Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COC(=O)Nc1cc(NC2CC2)n2ncc(/C=C3\NC(=O)NC3=O)c2n1
InChiKey
MHGYXMSVSFEOPY-WTKPLQERSA-N
Route Signature
9cc678536538199dd63f96bb6405ccbab70f44fbbf02918dd8eb4d17c70c403a
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_c72a6595ffd69c5264945607",
"signature": "9cc678536538199dd63f96bb6405ccbab70f44fbbf02918dd8eb4d17c70c403a",
"contentHash": "d30bdde7bb2aa338e8b46a267bc7d972b94a0a053e191364bad9a67f40968afa",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_4cc7927d9d3e2e6c6ab0e5b1",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00601",
"moleculeId": "sa_4917b5f073f2a8415ed8ca65",
"smiles": "COC(=O)Nc1cc(NC2CC2)n2ncc(/C=C3\\NC(=O)NC3=O)c2n1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_4917b5f073f2a8415ed8ca65",
"inchikey": "MHGYXMSVSFEOPY-WTKPLQERSA-N",
"smiles": "COC(=O)Nc1cc(NC2CC2)n2ncc(/C=C3\\NC(=O)NC3=O)c2n1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "4557",
"routeId": "sa_c72a6595ffd69c5264945607",
"moleculeId": "sa_4917b5f073f2a8415ed8ca65",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_4917b5f073f2a8415ed8ca65",
"inchikey": "MHGYXMSVSFEOPY-WTKPLQERSA-N",
"smiles": "COC(=O)Nc1cc(NC2CC2)n2ncc(/C=C3\\NC(=O)NC3=O)c2n1"
},
"smiles": "COC(=O)Nc1cc(NC2CC2)n2ncc(/C=C3\\NC(=O)NC3=O)c2n1",
"reactionStepId": "sa_982f50a82e369e28ac1e4d3a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110152240A1;0453;1072559\",\"rsmi\":\"O=[CH:10][c:9]1[c:8]2[n:7][c:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[cH:26][c:21]([NH:22][CH:23]3[CH2:24][CH2:25]3)[n:20]2[n:19][cH:18]1.[CH2:11]1[NH:12][C:13](=[O:14])[NH:15][C:16]1=[O:17]>C1CCNCC1.CCO>[CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[n:7][c:8]2[c:9](/[CH:10]=[C:11]3\\\\[NH:12][C:13](=[O:14])[NH:15][C:16]3=[O:17])[cH:18][n:19][n:20]2[c:21]([NH:22][CH:23]2[CH2:24][CH2:25]2)[cH:26]1\"},\"mapped_reaction_smiles\":\"O=[CH:10][c:9]1[c:8]2[n:7][c:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[cH:26][c:21]([NH:22][CH:23]3[CH2:24][CH2:25]3)[n:20]2[n:19][cH:18]1.[CH2:11]1[NH:12][C:13](=[O:14])[NH:15][C:16]1=[O:17]>C1CCNCC1.CCO>[CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[n:7][c:8]2[c:9](/[CH:10]=[C:11]3\\\\[NH:12][C:13](=[O:14])[NH:15][C:16]3=[O:17])[cH:18][n:19][n:20]2[c:21]([NH:22][CH:23]2[CH2:24][CH2:25]2)[cH:26]1\"}",
"reactionStep": {
"id": "sa_982f50a82e369e28ac1e4d3a",
"reactionHash": "3e628960b5b5b02dc9f7e88fab3233fe51a16ac9292fc54c27f6a38b76f1f5f8"
},
"children": [
{
"id": "4558",
"routeId": "sa_c72a6595ffd69c5264945607",
"moleculeId": "sa_eefea854c7a8157e049015e9",
"parentId": "4557",
"isLeaf": false,
"molecule": {
"id": "sa_eefea854c7a8157e049015e9",
"inchikey": "OVSCXQDHQNPFRR-UHFFFAOYSA-N",
"smiles": "COC(=O)Nc1cc(NC2CC2)n2ncc(C=O)c2n1"
},
"smiles": "COC(=O)Nc1cc(NC2CC2)n2ncc(C=O)c2n1",
"reactionStepId": "sa_cfbd5129b2d3f93878fa635d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110152240A1;0451;1072558\",\"rsmi\":\"Cl[C:3]([O:2][CH3:1])=[O:4].[NH2:5][c:6]1[n:7][c:8]2[c:9]([CH:10]=[O:11])[cH:12][n:13][n:14]2[c:15]([NH:16][CH:17]2[CH2:18][CH2:19]2)[cH:20]1>C1CCOC1.CCN(C(C)C)C(C)C>[CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[n:7][c:8]2[c:9]([CH:10]=[O:11])[cH:12][n:13][n:14]2[c:15]([NH:16][CH:17]2[CH2:18][CH2:19]2)[cH:20]1\"},\"mapped_reaction_smiles\":\"Cl[C:3]([O:2][CH3:1])=[O:4].[NH2:5][c:6]1[n:7][c:8]2[c:9]([CH:10]=[O:11])[cH:12][n:13][n:14]2[c:15]([NH:16][CH:17]2[CH2:18][CH2:19]2)[cH:20]1>C1CCOC1.CCN(C(C)C)C(C)C>[CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[n:7][c:8]2[c:9]([CH:10]=[O:11])[cH:12][n:13][n:14]2[c:15]([NH:16][CH:17]2[CH2:18][CH2:19]2)[cH:20]1\"}",
"reactionStep": {
"id": "sa_cfbd5129b2d3f93878fa635d",
"reactionHash": "0704622b5a28c3dab370c78b53b60f43519e68e5abc7f02fda0373887d63e13f"
},
"children": [
{
"id": "4559",
"routeId": "sa_c72a6595ffd69c5264945607",
"moleculeId": "sa_1951b5edec1e6be07ebc3026",
"parentId": "4558",
"isLeaf": false,
"molecule": {
"id": "sa_1951b5edec1e6be07ebc3026",
"inchikey": "DNKCWCSIJWZWCD-UHFFFAOYSA-N",
"smiles": "Nc1cc(NC2CC2)n2ncc(C=O)c2n1"
},
"smiles": "Nc1cc(NC2CC2)n2ncc(C=O)c2n1",
"reactionStepId": "sa_8b5682b4feb9f875af23a0a4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110152240A1;1086;1072682\",\"rsmi\":\"[N-]=[N+]=[N:1][c:2]1[n:3][c:4]2[c:5]([CH:6]=[O:7])[cH:8][n:9][n:10]2[c:11]([NH:12][CH:13]2[CH2:14][CH2:15]2)[cH:16]1>CCO.[Pd]>[NH2:1][c:2]1[n:3][c:4]2[c:5]([CH:6]=[O:7])[cH:8][n:9][n:10]2[c:11]([NH:12][CH:13]2[CH2:14][CH2:15]2)[cH:16]1\"},\"mapped_reaction_smiles\":\"[N-]=[N+]=[N:1][c:2]1[n:3][c:4]2[c:5]([CH:6]=[O:7])[cH:8][n:9][n:10]2[c:11]([NH:12][CH:13]2[CH2:14][CH2:15]2)[cH:16]1>CCO.[Pd]>[NH2:1][c:2]1[n:3][c:4]2[c:5]([CH:6]=[O:7])[cH:8][n:9][n:10]2[c:11]([NH:12][CH:13]2[CH2:14][CH2:15]2)[cH:16]1\"}",
"reactionStep": {
"id": "sa_8b5682b4feb9f875af23a0a4",
"reactionHash": "ed534632416cafc674f39421fc32dc756e62d62f161e915c68487e0da2559e7d"
},
"children": [
{
"id": "4560",
"routeId": "sa_c72a6595ffd69c5264945607",
"moleculeId": "sa_01fd533654531e4b7d15330e",
"parentId": "4559",
"isLeaf": false,
"molecule": {
"id": "sa_01fd533654531e4b7d15330e",
"inchikey": "BHBLUQKXXFKFBB-UHFFFAOYSA-N",
"smiles": "[N-]=[N+]=Nc1cc(NC2CC2)n2ncc(C=O)c2n1"
},
"smiles": "[N-]=[N+]=Nc1cc(NC2CC2)n2ncc(C=O)c2n1",
"reactionStepId": "sa_9250829e62f1f817c75e2fbe",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110152240A1;1084;1072681\",\"rsmi\":\"Cl[c:4]1[n:5][c:6]2[c:7]([CH:8]=[O:9])[cH:10][n:11][n:12]2[c:13]([NH:14][CH:15]2[CH2:16][CH2:17]2)[cH:18]1.[N-:1]=[N+:2]=[N-:3]>CN(C)C=O.O.[Na+]>[N-:1]=[N+:2]=[N:3][c:4]1[n:5][c:6]2[c:7]([CH:8]=[O:9])[cH:10][n:11][n:12]2[c:13]([NH:14][CH:15]2[CH2:16][CH2:17]2)[cH:18]1\"},\"mapped_reaction_smiles\":\"Cl[c:4]1[n:5][c:6]2[c:7]([CH:8]=[O:9])[cH:10][n:11][n:12]2[c:13]([NH:14][CH:15]2[CH2:16][CH2:17]2)[cH:18]1.[N-:1]=[N+:2]=[N-:3]>CN(C)C=O.O.[Na+]>[N-:1]=[N+:2]=[N:3][c:4]1[n:5][c:6]2[c:7]([CH:8]=[O:9])[cH:10][n:11][n:12]2[c:13]([NH:14][CH:15]2[CH2:16][CH2:17]2)[cH:18]1\"}",
"reactionStep": {
"id": "sa_9250829e62f1f817c75e2fbe",
"reactionHash": "d8fa31cb4c8bca031a18efc248b40dd96f78044efdcbabc51ff86f65cf49a8f3"
},
"children": [
{
"id": "4561",
"routeId": "sa_c72a6595ffd69c5264945607",
"moleculeId": "sa_50a8f83dd89c267fbada1205",
"parentId": "4560",
"isLeaf": true,
"molecule": {
"id": "sa_50a8f83dd89c267fbada1205",
"inchikey": "IVRMZWNICZWHMI-UHFFFAOYSA-N",
"smiles": "[N]N=[N-]"
},
"smiles": "[N-]=[N+]=[N-]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4562",
"routeId": "sa_c72a6595ffd69c5264945607",
"moleculeId": "sa_64ef17642cb94fd0e97321dd",
"parentId": "4560",
"isLeaf": false,
"molecule": {
"id": "sa_64ef17642cb94fd0e97321dd",
"inchikey": "YSOZCUCGNNFPOR-UHFFFAOYSA-N",
"smiles": "O=Cc1cnn2c(NC3CC3)cc(Cl)nc12"
},
"smiles": "O=Cc1cnn2c(NC3CC3)cc(Cl)nc12",
"reactionStepId": "sa_07db177dd99a345586886d7e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110152240A1;0421;1072551\",\"rsmi\":\"CN(C)[CH:2]=[O:1].[cH:3]1[c:4]2[n:5][c:6]([Cl:7])[cH:8][c:9]([NH:10][CH:11]3[CH2:12][CH2:13]3)[n:14]2[n:15][cH:16]1>O=P(Cl)(Cl)Cl>[O:1]=[CH:2][c:3]1[c:4]2[n:5][c:6]([Cl:7])[cH:8][c:9]([NH:10][CH:11]3[CH2:12][CH2:13]3)[n:14]2[n:15][cH:16]1\"},\"mapped_reaction_smiles\":\"CN(C)[CH:2]=[O:1].[cH:3]1[c:4]2[n:5][c:6]([Cl:7])[cH:8][c:9]([NH:10][CH:11]3[CH2:12][CH2:13]3)[n:14]2[n:15][cH:16]1>O=P(Cl)(Cl)Cl>[O:1]=[CH:2][c:3]1[c:4]2[n:5][c:6]([Cl:7])[cH:8][c:9]([NH:10][CH:11]3[CH2:12][CH2:13]3)[n:14]2[n:15][cH:16]1\"}",
"reactionStep": {
"id": "sa_07db177dd99a345586886d7e",
"reactionHash": "60a064b32db177156babc28391b3c23a32044af13013b8353fb4a11654a0b10c"
},
"children": [
{
"id": "4563",
"routeId": "sa_c72a6595ffd69c5264945607",
"moleculeId": "sa_3f35342afc93236f338d6c81",
"parentId": "4562",
"isLeaf": false,
"molecule": {
"id": "sa_3f35342afc93236f338d6c81",
"inchikey": "HDGHKFGXIUXTKS-UHFFFAOYSA-N",
"smiles": "Clc1cc(NC2CC2)n2nccc2n1"
},
"smiles": "Clc1cc(NC2CC2)n2nccc2n1",
"reactionStepId": "sa_01c8a56849ab754201ead88c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110152240A1;0419;1072550\",\"rsmi\":\"Cl[c:9]1[n:8]2[c:4]([n:3][c:2]([Cl:1])[cH:14]1)[cH:5][cH:6][n:7]2.[NH2:10][CH:11]1[CH2:12][CH2:13]1>CC#N.CCN(CC)CC>[Cl:1][c:2]1[n:3][c:4]2[cH:5][cH:6][n:7][n:8]2[c:9]([NH:10][CH:11]2[CH2:12][CH2:13]2)[cH:14]1\"},\"mapped_reaction_smiles\":\"Cl[c:9]1[n:8]2[c:4]([n:3][c:2]([Cl:1])[cH:14]1)[cH:5][cH:6][n:7]2.[NH2:10][CH:11]1[CH2:12][CH2:13]1>CC#N.CCN(CC)CC>[Cl:1][c:2]1[n:3][c:4]2[cH:5][cH:6][n:7][n:8]2[c:9]([NH:10][CH:11]2[CH2:12][CH2:13]2)[cH:14]1\"}",
"reactionStep": {
"id": "sa_01c8a56849ab754201ead88c",
"reactionHash": "d68f3efc2eb21760bc14e03990611eb27124ad8d8afb29e5b6071e5ee3592591"
},
"children": [
{
"id": "4564",
"routeId": "sa_c72a6595ffd69c5264945607",
"moleculeId": "sa_f7b02628c6b00fb9d50a0f6c",
"parentId": "4563",
"isLeaf": true,
"molecule": {
"id": "sa_f7b02628c6b00fb9d50a0f6c",
"inchikey": "HTJDQJBWANPRPF-UHFFFAOYSA-N",
"smiles": "NC1CC1"
},
"smiles": "NC1CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4565",
"routeId": "sa_c72a6595ffd69c5264945607",
"moleculeId": "sa_2004fdd4c16c0675a8099bc7",
"parentId": "4563",
"isLeaf": true,
"molecule": {
"id": "sa_2004fdd4c16c0675a8099bc7",
"inchikey": "JMTFWCYVZOFHLR-UHFFFAOYSA-N",
"smiles": "Clc1cc(Cl)n2nccc2n1"
},
"smiles": "Clc1cc(Cl)n2nccc2n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "4566",
"routeId": "sa_c72a6595ffd69c5264945607",
"moleculeId": "sa_e0b5e93d36242e79e81ef68c",
"parentId": "4562",
"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": []
}
]
}
]
}
]
},
{
"id": "4567",
"routeId": "sa_c72a6595ffd69c5264945607",
"moleculeId": "sa_786c6159be77bb31e43bff8a",
"parentId": "4558",
"isLeaf": true,
"molecule": {
"id": "sa_786c6159be77bb31e43bff8a",
"inchikey": "XMJHPCRAQCTCFT-UHFFFAOYSA-N",
"smiles": "COC(=O)Cl"
},
"smiles": "COC(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "4568",
"routeId": "sa_c72a6595ffd69c5264945607",
"moleculeId": "sa_d79006b2e02b7a3149ef3435",
"parentId": "4557",
"isLeaf": true,
"molecule": {
"id": "sa_d79006b2e02b7a3149ef3435",
"inchikey": "WJRBRSLFGCUECM-UHFFFAOYSA-N",
"smiles": "O=C1CNC(=O)N1"
},
"smiles": "O=C1CNC(=O)N1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}