Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1cc(C)nc(OCc2ccccc2)c1CN1CCc2c(Cl)cc(Br)c(Cl)c2C1=O
InChiKey
DWWIRJUBYWYGQA-UHFFFAOYSA-N
Route Signature
f25c940e80288950cb2f44c927be2d55566199b167dfaa30571b67ae8cf988d4
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_18289bedb5d5d539bfad5f6d",
"signature": "f25c940e80288950cb2f44c927be2d55566199b167dfaa30571b67ae8cf988d4",
"contentHash": "8a1587dcbbc59c9d57af48efb20d892b61c9778269db1b7a96e584770b352a61",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_f7ebd46c9040dbf8558187a8",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00830",
"moleculeId": "sa_7220eb514dc868acf5682fe6",
"smiles": "COc1cc(C)nc(OCc2ccccc2)c1CN1CCc2c(Cl)cc(Br)c(Cl)c2C1=O",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_7220eb514dc868acf5682fe6",
"inchikey": "DWWIRJUBYWYGQA-UHFFFAOYSA-N",
"smiles": "COc1cc(C)nc(OCc2ccccc2)c1CN1CCc2c(Cl)cc(Br)c(Cl)c2C1=O"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9767",
"routeId": "sa_18289bedb5d5d539bfad5f6d",
"moleculeId": "sa_7220eb514dc868acf5682fe6",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_7220eb514dc868acf5682fe6",
"inchikey": "DWWIRJUBYWYGQA-UHFFFAOYSA-N",
"smiles": "COc1cc(C)nc(OCc2ccccc2)c1CN1CCc2c(Cl)cc(Br)c(Cl)c2C1=O"
},
"smiles": "COc1cc(C)nc(OCc2ccccc2)c1CN1CCc2c(Cl)cc(Br)c(Cl)c2C1=O",
"reactionStepId": "sa_c9d7b73702e9a4ac9e1fed87",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150361067A1;0526;1802301\",\"rsmi\":\"Cl[CH2:5][c:4]1[c:3]([O:2][CH3:1])[cH:32][c:30]([CH3:31])[n:29][c:20]1[O:21][CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[NH:6]1[CH2:7][CH2:8][c:9]2[c:10]([Cl:11])[cH:12][c:13]([Br:14])[c:15]([Cl:16])[c:17]2[C:18]1=[O:19]>CC(C)(C)O.CCOC(C)=O.[K+]>[CH3:1][O:2][c:3]1[c:4]([CH2:5][N:6]2[CH2:7][CH2:8][c:9]3[c:10]([Cl:11])[cH:12][c:13]([Br:14])[c:15]([Cl:16])[c:17]3[C:18]2=[O:19])[c:20]([O:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[n:29][c:30]([CH3:31])[cH:32]1\"},\"mapped_reaction_smiles\":\"Cl[CH2:5][c:4]1[c:3]([O:2][CH3:1])[cH:32][c:30]([CH3:31])[n:29][c:20]1[O:21][CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[NH:6]1[CH2:7][CH2:8][c:9]2[c:10]([Cl:11])[cH:12][c:13]([Br:14])[c:15]([Cl:16])[c:17]2[C:18]1=[O:19]>CC(C)(C)O.CCOC(C)=O.[K+]>[CH3:1][O:2][c:3]1[c:4]([CH2:5][N:6]2[CH2:7][CH2:8][c:9]3[c:10]([Cl:11])[cH:12][c:13]([Br:14])[c:15]([Cl:16])[c:17]3[C:18]2=[O:19])[c:20]([O:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[n:29][c:30]([CH3:31])[cH:32]1\"}",
"reactionStep": {
"id": "sa_c9d7b73702e9a4ac9e1fed87",
"reactionHash": "0f4dacfdeef22584c9ab0c3e16f2159d7215c03c3b94dbd0864fd132e162d489"
},
"children": [
{
"id": "9768",
"routeId": "sa_18289bedb5d5d539bfad5f6d",
"moleculeId": "sa_3cec72b1c72617e380fdbb03",
"parentId": "9767",
"isLeaf": false,
"molecule": {
"id": "sa_3cec72b1c72617e380fdbb03",
"inchikey": "SLDUAUANOWLKTP-UHFFFAOYSA-N",
"smiles": "O=C1NCCc2c(Cl)cc(Br)c(Cl)c21"
},
"smiles": "O=C1NCCc2c(Cl)cc(Br)c(Cl)c21",
"reactionStepId": "sa_27773b343a0727486ca7cb03",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150361067A1;0492;1802278\",\"rsmi\":\"O=C1CCC(=O)N1[Br:11].[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][c:6]2[c:7]([Cl:8])[cH:9][cH:10][c:12]([Cl:13])[c:14]21>O=S(=O)(O)O>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][c:6]2[c:7]([Cl:8])[cH:9][c:10]([Br:11])[c:12]([Cl:13])[c:14]21\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:11].[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][c:6]2[c:7]([Cl:8])[cH:9][cH:10][c:12]([Cl:13])[c:14]21>O=S(=O)(O)O>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][c:6]2[c:7]([Cl:8])[cH:9][c:10]([Br:11])[c:12]([Cl:13])[c:14]21\"}",
"reactionStep": {
"id": "sa_27773b343a0727486ca7cb03",
"reactionHash": "b0368042b80b4c173bd458e86139fae079d50de4baba8f1365808e1090ba6dde"
},
"children": [
{
"id": "9769",
"routeId": "sa_18289bedb5d5d539bfad5f6d",
"moleculeId": "sa_ccdcf23ac83e7a68bfa4f2e5",
"parentId": "9768",
"isLeaf": true,
"molecule": {
"id": "sa_ccdcf23ac83e7a68bfa4f2e5",
"inchikey": "PCLIMKBDDGJMGD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Br"
},
"smiles": "O=C1CCC(=O)N1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9770",
"routeId": "sa_18289bedb5d5d539bfad5f6d",
"moleculeId": "sa_0a3087093bf83660eaf4272d",
"parentId": "9768",
"isLeaf": true,
"molecule": {
"id": "sa_0a3087093bf83660eaf4272d",
"inchikey": "PWUFZDFHINBNCE-UHFFFAOYSA-N",
"smiles": "O=C1NCCc2c(Cl)ccc(Cl)c21"
},
"smiles": "O=C1NCCc2c(Cl)ccc(Cl)c21",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "9771",
"routeId": "sa_18289bedb5d5d539bfad5f6d",
"moleculeId": "sa_a77264d13be667723d978b04",
"parentId": "9767",
"isLeaf": false,
"molecule": {
"id": "sa_a77264d13be667723d978b04",
"inchikey": "VTLCTOJLDMFEHV-UHFFFAOYSA-N",
"smiles": "COc1cc(C)nc(OCc2ccccc2)c1CCl"
},
"smiles": "COc1cc(C)nc(OCc2ccccc2)c1CCl",
"reactionStepId": "sa_1e35ade61ddda0a45eba3285",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150361067A1;0516;1802295\",\"rsmi\":\"O=S(Cl)[Cl:6].O[CH2:5][c:4]1[c:3]([O:2][CH3:1])[cH:19][c:17]([CH3:18])[n:16][c:7]1[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>CCOC(C)=O.O>[CH3:1][O:2][c:3]1[c:4]([CH2:5][Cl:6])[c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16][c:17]([CH3:18])[cH:19]1\"},\"mapped_reaction_smiles\":\"O=S(Cl)[Cl:6].O[CH2:5][c:4]1[c:3]([O:2][CH3:1])[cH:19][c:17]([CH3:18])[n:16][c:7]1[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>CCOC(C)=O.O>[CH3:1][O:2][c:3]1[c:4]([CH2:5][Cl:6])[c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16][c:17]([CH3:18])[cH:19]1\"}",
"reactionStep": {
"id": "sa_1e35ade61ddda0a45eba3285",
"reactionHash": "e723720b1f401fcffd10c7535a0610ce1f9640491970259d987b6c83ca1921ff"
},
"children": [
{
"id": "9772",
"routeId": "sa_18289bedb5d5d539bfad5f6d",
"moleculeId": "sa_cd67ce42f230ef1a4063353c",
"parentId": "9771",
"isLeaf": true,
"molecule": {
"id": "sa_cd67ce42f230ef1a4063353c",
"inchikey": "FYSNRJHAOHDILO-UHFFFAOYSA-N",
"smiles": "O=S(Cl)Cl"
},
"smiles": "O=S(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9773",
"routeId": "sa_18289bedb5d5d539bfad5f6d",
"moleculeId": "sa_c7c8435efced195e50ffc0ca",
"parentId": "9771",
"isLeaf": false,
"molecule": {
"id": "sa_c7c8435efced195e50ffc0ca",
"inchikey": "KDNKSHYVQXHFMP-UHFFFAOYSA-N",
"smiles": "COc1cc(C)nc(OCc2ccccc2)c1CO"
},
"smiles": "COc1cc(C)nc(OCc2ccccc2)c1CO",
"reactionStepId": "sa_4adbc1a37fbf068b75050a83",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150361067A1;0515;1802294\",\"rsmi\":\"CCO[C:5]([c:4]1[c:3]([O:2][CH3:1])[cH:19][c:17]([CH3:18])[n:16][c:7]1[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:6]>C1CCOC1.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][O:2][c:3]1[c:4]([CH2:5][OH:6])[c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16][c:17]([CH3:18])[cH:19]1\"},\"mapped_reaction_smiles\":\"CCO[C:5]([c:4]1[c:3]([O:2][CH3:1])[cH:19][c:17]([CH3:18])[n:16][c:7]1[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:6]>C1CCOC1.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][O:2][c:3]1[c:4]([CH2:5][OH:6])[c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16][c:17]([CH3:18])[cH:19]1\"}",
"reactionStep": {
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"reactionHash": "aab66eb50fc8766ef69134dd6441b19f883c0ac52eb0657c69491d3b7094bea3"
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"children": [
{
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"routeId": "sa_18289bedb5d5d539bfad5f6d",
"moleculeId": "sa_942fece0ee093948f779a055",
"parentId": "9773",
"isLeaf": false,
"molecule": {
"id": "sa_942fece0ee093948f779a055",
"inchikey": "WQXJNMHUNVAZNK-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1c(OC)cc(C)nc1OCc1ccccc1"
},
"smiles": "CCOC(=O)c1c(OC)cc(C)nc1OCc1ccccc1",
"reactionStepId": "sa_8df4190a618e931f18747b6f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150361067A1;0514;1802293\",\"rsmi\":\"I[CH3:22].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16][c:17]([CH3:18])[cH:19][c:20]1[OH:21]>CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16][c:17]([CH3:18])[cH:19][c:20]1[O:21][CH3:22]\"},\"mapped_reaction_smiles\":\"I[CH3:22].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16][c:17]([CH3:18])[cH:19][c:20]1[OH:21]>CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16][c:17]([CH3:18])[cH:19][c:20]1[O:21][CH3:22]\"}",
"reactionStep": {
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"reactionHash": "919d28482503ae7de2cefe94ba8fb4647706fdb1dabd9207105f5e715c6a0905"
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"children": [
{
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"routeId": "sa_18289bedb5d5d539bfad5f6d",
"moleculeId": "sa_b2cce2647e972ede9c635683",
"parentId": "9774",
"isLeaf": false,
"molecule": {
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"inchikey": "BWHPMEYQIOQJBE-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1c(O)cc(C)nc1OCc1ccccc1"
},
"smiles": "CCOC(=O)c1c(O)cc(C)nc1OCc1ccccc1",
"reactionStepId": "sa_530a4cfbd25b8263f18ad503",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150361067A1;0513;1802292\",\"rsmi\":\"Br[CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([OH:8])[n:16][c:17]([CH3:18])[cH:19][c:20]1[OH:21]>C1CCOC1.O=C(O)O.[Ag+2]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16][c:17]([CH3:18])[cH:19][c:20]1[OH:21]\"},\"mapped_reaction_smiles\":\"Br[CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([OH:8])[n:16][c:17]([CH3:18])[cH:19][c:20]1[OH:21]>C1CCOC1.O=C(O)O.[Ag+2]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16][c:17]([CH3:18])[cH:19][c:20]1[OH:21]\"}",
"reactionStep": {
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"reactionHash": "fe39a8f546a919a267a9143b77b0535ce15bd2c702872c53e20ab35f82118219"
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"children": [
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"moleculeId": "sa_4ff2e4de9d80150de333c065",
"parentId": "9775",
"isLeaf": true,
"molecule": {
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"inchikey": "AGEZXYOZHKGVCM-UHFFFAOYSA-N",
"smiles": "BrCc1ccccc1"
},
"smiles": "BrCc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "9777",
"routeId": "sa_18289bedb5d5d539bfad5f6d",
"moleculeId": "sa_e4ca579f0f35bf88aaaf163f",
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"molecule": {
"id": "sa_e4ca579f0f35bf88aaaf163f",
"inchikey": "CMCZAWPDHHYFPU-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1c(O)cc(C)[nH]c1=O"
},
"smiles": "CCOC(=O)c1c(O)cc(C)nc1O",
"reactionStepId": null,
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}
]
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{
"id": "9778",
"routeId": "sa_18289bedb5d5d539bfad5f6d",
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"molecule": {
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"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
},
"smiles": "CI",
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"children": []
}
]
}
]
}
]
}
]
}
}