Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=c1[nH]c2cc(Cl)c(Cl)cc2n1CCCN1CCN(C(c2ccccc2)c2ccccc2)CC1
InChiKey
PARKUCOPVUPEMZ-UHFFFAOYSA-N
Route Signature
a15dab109220be07850d5adde7b34b85e4b37d23b1bee8cc2a90832a8904fd82
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_a1b2eb80c9a8f1262d2b98bd",
"signature": "a15dab109220be07850d5adde7b34b85e4b37d23b1bee8cc2a90832a8904fd82",
"contentHash": "75ecdbbd27231ebc71f64a59ae752d3f72e16b1a2adf9784ec113d0807467b16",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_62729ab30a2c2a5cc2e7a21b",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-01055",
"moleculeId": "sa_64838f779335a0cdb7d6c4f0",
"smiles": "O=c1[nH]c2cc(Cl)c(Cl)cc2n1CCCN1CCN(C(c2ccccc2)c2ccccc2)CC1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_64838f779335a0cdb7d6c4f0",
"inchikey": "PARKUCOPVUPEMZ-UHFFFAOYSA-N",
"smiles": "O=c1[nH]c2cc(Cl)c(Cl)cc2n1CCCN1CCN(C(c2ccccc2)c2ccccc2)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "5244",
"routeId": "sa_a1b2eb80c9a8f1262d2b98bd",
"moleculeId": "sa_64838f779335a0cdb7d6c4f0",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_64838f779335a0cdb7d6c4f0",
"inchikey": "PARKUCOPVUPEMZ-UHFFFAOYSA-N",
"smiles": "O=c1[nH]c2cc(Cl)c(Cl)cc2n1CCCN1CCN(C(c2ccccc2)c2ccccc2)CC1"
},
"smiles": "O=c1[nH]c2cc(Cl)c(Cl)cc2n1CCCN1CCN(C(c2ccccc2)c2ccccc2)CC1",
"reactionStepId": "sa_06c7641b139e8b806ce37322",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US04200641;;66549\",\"rsmi\":\"N[C:2](N)=[O:1].[NH2:3][c:4]1[c:5]([NH:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][N:19]([CH:20]([c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[c:27]3[cH:28][cH:29][cH:30][cH:31][cH:32]3)[CH2:33][CH2:34]2)[cH:6][c:7]([Cl:8])[c:9]([Cl:10])[cH:11]1>ClC(Cl)Cl.O>[O:1]=[c:2]1[nH:3][c:4]2[c:5]([cH:6][c:7]([Cl:8])[c:9]([Cl:10])[cH:11]2)[n:12]1[CH2:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][N:19]([CH:20]([c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[CH2:33][CH2:34]1\"},\"mapped_reaction_smiles\":\"N[C:2](N)=[O:1].[NH2:3][c:4]1[c:5]([NH:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][N:19]([CH:20]([c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[c:27]3[cH:28][cH:29][cH:30][cH:31][cH:32]3)[CH2:33][CH2:34]2)[cH:6][c:7]([Cl:8])[c:9]([Cl:10])[cH:11]1>ClC(Cl)Cl.O>[O:1]=[c:2]1[nH:3][c:4]2[c:5]([cH:6][c:7]([Cl:8])[c:9]([Cl:10])[cH:11]2)[n:12]1[CH2:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][N:19]([CH:20]([c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[CH2:33][CH2:34]1\"}",
"reactionStep": {
"id": "sa_06c7641b139e8b806ce37322",
"reactionHash": "c846cb0f331f183233b92936611444293762da4039b74e557608694e0d3726b4"
},
"children": [
{
"id": "5245",
"routeId": "sa_a1b2eb80c9a8f1262d2b98bd",
"moleculeId": "sa_ef08c3bbaa6515e445564c15",
"parentId": "5244",
"isLeaf": false,
"molecule": {
"id": "sa_ef08c3bbaa6515e445564c15",
"inchikey": "DCWINZULDVVUSH-UHFFFAOYSA-N",
"smiles": "Nc1cc(Cl)c(Cl)cc1NCCCN1CCN(C(c2ccccc2)c2ccccc2)CC1"
},
"smiles": "Nc1cc(Cl)c(Cl)cc1NCCCN1CCN(C(c2ccccc2)c2ccccc2)CC1",
"reactionStepId": "sa_13a6cb662d2115c03904793d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US04200641;;66505\",\"rsmi\":\"O=[N+:1]([O-])[c:2]1[cH:3][c:4]([Cl:5])[c:6]([Cl:7])[cH:8][c:9]1[NH:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][N:17]([CH:18]([c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[CH2:31][CH2:32]1>CO.[H][H].[Ni]>[NH2:1][c:2]1[cH:3][c:4]([Cl:5])[c:6]([Cl:7])[cH:8][c:9]1[NH:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][N:17]([CH:18]([c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[CH2:31][CH2:32]1\"},\"mapped_reaction_smiles\":\"O=[N+:1]([O-])[c:2]1[cH:3][c:4]([Cl:5])[c:6]([Cl:7])[cH:8][c:9]1[NH:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][N:17]([CH:18]([c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[CH2:31][CH2:32]1>CO.[H][H].[Ni]>[NH2:1][c:2]1[cH:3][c:4]([Cl:5])[c:6]([Cl:7])[cH:8][c:9]1[NH:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][N:17]([CH:18]([c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[CH2:31][CH2:32]1\"}",
"reactionStep": {
"id": "sa_13a6cb662d2115c03904793d",
"reactionHash": "ea1d272b50433e0518db3f374eff2d0324553cea3df732fe5ed6f9a737d8b0b6"
},
"children": [
{
"id": "5246",
"routeId": "sa_a1b2eb80c9a8f1262d2b98bd",
"moleculeId": "sa_6a1498c7c04d5db90072fde5",
"parentId": "5245",
"isLeaf": false,
"molecule": {
"id": "sa_6a1498c7c04d5db90072fde5",
"inchikey": "VZVZOOZEOZJTTE-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cc(Cl)c(Cl)cc1NCCCN1CCN(C(c2ccccc2)c2ccccc2)CC1"
},
"smiles": "O=[N+]([O-])c1cc(Cl)c(Cl)cc1NCCCN1CCN(C(c2ccccc2)c2ccccc2)CC1",
"reactionStepId": "sa_0961eabaf99373b36f7379a9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US04200641;;66504\",\"rsmi\":\"Cl[CH2:9][CH2:8][CH2:7][NH:6][c:5]1[c:4]([N+:2](=[O:1])[O-:3])[cH:34][c:32]([Cl:33])[c:30]([Cl:31])[cH:29]1.[NH:10]1[CH2:11][CH2:12][N:13]([CH:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH2:27][CH2:28]1>CC(=O)CC(C)C.O.O=C(O)O.I.[K+].[Na+].[Na+]>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([NH:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][N:13]([CH:14]([c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][c:30]([Cl:31])[c:32]([Cl:33])[cH:34]1\"},\"mapped_reaction_smiles\":\"Cl[CH2:9][CH2:8][CH2:7][NH:6][c:5]1[c:4]([N+:2](=[O:1])[O-:3])[cH:34][c:32]([Cl:33])[c:30]([Cl:31])[cH:29]1.[NH:10]1[CH2:11][CH2:12][N:13]([CH:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[CH2:27][CH2:28]1>CC(=O)CC(C)C.O.O=C(O)O.I.[K+].[Na+].[Na+]>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([NH:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][N:13]([CH:14]([c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[CH2:27][CH2:28]2)[cH:29][c:30]([Cl:31])[c:32]([Cl:33])[cH:34]1\"}",
"reactionStep": {
"id": "sa_0961eabaf99373b36f7379a9",
"reactionHash": "77f1781a84c73f61af28d87079dfdc81774334f646deddc3f7e245d6afffd576"
},
"children": [
{
"id": "5247",
"routeId": "sa_a1b2eb80c9a8f1262d2b98bd",
"moleculeId": "sa_7041f0796b3d21a49a6d2bbb",
"parentId": "5246",
"isLeaf": true,
"molecule": {
"id": "sa_7041f0796b3d21a49a6d2bbb",
"inchikey": "NWVNXDKZIQLBNM-UHFFFAOYSA-N",
"smiles": "c1ccc(C(c2ccccc2)N2CCNCC2)cc1"
},
"smiles": "c1ccc(C(c2ccccc2)N2CCNCC2)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5248",
"routeId": "sa_a1b2eb80c9a8f1262d2b98bd",
"moleculeId": "sa_6cd0bd1a95d0b25bb262abf9",
"parentId": "5246",
"isLeaf": false,
"molecule": {
"id": "sa_6cd0bd1a95d0b25bb262abf9",
"inchikey": "OEIUPGGSXIKZBB-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cc(Cl)c(Cl)cc1NCCCCl"
},
"smiles": "O=[N+]([O-])c1cc(Cl)c(Cl)cc1NCCCCl",
"reactionStepId": "sa_15592c349e47d08cbbb7d9d2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US04200641;;66503\",\"rsmi\":\"ClC(Cl)[Cl:10].O[CH2:9][CH2:8][CH2:7][NH:6][c:5]1[c:4]([N+:2](=[O:1])[O-:3])[cH:16][c:14]([Cl:15])[c:12]([Cl:13])[cH:11]1>O=S(Cl)Cl>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([NH:6][CH2:7][CH2:8][CH2:9][Cl:10])[cH:11][c:12]([Cl:13])[c:14]([Cl:15])[cH:16]1\"},\"mapped_reaction_smiles\":\"ClC(Cl)[Cl:10].O[CH2:9][CH2:8][CH2:7][NH:6][c:5]1[c:4]([N+:2](=[O:1])[O-:3])[cH:16][c:14]([Cl:15])[c:12]([Cl:13])[cH:11]1>O=S(Cl)Cl>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([NH:6][CH2:7][CH2:8][CH2:9][Cl:10])[cH:11][c:12]([Cl:13])[c:14]([Cl:15])[cH:16]1\"}",
"reactionStep": {
"id": "sa_15592c349e47d08cbbb7d9d2",
"reactionHash": "c411bba376ffa28245975920fbd25ae2d76d7899dc8284d5a461001492432356"
},
"children": [
{
"id": "5249",
"routeId": "sa_a1b2eb80c9a8f1262d2b98bd",
"moleculeId": "sa_dc22e7a2b152e64af529fbf5",
"parentId": "5248",
"isLeaf": true,
"molecule": {
"id": "sa_dc22e7a2b152e64af529fbf5",
"inchikey": "HEDRZPFGACZZDS-UHFFFAOYSA-N",
"smiles": "ClC(Cl)Cl"
},
"smiles": "ClC(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5250",
"routeId": "sa_a1b2eb80c9a8f1262d2b98bd",
"moleculeId": "sa_24b3f385b0626dee8331a3c6",
"parentId": "5248",
"isLeaf": false,
"molecule": {
"id": "sa_24b3f385b0626dee8331a3c6",
"inchikey": "UDXBXNMUCAZWPI-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cc(Cl)c(Cl)cc1NCCCO"
},
"smiles": "O=[N+]([O-])c1cc(Cl)c(Cl)cc1NCCCO",
"reactionStepId": "sa_4aba2dff9dd04c8b7c66665d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US04200641;;66502\",\"rsmi\":\"Cl[c:5]1[c:4]([N+:2](=[O:1])[O-:3])[cH:16][c:14]([Cl:15])[c:12]([Cl:13])[cH:11]1.[NH2:6][CH2:7][CH2:8][CH2:9][OH:10]>CCCCO.I.[K+]>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([NH:6][CH2:7][CH2:8][CH2:9][OH:10])[cH:11][c:12]([Cl:13])[c:14]([Cl:15])[cH:16]1\"},\"mapped_reaction_smiles\":\"Cl[c:5]1[c:4]([N+:2](=[O:1])[O-:3])[cH:16][c:14]([Cl:15])[c:12]([Cl:13])[cH:11]1.[NH2:6][CH2:7][CH2:8][CH2:9][OH:10]>CCCCO.I.[K+]>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([NH:6][CH2:7][CH2:8][CH2:9][OH:10])[cH:11][c:12]([Cl:13])[c:14]([Cl:15])[cH:16]1\"}",
"reactionStep": {
"id": "sa_4aba2dff9dd04c8b7c66665d",
"reactionHash": "40c831fab4fa764d75ceb78e394d9d53e712f1a998adccdaf03727d26f96593e"
},
"children": [
{
"id": "5251",
"routeId": "sa_a1b2eb80c9a8f1262d2b98bd",
"moleculeId": "sa_0ac5c9f05eded829b5d58297",
"parentId": "5250",
"isLeaf": true,
"molecule": {
"id": "sa_0ac5c9f05eded829b5d58297",
"inchikey": "IBRBMZRLVYKVRF-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cc(Cl)c(Cl)cc1Cl"
},
"smiles": "O=[N+]([O-])c1cc(Cl)c(Cl)cc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5252",
"routeId": "sa_a1b2eb80c9a8f1262d2b98bd",
"moleculeId": "sa_7f4a9cfde0c95e580eb65167",
"parentId": "5250",
"isLeaf": true,
"molecule": {
"id": "sa_7f4a9cfde0c95e580eb65167",
"inchikey": "WUGQZFFCHPXWKQ-UHFFFAOYSA-N",
"smiles": "NCCCO"
},
"smiles": "NCCCO",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
]
}
]
},
{
"id": "5253",
"routeId": "sa_a1b2eb80c9a8f1262d2b98bd",
"moleculeId": "sa_ff9c192eabf68896f2512671",
"parentId": "5244",
"isLeaf": true,
"molecule": {
"id": "sa_ff9c192eabf68896f2512671",
"inchikey": "XSQUKJJJFZCRTK-UHFFFAOYSA-N",
"smiles": "NC(N)=O"
},
"smiles": "NC(N)=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}