Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCC(CC)c1ccc(Cl)c2nc3n(c12)CCCCN3c1c[nH]c(=O)cc1C
InChiKey
FRHMCXUCLPCLHB-UHFFFAOYSA-N
Route Signature
3c0eeb8ac5465bce123ad2bad7014fa224a2213fa5445b0232edc270ed58c902
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_fd57d66f124090ba5c64aac8",
"signature": "3c0eeb8ac5465bce123ad2bad7014fa224a2213fa5445b0232edc270ed58c902",
"contentHash": "f5cf0e045526f67ed0c2e72fe3b64653df875b4c6c9db2848d588008084e628a",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_3537d45ba26db43d18931345",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-01538",
"moleculeId": "sa_2e040ffa0133300d2a695e6d",
"smiles": "CCC(CC)c1ccc(Cl)c2nc3n(c12)CCCCN3c1c[nH]c(=O)cc1C",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_2e040ffa0133300d2a695e6d",
"inchikey": "FRHMCXUCLPCLHB-UHFFFAOYSA-N",
"smiles": "CCC(CC)c1ccc(Cl)c2nc3n(c12)CCCCN3c1c[nH]c(=O)cc1C"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "14426",
"routeId": "sa_fd57d66f124090ba5c64aac8",
"moleculeId": "sa_2e040ffa0133300d2a695e6d",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_2e040ffa0133300d2a695e6d",
"inchikey": "FRHMCXUCLPCLHB-UHFFFAOYSA-N",
"smiles": "CCC(CC)c1ccc(Cl)c2nc3n(c12)CCCCN3c1c[nH]c(=O)cc1C"
},
"smiles": "CCC(CC)c1ccc(Cl)c2nc3n(c12)CCCCN3c1c[nH]c(=O)cc1C",
"reactionStepId": "sa_7770c4afc5facc857a5dcfb3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090186879A1;1735;742119\",\"rsmi\":\"C[O:23][c:22]1[n:21][cH:20][c:19]([N:18]2[CH2:17][CH2:16][CH2:15][CH2:14][n:13]3[c:12]4[c:6]([CH:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[cH:7][cH:8][c:9]([Cl:10])[c:11]4[n:28][c:27]32)[c:25]([CH3:26])[cH:24]1>CC#N.C[Si](C)(C)Cl.O=C(O)O.I.[Na+].[Na+]>[CH3:1][CH2:2][CH:3]([CH2:4][CH3:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[c:11]2[c:12]1[n:13]1[c:27]([n:28]2)[N:18]([c:19]2[cH:20][nH:21][c:22](=[O:23])[cH:24][c:25]2[CH3:26])[CH2:17][CH2:16][CH2:15][CH2:14]1\"},\"mapped_reaction_smiles\":\"C[O:23][c:22]1[n:21][cH:20][c:19]([N:18]2[CH2:17][CH2:16][CH2:15][CH2:14][n:13]3[c:12]4[c:6]([CH:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[cH:7][cH:8][c:9]([Cl:10])[c:11]4[n:28][c:27]32)[c:25]([CH3:26])[cH:24]1>CC#N.C[Si](C)(C)Cl.O=C(O)O.I.[Na+].[Na+]>[CH3:1][CH2:2][CH:3]([CH2:4][CH3:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[c:11]2[c:12]1[n:13]1[c:27]([n:28]2)[N:18]([c:19]2[cH:20][nH:21][c:22](=[O:23])[cH:24][c:25]2[CH3:26])[CH2:17][CH2:16][CH2:15][CH2:14]1\"}",
"reactionStep": {
"id": "sa_7770c4afc5facc857a5dcfb3",
"reactionHash": "40406946176a8b3a2a4996f87a306ae46b270cd5f3c2d492b8c51c461d12b739"
},
"children": [
{
"id": "14427",
"routeId": "sa_fd57d66f124090ba5c64aac8",
"moleculeId": "sa_f544b8ae26b8c1cdb34f5239",
"parentId": "14426",
"isLeaf": false,
"molecule": {
"id": "sa_f544b8ae26b8c1cdb34f5239",
"inchikey": "DNYUZJBNRLKIPV-UHFFFAOYSA-N",
"smiles": "CCC(CC)c1ccc(Cl)c2nc3n(c12)CCCCN3c1cnc(OC)cc1C"
},
"smiles": "CCC(CC)c1ccc(Cl)c2nc3n(c12)CCCCN3c1cnc(OC)cc1C",
"reactionStepId": "sa_6904a7a0bad017309518a2e9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090186879A1;1617;742102\",\"rsmi\":\"O[CH2:17][CH2:16][CH2:15][CH2:14][n:13]1[c:12]2[c:6]([CH:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[cH:7][cH:8][c:9]([Cl:10])[c:11]2[n:29][c:28]1[NH:18][c:19]1[c:20]([CH3:21])[cH:22][c:23]([O:24][CH3:25])[n:26][cH:27]1>CS(=O)(=O)Cl.O.O=C(O)O.O=C(O)O.[K+].[K+].[Na+].c1ccncc1>[CH3:1][CH2:2][CH:3]([CH2:4][CH3:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[c:11]2[c:12]1[n:13]1[c:28]([n:29]2)[N:18]([c:19]2[c:20]([CH3:21])[cH:22][c:23]([O:24][CH3:25])[n:26][cH:27]2)[CH2:17][CH2:16][CH2:15][CH2:14]1\"},\"mapped_reaction_smiles\":\"O[CH2:17][CH2:16][CH2:15][CH2:14][n:13]1[c:12]2[c:6]([CH:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[cH:7][cH:8][c:9]([Cl:10])[c:11]2[n:29][c:28]1[NH:18][c:19]1[c:20]([CH3:21])[cH:22][c:23]([O:24][CH3:25])[n:26][cH:27]1>CS(=O)(=O)Cl.O.O=C(O)O.O=C(O)O.[K+].[K+].[Na+].c1ccncc1>[CH3:1][CH2:2][CH:3]([CH2:4][CH3:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[c:11]2[c:12]1[n:13]1[c:28]([n:29]2)[N:18]([c:19]2[c:20]([CH3:21])[cH:22][c:23]([O:24][CH3:25])[n:26][cH:27]2)[CH2:17][CH2:16][CH2:15][CH2:14]1\"}",
"reactionStep": {
"id": "sa_6904a7a0bad017309518a2e9",
"reactionHash": "c7be9a9f85c766bd17d69612963fbf9da66e9b5fcccc995d29fd131e2fac330c"
},
"children": [
{
"id": "14428",
"routeId": "sa_fd57d66f124090ba5c64aac8",
"moleculeId": "sa_7ccf1ec7b7d3a3625b599c65",
"parentId": "14427",
"isLeaf": false,
"molecule": {
"id": "sa_7ccf1ec7b7d3a3625b599c65",
"inchikey": "ZBMFRHSEVIVKHQ-UHFFFAOYSA-N",
"smiles": "CCC(CC)c1ccc(Cl)c2nc(Nc3cnc(OC)cc3C)n(CCCCO)c12"
},
"smiles": "CCC(CC)c1ccc(Cl)c2nc(Nc3cnc(OC)cc3C)n(CCCCO)c12",
"reactionStepId": "sa_8d081ab0790f3fc3fb016b16",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090186879A1;0915;741902\",\"rsmi\":\"CCO[C:17]([CH2:16][CH2:15][CH2:14][n:13]1[c:12]2[c:6]([CH:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[cH:7][cH:8][c:9]([Cl:10])[c:11]2[n:30][c:19]1[NH:20][c:21]1[c:22]([CH3:23])[cH:24][c:25]([O:26][CH3:27])[n:28][cH:29]1)=[O:18]>C1CCOC1.O.B.[Li+]>[CH3:1][CH2:2][CH:3]([CH2:4][CH3:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[c:11]2[c:12]1[n:13]([CH2:14][CH2:15][CH2:16][CH2:17][OH:18])[c:19]([NH:20][c:21]1[c:22]([CH3:23])[cH:24][c:25]([O:26][CH3:27])[n:28][cH:29]1)[n:30]2\"},\"mapped_reaction_smiles\":\"CCO[C:17]([CH2:16][CH2:15][CH2:14][n:13]1[c:12]2[c:6]([CH:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[cH:7][cH:8][c:9]([Cl:10])[c:11]2[n:30][c:19]1[NH:20][c:21]1[c:22]([CH3:23])[cH:24][c:25]([O:26][CH3:27])[n:28][cH:29]1)=[O:18]>C1CCOC1.O.B.[Li+]>[CH3:1][CH2:2][CH:3]([CH2:4][CH3:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[c:11]2[c:12]1[n:13]([CH2:14][CH2:15][CH2:16][CH2:17][OH:18])[c:19]([NH:20][c:21]1[c:22]([CH3:23])[cH:24][c:25]([O:26][CH3:27])[n:28][cH:29]1)[n:30]2\"}",
"reactionStep": {
"id": "sa_8d081ab0790f3fc3fb016b16",
"reactionHash": "3145a417c7b43599e1396310902e69ea5e9451b07e1ed4c76adf4023e3d0bb9f"
},
"children": [
{
"id": "14429",
"routeId": "sa_fd57d66f124090ba5c64aac8",
"moleculeId": "sa_00c7e67435de2ddccb31c7d8",
"parentId": "14428",
"isLeaf": false,
"molecule": {
"id": "sa_00c7e67435de2ddccb31c7d8",
"inchikey": "JFFLCCUWOMVOGY-UHFFFAOYSA-N",
"smiles": "CCOC(=O)CCCn1c(Nc2cnc(OC)cc2C)nc2c(Cl)ccc(C(CC)CC)c21"
},
"smiles": "CCOC(=O)CCCn1c(Nc2cnc(OC)cc2C)nc2c(Cl)ccc(C(CC)CC)c21",
"reactionStepId": "sa_51711742d5c4e2474914ae8c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090186879A1;0911;741901\",\"rsmi\":\"Cl[c:10]1[n:9]([CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:23]2[c:22]([n:21]1)[c:32]([Cl:33])[cH:31][cH:30][c:24]2[CH:25]([CH2:26][CH3:27])[CH2:28][CH3:29].[NH2:11][c:12]1[c:13]([CH3:14])[cH:15][c:16]([O:17][CH3:18])[n:19][cH:20]1>CCOC(C)=O.CN1CCCC1=O.Cc1ccc(S(=O)(=O)O)cc1.O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][n:9]1[c:10]([NH:11][c:12]2[c:13]([CH3:14])[cH:15][c:16]([O:17][CH3:18])[n:19][cH:20]2)[n:21][c:22]2[c:23]1[c:24]([CH:25]([CH2:26][CH3:27])[CH2:28][CH3:29])[cH:30][cH:31][c:32]2[Cl:33]\"},\"mapped_reaction_smiles\":\"Cl[c:10]1[n:9]([CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:23]2[c:22]([n:21]1)[c:32]([Cl:33])[cH:31][cH:30][c:24]2[CH:25]([CH2:26][CH3:27])[CH2:28][CH3:29].[NH2:11][c:12]1[c:13]([CH3:14])[cH:15][c:16]([O:17][CH3:18])[n:19][cH:20]1>CCOC(C)=O.CN1CCCC1=O.Cc1ccc(S(=O)(=O)O)cc1.O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][n:9]1[c:10]([NH:11][c:12]2[c:13]([CH3:14])[cH:15][c:16]([O:17][CH3:18])[n:19][cH:20]2)[n:21][c:22]2[c:23]1[c:24]([CH:25]([CH2:26][CH3:27])[CH2:28][CH3:29])[cH:30][cH:31][c:32]2[Cl:33]\"}",
"reactionStep": {
"id": "sa_51711742d5c4e2474914ae8c",
"reactionHash": "f7a7288d9128435bdb1f8a5b4487b42cac78be0d8f71f36977c51351f03ec1a8"
},
"children": [
{
"id": "14430",
"routeId": "sa_fd57d66f124090ba5c64aac8",
"moleculeId": "sa_4ead272dcff16dcd946f8e20",
"parentId": "14429",
"isLeaf": false,
"molecule": {
"id": "sa_4ead272dcff16dcd946f8e20",
"inchikey": "DCGRCFSAAVNKLO-UHFFFAOYSA-N",
"smiles": "CCOC(=O)CCCn1c(Cl)nc2c(Cl)ccc(C(CC)CC)c21"
},
"smiles": "CCOC(=O)CCCn1c(Cl)nc2c(Cl)ccc(C(CC)CC)c21",
"reactionStepId": "sa_f7bf3cc7d61aacf51bfd8423",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090186879A1;0848;741886\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:11].O=[c:10]1[n:9]([CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:14]2[c:13]([nH:12]1)[c:23]([Cl:24])[cH:22][cH:21][c:15]2[CH:16]([CH2:17][CH3:18])[CH2:19][CH3:20]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][n:9]1[c:10]([Cl:11])[n:12][c:13]2[c:14]1[c:15]([CH:16]([CH2:17][CH3:18])[CH2:19][CH3:20])[cH:21][cH:22][c:23]2[Cl:24]\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:11].O=[c:10]1[n:9]([CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:14]2[c:13]([nH:12]1)[c:23]([Cl:24])[cH:22][cH:21][c:15]2[CH:16]([CH2:17][CH3:18])[CH2:19][CH3:20]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][n:9]1[c:10]([Cl:11])[n:12][c:13]2[c:14]1[c:15]([CH:16]([CH2:17][CH3:18])[CH2:19][CH3:20])[cH:21][cH:22][c:23]2[Cl:24]\"}",
"reactionStep": {
"id": "sa_f7bf3cc7d61aacf51bfd8423",
"reactionHash": "c31b280dd3bbef47116d91a53105bd31e2695c9f60c79b34b23de8128ed3ce99"
},
"children": [
{
"id": "14431",
"routeId": "sa_fd57d66f124090ba5c64aac8",
"moleculeId": "sa_ea599569f088057dce49c9d1",
"parentId": "14430",
"isLeaf": true,
"molecule": {
"id": "sa_ea599569f088057dce49c9d1",
"inchikey": "MQYSTZYWRDLIDB-UHFFFAOYSA-N",
"smiles": "CCOC(=O)CCCn1c(=O)[nH]c2c(Cl)ccc(C(CC)CC)c21"
},
"smiles": "CCOC(=O)CCCn1c(=O)[nH]c2c(Cl)ccc(C(CC)CC)c21",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14432",
"routeId": "sa_fd57d66f124090ba5c64aac8",
"moleculeId": "sa_312a7cd3d48a055e9bc98180",
"parentId": "14430",
"isLeaf": true,
"molecule": {
"id": "sa_312a7cd3d48a055e9bc98180",
"inchikey": "XHXFXVLFKHQFAL-UHFFFAOYSA-N",
"smiles": "O=P(Cl)(Cl)Cl"
},
"smiles": "O=P(Cl)(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "14433",
"routeId": "sa_fd57d66f124090ba5c64aac8",
"moleculeId": "sa_3c8727aa6ff003226fadd08f",
"parentId": "14429",
"isLeaf": true,
"molecule": {
"id": "sa_3c8727aa6ff003226fadd08f",
"inchikey": "PADDNCJJHROILV-UHFFFAOYSA-N",
"smiles": "COc1cc(C)c(N)cn1"
},
"smiles": "COc1cc(C)c(N)cn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
}