Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1n[nH]c2c1C(c1ccc(Cl)cc1)N(c1cc(C)c3nnc(C)n3c1)C2=O
InChiKey
PKWSPAGTIXNWLL-UHFFFAOYSA-N
Route Signature
ac78cbbc08016dff14b78ef98e7b00f37eef3f12bc3156a078ce5c509a437583
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_7e44e6d336ddfa505573c5d8",
"signature": "ac78cbbc08016dff14b78ef98e7b00f37eef3f12bc3156a078ce5c509a437583",
"contentHash": "8e80bf3d76d50149c6a88f265bd3b8b4d6f506bef7c405787b0624ba0d4c4b55",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_21f0a15cf099e2a34b9c225c",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00341",
"moleculeId": "sa_856b65af8b07ff894f5020f0",
"smiles": "Cc1n[nH]c2c1C(c1ccc(Cl)cc1)N(c1cc(C)c3nnc(C)n3c1)C2=O",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_856b65af8b07ff894f5020f0",
"inchikey": "PKWSPAGTIXNWLL-UHFFFAOYSA-N",
"smiles": "Cc1n[nH]c2c1C(c1ccc(Cl)cc1)N(c1cc(C)c3nnc(C)n3c1)C2=O"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 4
},
"rootNode": {
"id": "4062",
"routeId": "sa_7e44e6d336ddfa505573c5d8",
"moleculeId": "sa_856b65af8b07ff894f5020f0",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_856b65af8b07ff894f5020f0",
"inchikey": "PKWSPAGTIXNWLL-UHFFFAOYSA-N",
"smiles": "Cc1n[nH]c2c1C(c1ccc(Cl)cc1)N(c1cc(C)c3nnc(C)n3c1)C2=O"
},
"smiles": "Cc1n[nH]c2c1C(c1ccc(Cl)cc1)N(c1cc(C)c3nnc(C)n3c1)C2=O",
"reactionStepId": "sa_323261989071317714040866",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140349990A1;1004;1617870\",\"rsmi\":\"O=[C:10]([C:9]1=[C:8](O)[C:6](=[O:7])[N:5]([c:4]2[cH:3][c:2]([CH3:1])[c:28]3[n:23]([cH:22]2)[c:24]([CH3:25])[n:26][n:27]3)[CH:14]1[c:15]1[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]1)[CH3:11].[NH2:12][NH2:13]>O>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[C:6](=[O:7])[c:8]3[c:9]([c:10]([CH3:11])[n:12][nH:13]3)[CH:14]2[c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]2)[cH:22][n:23]2[c:24]([CH3:25])[n:26][n:27][c:28]12\"},\"mapped_reaction_smiles\":\"O=[C:10]([C:9]1=[C:8](O)[C:6](=[O:7])[N:5]([c:4]2[cH:3][c:2]([CH3:1])[c:28]3[n:23]([cH:22]2)[c:24]([CH3:25])[n:26][n:27]3)[CH:14]1[c:15]1[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]1)[CH3:11].[NH2:12][NH2:13]>O>[CH3:1][c:2]1[cH:3][c:4]([N:5]2[C:6](=[O:7])[c:8]3[c:9]([c:10]([CH3:11])[n:12][nH:13]3)[CH:14]2[c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]2)[cH:22][n:23]2[c:24]([CH3:25])[n:26][n:27][c:28]12\"}",
"reactionStep": {
"id": "sa_323261989071317714040866",
"reactionHash": "9dad9cd50427811e6ad20159cde78e15e6142cd5890f33411fe556dadb77ae4a"
},
"children": [
{
"id": "4063",
"routeId": "sa_7e44e6d336ddfa505573c5d8",
"moleculeId": "sa_681b90bfe3789a310096845b",
"parentId": "4062",
"isLeaf": true,
"molecule": {
"id": "sa_681b90bfe3789a310096845b",
"inchikey": "OAKJQQAXSVQMHS-UHFFFAOYSA-N",
"smiles": "NN"
},
"smiles": "NN",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4064",
"routeId": "sa_7e44e6d336ddfa505573c5d8",
"moleculeId": "sa_39bf62eee5ba7a83fe347cc1",
"parentId": "4062",
"isLeaf": false,
"molecule": {
"id": "sa_39bf62eee5ba7a83fe347cc1",
"inchikey": "UAOZFBSJKCSENQ-UHFFFAOYSA-N",
"smiles": "CC(=O)C1=C(O)C(=O)N(c2cc(C)c3nnc(C)n3c2)C1c1ccc(Cl)cc1"
},
"smiles": "CC(=O)C1=C(O)C(=O)N(c2cc(C)c3nnc(C)n3c2)C1c1ccc(Cl)cc1",
"reactionStepId": "sa_1b67a30cf2e718ce5736a09d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140349990A1;0975;1617860\",\"rsmi\":\"CCO[C:7]([C:5]([CH2:4][C:2]([CH3:1])=[O:3])=[O:6])=[O:8].O=[CH:21][c:22]1[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]1.[NH2:9][c:10]1[cH:11][n:12]2[c:13]([CH3:14])[n:15][n:16][c:17]2[c:18]([CH3:19])[cH:20]1>>[CH3:1][C:2](=[O:3])[C:4]1=[C:5]([OH:6])[C:7](=[O:8])[N:9]([c:10]2[cH:11][n:12]3[c:13]([CH3:14])[n:15][n:16][c:17]3[c:18]([CH3:19])[cH:20]2)[CH:21]1[c:22]1[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]1\"},\"mapped_reaction_smiles\":\"CCO[C:7]([C:5]([CH2:4][C:2]([CH3:1])=[O:3])=[O:6])=[O:8].O=[CH:21][c:22]1[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]1.[NH2:9][c:10]1[cH:11][n:12]2[c:13]([CH3:14])[n:15][n:16][c:17]2[c:18]([CH3:19])[cH:20]1>>[CH3:1][C:2](=[O:3])[C:4]1=[C:5]([OH:6])[C:7](=[O:8])[N:9]([c:10]2[cH:11][n:12]3[c:13]([CH3:14])[n:15][n:16][c:17]3[c:18]([CH3:19])[cH:20]2)[CH:21]1[c:22]1[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]1\"}",
"reactionStep": {
"id": "sa_1b67a30cf2e718ce5736a09d",
"reactionHash": "f1692c8b06f0247899b35b2ab31d1314cfc9dd5f3a133dca7ed7369c14388cf2"
},
"children": [
{
"id": "4065",
"routeId": "sa_7e44e6d336ddfa505573c5d8",
"moleculeId": "sa_95255078a9b1044823d7ec55",
"parentId": "4064",
"isLeaf": true,
"molecule": {
"id": "sa_95255078a9b1044823d7ec55",
"inchikey": "AVPYQKSLYISFPO-UHFFFAOYSA-N",
"smiles": "O=Cc1ccc(Cl)cc1"
},
"smiles": "O=Cc1ccc(Cl)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4066",
"routeId": "sa_7e44e6d336ddfa505573c5d8",
"moleculeId": "sa_15c87518dcadcfdffc560bc4",
"parentId": "4064",
"isLeaf": false,
"molecule": {
"id": "sa_15c87518dcadcfdffc560bc4",
"inchikey": "OIQBRQXGHWVXKY-UHFFFAOYSA-N",
"smiles": "Cc1cc(N)cn2c(C)nnc12"
},
"smiles": "Cc1cc(N)cn2c(C)nnc12",
"reactionStepId": "sa_624e0cc041a5e24768761a5f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140349990A1;0874;1617830\",\"rsmi\":\"O=[N+:5]([O-])[c:4]1[cH:3][c:2]([CH3:1])[c:12]2[n:7]([cH:6]1)[c:8]([CH3:9])[n:10][n:11]2>CO.[H][H].[Pd]>[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[cH:6][n:7]2[c:8]([CH3:9])[n:10][n:11][c:12]12\"},\"mapped_reaction_smiles\":\"O=[N+:5]([O-])[c:4]1[cH:3][c:2]([CH3:1])[c:12]2[n:7]([cH:6]1)[c:8]([CH3:9])[n:10][n:11]2>CO.[H][H].[Pd]>[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[cH:6][n:7]2[c:8]([CH3:9])[n:10][n:11][c:12]12\"}",
"reactionStep": {
"id": "sa_624e0cc041a5e24768761a5f",
"reactionHash": "4057bf02b11dc3d5aa61b57550fb963cbc4a6e1a40d018796e2d16289e8c37ec"
},
"children": [
{
"id": "4067",
"routeId": "sa_7e44e6d336ddfa505573c5d8",
"moleculeId": "sa_211c42e4f0bd85919f18ca58",
"parentId": "4066",
"isLeaf": false,
"molecule": {
"id": "sa_211c42e4f0bd85919f18ca58",
"inchikey": "GKMNUWYJEWYKIS-UHFFFAOYSA-N",
"smiles": "Cc1cc([N+](=O)[O-])cn2c(C)nnc12"
},
"smiles": "Cc1cc([N+](=O)[O-])cn2c(C)nnc12",
"reactionStepId": "sa_41c994fc3298f17ec62ddbd9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140349990A1;0872;1617829\",\"rsmi\":\"O=[C:10]([CH3:11])[NH:12][NH:13][c:14]1[c:2]([CH3:1])[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][n:9]1>C1COCCO1.CC(=O)O>[CH3:1][c:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][n:9]2[c:10]([CH3:11])[n:12][n:13][c:14]12\"},\"mapped_reaction_smiles\":\"O=[C:10]([CH3:11])[NH:12][NH:13][c:14]1[c:2]([CH3:1])[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][n:9]1>C1COCCO1.CC(=O)O>[CH3:1][c:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][n:9]2[c:10]([CH3:11])[n:12][n:13][c:14]12\"}",
"reactionStep": {
"id": "sa_41c994fc3298f17ec62ddbd9",
"reactionHash": "67c1cc715f9544deac232b29d6e59f88dd0545604efba474e5d150509c980ce5"
},
"children": [
{
"id": "4068",
"routeId": "sa_7e44e6d336ddfa505573c5d8",
"moleculeId": "sa_0e024c2181975fbc9a8edead",
"parentId": "4067",
"isLeaf": false,
"molecule": {
"id": "sa_0e024c2181975fbc9a8edead",
"inchikey": "HXTKJUJJTJXIET-UHFFFAOYSA-N",
"smiles": "CC(=O)NNc1ncc([N+](=O)[O-])cc1C"
},
"smiles": "CC(=O)NNc1ncc([N+](=O)[O-])cc1C",
"reactionStepId": "sa_315da0c7265a1930f1724f12",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140349990A1;0870;1617828\",\"rsmi\":\"CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][NH:5][c:6]1[n:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][c:14]1[CH3:15]>C1COCCO1>[CH3:1][C:2](=[O:3])[NH:4][NH:5][c:6]1[n:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][c:14]1[CH3:15]\"},\"mapped_reaction_smiles\":\"CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][NH:5][c:6]1[n:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][c:14]1[CH3:15]>C1COCCO1>[CH3:1][C:2](=[O:3])[NH:4][NH:5][c:6]1[n:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][c:14]1[CH3:15]\"}",
"reactionStep": {
"id": "sa_315da0c7265a1930f1724f12",
"reactionHash": "6862a53b40132444313f621ead66ac46be70705c659648231974f93494cff4a6"
},
"children": [
{
"id": "4069",
"routeId": "sa_7e44e6d336ddfa505573c5d8",
"moleculeId": "sa_c3428ab791c5d17db3ee61bd",
"parentId": "4068",
"isLeaf": false,
"molecule": {
"id": "sa_c3428ab791c5d17db3ee61bd",
"inchikey": "CSHKMLIZQJQZBQ-UHFFFAOYSA-N",
"smiles": "Cc1cc([N+](=O)[O-])cnc1NN"
},
"smiles": "Cc1cc([N+](=O)[O-])cnc1NN",
"reactionStepId": "sa_5d0c6e979dbed8e0881c230c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140349990A1;0868;1617827\",\"rsmi\":\"Cl[c:10]1[c:2]([CH3:1])[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][n:9]1.[NH2:11][NH2:12]>CCO.O>[CH3:1][c:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][n:9][c:10]1[NH:11][NH2:12]\"},\"mapped_reaction_smiles\":\"Cl[c:10]1[c:2]([CH3:1])[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][n:9]1.[NH2:11][NH2:12]>CCO.O>[CH3:1][c:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][n:9][c:10]1[NH:11][NH2:12]\"}",
"reactionStep": {
"id": "sa_5d0c6e979dbed8e0881c230c",
"reactionHash": "2da73a56d4277bf1d2893ff809a8a421237b1eced67701118520817b00cb90f8"
},
"children": [
{
"id": "4070",
"routeId": "sa_7e44e6d336ddfa505573c5d8",
"moleculeId": "sa_681b90bfe3789a310096845b",
"parentId": "4069",
"isLeaf": true,
"molecule": {
"id": "sa_681b90bfe3789a310096845b",
"inchikey": "OAKJQQAXSVQMHS-UHFFFAOYSA-N",
"smiles": "NN"
},
"smiles": "NN",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4071",
"routeId": "sa_7e44e6d336ddfa505573c5d8",
"moleculeId": "sa_323f68bc824e82f5e3830880",
"parentId": "4069",
"isLeaf": true,
"molecule": {
"id": "sa_323f68bc824e82f5e3830880",
"inchikey": "OSIOIGXJUZTWRI-UHFFFAOYSA-N",
"smiles": "Cc1cc([N+](=O)[O-])cnc1Cl"
},
"smiles": "Cc1cc([N+](=O)[O-])cnc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "4072",
"routeId": "sa_7e44e6d336ddfa505573c5d8",
"moleculeId": "sa_a7893fcf81826693d9b4bed4",
"parentId": "4068",
"isLeaf": true,
"molecule": {
"id": "sa_a7893fcf81826693d9b4bed4",
"inchikey": "WFDIJRYMOXRFFG-UHFFFAOYSA-N",
"smiles": "CC(=O)OC(C)=O"
},
"smiles": "CC(=O)OC(C)=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "4073",
"routeId": "sa_7e44e6d336ddfa505573c5d8",
"moleculeId": "sa_7ae9859c63b78315846fc60d",
"parentId": "4064",
"isLeaf": true,
"molecule": {
"id": "sa_7ae9859c63b78315846fc60d",
"inchikey": "OYQVQWIASIXXRT-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C(=O)CC(C)=O"
},
"smiles": "CCOC(=O)C(=O)CC(C)=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}