOC(C)=O.[Na+].[Na+].[Na+]>[CH3:1][NH:2][c:3]1[cH:4][c:5]([Cl:6])[c:7](-[n:8]2[n:9][c:10]([CH:11]3[CH2:12][CH2:13]3)[c:14]3[c:15]2-[c:16]2[c:17]([n:20][c:21]([NH:22][C:23]([CH3:24])=[O:25])[s:26]2)[CH2:18][CH2:19]3)[cH:27][cH:28]1\"},\"mapped_reaction_smiles\":\"O=[CH2:1].[NH2:2][c:3]1[cH:4][c:5]([Cl:6])[c:7](-[n:8]2[n:9][c:10]([CH:11]3[CH2:12][CH2:13]3)[c:14]3[c:15]2-[c:16]2[c:17]([n:20][c:21]([NH:22][C:23]([CH3:24])=[O:25])[s:26]2)[CH2:18][CH2:19]3)[cH:27][cH:28]1>C1CCOC1.CC(=O)O.O=C(O)O.BOC(C)=O.[Na+].[Na+].[Na+]>[CH3:1][NH:2][c:3]1[cH:4][c:5]([Cl:6])[c:7](-[n:8]2[n:9][c:10]([CH:11]3[CH2:12][CH2:13]3)[c:14]3[c:15]2-[c:16]2[c:17]([n:20][c:21]([NH:22][C:23]([CH3:24])=[O:25])[s:26]2)[CH2:18][CH2:19]3)[cH:27][cH:28]1\"}",
"reactionStep": {
"id": "sa_e06f90b1ff34db9624437d0d",
"reactionHash": "aeaf2b927ed83b59f52a78cf12b9cb4844418e2a29248e6fc33d2a9b928d29f2"
},
"children": [
{
"id": "14661",
"routeId": "sa_8ea97d8b7f8b4d43d95a4e29",
"moleculeId": "sa_fa48b0311f9ecb906b2132fe",
"parentId": "14660",
"isLeaf": true,
"molecule": {
"id": "sa_fa48b0311f9ecb906b2132fe",
"inchikey": "WSFSSNUMVMOOMR-UHFFFAOYSA-N",
"smiles": "C=O"
},
"smiles": "C=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14662",
"routeId": "sa_8ea97d8b7f8b4d43d95a4e29",
"moleculeId": "sa_dd761f6fd77cbfd98134a8fe",
"parentId": "14660",
"isLeaf": false,
"molecule": {
"id": "sa_dd761f6fd77cbfd98134a8fe",
"inchikey": "YZWGICSOSGPVHR-UHFFFAOYSA-N",
"smiles": "CC(=O)Nc1nc2c(s1)-c1c(c(C3CC3)nn1-c1ccc(N)cc1Cl)CC2"
},
"smiles": "CC(=O)Nc1nc2c(s1)-c1c(c(C3CC3)nn1-c1ccc(N)cc1Cl)CC2",
"reactionStepId": "sa_061ee92a21aadbe14f0f0c36",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070238718A1;0324;505350\",\"rsmi\":\"O=[N+:25]([O-])[c:24]1[cH:23][c:21]([Cl:22])[c:20](-[n:19]2[c:10]3[c:11]([c:14]([CH:15]4[CH2:16][CH2:17]4)[n:18]2)[CH2:12][CH2:13][c:7]2[n:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[s:9][c:8]2-3)[cH:27][cH:26]1>CC(=O)O.[Fe]>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[n:6][c:7]2[c:8]([s:9]1)-[c:10]1[c:11]([c:14]([CH:15]3[CH2:16][CH2:17]3)[n:18][n:19]1-[c:20]1[c:21]([Cl:22])[cH:23][c:24]([NH2:25])[cH:26][cH:27]1)[CH2:12][CH2:13]2\"},\"mapped_reaction_smiles\":\"O=[N+:25]([O-])[c:24]1[cH:23][c:21]([Cl:22])[c:20](-[n:19]2[c:10]3[c:11]([c:14]([CH:15]4[CH2:16][CH2:17]4)[n:18]2)[CH2:12][CH2:13][c:7]2[n:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[s:9][c:8]2-3)[cH:27][cH:26]1>CC(=O)O.[Fe]>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[n:6][c:7]2[c:8]([s:9]1)-[c:10]1[c:11]([c:14]([CH:15]3[CH2:16][CH2:17]3)[n:18][n:19]1-[c:20]1[c:21]([Cl:22])[cH:23][c:24]([NH2:25])[cH:26][cH:27]1)[CH2:12][CH2:13]2\"}",
"reactionStep": {
"id": "sa_061ee92a21aadbe14f0f0c36",
"reactionHash": "6bbcaa15ecc84565b180df1514d9fb71a297ee4ee47997d45d53fb0742c071fa"
},
"children": [
{
"id": "14663",
"routeId": "sa_8ea97d8b7f8b4d43d95a4e29",
"moleculeId": "sa_6063889a4392bbd3f07cda6c",
"parentId": "14662",
"isLeaf": false,
"molecule": {
"id": "sa_6063889a4392bbd3f07cda6c",
"inchikey": "IWQYTVDSZUXRDA-UHFFFAOYSA-N",
"smiles": "CC(=O)Nc1nc2c(s1)-c1c(c(C3CC3)nn1-c1ccc([N+](=O)[O-])cc1Cl)CC2"
},
"smiles": "CC(=O)Nc1nc2c(s1)-c1c(c(C3CC3)nn1-c1ccc([N+](=O)[O-])cc1Cl)CC2",
"reactionStepId": "sa_2981f51e2500b21a6acef5de",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070238718A1;0281;505346\",\"rsmi\":\"O=[C:10]1[c:8]2[c:7]([n:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[s:9]2)[CH2:13][CH2:12][CH:11]1[C:14](=O)[CH:15]1[CH2:16][CH2:17]1.[NH2:18][NH:19][c:20]1[c:21]([Cl:22])[cH:23][c:24]([N+:25](=[O:26])[O-:27])[cH:28][cH:29]1>CC(=O)O.Cl>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[n:6][c:7]2[c:8]([s:9]1)-[c:10]1[c:11]([c:14]([CH:15]3[CH2:16][CH2:17]3)[n:18][n:19]1-[c:20]1[c:21]([Cl:22])[cH:23][c:24]([N+:25](=[O:26])[O-:27])[cH:28][cH:29]1)[CH2:12][CH2:13]2\"},\"mapped_reaction_smiles\":\"O=[C:10]1[c:8]2[c:7]([n:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[s:9]2)[CH2:13][CH2:12][CH:11]1[C:14](=O)[CH:15]1[CH2:16][CH2:17]1.[NH2:18][NH:19][c:20]1[c:21]([Cl:22])[cH:23][c:24]([N+:25](=[O:26])[O-:27])[cH:28][cH:29]1>CC(=O)O.Cl>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[n:6][c:7]2[c:8]([s:9]1)-[c:10]1[c:11]([c:14]([CH:15]3[CH2:16][CH2:17]3)[n:18][n:19]1-[c:20]1[c:21]([Cl:22])[cH:23][c:24]([N+:25](=[O:26])[O-:27])[cH:28][cH:29]1)[CH2:12][CH2:13]2\"}",
"reactionStep": {
"id": "sa_2981f51e2500b21a6acef5de",
"reactionHash": "c82bd9d19ba8ea705025acfdcd50ffc1ca8ffcbb1e3707341acda425a30cda0e"
},
"children": [
{
"id": "14664",
"routeId": "sa_8ea97d8b7f8b4d43d95a4e29",
"moleculeId": "sa_8dfb9719ce9825cebe92870d",
"parentId": "14663",
"isLeaf": true,
"molecule": {
"id": "sa_8dfb9719ce9825cebe92870d",
"inchikey": "JBFZYCIJRNJFOG-UHFFFAOYSA-N",
"smiles": "NNc1ccc([N+](=O)[O-])cc1Cl"
},
"smiles": "NNc1ccc([N+](=O)[O-])cc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14665",
"routeId": "sa_8ea97d8b7f8b4d43d95a4e29",
"moleculeId": "sa_5dad7dca41283a8fbf4bcd3e",
"parentId": "14663",
"isLeaf": true,
"molecule": {
"id": "sa_5dad7dca41283a8fbf4bcd3e",
"inchikey": "KWWDWFPEBPAHPJ-UHFFFAOYSA-N",
"smiles": "CC(=O)Nc1nc2c(s1)C(=O)C(C(=O)C1CC1)CC2"
},
"smiles": "CC(=O)Nc1nc2c(s1)C(=O)C(C(=O)C1CC1)CC2",
"reactionStepId": null,
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}
]
}
]
}
]
},
{
"id": "14666",
"routeId": "sa_8ea97d8b7f8b4d43d95a4e29",
"moleculeId": "sa_12e98adee45935b95a972d8a",
"parentId": "14659",
"isLeaf": true,
"molecule": {
"id": "sa_12e98adee45935b95a972d8a",
"inchikey": "QWOKUEHKTGNNIV-UHFFFAOYSA-N",
"smiles": "CCCN1CCC(C(=O)Cl)CC1"
},
"smiles": "CCCN1CCC(C(=O)Cl)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
}