Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(=O)c1ccc(OCc2ccc(C(OC3CCCCO3)c3cccc(C#N)c3)cc2)c(Cl)c1O
InChiKey
SUHQFWWEYGQWNR-UHFFFAOYSA-N
Route Signature
c859596654ec9ddae11cf49b2c4ca7ac63d15ee4e2b532db7576715425f6140b
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_d1ceac15c5f5c659e95cbbbe",
"signature": "c859596654ec9ddae11cf49b2c4ca7ac63d15ee4e2b532db7576715425f6140b",
"contentHash": "eed1fba0a0014c58f9947730283fa9b35f69fd98ceae1e0c862e1aa41e403a4f",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_076c9ec180a83f3c197eb05b",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-00349",
"moleculeId": "sa_0d5c93c8ffe2d1848b09dfd2",
"smiles": "CC(=O)c1ccc(OCc2ccc(C(OC3CCCCO3)c3cccc(C#N)c3)cc2)c(Cl)c1O",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_0d5c93c8ffe2d1848b09dfd2",
"inchikey": "SUHQFWWEYGQWNR-UHFFFAOYSA-N",
"smiles": "CC(=O)c1ccc(OCc2ccc(C(OC3CCCCO3)c3cccc(C#N)c3)cc2)c(Cl)c1O"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "639",
"routeId": "sa_d1ceac15c5f5c659e95cbbbe",
"moleculeId": "sa_0d5c93c8ffe2d1848b09dfd2",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_0d5c93c8ffe2d1848b09dfd2",
"inchikey": "SUHQFWWEYGQWNR-UHFFFAOYSA-N",
"smiles": "CC(=O)c1ccc(OCc2ccc(C(OC3CCCCO3)c3cccc(C#N)c3)cc2)c(Cl)c1O"
},
"smiles": "CC(=O)c1ccc(OCc2ccc(C(OC3CCCCO3)c3cccc(C#N)c3)cc2)c(Cl)c1O",
"reactionStepId": "sa_19da96791977655bf9c390e7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090318483A1;0375;812085\",\"rsmi\":\"O[c:9]1[c:7]([Cl:8])[c:5]([OH:6])[c:4]([C:2]([CH3:1])=[O:3])[cH:35][cH:34]1.[OH:10][CH2:11][c:12]1[cH:13][cH:14][c:15]([CH:16]([O:17][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][O:23]2)[c:24]2[cH:25][cH:26][cH:27][c:28]([C:29]#[N:30])[cH:31]2)[cH:32][cH:33]1>C1CCOC1.CC(C)OC(=O)/N=N/C(=O)OC(C)C.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][C:2](=[O:3])[c:4]1[c:5]([OH:6])[c:7]([Cl:8])[c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][c:15]([CH:16]([O:17][CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][O:23]3)[c:24]3[cH:25][cH:26][cH:27][c:28]([C:29]#[N:30])[cH:31]3)[cH:32][cH:33]2)[cH:34][cH:35]1\"},\"mapped_reaction_smiles\":\"O[c:9]1[c:7]([Cl:8])[c:5]([OH:6])[c:4]([C:2]([CH3:1])=[O:3])[cH:35][cH:34]1.[OH:10][CH2:11][c:12]1[cH:13][cH:14][c:15]([CH:16]([O:17][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][O:23]2)[c:24]2[cH:25][cH:26][cH:27][c:28]([C:29]#[N:30])[cH:31]2)[cH:32][cH:33]1>C1CCOC1.CC(C)OC(=O)/N=N/C(=O)OC(C)C.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][C:2](=[O:3])[c:4]1[c:5]([OH:6])[c:7]([Cl:8])[c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][c:15]([CH:16]([O:17][CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][O:23]3)[c:24]3[cH:25][cH:26][cH:27][c:28]([C:29]#[N:30])[cH:31]3)[cH:32][cH:33]2)[cH:34][cH:35]1\"}",
"reactionStep": {
"id": "sa_19da96791977655bf9c390e7",
"reactionHash": "19d697ec3361ad9d2fca9ec7a29de3798cf1d595c4564cfca15edc8aa7d99fbd"
},
"children": [
{
"id": "640",
"routeId": "sa_d1ceac15c5f5c659e95cbbbe",
"moleculeId": "sa_a6c236118ce07a4209bc6dd0",
"parentId": "639",
"isLeaf": false,
"molecule": {
"id": "sa_a6c236118ce07a4209bc6dd0",
"inchikey": "NNAUCAUMKGFRFF-UHFFFAOYSA-N",
"smiles": "CC(=O)c1ccc(O)c(Cl)c1O"
},
"smiles": "CC(=O)c1ccc(O)c(Cl)c1O",
"reactionStepId": "sa_c1f58a67b1714b4f2c31787d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090318483A1;0226;812009\",\"rsmi\":\"[CH3:1][C:2](=[O:3])[c:4]1[c:5]([OH:6])[cH:7][c:9]([OH:10])[cH:11][cH:12]1.O[Cl:8]>Cl.O.[Na+].[Na+].O>[CH3:1][C:2](=[O:3])[c:4]1[c:5]([OH:6])[c:7]([Cl:8])[c:9]([OH:10])[cH:11][cH:12]1\"},\"mapped_reaction_smiles\":\"[CH3:1][C:2](=[O:3])[c:4]1[c:5]([OH:6])[cH:7][c:9]([OH:10])[cH:11][cH:12]1.O[Cl:8]>Cl.O.[Na+].[Na+].O>[CH3:1][C:2](=[O:3])[c:4]1[c:5]([OH:6])[c:7]([Cl:8])[c:9]([OH:10])[cH:11][cH:12]1\"}",
"reactionStep": {
"id": "sa_c1f58a67b1714b4f2c31787d",
"reactionHash": "910743c50e9eb4e7bc3bd5d4a4796333cbbb04c34c81cea36a086a8ab56a0c65"
},
"children": [
{
"id": "641",
"routeId": "sa_d1ceac15c5f5c659e95cbbbe",
"moleculeId": "sa_58d5aeb62571b971c228da63",
"parentId": "640",
"isLeaf": true,
"molecule": {
"id": "sa_58d5aeb62571b971c228da63",
"inchikey": "QWPPOHNGKGFGJK-UHFFFAOYSA-N",
"smiles": "OCl"
},
"smiles": "OCl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "642",
"routeId": "sa_d1ceac15c5f5c659e95cbbbe",
"moleculeId": "sa_d6b855a5b6a15748d8f16830",
"parentId": "640",
"isLeaf": true,
"molecule": {
"id": "sa_d6b855a5b6a15748d8f16830",
"inchikey": "SULYEHHGGXARJS-UHFFFAOYSA-N",
"smiles": "CC(=O)c1ccc(O)cc1O"
},
"smiles": "CC(=O)c1ccc(O)cc1O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "643",
"routeId": "sa_d1ceac15c5f5c659e95cbbbe",
"moleculeId": "sa_2cdea5f35e558382c3e20afe",
"parentId": "639",
"isLeaf": false,
"molecule": {
"id": "sa_2cdea5f35e558382c3e20afe",
"inchikey": "RSKYMAVGNXGDKQ-UHFFFAOYSA-N",
"smiles": "N#Cc1cccc(C(OC2CCCCO2)c2ccc(CO)cc2)c1"
},
"smiles": "N#Cc1cccc(C(OC2CCCCO2)c2ccc(CO)cc2)c1",
"reactionStepId": "sa_2a4a8b27395c9e9185a2f603",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090318483A1;0232;812014\",\"rsmi\":\"CC(C)[Si](C(C)C)(C(C)C)[O:19][CH2:18][c:17]1[cH:16][cH:15][c:14]([CH:6]([c:5]2[cH:4][c:3]([C:2]#[N:1])[cH:24][cH:23][cH:22]2)[O:7][CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][O:13]2)[cH:21][cH:20]1>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.O.F>[N:1]#[C:2][c:3]1[cH:4][c:5]([CH:6]([O:7][CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][O:13]2)[c:14]2[cH:15][cH:16][c:17]([CH2:18][OH:19])[cH:20][cH:21]2)[cH:22][cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"CC(C)[Si](C(C)C)(C(C)C)[O:19][CH2:18][c:17]1[cH:16][cH:15][c:14]([CH:6]([c:5]2[cH:4][c:3]([C:2]#[N:1])[cH:24][cH:23][cH:22]2)[O:7][CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][O:13]2)[cH:21][cH:20]1>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.O.F>[N:1]#[C:2][c:3]1[cH:4][c:5]([CH:6]([O:7][CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][O:13]2)[c:14]2[cH:15][cH:16][c:17]([CH2:18][OH:19])[cH:20][cH:21]2)[cH:22][cH:23][cH:24]1\"}",
"reactionStep": {
"id": "sa_2a4a8b27395c9e9185a2f603",
"reactionHash": "c6b3537c9820a0a59c67cfd811560221fac8b385f2a7e69892dd745fcdfaaa52"
},
"children": [
{
"id": "644",
"routeId": "sa_d1ceac15c5f5c659e95cbbbe",
"moleculeId": "sa_c9b195822209337c7d6851d4",
"parentId": "643",
"isLeaf": false,
"molecule": {
"id": "sa_c9b195822209337c7d6851d4",
"inchikey": "DJFGZVVHSIXYIS-UHFFFAOYSA-N",
"smiles": "CC(C)[Si](OCc1ccc(C(OC2CCCCO2)c2cccc(C#N)c2)cc1)(C(C)C)C(C)C"
},
"smiles": "CC(C)[Si](OCc1ccc(C(OC2CCCCO2)c2cccc(C#N)c2)cc1)(C(C)C)C(C)C",
"reactionStepId": "sa_985bacb97bb00360d3bf5f28",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090318483A1;0231;812013\",\"rsmi\":\"[CH3:1][CH:2]([CH3:3])[Si:4]([O:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH:11]([OH:12])[c:19]2[cH:20][cH:21][cH:22][c:23]([C:24]#[N:25])[cH:26]2)[cH:27][cH:28]1)([CH:29]([CH3:30])[CH3:31])[CH:32]([CH3:33])[CH3:34].[CH:13]1=[CH:14][CH2:15][CH2:16][CH2:17][O:18]1>Cc1ccc(S(=O)(=O)O)cc1.ClCCl.O=C(O)O.[Na+].c1ccncc1>[CH3:1][CH:2]([CH3:3])[Si:4]([O:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH:11]([O:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:18]2)[c:19]2[cH:20][cH:21][cH:22][c:23]([C:24]#[N:25])[cH:26]2)[cH:27][cH:28]1)([CH:29]([CH3:30])[CH3:31])[CH:32]([CH3:33])[CH3:34]\"},\"mapped_reaction_smiles\":\"[CH3:1][CH:2]([CH3:3])[Si:4]([O:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH:11]([OH:12])[c:19]2[cH:20][cH:21][cH:22][c:23]([C:24]#[N:25])[cH:26]2)[cH:27][cH:28]1)([CH:29]([CH3:30])[CH3:31])[CH:32]([CH3:33])[CH3:34].[CH:13]1=[CH:14][CH2:15][CH2:16][CH2:17][O:18]1>Cc1ccc(S(=O)(=O)O)cc1.ClCCl.O=C(O)O.[Na+].c1ccncc1>[CH3:1][CH:2]([CH3:3])[Si:4]([O:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH:11]([O:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:18]2)[c:19]2[cH:20][cH:21][cH:22][c:23]([C:24]#[N:25])[cH:26]2)[cH:27][cH:28]1)([CH:29]([CH3:30])[CH3:31])[CH:32]([CH3:33])[CH3:34]\"}",
"reactionStep": {
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"reactionHash": "73a4a74f4898f1818e3ae99adfdfc6339f79a83f442b7214dc0b9d038b256930"
},
"children": [
{
"id": "645",
"routeId": "sa_d1ceac15c5f5c659e95cbbbe",
"moleculeId": "sa_359472b115a712c065ff6c19",
"parentId": "644",
"isLeaf": true,
"molecule": {
"id": "sa_359472b115a712c065ff6c19",
"inchikey": "BUDQDWGNQVEFAC-UHFFFAOYSA-N",
"smiles": "C1=COCCC1"
},
"smiles": "C1=COCCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "646",
"routeId": "sa_d1ceac15c5f5c659e95cbbbe",
"moleculeId": "sa_20c8152a15b5015746b70982",
"parentId": "644",
"isLeaf": false,
"molecule": {
"id": "sa_20c8152a15b5015746b70982",
"inchikey": "PCHYITCBRPBSNH-UHFFFAOYSA-N",
"smiles": "CC(C)[Si](OCc1ccc(C(O)c2cccc(C#N)c2)cc1)(C(C)C)C(C)C"
},
"smiles": "CC(C)[Si](OCc1ccc(C(O)c2cccc(C#N)c2)cc1)(C(C)C)C(C)C",
"reactionStepId": "sa_e3a8dcca0f72d12117b7e3ae",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090318483A1;0230;812012\",\"rsmi\":\"Br[c:10]1[cH:9][cH:8][c:7]([CH2:6][O:5][Si:4]([CH:2]([CH3:1])[CH3:3])([CH:23]([CH3:24])[CH3:25])[CH:26]([CH3:27])[CH3:28])[cH:22][cH:21]1.[CH:11](=[O:12])[c:13]1[cH:14][cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20]1>C1CCOC1.CCOC(C)=O.Cl.[Li]CCCC.N>[CH3:1][CH:2]([CH3:3])[Si:4]([O:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH:11]([OH:12])[c:13]2[cH:14][cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20]2)[cH:21][cH:22]1)([CH:23]([CH3:24])[CH3:25])[CH:26]([CH3:27])[CH3:28]\"},\"mapped_reaction_smiles\":\"Br[c:10]1[cH:9][cH:8][c:7]([CH2:6][O:5][Si:4]([CH:2]([CH3:1])[CH3:3])([CH:23]([CH3:24])[CH3:25])[CH:26]([CH3:27])[CH3:28])[cH:22][cH:21]1.[CH:11](=[O:12])[c:13]1[cH:14][cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20]1>C1CCOC1.CCOC(C)=O.Cl.[Li]CCCC.N>[CH3:1][CH:2]([CH3:3])[Si:4]([O:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH:11]([OH:12])[c:13]2[cH:14][cH:15][cH:16][c:17]([C:18]#[N:19])[cH:20]2)[cH:21][cH:22]1)([CH:23]([CH3:24])[CH3:25])[CH:26]([CH3:27])[CH3:28]\"}",
"reactionStep": {
"id": "sa_e3a8dcca0f72d12117b7e3ae",
"reactionHash": "4cc752beb827067d8ca805a25bfc15b595de96b41e8cab508720b8681aecdafa"
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"children": [
{
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"routeId": "sa_d1ceac15c5f5c659e95cbbbe",
"moleculeId": "sa_7fc369bb44de55bd397a1580",
"parentId": "646",
"isLeaf": false,
"molecule": {
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"inchikey": "DWOFTILJYCEQSC-UHFFFAOYSA-N",
"smiles": "CC(C)[Si](OCc1ccc(Br)cc1)(C(C)C)C(C)C"
},
"smiles": "CC(C)[Si](OCc1ccc(Br)cc1)(C(C)C)C(C)C",
"reactionStepId": "sa_6f5e669fe1e1eccad14a348f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090318483A1;0228;812011\",\"rsmi\":\"Cl[Si:4]([CH:2]([CH3:1])[CH3:3])([CH:14]([CH3:15])[CH3:16])[CH:17]([CH3:18])[CH3:19].[OH:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1>C1CCC2=NCCCN2CC1.ClCCl>[CH3:1][CH:2]([CH3:3])[Si:4]([O:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1)([CH:14]([CH3:15])[CH3:16])[CH:17]([CH3:18])[CH3:19]\"},\"mapped_reaction_smiles\":\"Cl[Si:4]([CH:2]([CH3:1])[CH3:3])([CH:14]([CH3:15])[CH3:16])[CH:17]([CH3:18])[CH3:19].[OH:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1>C1CCC2=NCCCN2CC1.ClCCl>[CH3:1][CH:2]([CH3:3])[Si:4]([O:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1)([CH:14]([CH3:15])[CH3:16])[CH:17]([CH3:18])[CH3:19]\"}",
"reactionStep": {
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"reactionHash": "376285eb936d697eda0956fe2e2f77cd1a83dddc2b15395b920f6cd895dac84e"
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"molecule": {
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"inchikey": "KQIADDMXRMTWHZ-UHFFFAOYSA-N",
"smiles": "CC(C)[Si](Cl)(C(C)C)C(C)C"
},
"smiles": "CC(C)[Si](Cl)(C(C)C)C(C)C",
"reactionStepId": null,
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},
{
"id": "649",
"routeId": "sa_d1ceac15c5f5c659e95cbbbe",
"moleculeId": "sa_9a1609e10fe48217ca44155b",
"parentId": "647",
"isLeaf": true,
"molecule": {
"id": "sa_9a1609e10fe48217ca44155b",
"inchikey": "VEDDBHYQWFOITD-UHFFFAOYSA-N",
"smiles": "OCc1ccc(Br)cc1"
},
"smiles": "OCc1ccc(Br)cc1",
"reactionStepId": null,
"template": null,
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}
]
},
{
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"parentId": "646",
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"molecule": {
"id": "sa_a8d6d6e6de4ceb901383b5a2",
"inchikey": "HGZJJKZPPMFIBU-UHFFFAOYSA-N",
"smiles": "N#Cc1cccc(C=O)c1"
},
"smiles": "N#Cc1cccc(C=O)c1",
"reactionStepId": null,
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"children": []
}
]
}
]
}
]
}
]
}
}