Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1cc(OC)cc(-c2cc3cnc(Cl)nc3cc2OC)c1
InChiKey
CZCORHFDBJFJRX-UHFFFAOYSA-N
Route Signature
3415f2cf2100bc73bd835c95a83d3063bfc4a71dea8f8acbc96e17855e7275f3
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_ff5e3a63068128931f9bb5f3",
"signature": "3415f2cf2100bc73bd835c95a83d3063bfc4a71dea8f8acbc96e17855e7275f3",
"contentHash": "82612104da79fb25e8eec05ef7a7ff3ec2355c3147c1b00eca37562f74e4c548",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_ad5271baec29fa01279d8184",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00179",
"moleculeId": "sa_29a867fec01f0beeb194e161",
"smiles": "COc1cc(OC)cc(-c2cc3cnc(Cl)nc3cc2OC)c1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_29a867fec01f0beeb194e161",
"inchikey": "CZCORHFDBJFJRX-UHFFFAOYSA-N",
"smiles": "COc1cc(OC)cc(-c2cc3cnc(Cl)nc3cc2OC)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 4
},
"rootNode": {
"id": "3621",
"routeId": "sa_ff5e3a63068128931f9bb5f3",
"moleculeId": "sa_29a867fec01f0beeb194e161",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_29a867fec01f0beeb194e161",
"inchikey": "CZCORHFDBJFJRX-UHFFFAOYSA-N",
"smiles": "COc1cc(OC)cc(-c2cc3cnc(Cl)nc3cc2OC)c1"
},
"smiles": "COc1cc(OC)cc(-c2cc3cnc(Cl)nc3cc2OC)c1",
"reactionStepId": "sa_8cce2da39e9fb24277059e22",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150210694A1;0256;1727536\",\"rsmi\":\"Br[c:10]1[c:11]([O:12][CH3:13])[cH:14][c:15]2[n:16][c:17]([Cl:18])[n:19][cH:20][c:21]2[cH:22]1.OB(O)[c:9]1[cH:8][c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[cH:23]1>C1CCOC1.C1COCCO1.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.O=C(O)O.O=C(O)O.O=C(O)O.[Ce+3].[Ce+3]>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[cH:8][c:9](-[c:10]2[c:11]([O:12][CH3:13])[cH:14][c:15]3[n:16][c:17]([Cl:18])[n:19][cH:20][c:21]3[cH:22]2)[cH:23]1\"},\"mapped_reaction_smiles\":\"Br[c:10]1[c:11]([O:12][CH3:13])[cH:14][c:15]2[n:16][c:17]([Cl:18])[n:19][cH:20][c:21]2[cH:22]1.OB(O)[c:9]1[cH:8][c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[cH:23]1>C1CCOC1.C1COCCO1.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.O=C(O)O.O=C(O)O.O=C(O)O.[Ce+3].[Ce+3]>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[cH:8][c:9](-[c:10]2[c:11]([O:12][CH3:13])[cH:14][c:15]3[n:16][c:17]([Cl:18])[n:19][cH:20][c:21]3[cH:22]2)[cH:23]1\"}",
"reactionStep": {
"id": "sa_8cce2da39e9fb24277059e22",
"reactionHash": "ddb6d7f04e132cc9febb96f9175502f839f3b290598571ee1b8908dcac60b493"
},
"children": [
{
"id": "3622",
"routeId": "sa_ff5e3a63068128931f9bb5f3",
"moleculeId": "sa_2edbef7100503d8a5fbcf64d",
"parentId": "3621",
"isLeaf": false,
"molecule": {
"id": "sa_2edbef7100503d8a5fbcf64d",
"inchikey": "DQXKBPJZXVQDEU-UHFFFAOYSA-N",
"smiles": "COc1cc2nc(Cl)ncc2cc1Br"
},
"smiles": "COc1cc2nc(Cl)ncc2cc1Br",
"reactionStepId": "sa_d653c125cb71b131e6c49d7e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150210694A1;0254;1727535\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:11].O[c:10]1[n:9][cH:8][c:7]2[cH:6][c:4]([Br:5])[c:3]([O:2][CH3:1])[cH:14][c:13]2[n:12]1>>[CH3:1][O:2][c:3]1[c:4]([Br:5])[cH:6][c:7]2[cH:8][n:9][c:10]([Cl:11])[n:12][c:13]2[cH:14]1\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:11].O[c:10]1[n:9][cH:8][c:7]2[cH:6][c:4]([Br:5])[c:3]([O:2][CH3:1])[cH:14][c:13]2[n:12]1>>[CH3:1][O:2][c:3]1[c:4]([Br:5])[cH:6][c:7]2[cH:8][n:9][c:10]([Cl:11])[n:12][c:13]2[cH:14]1\"}",
"reactionStep": {
"id": "sa_d653c125cb71b131e6c49d7e",
"reactionHash": "2c77b7ae224109ef4a7ddb2d2cea402bc896bf1eb7f448382156641b5d2d1cca"
},
"children": [
{
"id": "3623",
"routeId": "sa_ff5e3a63068128931f9bb5f3",
"moleculeId": "sa_973e739469c489a518fbb66d",
"parentId": "3622",
"isLeaf": false,
"molecule": {
"id": "sa_973e739469c489a518fbb66d",
"inchikey": "GTIKGUSZNROYHB-UHFFFAOYSA-N",
"smiles": "COc1cc2nc(O)ncc2cc1Br"
},
"smiles": "COc1cc2nc(O)ncc2cc1Br",
"reactionStepId": "sa_098cc757ed99dd6ac20f82e3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150210694A1;0252;1727534\",\"rsmi\":\"N[c:13]1[c:7]([CH:8]=O)[cH:6][c:4]([Br:5])[c:3]([O:2][CH3:1])[cH:14]1.[NH2:9][C:10](=[O:11])[NH2:12]>>[CH3:1][O:2][c:3]1[c:4]([Br:5])[cH:6][c:7]2[cH:8][n:9][c:10]([OH:11])[n:12][c:13]2[cH:14]1\"},\"mapped_reaction_smiles\":\"N[c:13]1[c:7]([CH:8]=O)[cH:6][c:4]([Br:5])[c:3]([O:2][CH3:1])[cH:14]1.[NH2:9][C:10](=[O:11])[NH2:12]>>[CH3:1][O:2][c:3]1[c:4]([Br:5])[cH:6][c:7]2[cH:8][n:9][c:10]([OH:11])[n:12][c:13]2[cH:14]1\"}",
"reactionStep": {
"id": "sa_098cc757ed99dd6ac20f82e3",
"reactionHash": "582b5c46cb84bba72b8663332c9ad7094f03827fb218c3e88620fbc89e644e41"
},
"children": [
{
"id": "3624",
"routeId": "sa_ff5e3a63068128931f9bb5f3",
"moleculeId": "sa_ea83fcca79510507d38ebd20",
"parentId": "3623",
"isLeaf": false,
"molecule": {
"id": "sa_ea83fcca79510507d38ebd20",
"inchikey": "ATTFTXASVWTGHE-UHFFFAOYSA-N",
"smiles": "COc1cc(N)c(C=O)cc1Br"
},
"smiles": "COc1cc(N)c(C=O)cc1Br",
"reactionStepId": "sa_44022d56538bf36baaf772f1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150210694A1;0250;1727533\",\"rsmi\":\"O=C1CCC(=O)N1[Br:12].[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]([CH:8]=[O:9])[cH:10][cH:11]1>ClCCl>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]([CH:8]=[O:9])[cH:10][c:11]1[Br:12]\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:12].[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]([CH:8]=[O:9])[cH:10][cH:11]1>ClCCl>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]([CH:8]=[O:9])[cH:10][c:11]1[Br:12]\"}",
"reactionStep": {
"id": "sa_44022d56538bf36baaf772f1",
"reactionHash": "975f5ab837c0fbeea96c31626fef43358c664273269f49748af56197abb02619"
},
"children": [
{
"id": "3625",
"routeId": "sa_ff5e3a63068128931f9bb5f3",
"moleculeId": "sa_343e4c5a0a6b7b65693612c4",
"parentId": "3624",
"isLeaf": false,
"molecule": {
"id": "sa_343e4c5a0a6b7b65693612c4",
"inchikey": "MFBXUCNGQIZZLN-UHFFFAOYSA-N",
"smiles": "COc1ccc(C=O)c(N)c1"
},
"smiles": "COc1ccc(C=O)c(N)c1",
"reactionStepId": "sa_ff1af938b853a88b455250a0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150210694A1;0248;1727532\",\"rsmi\":\"[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]([CH2:8][OH:9])[cH:10][cH:11]1>ClCCl.[Mn+2].[O-2]>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]([CH:8]=[O:9])[cH:10][cH:11]1\"},\"mapped_reaction_smiles\":\"[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]([CH2:8][OH:9])[cH:10][cH:11]1>ClCCl.[Mn+2].[O-2]>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]([CH:8]=[O:9])[cH:10][cH:11]1\"}",
"reactionStep": {
"id": "sa_ff1af938b853a88b455250a0",
"reactionHash": "67e3d1f1e223f52d9f9b5c69aa741fa7761295d73d87900dd48bf0156a09da57"
},
"children": [
{
"id": "3626",
"routeId": "sa_ff5e3a63068128931f9bb5f3",
"moleculeId": "sa_cb557d2bae8928d6b6a7622b",
"parentId": "3625",
"isLeaf": false,
"molecule": {
"id": "sa_cb557d2bae8928d6b6a7622b",
"inchikey": "AIRVVOQVTLZCFV-UHFFFAOYSA-N",
"smiles": "COc1ccc(CO)c(N)c1"
},
"smiles": "COc1ccc(CO)c(N)c1",
"reactionStepId": "sa_401befd8be592a31b1952174",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150210694A1;0246;1727531\",\"rsmi\":\"O=[C:8]([c:7]1[c:5]([NH2:6])[cH:4][c:3]([O:2][CH3:1])[cH:11][cH:10]1)[OH:9]>C1CCOC1.B>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]([CH2:8][OH:9])[cH:10][cH:11]1\"},\"mapped_reaction_smiles\":\"O=[C:8]([c:7]1[c:5]([NH2:6])[cH:4][c:3]([O:2][CH3:1])[cH:11][cH:10]1)[OH:9]>C1CCOC1.B>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[c:7]([CH2:8][OH:9])[cH:10][cH:11]1\"}",
"reactionStep": {
"id": "sa_401befd8be592a31b1952174",
"reactionHash": "ab28aedab21adedb90e03dd507a102260ef73c67909fd75fef34430c97afa2d6"
},
"children": [
{
"id": "3627",
"routeId": "sa_ff5e3a63068128931f9bb5f3",
"moleculeId": "sa_58c94ddf82fcae5e8c7f7a43",
"parentId": "3626",
"isLeaf": true,
"molecule": {
"id": "sa_58c94ddf82fcae5e8c7f7a43",
"inchikey": "HHNWXQCVWVVVQZ-UHFFFAOYSA-N",
"smiles": "COc1ccc(C(=O)O)c(N)c1"
},
"smiles": "COc1ccc(C(=O)O)c(N)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "3628",
"routeId": "sa_ff5e3a63068128931f9bb5f3",
"moleculeId": "sa_ccdcf23ac83e7a68bfa4f2e5",
"parentId": "3624",
"isLeaf": true,
"molecule": {
"id": "sa_ccdcf23ac83e7a68bfa4f2e5",
"inchikey": "PCLIMKBDDGJMGD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Br"
},
"smiles": "O=C1CCC(=O)N1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "3629",
"routeId": "sa_ff5e3a63068128931f9bb5f3",
"moleculeId": "sa_ff9c192eabf68896f2512671",
"parentId": "3623",
"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": "3630",
"routeId": "sa_ff5e3a63068128931f9bb5f3",
"moleculeId": "sa_312a7cd3d48a055e9bc98180",
"parentId": "3622",
"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": "3631",
"routeId": "sa_ff5e3a63068128931f9bb5f3",
"moleculeId": "sa_155e4e46d2daa798b9717a93",
"parentId": "3621",
"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": []
}
]
}
}