Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COC[C@H](C)Oc1cc(Oc2ccc3c(c2)OCN(C)C3=O)cc(C(=O)Nc2cc[nH]n2)c1
InChiKey
IPIOTOYOPYUTPP-AWEZNQCLSA-N
Route Signature
317c555e75ca6449af7145b390092204ef3633288e501896e52adc094d4533aa
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_54a9e503606476a760d9a128",
"signature": "317c555e75ca6449af7145b390092204ef3633288e501896e52adc094d4533aa",
"contentHash": "6240f767df50aa2a3ab8aed9d9efb5143673ddea6365e995d182fcf8c1546aa1",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_735f0a04b3ca9ee767f7a826",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-06434",
"moleculeId": "sa_c4388de6c60efc613c67466f",
"smiles": "COC[C@H](C)Oc1cc(Oc2ccc3c(c2)OCN(C)C3=O)cc(C(=O)Nc2cc[nH]n2)c1",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_c4388de6c60efc613c67466f",
"inchikey": "IPIOTOYOPYUTPP-AWEZNQCLSA-N",
"smiles": "COC[C@H](C)Oc1cc(Oc2ccc3c(c2)OCN(C)C3=O)cc(C(=O)Nc2cc[nH]n2)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "11604",
"routeId": "sa_54a9e503606476a760d9a128",
"moleculeId": "sa_c4388de6c60efc613c67466f",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_c4388de6c60efc613c67466f",
"inchikey": "IPIOTOYOPYUTPP-AWEZNQCLSA-N",
"smiles": "COC[C@H](C)Oc1cc(Oc2ccc3c(c2)OCN(C)C3=O)cc(C(=O)Nc2cc[nH]n2)c1"
},
"smiles": "COC[C@H](C)Oc1cc(Oc2ccc3c(c2)OCN(C)C3=O)cc(C(=O)Nc2cc[nH]n2)c1",
"reactionStepId": "sa_e6206d9a37016321e0045394",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090105214A1;0575;693571\",\"rsmi\":\"CC(C)(C)OC(=O)[n:30]1[n:29][c:28]([NH:27][C:25]([c:24]2[cH:23][c:9]([O:10][c:11]3[cH:12][c:13]4[c:14]([cH:15][cH:16]3)[C:17](=[O:18])[N:19]([CH3:20])[CH2:21][O:22]4)[cH:8][c:7]([O:6][C@H:4]([CH2:3][O:2][CH3:1])[CH3:5])[cH:33]2)=[O:26])[cH:32][cH:31]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][O:2][CH2:3][C@H:4]([CH3:5])[O:6][c:7]1[cH:8][c:9]([O:10][c:11]2[cH:12][c:13]3[c:14]([cH:15][cH:16]2)[C:17](=[O:18])[N:19]([CH3:20])[CH2:21][O:22]3)[cH:23][c:24]([C:25](=[O:26])[NH:27][c:28]2[n:29][nH:30][cH:31][cH:32]2)[cH:33]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[n:30]1[n:29][c:28]([NH:27][C:25]([c:24]2[cH:23][c:9]([O:10][c:11]3[cH:12][c:13]4[c:14]([cH:15][cH:16]3)[C:17](=[O:18])[N:19]([CH3:20])[CH2:21][O:22]4)[cH:8][c:7]([O:6][C@H:4]([CH2:3][O:2][CH3:1])[CH3:5])[cH:33]2)=[O:26])[cH:32][cH:31]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][O:2][CH2:3][C@H:4]([CH3:5])[O:6][c:7]1[cH:8][c:9]([O:10][c:11]2[cH:12][c:13]3[c:14]([cH:15][cH:16]2)[C:17](=[O:18])[N:19]([CH3:20])[CH2:21][O:22]3)[cH:23][c:24]([C:25](=[O:26])[NH:27][c:28]2[n:29][nH:30][cH:31][cH:32]2)[cH:33]1\"}",
"reactionStep": {
"id": "sa_e6206d9a37016321e0045394",
"reactionHash": "da6a87a5392a5f29f325e38ae3934c63bd0b7c4a8dabdac16e4c7f0d90cbb47b"
},
"children": [
{
"id": "11605",
"routeId": "sa_54a9e503606476a760d9a128",
"moleculeId": "sa_3a2a5a1e6173a76c0950c183",
"parentId": "11604",
"isLeaf": false,
"molecule": {
"id": "sa_3a2a5a1e6173a76c0950c183",
"inchikey": "SMGUWUUYWCMYEE-KRWDZBQOSA-N",
"smiles": "COC[C@H](C)Oc1cc(Oc2ccc3c(c2)OCN(C)C3=O)cc(C(=O)Nc2ccn(C(=O)OC(C)(C)C)n2)c1"
},
"smiles": "COC[C@H](C)Oc1cc(Oc2ccc3c(c2)OCN(C)C3=O)cc(C(=O)Nc2ccn(C(=O)OC(C)(C)C)n2)c1",
"reactionStepId": "sa_a68ae006fc2aec1f5822a3bc",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090105214A1;0579;693572\",\"rsmi\":\"O[C:25]([c:24]1[cH:23][c:9]([O:10][c:11]2[cH:12][c:13]3[c:14]([cH:15][cH:16]2)[C:17](=[O:18])[N:19]([CH3:20])[CH2:21][O:22]3)[cH:8][c:7]([O:6][C@H:4]([CH2:3][O:2][CH3:1])[CH3:5])[cH:40]1)=[O:26].[NH2:27][c:28]1[n:29][n:30]([C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37])[cH:38][cH:39]1>CC(C)=C(Cl)N(C)C.ClCCl.c1ccncc1>[CH3:1][O:2][CH2:3][C@H:4]([CH3:5])[O:6][c:7]1[cH:8][c:9]([O:10][c:11]2[cH:12][c:13]3[c:14]([cH:15][cH:16]2)[C:17](=[O:18])[N:19]([CH3:20])[CH2:21][O:22]3)[cH:23][c:24]([C:25](=[O:26])[NH:27][c:28]2[n:29][n:30]([C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37])[cH:38][cH:39]2)[cH:40]1\"},\"mapped_reaction_smiles\":\"O[C:25]([c:24]1[cH:23][c:9]([O:10][c:11]2[cH:12][c:13]3[c:14]([cH:15][cH:16]2)[C:17](=[O:18])[N:19]([CH3:20])[CH2:21][O:22]3)[cH:8][c:7]([O:6][C@H:4]([CH2:3][O:2][CH3:1])[CH3:5])[cH:40]1)=[O:26].[NH2:27][c:28]1[n:29][n:30]([C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37])[cH:38][cH:39]1>CC(C)=C(Cl)N(C)C.ClCCl.c1ccncc1>[CH3:1][O:2][CH2:3][C@H:4]([CH3:5])[O:6][c:7]1[cH:8][c:9]([O:10][c:11]2[cH:12][c:13]3[c:14]([cH:15][cH:16]2)[C:17](=[O:18])[N:19]([CH3:20])[CH2:21][O:22]3)[cH:23][c:24]([C:25](=[O:26])[NH:27][c:28]2[n:29][n:30]([C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37])[cH:38][cH:39]2)[cH:40]1\"}",
"reactionStep": {
"id": "sa_a68ae006fc2aec1f5822a3bc",
"reactionHash": "857f9804a4d9402922c2c062b3e6fbf0230af069116c0f66dd29212b029aca29"
},
"children": [
{
"id": "11606",
"routeId": "sa_54a9e503606476a760d9a128",
"moleculeId": "sa_cd3ec561198bd2166c0f7849",
"parentId": "11605",
"isLeaf": false,
"molecule": {
"id": "sa_cd3ec561198bd2166c0f7849",
"inchikey": "PPSTXULCXCAGFK-LBPRGKRZSA-N",
"smiles": "COC[C@H](C)Oc1cc(Oc2ccc3c(c2)OCN(C)C3=O)cc(C(=O)O)c1"
},
"smiles": "COC[C@H](C)Oc1cc(Oc2ccc3c(c2)OCN(C)C3=O)cc(C(=O)O)c1",
"reactionStepId": "sa_91c7dc521a671c19f628b318",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090105214A1;0586;693574\",\"rsmi\":\"F[c:11]1[cH:12][c:13]2[c:14]([cH:15][cH:16]1)[C:17](=[O:18])[N:19]([CH3:20])[CH2:21][O:22]2.[CH3:1][O:2][CH2:3][C@H:4]([CH3:5])[O:6][c:7]1[cH:8][c:9]([OH:10])[cH:23][c:24]([C:25](=[O:26])[OH:27])[cH:28]1>CC#N.CCOC(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][CH2:3][C@H:4]([CH3:5])[O:6][c:7]1[cH:8][c:9]([O:10][c:11]2[cH:12][c:13]3[c:14]([cH:15][cH:16]2)[C:17](=[O:18])[N:19]([CH3:20])[CH2:21][O:22]3)[cH:23][c:24]([C:25](=[O:26])[OH:27])[cH:28]1\"},\"mapped_reaction_smiles\":\"F[c:11]1[cH:12][c:13]2[c:14]([cH:15][cH:16]1)[C:17](=[O:18])[N:19]([CH3:20])[CH2:21][O:22]2.[CH3:1][O:2][CH2:3][C@H:4]([CH3:5])[O:6][c:7]1[cH:8][c:9]([OH:10])[cH:23][c:24]([C:25](=[O:26])[OH:27])[cH:28]1>CC#N.CCOC(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][CH2:3][C@H:4]([CH3:5])[O:6][c:7]1[cH:8][c:9]([O:10][c:11]2[cH:12][c:13]3[c:14]([cH:15][cH:16]2)[C:17](=[O:18])[N:19]([CH3:20])[CH2:21][O:22]3)[cH:23][c:24]([C:25](=[O:26])[OH:27])[cH:28]1\"}",
"reactionStep": {
"id": "sa_91c7dc521a671c19f628b318",
"reactionHash": "b5d60476bb6a167443048ef3c766bea0ad852cf33532014914abe64151576298"
},
"children": [
{
"id": "11607",
"routeId": "sa_54a9e503606476a760d9a128",
"moleculeId": "sa_146185de2e770f20a49d89e3",
"parentId": "11606",
"isLeaf": true,
"molecule": {
"id": "sa_146185de2e770f20a49d89e3",
"inchikey": "HDGWFTVUCOOVNT-UHFFFAOYSA-N",
"smiles": "CN1COc2cc(F)ccc2C1=O"
},
"smiles": "CN1COc2cc(F)ccc2C1=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11608",
"routeId": "sa_54a9e503606476a760d9a128",
"moleculeId": "sa_09e833006171c4d384bc1d33",
"parentId": "11606",
"isLeaf": true,
"molecule": {
"id": "sa_09e833006171c4d384bc1d33",
"inchikey": "IJHZTGIAQNRARD-ZETCQYMHSA-N",
"smiles": "COC[C@H](C)Oc1cc(O)cc(C(=O)O)c1"
},
"smiles": "COC[C@H](C)Oc1cc(O)cc(C(=O)O)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "11609",
"routeId": "sa_54a9e503606476a760d9a128",
"moleculeId": "sa_90f0fdb51ee3f7d18f40c63c",
"parentId": "11605",
"isLeaf": false,
"molecule": {
"id": "sa_90f0fdb51ee3f7d18f40c63c",
"inchikey": "SLWKHFGJHAEQPD-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)n1ccc(N)n1"
},
"smiles": "CC(C)(C)OC(=O)n1ccc(N)n1",
"reactionStepId": "sa_a5250f1bcd0045a3f883f655",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090105214A1;0583;693573\",\"rsmi\":\"CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[nH:8]1[cH:9][cH:10][c:11]([NH2:12])[n:13]1>CCOC(C)=O.CN(C)C=O.O=C(O)O.[HH].[Na+].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[cH:9][cH:10][c:11]([NH2:12])[n:13]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[nH:8]1[cH:9][cH:10][c:11]([NH2:12])[n:13]1>CCOC(C)=O.CN(C)C=O.O=C(O)O.[HH].[Na+].[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[n:8]1[cH:9][cH:10][c:11]([NH2:12])[n:13]1\"}",
"reactionStep": {
"id": "sa_a5250f1bcd0045a3f883f655",
"reactionHash": "a85d11775a7344d7b3b30b4d5babe175074e3192d5b22a3854f6e10263ab7a86"
},
"children": [
{
"id": "11610",
"routeId": "sa_54a9e503606476a760d9a128",
"moleculeId": "sa_b273d4d4546165bca2b249b5",
"parentId": "11609",
"isLeaf": true,
"molecule": {
"id": "sa_b273d4d4546165bca2b249b5",
"inchikey": "DYHSDKLCOJIUFX-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C"
},
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11611",
"routeId": "sa_54a9e503606476a760d9a128",
"moleculeId": "sa_121095baeeed9cf171d90473",
"parentId": "11609",
"isLeaf": true,
"molecule": {
"id": "sa_121095baeeed9cf171d90473",
"inchikey": "JVVRJMXHNUAPHW-UHFFFAOYSA-N",
"smiles": "Nc1cc[nH]n1"
},
"smiles": "Nc1cc[nH]n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
}