Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1cc(OC)cc(-c2cc3cnc(Cl)nc3cc2Cl)c1
InChiKey
DLIRSSNKVAIFDD-UHFFFAOYSA-N
Route Signature
c25056079761723fc7c32055840d826ac7c3c980dedbb0605639b567e68ecb39
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_abaa43162c30711bc7bed3be",
"signature": "c25056079761723fc7c32055840d826ac7c3c980dedbb0605639b567e68ecb39",
"contentHash": "26b76ba8a7ea3780be14eb334ab061dc57150002a4ace8c522e56d6891399055",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_539369e8ba905abc5fe26ae4",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-01057",
"moleculeId": "sa_b1eb6ba51bed35cc09a8c8d6",
"smiles": "COc1cc(OC)cc(-c2cc3cnc(Cl)nc3cc2Cl)c1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_b1eb6ba51bed35cc09a8c8d6",
"inchikey": "DLIRSSNKVAIFDD-UHFFFAOYSA-N",
"smiles": "COc1cc(OC)cc(-c2cc3cnc(Cl)nc3cc2Cl)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "14036",
"routeId": "sa_abaa43162c30711bc7bed3be",
"moleculeId": "sa_b1eb6ba51bed35cc09a8c8d6",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_b1eb6ba51bed35cc09a8c8d6",
"inchikey": "DLIRSSNKVAIFDD-UHFFFAOYSA-N",
"smiles": "COc1cc(OC)cc(-c2cc3cnc(Cl)nc3cc2Cl)c1"
},
"smiles": "COc1cc(OC)cc(-c2cc3cnc(Cl)nc3cc2Cl)c1",
"reactionStepId": "sa_673a44dd01ab368d3bc514f8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150119405A1;0419;1684021\",\"rsmi\":\"Br[c:10]1[c:11]([Cl:12])[cH:13][c:14]2[n:15][c:16]([Cl:17])[n:18][cH:19][c:20]2[cH:21]1.OB(O)[c:9]1[cH:8][c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[cH:22]1>C1CCOC1.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[cH:8][c:9](-[c:10]2[c:11]([Cl:12])[cH:13][c:14]3[n:15][c:16]([Cl:17])[n:18][cH:19][c:20]3[cH:21]2)[cH:22]1\"},\"mapped_reaction_smiles\":\"Br[c:10]1[c:11]([Cl:12])[cH:13][c:14]2[n:15][c:16]([Cl:17])[n:18][cH:19][c:20]2[cH:21]1.OB(O)[c:9]1[cH:8][c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[cH:22]1>C1CCOC1.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[cH:8][c:9](-[c:10]2[c:11]([Cl:12])[cH:13][c:14]3[n:15][c:16]([Cl:17])[n:18][cH:19][c:20]3[cH:21]2)[cH:22]1\"}",
"reactionStep": {
"id": "sa_673a44dd01ab368d3bc514f8",
"reactionHash": "e9360e036db21ea87310c38df997c0056026e9530797b2ef2a11033e56d56eec"
},
"children": [
{
"id": "14037",
"routeId": "sa_abaa43162c30711bc7bed3be",
"moleculeId": "sa_5f5c49e031bc0d9c997eb984",
"parentId": "14036",
"isLeaf": false,
"molecule": {
"id": "sa_5f5c49e031bc0d9c997eb984",
"inchikey": "APEAOBLDQOPTNT-UHFFFAOYSA-N",
"smiles": "Clc1ncc2cc(Br)c(Cl)cc2n1"
},
"smiles": "Clc1ncc2cc(Br)c(Cl)cc2n1",
"reactionStepId": "sa_677bc4ed86656a1f0ee279ff",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150119405A1;0417;1684020\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:1].O[c:2]1[n:3][c:4]2[cH:5][c:6]([Cl:7])[c:8]([Br:9])[cH:10][c:11]2[cH:12][n:13]1>>[Cl:1][c:2]1[n:3][c:4]2[cH:5][c:6]([Cl:7])[c:8]([Br:9])[cH:10][c:11]2[cH:12][n:13]1\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:1].O[c:2]1[n:3][c:4]2[cH:5][c:6]([Cl:7])[c:8]([Br:9])[cH:10][c:11]2[cH:12][n:13]1>>[Cl:1][c:2]1[n:3][c:4]2[cH:5][c:6]([Cl:7])[c:8]([Br:9])[cH:10][c:11]2[cH:12][n:13]1\"}",
"reactionStep": {
"id": "sa_677bc4ed86656a1f0ee279ff",
"reactionHash": "60071e8af28f1afef74db79c93c4abbd956a911d6ae025407d22900c5a86a280"
},
"children": [
{
"id": "14038",
"routeId": "sa_abaa43162c30711bc7bed3be",
"moleculeId": "sa_89296d9d3d9de2b81b05b62b",
"parentId": "14037",
"isLeaf": false,
"molecule": {
"id": "sa_89296d9d3d9de2b81b05b62b",
"inchikey": "CTNDZOBVJZGQQF-UHFFFAOYSA-N",
"smiles": "Oc1ncc2cc(Br)c(Cl)cc2n1"
},
"smiles": "Oc1ncc2cc(Br)c(Cl)cc2n1",
"reactionStepId": "sa_3aaff61d66ddf7b96e08295b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150119405A1;0415;1684019\",\"rsmi\":\"N[C:2](=[O:1])[NH2:13].O=[CH:12][c:11]1[c:4]([NH2:3])[cH:5][c:6]([Cl:7])[c:8]([Br:9])[cH:10]1>>[OH:1][c:2]1[n:3][c:4]2[cH:5][c:6]([Cl:7])[c:8]([Br:9])[cH:10][c:11]2[cH:12][n:13]1\"},\"mapped_reaction_smiles\":\"N[C:2](=[O:1])[NH2:13].O=[CH:12][c:11]1[c:4]([NH2:3])[cH:5][c:6]([Cl:7])[c:8]([Br:9])[cH:10]1>>[OH:1][c:2]1[n:3][c:4]2[cH:5][c:6]([Cl:7])[c:8]([Br:9])[cH:10][c:11]2[cH:12][n:13]1\"}",
"reactionStep": {
"id": "sa_3aaff61d66ddf7b96e08295b",
"reactionHash": "64e16d7ee5c34f894dfb483ef72fe22e3dd46c6147285d0e93d19b1d290dbf4f"
},
"children": [
{
"id": "14039",
"routeId": "sa_abaa43162c30711bc7bed3be",
"moleculeId": "sa_dc9adebfc6f3228023d9c98d",
"parentId": "14038",
"isLeaf": false,
"molecule": {
"id": "sa_dc9adebfc6f3228023d9c98d",
"inchikey": "PROWVWALAHUEHK-UHFFFAOYSA-N",
"smiles": "Nc1cc(Cl)c(Br)cc1C=O"
},
"smiles": "Nc1cc(Cl)c(Br)cc1C=O",
"reactionStepId": "sa_76a9a6a02c7c1be1957836d2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150119405A1;0413;1684018\",\"rsmi\":\"[NH2:1][c:2]1[c:3]([CH2:4][OH:5])[cH:6][c:7]([Br:8])[c:9]([Cl:10])[cH:11]1>ClCCl.[Mn+4].[O-2].[O-2]>[NH2:1][c:2]1[c:3]([CH:4]=[O:5])[cH:6][c:7]([Br:8])[c:9]([Cl:10])[cH:11]1\"},\"mapped_reaction_smiles\":\"[NH2:1][c:2]1[c:3]([CH2:4][OH:5])[cH:6][c:7]([Br:8])[c:9]([Cl:10])[cH:11]1>ClCCl.[Mn+4].[O-2].[O-2]>[NH2:1][c:2]1[c:3]([CH:4]=[O:5])[cH:6][c:7]([Br:8])[c:9]([Cl:10])[cH:11]1\"}",
"reactionStep": {
"id": "sa_76a9a6a02c7c1be1957836d2",
"reactionHash": "aeba9dabe7ec63c34ebf1dc939ab2f001b73a3fef90f3bc445a9f8cf2891a364"
},
"children": [
{
"id": "14040",
"routeId": "sa_abaa43162c30711bc7bed3be",
"moleculeId": "sa_7c9ce9833578074d9743bf6f",
"parentId": "14039",
"isLeaf": false,
"molecule": {
"id": "sa_7c9ce9833578074d9743bf6f",
"inchikey": "TUYSJQDXRVTMSR-UHFFFAOYSA-N",
"smiles": "Nc1cc(Cl)c(Br)cc1CO"
},
"smiles": "Nc1cc(Cl)c(Br)cc1CO",
"reactionStepId": "sa_c01d03a510577ded5280319e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150119405A1;0411;1684017\",\"rsmi\":\"O=[C:4]([c:3]1[c:2]([NH2:1])[cH:11][c:9]([Cl:10])[c:7]([Br:8])[cH:6]1)[OH:5]>C1CCOC1.B>[NH2:1][c:2]1[c:3]([CH2:4][OH:5])[cH:6][c:7]([Br:8])[c:9]([Cl:10])[cH:11]1\"},\"mapped_reaction_smiles\":\"O=[C:4]([c:3]1[c:2]([NH2:1])[cH:11][c:9]([Cl:10])[c:7]([Br:8])[cH:6]1)[OH:5]>C1CCOC1.B>[NH2:1][c:2]1[c:3]([CH2:4][OH:5])[cH:6][c:7]([Br:8])[c:9]([Cl:10])[cH:11]1\"}",
"reactionStep": {
"id": "sa_c01d03a510577ded5280319e",
"reactionHash": "90666881c977ed3bd3ccc1c8812e3f488af7703917f7c5115bce968bcc858a3e"
},
"children": [
{
"id": "14041",
"routeId": "sa_abaa43162c30711bc7bed3be",
"moleculeId": "sa_642ad1dc76b650d63c925ee1",
"parentId": "14040",
"isLeaf": false,
"molecule": {
"id": "sa_642ad1dc76b650d63c925ee1",
"inchikey": "TUDNMLBIHIWVJM-UHFFFAOYSA-N",
"smiles": "Nc1cc(Cl)c(Br)cc1C(=O)O"
},
"smiles": "Nc1cc(Cl)c(Br)cc1C(=O)O",
"reactionStepId": "sa_f91716705c2c9ebe7a9405ce",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150119405A1;0409;1684016\",\"rsmi\":\"Br[Br:9].[NH2:1][c:2]1[c:3]([C:4](=[O:5])[OH:6])[cH:7][cH:8][c:10]([Cl:11])[cH:12]1>CO>[NH2:1][c:2]1[c:3]([C:4](=[O:5])[OH:6])[cH:7][c:8]([Br:9])[c:10]([Cl:11])[cH:12]1\"},\"mapped_reaction_smiles\":\"Br[Br:9].[NH2:1][c:2]1[c:3]([C:4](=[O:5])[OH:6])[cH:7][cH:8][c:10]([Cl:11])[cH:12]1>CO>[NH2:1][c:2]1[c:3]([C:4](=[O:5])[OH:6])[cH:7][c:8]([Br:9])[c:10]([Cl:11])[cH:12]1\"}",
"reactionStep": {
"id": "sa_f91716705c2c9ebe7a9405ce",
"reactionHash": "e8bc39290740dde5247b4d1b1da19191ebbafdc519ef90a189e6514f6c9fd90f"
},
"children": [
{
"id": "14042",
"routeId": "sa_abaa43162c30711bc7bed3be",
"moleculeId": "sa_24211e89e565c162ea935f73",
"parentId": "14041",
"isLeaf": true,
"molecule": {
"id": "sa_24211e89e565c162ea935f73",
"inchikey": "GDTBXPJZTBHREO-UHFFFAOYSA-N",
"smiles": "BrBr"
},
"smiles": "BrBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14043",
"routeId": "sa_abaa43162c30711bc7bed3be",
"moleculeId": "sa_18708ea3ebef9eeff7dfe2a4",
"parentId": "14041",
"isLeaf": true,
"molecule": {
"id": "sa_18708ea3ebef9eeff7dfe2a4",
"inchikey": "JYYLQSCZISREGY-UHFFFAOYSA-N",
"smiles": "Nc1cc(Cl)ccc1C(=O)O"
},
"smiles": "Nc1cc(Cl)ccc1C(=O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "14044",
"routeId": "sa_abaa43162c30711bc7bed3be",
"moleculeId": "sa_ff9c192eabf68896f2512671",
"parentId": "14038",
"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": []
}
]
},
{
"id": "14045",
"routeId": "sa_abaa43162c30711bc7bed3be",
"moleculeId": "sa_312a7cd3d48a055e9bc98180",
"parentId": "14037",
"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": "14046",
"routeId": "sa_abaa43162c30711bc7bed3be",
"moleculeId": "sa_155e4e46d2daa798b9717a93",
"parentId": "14036",
"isLeaf": true,
"molecule": {
"id": "sa_155e4e46d2daa798b9717a93",
"inchikey": "XUIURRYWQBBCCK-UHFFFAOYSA-N",
"smiles": "COc1cc(OC)cc(B(O)O)c1"
},
"smiles": "COc1cc(OC)cc(B(O)O)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}