Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=C(CCCc1c[nH]nn1)NC1CCN(C(=O)OCc2cc(Cl)cc(Cl)c2)CC1
InChiKey
GAMSNABJTRSYDT-UHFFFAOYSA-N
Route Signature
d500d18620b67b454607bf096a3c6355336101c437a00abdd77bf09f3629dc96
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_68b4592b60822171b63567f9",
"signature": "d500d18620b67b454607bf096a3c6355336101c437a00abdd77bf09f3629dc96",
"contentHash": "c1d9b8f9baab8c3f97a3391eaa8f1fa3a60feec0d5d6f9248b1aa3c80b8e5b79",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_1157ce4fe5ca39ff513bde11",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00862",
"moleculeId": "sa_3092221379a688b1d0f434ba",
"smiles": "O=C(CCCc1c[nH]nn1)NC1CCN(C(=O)OCc2cc(Cl)cc(Cl)c2)CC1",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_3092221379a688b1d0f434ba",
"inchikey": "GAMSNABJTRSYDT-UHFFFAOYSA-N",
"smiles": "O=C(CCCc1c[nH]nn1)NC1CCN(C(=O)OCc2cc(Cl)cc(Cl)c2)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9779",
"routeId": "sa_68b4592b60822171b63567f9",
"moleculeId": "sa_3092221379a688b1d0f434ba",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_3092221379a688b1d0f434ba",
"inchikey": "GAMSNABJTRSYDT-UHFFFAOYSA-N",
"smiles": "O=C(CCCc1c[nH]nn1)NC1CCN(C(=O)OCc2cc(Cl)cc(Cl)c2)CC1"
},
"smiles": "O=C(CCCc1c[nH]nn1)NC1CCN(C(=O)OCc2cc(Cl)cc(Cl)c2)CC1",
"reactionStepId": "sa_9b5adc9930c5172265bc454a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140171403A1;0696;1538836\",\"rsmi\":\"O[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][c:6]1[cH:7][nH:8][n:9][n:10]1.[NH2:11][CH:12]1[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][CH2:19][c:20]2[cH:21][c:22]([Cl:23])[cH:24][c:25]([Cl:26])[cH:27]2)[CH2:28][CH2:29]1>CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1.CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C=O.Cl>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][c:6]1[cH:7][nH:8][n:9][n:10]1)[NH:11][CH:12]1[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][CH2:19][c:20]2[cH:21][c:22]([Cl:23])[cH:24][c:25]([Cl:26])[cH:27]2)[CH2:28][CH2:29]1\"},\"mapped_reaction_smiles\":\"O[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][c:6]1[cH:7][nH:8][n:9][n:10]1.[NH2:11][CH:12]1[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][CH2:19][c:20]2[cH:21][c:22]([Cl:23])[cH:24][c:25]([Cl:26])[cH:27]2)[CH2:28][CH2:29]1>CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1.CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C=O.Cl>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][c:6]1[cH:7][nH:8][n:9][n:10]1)[NH:11][CH:12]1[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][CH2:19][c:20]2[cH:21][c:22]([Cl:23])[cH:24][c:25]([Cl:26])[cH:27]2)[CH2:28][CH2:29]1\"}",
"reactionStep": {
"id": "sa_9b5adc9930c5172265bc454a",
"reactionHash": "d85006d5c3901f51fa1b821a2359ad9bf6a15528ca8c218a5a528570dd5d9e3e"
},
"children": [
{
"id": "9780",
"routeId": "sa_68b4592b60822171b63567f9",
"moleculeId": "sa_d34ec7987c8478d3335d3574",
"parentId": "9779",
"isLeaf": false,
"molecule": {
"id": "sa_d34ec7987c8478d3335d3574",
"inchikey": "JJYUJRZNPOGWAM-UHFFFAOYSA-N",
"smiles": "O=C(O)CCCc1cnn[nH]1"
},
"smiles": "O=C(O)CCCc1c[nH]nn1",
"reactionStepId": "sa_1aaf54ee506a86ee97e563e5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140171403A1;0694;1538835\",\"rsmi\":\"c1ccc(C[n:9]2[cH:8][c:7]([CH2:6][CH2:5][CH2:4][C:2](=[O:1])[OH:3])[n:11][n:10]2)cc1>CCO.[Pd]>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][c:7]1[cH:8][nH:9][n:10][n:11]1\"},\"mapped_reaction_smiles\":\"c1ccc(C[n:9]2[cH:8][c:7]([CH2:6][CH2:5][CH2:4][C:2](=[O:1])[OH:3])[n:11][n:10]2)cc1>CCO.[Pd]>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][c:7]1[cH:8][nH:9][n:10][n:11]1\"}",
"reactionStep": {
"id": "sa_1aaf54ee506a86ee97e563e5",
"reactionHash": "97e494d81e02089dc533261da20a4fe081f7316554ef44dacebf9aafdad53c86"
},
"children": [
{
"id": "9781",
"routeId": "sa_68b4592b60822171b63567f9",
"moleculeId": "sa_65a81f82d21ebd227c2d7418",
"parentId": "9780",
"isLeaf": false,
"molecule": {
"id": "sa_65a81f82d21ebd227c2d7418",
"inchikey": "OAWCYVBOWRJWMA-UHFFFAOYSA-N",
"smiles": "O=C(O)CCCc1cn(Cc2ccccc2)nn1"
},
"smiles": "O=C(O)CCCc1cn(Cc2ccccc2)nn1",
"reactionStepId": "sa_2a53e80dad1f8ace3f5de1f3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140171403A1;0692;1538834\",\"rsmi\":\"[N:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)=[N+:17]=[N-:18].[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][C:7]#[CH:8]>CC(=O)O.CC(=O)O.CC(C)(C)O.CCOC(C)=O.O.O=C1O[C@H]([C@@H](O)CO)C(O)=C1O.Cl.[Cu+2].[Na+].[Na+]>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][c:7]1[cH:8][n:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[n:17][n:18]1\"},\"mapped_reaction_smiles\":\"[N:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)=[N+:17]=[N-:18].[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][C:7]#[CH:8]>CC(=O)O.CC(=O)O.CC(C)(C)O.CCOC(C)=O.O.O=C1O[C@H]([C@@H](O)CO)C(O)=C1O.Cl.[Cu+2].[Na+].[Na+]>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][c:7]1[cH:8][n:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[n:17][n:18]1\"}",
"reactionStep": {
"id": "sa_2a53e80dad1f8ace3f5de1f3",
"reactionHash": "45ed044d5ca031591c8c2967bb44200f6c76a2a311d1bc99198c1792b45419e2"
},
"children": [
{
"id": "9782",
"routeId": "sa_68b4592b60822171b63567f9",
"moleculeId": "sa_70759a5dcc37815c2e14581f",
"parentId": "9781",
"isLeaf": true,
"molecule": {
"id": "sa_70759a5dcc37815c2e14581f",
"inchikey": "UDLLFLQFQMACJB-UHFFFAOYSA-N",
"smiles": "[N-]=[N+]=NCc1ccccc1"
},
"smiles": "[N-]=[N+]=NCc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9783",
"routeId": "sa_68b4592b60822171b63567f9",
"moleculeId": "sa_121d9ad731349d9313a0bd1b",
"parentId": "9781",
"isLeaf": true,
"molecule": {
"id": "sa_121d9ad731349d9313a0bd1b",
"inchikey": "VPFMEXRVUOPYRG-UHFFFAOYSA-N",
"smiles": "C#CCCCC(=O)O"
},
"smiles": "C#CCCCC(=O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "9784",
"routeId": "sa_68b4592b60822171b63567f9",
"moleculeId": "sa_1e9d03bc1e30f547de674547",
"parentId": "9779",
"isLeaf": false,
"molecule": {
"id": "sa_1e9d03bc1e30f547de674547",
"inchikey": "XCROTBMOUYYYIP-UHFFFAOYSA-N",
"smiles": "NC1CCN(C(=O)OCc2cc(Cl)cc(Cl)c2)CC1"
},
"smiles": "NC1CCN(C(=O)OCc2cc(Cl)cc(Cl)c2)CC1",
"reactionStepId": "sa_4de19c8b729659162eb16551",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140171403A1;0641;1538818\",\"rsmi\":\"CC(C)(C)OC(=O)[NH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][c:12]([Cl:13])[cH:14][c:15]([Cl:16])[cH:17]2)[CH2:18][CH2:19]1>C1COCCO1.Cl.ClCCl>[NH2:1][CH:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][c:12]([Cl:13])[cH:14][c:15]([Cl:16])[cH:17]2)[CH2:18][CH2:19]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[NH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][c:12]([Cl:13])[cH:14][c:15]([Cl:16])[cH:17]2)[CH2:18][CH2:19]1>C1COCCO1.Cl.ClCCl>[NH2:1][CH:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][c:12]([Cl:13])[cH:14][c:15]([Cl:16])[cH:17]2)[CH2:18][CH2:19]1\"}",
"reactionStep": {
"id": "sa_4de19c8b729659162eb16551",
"reactionHash": "81acce717ade9438bcfaa049fcd5c6bc206615bc8ff197989327656b4302ee8a"
},
"children": [
{
"id": "9785",
"routeId": "sa_68b4592b60822171b63567f9",
"moleculeId": "sa_00146bd1d9da7491c141ef1d",
"parentId": "9784",
"isLeaf": false,
"molecule": {
"id": "sa_00146bd1d9da7491c141ef1d",
"inchikey": "JLJCYMNNCJEAGG-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)NC1CCN(C(=O)OCc2cc(Cl)cc(Cl)c2)CC1"
},
"smiles": "CC(C)(C)OC(=O)NC1CCN(C(=O)OCc2cc(Cl)cc(Cl)c2)CC1",
"reactionStepId": "sa_10a87588e01ae5c44830ad11",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140171403A1;0639;1538817\",\"rsmi\":\"CN(C)[CH:13]=[O:14].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][NH:12][CH2:25][CH2:26]1.[OH:15][CH2:16][c:17]1[cH:18][c:19]([Cl:20])[cH:21][c:22]([Cl:23])[cH:24]1>O=C(n1ccnc1)n1ccnc1>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][CH2:16][c:17]2[cH:18][c:19]([Cl:20])[cH:21][c:22]([Cl:23])[cH:24]2)[CH2:25][CH2:26]1\"},\"mapped_reaction_smiles\":\"CN(C)[CH:13]=[O:14].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][NH:12][CH2:25][CH2:26]1.[OH:15][CH2:16][c:17]1[cH:18][c:19]([Cl:20])[cH:21][c:22]([Cl:23])[cH:24]1>O=C(n1ccnc1)n1ccnc1>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][CH2:16][c:17]2[cH:18][c:19]([Cl:20])[cH:21][c:22]([Cl:23])[cH:24]2)[CH2:25][CH2:26]1\"}",
"reactionStep": {
"id": "sa_10a87588e01ae5c44830ad11",
"reactionHash": "2a740f08c78d4e39c0e9413b02ae56b900c20c595d19976d9de6db9dd62c639a"
},
"children": [
{
"id": "9786",
"routeId": "sa_68b4592b60822171b63567f9",
"moleculeId": "sa_ad1bf3178408345827eeb74f",
"parentId": "9785",
"isLeaf": true,
"molecule": {
"id": "sa_ad1bf3178408345827eeb74f",
"inchikey": "CKXZPVPIDOJLLM-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(O)=NC1CCNCC1"
},
"smiles": "CC(C)(C)OC(=O)NC1CCNCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9787",
"routeId": "sa_68b4592b60822171b63567f9",
"moleculeId": "sa_226befd3f20e33ba8858ec30",
"parentId": "9785",
"isLeaf": true,
"molecule": {
"id": "sa_226befd3f20e33ba8858ec30",
"inchikey": "VSNNLLQKDRCKCB-UHFFFAOYSA-N",
"smiles": "OCc1cc(Cl)cc(Cl)c1"
},
"smiles": "OCc1cc(Cl)cc(Cl)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9788",
"routeId": "sa_68b4592b60822171b63567f9",
"moleculeId": "sa_e0b5e93d36242e79e81ef68c",
"parentId": "9785",
"isLeaf": true,
"molecule": {
"id": "sa_e0b5e93d36242e79e81ef68c",
"inchikey": "ZMXDDKWLCZADIW-UHFFFAOYSA-N",
"smiles": "CN(C)C=O"
},
"smiles": "CN(C)C=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
}