Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
NC(=O)/C=C/c1ccc(C(=C2CCCCCC2)c2ccc(O)cc2)cc1
InChiKey
YEZMYWLJHQMEKH-CXUHLZMHSA-N
Route Signature
1a3acf63fc6edcdf094acc58de26ce765e04761926e1563728adfadb08aee9de
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_84a41d3807a3a1d0348d7ce8",
"signature": "1a3acf63fc6edcdf094acc58de26ce765e04761926e1563728adfadb08aee9de",
"contentHash": "6c9c3ca966e4206f611a52426a1ad8daa30975734a16151da4eacee59c206bb3",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_5ca76513bc05a84435d99f2a",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-02278",
"moleculeId": "sa_7a63a62a29223f3960c3f1d6",
"smiles": "NC(=O)/C=C/c1ccc(C(=C2CCCCCC2)c2ccc(O)cc2)cc1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_7a63a62a29223f3960c3f1d6",
"inchikey": "YEZMYWLJHQMEKH-CXUHLZMHSA-N",
"smiles": "NC(=O)/C=C/c1ccc(C(=C2CCCCCC2)c2ccc(O)cc2)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 3
},
"rootNode": {
"id": "6266",
"routeId": "sa_84a41d3807a3a1d0348d7ce8",
"moleculeId": "sa_7a63a62a29223f3960c3f1d6",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_7a63a62a29223f3960c3f1d6",
"inchikey": "YEZMYWLJHQMEKH-CXUHLZMHSA-N",
"smiles": "NC(=O)/C=C/c1ccc(C(=C2CCCCCC2)c2ccc(O)cc2)cc1"
},
"smiles": "NC(=O)/C=C/c1ccc(C(=C2CCCCCC2)c2ccc(O)cc2)cc1",
"reactionStepId": "sa_af50dd59feff2ef3c6d3890a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07799828B2;0290;1014828\",\"rsmi\":\"O[C:2](=[O:3])/[CH:4]=[CH:5]/[c:6]1[cH:7][cH:8][c:9]([C:10]([c:11]2[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]2)=[C:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[cH:25][cH:26]1.[NH3:1]>CN(C)C=O.Cc1ccccc1.ClCCl.O=C(Cl)C(=O)Cl>[NH2:1][C:2](=[O:3])/[CH:4]=[CH:5]/[c:6]1[cH:7][cH:8][c:9]([C:10]([c:11]2[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]2)=[C:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[cH:25][cH:26]1\"},\"mapped_reaction_smiles\":\"O[C:2](=[O:3])/[CH:4]=[CH:5]/[c:6]1[cH:7][cH:8][c:9]([C:10]([c:11]2[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]2)=[C:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[cH:25][cH:26]1.[NH3:1]>CN(C)C=O.Cc1ccccc1.ClCCl.O=C(Cl)C(=O)Cl>[NH2:1][C:2](=[O:3])/[CH:4]=[CH:5]/[c:6]1[cH:7][cH:8][c:9]([C:10]([c:11]2[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]2)=[C:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[cH:25][cH:26]1\"}",
"reactionStep": {
"id": "sa_af50dd59feff2ef3c6d3890a",
"reactionHash": "6d20664934696526e2e8860d66268d88b42559b035e14667b867b8af18859542"
},
"children": [
{
"id": "6267",
"routeId": "sa_84a41d3807a3a1d0348d7ce8",
"moleculeId": "sa_7b38097f0b02fec6440e12de",
"parentId": "6266",
"isLeaf": false,
"molecule": {
"id": "sa_7b38097f0b02fec6440e12de",
"inchikey": "FIXMRJCBRFHJKY-CXUHLZMHSA-N",
"smiles": "O=C(O)/C=C/c1ccc(C(=C2CCCCCC2)c2ccc(O)cc2)cc1"
},
"smiles": "O=C(O)/C=C/c1ccc(C(=C2CCCCCC2)c2ccc(O)cc2)cc1",
"reactionStepId": "sa_668baa8d5027d8c00de58161",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07799828B2;0286;1014826\",\"rsmi\":\"CC(C)(C)[O:3][C:2](=[O:1])/[CH:4]=[CH:5]/[c:6]1[cH:7][cH:8][c:9]([C:10]([c:11]2[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]2)=[C:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[cH:25][cH:26]1>ClCCl.O=C(O)C(F)(F)F>[O:1]=[C:2]([OH:3])/[CH:4]=[CH:5]/[c:6]1[cH:7][cH:8][c:9]([C:10]([c:11]2[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]2)=[C:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[cH:25][cH:26]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)[O:3][C:2](=[O:1])/[CH:4]=[CH:5]/[c:6]1[cH:7][cH:8][c:9]([C:10]([c:11]2[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]2)=[C:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[cH:25][cH:26]1>ClCCl.O=C(O)C(F)(F)F>[O:1]=[C:2]([OH:3])/[CH:4]=[CH:5]/[c:6]1[cH:7][cH:8][c:9]([C:10]([c:11]2[cH:12][cH:13][c:14]([OH:15])[cH:16][cH:17]2)=[C:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[cH:25][cH:26]1\"}",
"reactionStep": {
"id": "sa_668baa8d5027d8c00de58161",
"reactionHash": "09b5c9d66f84c6a503656e97b4366ad095eeda5be687d650af8d51746a674922"
},
"children": [
{
"id": "6268",
"routeId": "sa_84a41d3807a3a1d0348d7ce8",
"moleculeId": "sa_002759aa2d37a0c5ec4cf860",
"parentId": "6267",
"isLeaf": false,
"molecule": {
"id": "sa_002759aa2d37a0c5ec4cf860",
"inchikey": "BRVFDZFIHAJURA-XDHOZWIPSA-N",
"smiles": "CC(C)(C)OC(=O)/C=C/c1ccc(C(=C2CCCCCC2)c2ccc(O)cc2)cc1"
},
"smiles": "CC(C)(C)OC(=O)/C=C/c1ccc(C(=C2CCCCCC2)c2ccc(O)cc2)cc1",
"reactionStepId": "sa_c233e5c8215b6575d23230e6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07799828B2;0285;1014825\",\"rsmi\":\"Br[c:10]1[cH:11][cH:12][c:13]([C:14]([c:15]2[cH:16][cH:17][c:18]([OH:19])[cH:20][cH:21]2)=[C:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[cH:29][cH:30]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH:8]=[CH2:9]>CC#N.CC(=O)O.CC(=O)O.CCN(CC)CC.CCOC(C)=O.Cc1ccccc1P(c1ccccc1C)c1ccccc1C.O.[Pd+2]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])/[CH:8]=[CH:9]/[c:10]1[cH:11][cH:12][c:13]([C:14]([c:15]2[cH:16][cH:17][c:18]([OH:19])[cH:20][cH:21]2)=[C:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"Br[c:10]1[cH:11][cH:12][c:13]([C:14]([c:15]2[cH:16][cH:17][c:18]([OH:19])[cH:20][cH:21]2)=[C:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[cH:29][cH:30]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH:8]=[CH2:9]>CC#N.CC(=O)O.CC(=O)O.CCN(CC)CC.CCOC(C)=O.Cc1ccccc1P(c1ccccc1C)c1ccccc1C.O.[Pd+2]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])/[CH:8]=[CH:9]/[c:10]1[cH:11][cH:12][c:13]([C:14]([c:15]2[cH:16][cH:17][c:18]([OH:19])[cH:20][cH:21]2)=[C:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[cH:29][cH:30]1\"}",
"reactionStep": {
"id": "sa_c233e5c8215b6575d23230e6",
"reactionHash": "515e43bb406610d0d742297d8f1388dcd91b758f1a1a715135fe509fc00a2e12"
},
"children": [
{
"id": "6269",
"routeId": "sa_84a41d3807a3a1d0348d7ce8",
"moleculeId": "sa_3100f8ae32a804214fc4c82e",
"parentId": "6268",
"isLeaf": false,
"molecule": {
"id": "sa_3100f8ae32a804214fc4c82e",
"inchikey": "BOVKWNXSOADTJJ-UHFFFAOYSA-N",
"smiles": "Oc1ccc(C(=C2CCCCCC2)c2ccc(Br)cc2)cc1"
},
"smiles": "Oc1ccc(C(=C2CCCCCC2)c2ccc(Br)cc2)cc1",
"reactionStepId": "sa_8afddfd175000db78e2fdf74",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07799828B2;0284;1014824\",\"rsmi\":\"O=[C:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1.O=[C:6]([c:5]1[cH:4][cH:3][c:2]([OH:1])[cH:22][cH:21]1)[c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1>C1CCOC1.Cl[Ti](Cl)(Cl)Cl.[Zn]>[OH:1][c:2]1[cH:3][cH:4][c:5]([C:6]([c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]2)=[C:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[cH:21][cH:22]1\"},\"mapped_reaction_smiles\":\"O=[C:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1.O=[C:6]([c:5]1[cH:4][cH:3][c:2]([OH:1])[cH:22][cH:21]1)[c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1>C1CCOC1.Cl[Ti](Cl)(Cl)Cl.[Zn]>[OH:1][c:2]1[cH:3][cH:4][c:5]([C:6]([c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]2)=[C:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[cH:21][cH:22]1\"}",
"reactionStep": {
"id": "sa_8afddfd175000db78e2fdf74",
"reactionHash": "ba6e9cb02d66aeb07628950460f17bfef00b67f0ea49cc1ccf71f55a6d87538d"
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"children": [
{
"id": "6270",
"routeId": "sa_84a41d3807a3a1d0348d7ce8",
"moleculeId": "sa_62bf35e4599b33928c3ebb43",
"parentId": "6269",
"isLeaf": true,
"molecule": {
"id": "sa_62bf35e4599b33928c3ebb43",
"inchikey": "CGZZMOTZOONQIA-UHFFFAOYSA-N",
"smiles": "O=C1CCCCCC1"
},
"smiles": "O=C1CCCCCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "6271",
"routeId": "sa_84a41d3807a3a1d0348d7ce8",
"moleculeId": "sa_74c7ea29fc8bab2fc342313d",
"parentId": "6269",
"isLeaf": false,
"molecule": {
"id": "sa_74c7ea29fc8bab2fc342313d",
"inchikey": "GCSYLFJQFPSOBR-UHFFFAOYSA-N",
"smiles": "O=C(c1ccc(O)cc1)c1ccc(Br)cc1"
},
"smiles": "O=C(c1ccc(O)cc1)c1ccc(Br)cc1",
"reactionStepId": "sa_cd29e601e8f4a0ebe4b72643",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07799828B2;0275;1014817\",\"rsmi\":\"C[O:7][c:6]1[cH:5][cH:4][c:3]([C:2](=[O:1])[c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]2)[cH:9][cH:8]1>Cc1ccccc1.Cl.N#N.[Al+3].Cl.Cl.Cl>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]1\"},\"mapped_reaction_smiles\":\"C[O:7][c:6]1[cH:5][cH:4][c:3]([C:2](=[O:1])[c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]2)[cH:9][cH:8]1>Cc1ccccc1.Cl.N#N.[Al+3].Cl.Cl.Cl>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]1\"}",
"reactionStep": {
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"reactionHash": "238c854f1b2c5842767a1b0262722d266c10c5b4f76974397bae3c5bea8d150d"
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"children": [
{
"id": "6272",
"routeId": "sa_84a41d3807a3a1d0348d7ce8",
"moleculeId": "sa_e89e814f6ee5193be95a34ec",
"parentId": "6271",
"isLeaf": false,
"molecule": {
"id": "sa_e89e814f6ee5193be95a34ec",
"inchikey": "VFMPCNWWYIQPCN-UHFFFAOYSA-N",
"smiles": "COc1ccc(C(=O)c2ccc(Br)cc2)cc1"
},
"smiles": "COc1ccc(C(=O)c2ccc(Br)cc2)cc1",
"reactionStepId": "sa_24850b01dad224d4217c5f46",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07799828B2;0274;1014816\",\"rsmi\":\"Cl[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:16][cH:17]1>Cl.ClCCl.[Al+3].Cl.Cl.Cl>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]2)[cH:16][cH:17]1\"},\"mapped_reaction_smiles\":\"Cl[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:16][cH:17]1>Cl.ClCCl.[Al+3].Cl.Cl.Cl>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]2)[cH:16][cH:17]1\"}",
"reactionStep": {
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"reactionHash": "e26618026d061f8afc19f9861b533dc99ff9c8765353b59095124f8c815a2793"
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"children": [
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"routeId": "sa_84a41d3807a3a1d0348d7ce8",
"moleculeId": "sa_f99b5e8b3add73d6b7cc68e9",
"parentId": "6272",
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"molecule": {
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"inchikey": "DENKGPBHLYFNGK-UHFFFAOYSA-N",
"smiles": "O=C(Cl)c1ccc(Br)cc1"
},
"smiles": "O=C(Cl)c1ccc(Br)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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{
"id": "6274",
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"molecule": {
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"inchikey": "RDOXTESZEPMUJZ-UHFFFAOYSA-N",
"smiles": "COc1ccccc1"
},
"smiles": "COc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
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]
}
]
},
{
"id": "6275",
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"moleculeId": "sa_43021b3c4d107e3a8c19ba64",
"parentId": "6268",
"isLeaf": true,
"molecule": {
"id": "sa_43021b3c4d107e3a8c19ba64",
"inchikey": "ISXSCDLOGDJUNJ-UHFFFAOYSA-N",
"smiles": "C=CC(=O)OC(C)(C)C"
},
"smiles": "C=CC(=O)OC(C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "6276",
"routeId": "sa_84a41d3807a3a1d0348d7ce8",
"moleculeId": "sa_c9679fdd876f32f86b77fb69",
"parentId": "6266",
"isLeaf": true,
"molecule": {
"id": "sa_c9679fdd876f32f86b77fb69",
"inchikey": "QGZKDVFQNNGYKY-UHFFFAOYSA-N",
"smiles": "N"
},
"smiles": "N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}