Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=C(COc1cccnc1)N1CCc2cc(NS(=O)(=O)C3CCN(C4COC4)CC3)ccc2C1
InChiKey
GPYPJEKBDVMLSW-UHFFFAOYSA-N
Route Signature
8e958cb5b6059aa9309f958f86a823208c3c53ff0ebf4e8eb0aadcbc9bd7986a
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_e91d0afba48f235ba2d8ad32",
"signature": "8e958cb5b6059aa9309f958f86a823208c3c53ff0ebf4e8eb0aadcbc9bd7986a",
"contentHash": "4a845a155e61a61024153fdc606175b280855b2b4a5e257338b16e3092fda451",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_321346f452e9d5912d365431",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-01636",
"moleculeId": "sa_5eaf4407977760fa0f985cbc",
"smiles": "O=C(COc1cccnc1)N1CCc2cc(NS(=O)(=O)C3CCN(C4COC4)CC3)ccc2C1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_5eaf4407977760fa0f985cbc",
"inchikey": "GPYPJEKBDVMLSW-UHFFFAOYSA-N",
"smiles": "O=C(COc1cccnc1)N1CCc2cc(NS(=O)(=O)C3CCN(C4COC4)CC3)ccc2C1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "5897",
"routeId": "sa_e91d0afba48f235ba2d8ad32",
"moleculeId": "sa_5eaf4407977760fa0f985cbc",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_5eaf4407977760fa0f985cbc",
"inchikey": "GPYPJEKBDVMLSW-UHFFFAOYSA-N",
"smiles": "O=C(COc1cccnc1)N1CCc2cc(NS(=O)(=O)C3CCN(C4COC4)CC3)ccc2C1"
},
"smiles": "O=C(COc1cccnc1)N1CCc2cc(NS(=O)(=O)C3CCN(C4COC4)CC3)ccc2C1",
"reactionStepId": "sa_5ecd63f506343a1c0cbe657d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160229835A1;0116;1918339\",\"rsmi\":\"O=[C:25]1[CH2:26][O:27][CH2:28]1.[O:1]=[C:2]([CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1)[N:11]1[CH2:12][CH2:13][c:14]2[cH:15][c:16]([NH:17][S:18](=[O:19])(=[O:20])[CH:21]3[CH2:22][CH2:23][NH:24][CH2:29][CH2:30]3)[cH:31][cH:32][c:33]2[CH2:34]1>CC(=O)OB(OC(C)=O)OC(C)=O.ClCCl.[Na+]>[O:1]=[C:2]([CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1)[N:11]1[CH2:12][CH2:13][c:14]2[cH:15][c:16]([NH:17][S:18](=[O:19])(=[O:20])[CH:21]3[CH2:22][CH2:23][N:24]([CH:25]4[CH2:26][O:27][CH2:28]4)[CH2:29][CH2:30]3)[cH:31][cH:32][c:33]2[CH2:34]1\"},\"mapped_reaction_smiles\":\"O=[C:25]1[CH2:26][O:27][CH2:28]1.[O:1]=[C:2]([CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1)[N:11]1[CH2:12][CH2:13][c:14]2[cH:15][c:16]([NH:17][S:18](=[O:19])(=[O:20])[CH:21]3[CH2:22][CH2:23][NH:24][CH2:29][CH2:30]3)[cH:31][cH:32][c:33]2[CH2:34]1>CC(=O)OB(OC(C)=O)OC(C)=O.ClCCl.[Na+]>[O:1]=[C:2]([CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1)[N:11]1[CH2:12][CH2:13][c:14]2[cH:15][c:16]([NH:17][S:18](=[O:19])(=[O:20])[CH:21]3[CH2:22][CH2:23][N:24]([CH:25]4[CH2:26][O:27][CH2:28]4)[CH2:29][CH2:30]3)[cH:31][cH:32][c:33]2[CH2:34]1\"}",
"reactionStep": {
"id": "sa_5ecd63f506343a1c0cbe657d",
"reactionHash": "f9e39f732cfeecb473a1ec3973fe3232158b4c90af20ad9053146179e0f70f19"
},
"children": [
{
"id": "5898",
"routeId": "sa_e91d0afba48f235ba2d8ad32",
"moleculeId": "sa_45ce2bd3a7699635775e615a",
"parentId": "5897",
"isLeaf": false,
"molecule": {
"id": "sa_45ce2bd3a7699635775e615a",
"inchikey": "KHGDZTKVYOZBDN-UHFFFAOYSA-N",
"smiles": "O=C(COc1cccnc1)N1CCc2cc(NS(=O)(=O)C3CCNCC3)ccc2C1"
},
"smiles": "O=C(COc1cccnc1)N1CCc2cc(NS(=O)(=O)C3CCNCC3)ccc2C1",
"reactionStepId": "sa_9c96864d9edf46f4487677ce",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160229835A1;0079;1918323\",\"rsmi\":\"CC(C)(C)OC(=O)[N:24]1[CH2:23][CH2:22][CH:21]([S:18]([NH:17][c:16]2[cH:15][c:14]3[c:29]([cH:28][cH:27]2)[CH2:30][N:11]([C:2](=[O:1])[CH2:3][O:4][c:5]2[cH:6][cH:7][cH:8][n:9][cH:10]2)[CH2:12][CH2:13]3)(=[O:19])=[O:20])[CH2:26][CH2:25]1>Cl.ClCCl>[O:1]=[C:2]([CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1)[N:11]1[CH2:12][CH2:13][c:14]2[cH:15][c:16]([NH:17][S:18](=[O:19])(=[O:20])[CH:21]3[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]3)[cH:27][cH:28][c:29]2[CH2:30]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:24]1[CH2:23][CH2:22][CH:21]([S:18]([NH:17][c:16]2[cH:15][c:14]3[c:29]([cH:28][cH:27]2)[CH2:30][N:11]([C:2](=[O:1])[CH2:3][O:4][c:5]2[cH:6][cH:7][cH:8][n:9][cH:10]2)[CH2:12][CH2:13]3)(=[O:19])=[O:20])[CH2:26][CH2:25]1>Cl.ClCCl>[O:1]=[C:2]([CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1)[N:11]1[CH2:12][CH2:13][c:14]2[cH:15][c:16]([NH:17][S:18](=[O:19])(=[O:20])[CH:21]3[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]3)[cH:27][cH:28][c:29]2[CH2:30]1\"}",
"reactionStep": {
"id": "sa_9c96864d9edf46f4487677ce",
"reactionHash": "82caf3b3b741086645fa666b863fc263bd2904fac94028846674439096384ef5"
},
"children": [
{
"id": "5899",
"routeId": "sa_e91d0afba48f235ba2d8ad32",
"moleculeId": "sa_b95054a20272f3e4678891ff",
"parentId": "5898",
"isLeaf": false,
"molecule": {
"id": "sa_b95054a20272f3e4678891ff",
"inchikey": "DZYVQACAFTYBPW-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(S(=O)(=O)Nc2ccc3c(c2)CCN(C(=O)COc2cccnc2)C3)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(S(=O)(=O)Nc2ccc3c(c2)CCN(C(=O)COc2cccnc2)C3)CC1",
"reactionStepId": "sa_6d3ca78ef57186deeb610875",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160229835A1;0077;1918322\",\"rsmi\":\"Cl[S:12]([CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:37][CH2:36]1)(=[O:13])=[O:14].[NH2:15][c:16]1[cH:17][cH:18][c:19]2[c:34]([cH:35]1)[CH2:33][CH2:32][N:21]([C:22](=[O:23])[CH2:24][O:25][c:26]1[cH:27][cH:28][cH:29][n:30][cH:31]1)[CH2:20]2>CCN(CC)CC.ClCCl>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([S:12](=[O:13])(=[O:14])[NH:15][c:16]2[cH:17][cH:18][c:19]3[c:34]([cH:35]2)[CH2:33][CH2:32][N:21]([C:22](=[O:23])[CH2:24][O:25][c:26]2[cH:27][cH:28][cH:29][n:30][cH:31]2)[CH2:20]3)[CH2:36][CH2:37]1\"},\"mapped_reaction_smiles\":\"Cl[S:12]([CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:37][CH2:36]1)(=[O:13])=[O:14].[NH2:15][c:16]1[cH:17][cH:18][c:19]2[c:34]([cH:35]1)[CH2:33][CH2:32][N:21]([C:22](=[O:23])[CH2:24][O:25][c:26]1[cH:27][cH:28][cH:29][n:30][cH:31]1)[CH2:20]2>CCN(CC)CC.ClCCl>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([S:12](=[O:13])(=[O:14])[NH:15][c:16]2[cH:17][cH:18][c:19]3[c:34]([cH:35]2)[CH2:33][CH2:32][N:21]([C:22](=[O:23])[CH2:24][O:25][c:26]2[cH:27][cH:28][cH:29][n:30][cH:31]2)[CH2:20]3)[CH2:36][CH2:37]1\"}",
"reactionStep": {
"id": "sa_6d3ca78ef57186deeb610875",
"reactionHash": "ca73df0f2532e6000b31b513be0a515393229b22bafde071ed5f17d215fd4956"
},
"children": [
{
"id": "5900",
"routeId": "sa_e91d0afba48f235ba2d8ad32",
"moleculeId": "sa_3a2279cc186395761ead4539",
"parentId": "5899",
"isLeaf": false,
"molecule": {
"id": "sa_3a2279cc186395761ead4539",
"inchikey": "BQNNQZJGOJXRPU-UHFFFAOYSA-N",
"smiles": "Nc1ccc2c(c1)CCN(C(=O)COc1cccnc1)C2"
},
"smiles": "Nc1ccc2c(c1)CCN(C(=O)COc1cccnc1)C2",
"reactionStepId": "sa_98fe0a2de571029d8cc29dea",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160229835A1;0075;1918321\",\"rsmi\":\"O[C:8](=[O:9])[CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][n:16][cH:17]1.[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:20]([cH:21]1)[CH2:19][CH2:18][NH:7][CH2:6]2>CN(C)C=O.O=C(n1ccnc1)n1ccnc1>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:20]([cH:21]1)[CH2:19][CH2:18][N:7]([C:8](=[O:9])[CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][n:16][cH:17]1)[CH2:6]2\"},\"mapped_reaction_smiles\":\"O[C:8](=[O:9])[CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][n:16][cH:17]1.[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:20]([cH:21]1)[CH2:19][CH2:18][NH:7][CH2:6]2>CN(C)C=O.O=C(n1ccnc1)n1ccnc1>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:20]([cH:21]1)[CH2:19][CH2:18][N:7]([C:8](=[O:9])[CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][n:16][cH:17]1)[CH2:6]2\"}",
"reactionStep": {
"id": "sa_98fe0a2de571029d8cc29dea",
"reactionHash": "0bc730a57333f489ae909b71b4b38a32adf6d8394cafebea9bca118a265eec41"
},
"children": [
{
"id": "5901",
"routeId": "sa_e91d0afba48f235ba2d8ad32",
"moleculeId": "sa_56fd9c569e177d153e12d40c",
"parentId": "5900",
"isLeaf": true,
"molecule": {
"id": "sa_56fd9c569e177d153e12d40c",
"inchikey": "MBEPWLCDXKKANL-UHFFFAOYSA-N",
"smiles": "O=C(O)COc1cccnc1"
},
"smiles": "O=C(O)COc1cccnc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5902",
"routeId": "sa_e91d0afba48f235ba2d8ad32",
"moleculeId": "sa_f0cd80620ebef56174cd07ff",
"parentId": "5900",
"isLeaf": false,
"molecule": {
"id": "sa_f0cd80620ebef56174cd07ff",
"inchikey": "SAAFIVJVSQVSSW-UHFFFAOYSA-N",
"smiles": "Nc1ccc2c(c1)CCNC2"
},
"smiles": "Nc1ccc2c(c1)CCNC2",
"reactionStepId": "sa_2eb03fce8220fcb476c91ec1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160229835A1;0073;1918320\",\"rsmi\":\"CC(C)(C)OC(=O)[N:7]1[CH2:6][c:5]2[cH:4][cH:3][c:2]([NH2:1])[cH:11][c:10]2[CH2:9][CH2:8]1>Cl.ClCCl>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:10]([cH:11]1)[CH2:9][CH2:8][NH:7][CH2:6]2\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:7]1[CH2:6][c:5]2[cH:4][cH:3][c:2]([NH2:1])[cH:11][c:10]2[CH2:9][CH2:8]1>Cl.ClCCl>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:10]([cH:11]1)[CH2:9][CH2:8][NH:7][CH2:6]2\"}",
"reactionStep": {
"id": "sa_2eb03fce8220fcb476c91ec1",
"reactionHash": "30b790453420bd9bcd3eb6dea01c6e89fabbd78661791a2fe1f51e37929a7966"
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"children": [
{
"id": "5903",
"routeId": "sa_e91d0afba48f235ba2d8ad32",
"moleculeId": "sa_ca969c13ea0eb44ff5ac5c8d",
"parentId": "5902",
"isLeaf": true,
"molecule": {
"id": "sa_ca969c13ea0eb44ff5ac5c8d",
"inchikey": "OLOIFCYZWOTWRO-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCc2cc(N)ccc2C1"
},
"smiles": "CC(C)(C)OC(=O)N1CCc2cc(N)ccc2C1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "5904",
"routeId": "sa_e91d0afba48f235ba2d8ad32",
"moleculeId": "sa_95f5ce9c3d7c9c91ccda03b0",
"parentId": "5899",
"isLeaf": true,
"molecule": {
"id": "sa_95f5ce9c3d7c9c91ccda03b0",
"inchikey": "VJAHMDQRVLEOFG-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(S(=O)(=O)Cl)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(S(=O)(=O)Cl)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
},
{
"id": "5905",
"routeId": "sa_e91d0afba48f235ba2d8ad32",
"moleculeId": "sa_ddfaebc0215df9379436d904",
"parentId": "5897",
"isLeaf": true,
"molecule": {
"id": "sa_ddfaebc0215df9379436d904",
"inchikey": "ROADCYAOHVSOLQ-UHFFFAOYSA-N",
"smiles": "O=C1COC1"
},
"smiles": "O=C1COC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}