Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1cc(C=C2CCC(N)CC2)cc(Oc2ccc(C(F)(F)F)cn2)c1
InChiKey
YBBPKAADFHMASI-UHFFFAOYSA-N
Route Signature
e4032c361c20d5c2580c24bcaa4530ad56c029619fe065e6d2f6721df04dbfb4
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_a6b387f410dea1e49383343d",
"signature": "e4032c361c20d5c2580c24bcaa4530ad56c029619fe065e6d2f6721df04dbfb4",
"contentHash": "862951563b78d983f050bf77c5d2bfe6c4eb544db94200bc166ec2b7b89ee44a",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_03dc433b45d22c225fa9eea5",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00160",
"moleculeId": "sa_6e7dab7dcffc68d94fbaab62",
"smiles": "Cc1cc(C=C2CCC(N)CC2)cc(Oc2ccc(C(F)(F)F)cn2)c1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_6e7dab7dcffc68d94fbaab62",
"inchikey": "YBBPKAADFHMASI-UHFFFAOYSA-N",
"smiles": "Cc1cc(C=C2CCC(N)CC2)cc(Oc2ccc(C(F)(F)F)cn2)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "3544",
"routeId": "sa_a6b387f410dea1e49383343d",
"moleculeId": "sa_6e7dab7dcffc68d94fbaab62",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_6e7dab7dcffc68d94fbaab62",
"inchikey": "YBBPKAADFHMASI-UHFFFAOYSA-N",
"smiles": "Cc1cc(C=C2CCC(N)CC2)cc(Oc2ccc(C(F)(F)F)cn2)c1"
},
"smiles": "Cc1cc(C=C2CCC(N)CC2)cc(Oc2ccc(C(F)(F)F)cn2)c1",
"reactionStepId": "sa_63b0a07f0475e3a4bc612a8b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150065464A1;0243;1658816\",\"rsmi\":\"O=[C:22]1[CH2:21][CH2:20][C:19](=[CH:18][c:17]2[cH:16][c:4]([O:5][c:6]3[n:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]3)[cH:3][c:2]([CH3:1])[cH:26]2)[CH2:25][CH2:24]1.[NH3:23]>CC(C)O.CC(C)O.CC(C)O.CC(C)O.CCO.B.[Na+].[Ti+4]>[CH3:1][c:2]1[cH:3][c:4]([O:5][c:6]2[n:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][c:17]([CH:18]=[C:19]2[CH2:20][CH2:21][CH:22]([NH2:23])[CH2:24][CH2:25]2)[cH:26]1\"},\"mapped_reaction_smiles\":\"O=[C:22]1[CH2:21][CH2:20][C:19](=[CH:18][c:17]2[cH:16][c:4]([O:5][c:6]3[n:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]3)[cH:3][c:2]([CH3:1])[cH:26]2)[CH2:25][CH2:24]1.[NH3:23]>CC(C)O.CC(C)O.CC(C)O.CC(C)O.CCO.B.[Na+].[Ti+4]>[CH3:1][c:2]1[cH:3][c:4]([O:5][c:6]2[n:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][c:17]([CH:18]=[C:19]2[CH2:20][CH2:21][CH:22]([NH2:23])[CH2:24][CH2:25]2)[cH:26]1\"}",
"reactionStep": {
"id": "sa_63b0a07f0475e3a4bc612a8b",
"reactionHash": "db2156ed44ba6cc60eca334bb8aa5012a6e9c8f15500849f8560fd8360cdff20"
},
"children": [
{
"id": "3545",
"routeId": "sa_a6b387f410dea1e49383343d",
"moleculeId": "sa_a3dc9a2dc9fca1de561fad12",
"parentId": "3544",
"isLeaf": false,
"molecule": {
"id": "sa_a3dc9a2dc9fca1de561fad12",
"inchikey": "IDRDYVXTULBCQA-UHFFFAOYSA-N",
"smiles": "Cc1cc(C=C2CCC(=O)CC2)cc(Oc2ccc(C(F)(F)F)cn2)c1"
},
"smiles": "Cc1cc(C=C2CCC(=O)CC2)cc(Oc2ccc(C(F)(F)F)cn2)c1",
"reactionStepId": "sa_482962946d838877cc886c98",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150065464A1;0241;1658815\",\"rsmi\":\"C1C[O:23][C:22]2(O1)[CH2:21][CH2:20][C:19](=[CH:18][c:17]1[cH:16][c:4]([O:5][c:6]3[n:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]3)[cH:3][c:2]([CH3:1])[cH:26]1)[CH2:25][CH2:24]2>CC(C)=O.Cl>[CH3:1][c:2]1[cH:3][c:4]([O:5][c:6]2[n:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][c:17]([CH:18]=[C:19]2[CH2:20][CH2:21][C:22](=[O:23])[CH2:24][CH2:25]2)[cH:26]1\"},\"mapped_reaction_smiles\":\"C1C[O:23][C:22]2(O1)[CH2:21][CH2:20][C:19](=[CH:18][c:17]1[cH:16][c:4]([O:5][c:6]3[n:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]3)[cH:3][c:2]([CH3:1])[cH:26]1)[CH2:25][CH2:24]2>CC(C)=O.Cl>[CH3:1][c:2]1[cH:3][c:4]([O:5][c:6]2[n:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][c:17]([CH:18]=[C:19]2[CH2:20][CH2:21][C:22](=[O:23])[CH2:24][CH2:25]2)[cH:26]1\"}",
"reactionStep": {
"id": "sa_482962946d838877cc886c98",
"reactionHash": "9e21efd09bdbfab4e0d35f798c3012d4c8b78f8e83f321ffb06172a2edb80c84"
},
"children": [
{
"id": "3546",
"routeId": "sa_a6b387f410dea1e49383343d",
"moleculeId": "sa_829ae88c60a7cf5bfe9472f4",
"parentId": "3545",
"isLeaf": false,
"molecule": {
"id": "sa_829ae88c60a7cf5bfe9472f4",
"inchikey": "OAZZXWOUIOQPMY-UHFFFAOYSA-N",
"smiles": "Cc1cc(C=C2CCC3(CC2)OCCO3)cc(Oc2ccc(C(F)(F)F)cn2)c1"
},
"smiles": "Cc1cc(C=C2CCC3(CC2)OCCO3)cc(Oc2ccc(C(F)(F)F)cn2)c1",
"reactionStepId": "sa_bb023e83255b029494c877d1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150065464A1;0239;1658814\",\"rsmi\":\"CCOP(=O)(OCC)[CH2:18][c:17]1[cH:16][c:4]([O:5][c:6]2[n:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:3][c:2]([CH3:1])[cH:29]1.O=[C:19]1[CH2:20][CH2:21][C:22]2([CH2:23][CH2:24]1)[O:25][CH2:26][CH2:27][O:28]2>C1CCOC1.[HH].[Na+]>[CH3:1][c:2]1[cH:3][c:4]([O:5][c:6]2[n:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][c:17]([CH:18]=[C:19]2[CH2:20][CH2:21][C:22]3([CH2:23][CH2:24]2)[O:25][CH2:26][CH2:27][O:28]3)[cH:29]1\"},\"mapped_reaction_smiles\":\"CCOP(=O)(OCC)[CH2:18][c:17]1[cH:16][c:4]([O:5][c:6]2[n:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:3][c:2]([CH3:1])[cH:29]1.O=[C:19]1[CH2:20][CH2:21][C:22]2([CH2:23][CH2:24]1)[O:25][CH2:26][CH2:27][O:28]2>C1CCOC1.[HH].[Na+]>[CH3:1][c:2]1[cH:3][c:4]([O:5][c:6]2[n:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][c:17]([CH:18]=[C:19]2[CH2:20][CH2:21][C:22]3([CH2:23][CH2:24]2)[O:25][CH2:26][CH2:27][O:28]3)[cH:29]1\"}",
"reactionStep": {
"id": "sa_bb023e83255b029494c877d1",
"reactionHash": "d5720ad6de54fc572dedda346a071d28e5ef1443580e78894e11c2d9b49c8974"
},
"children": [
{
"id": "3547",
"routeId": "sa_a6b387f410dea1e49383343d",
"moleculeId": "sa_aef998f3e5c07f5b38738ee3",
"parentId": "3546",
"isLeaf": false,
"molecule": {
"id": "sa_aef998f3e5c07f5b38738ee3",
"inchikey": "UEIJIPGIOKZRGT-UHFFFAOYSA-N",
"smiles": "CCOP(=O)(Cc1cc(C)cc(Oc2ccc(C(F)(F)F)cn2)c1)OCC"
},
"smiles": "CCOP(=O)(Cc1cc(C)cc(Oc2ccc(C(F)(F)F)cn2)c1)OCC",
"reactionStepId": "sa_d8e1b3db27f138b4c48463b9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150065464A1;0237;1658813\",\"rsmi\":\"CC[O:5][P:4]([O:3][CH2:2][CH3:1])[O:25][CH2:26][CH3:27].Cl[CH2:6][c:7]1[cH:8][c:9]([CH3:10])[cH:11][c:12]([O:13][c:14]2[n:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22][cH:23]2)[cH:24]1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][c:7]1[cH:8][c:9]([CH3:10])[cH:11][c:12]([O:13][c:14]2[n:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22][cH:23]2)[cH:24]1)[O:25][CH2:26][CH3:27]\"},\"mapped_reaction_smiles\":\"CC[O:5][P:4]([O:3][CH2:2][CH3:1])[O:25][CH2:26][CH3:27].Cl[CH2:6][c:7]1[cH:8][c:9]([CH3:10])[cH:11][c:12]([O:13][c:14]2[n:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22][cH:23]2)[cH:24]1>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][c:7]1[cH:8][c:9]([CH3:10])[cH:11][c:12]([O:13][c:14]2[n:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22][cH:23]2)[cH:24]1)[O:25][CH2:26][CH3:27]\"}",
"reactionStep": {
"id": "sa_d8e1b3db27f138b4c48463b9",
"reactionHash": "6ae2272407ddd97224c6aea110a3da0c6f73a1b5d9620e7b01551c64ba65dda0"
},
"children": [
{
"id": "3548",
"routeId": "sa_a6b387f410dea1e49383343d",
"moleculeId": "sa_89f1484a9c859438eeae3e6a",
"parentId": "3547",
"isLeaf": true,
"molecule": {
"id": "sa_89f1484a9c859438eeae3e6a",
"inchikey": "BDZBKCUKTQZUTL-UHFFFAOYSA-N",
"smiles": "CCOP(OCC)OCC"
},
"smiles": "CCOP(OCC)OCC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3549",
"routeId": "sa_a6b387f410dea1e49383343d",
"moleculeId": "sa_778e2201698171276ef343bd",
"parentId": "3547",
"isLeaf": false,
"molecule": {
"id": "sa_778e2201698171276ef343bd",
"inchikey": "GZHLRYQIMYOMRO-UHFFFAOYSA-N",
"smiles": "Cc1cc(CCl)cc(Oc2ccc(C(F)(F)F)cn2)c1"
},
"smiles": "Cc1cc(CCl)cc(Oc2ccc(C(F)(F)F)cn2)c1",
"reactionStepId": "sa_d4929020f5578ac2b47ae604",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150065464A1;0235;1658812\",\"rsmi\":\"ClC[Cl:19].O[CH2:18][c:17]1[cH:16][c:4]([O:5][c:6]2[n:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:3][c:2]([CH3:1])[cH:20]1>O=S(Cl)Cl>[CH3:1][c:2]1[cH:3][c:4]([O:5][c:6]2[n:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][c:17]([CH2:18][Cl:19])[cH:20]1\"},\"mapped_reaction_smiles\":\"ClC[Cl:19].O[CH2:18][c:17]1[cH:16][c:4]([O:5][c:6]2[n:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:3][c:2]([CH3:1])[cH:20]1>O=S(Cl)Cl>[CH3:1][c:2]1[cH:3][c:4]([O:5][c:6]2[n:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][c:17]([CH2:18][Cl:19])[cH:20]1\"}",
"reactionStep": {
"id": "sa_d4929020f5578ac2b47ae604",
"reactionHash": "559f388c220c16b61c7cfb5157217d9d0b1fe6a017c40a27cf400b47630d3a4f"
},
"children": [
{
"id": "3550",
"routeId": "sa_a6b387f410dea1e49383343d",
"moleculeId": "sa_29e8346b25e0a4286bee0257",
"parentId": "3549",
"isLeaf": false,
"molecule": {
"id": "sa_29e8346b25e0a4286bee0257",
"inchikey": "PBBKKUUWHARRGX-UHFFFAOYSA-N",
"smiles": "Cc1cc(CO)cc(Oc2ccc(C(F)(F)F)cn2)c1"
},
"smiles": "Cc1cc(CO)cc(Oc2ccc(C(F)(F)F)cn2)c1",
"reactionStepId": "sa_e681030b0d076fa3d8ced98c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150065464A1;0233;1658811\",\"rsmi\":\"Cl[c:6]1[n:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]1.[CH3:1][c:2]1[cH:3][c:4]([OH:5])[cH:16][c:17]([CH2:18][OH:19])[cH:20]1>CN(C)C=O.O.O=C(O)O.[K+].[K+]>[CH3:1][c:2]1[cH:3][c:4]([O:5][c:6]2[n:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][c:17]([CH2:18][OH:19])[cH:20]1\"},\"mapped_reaction_smiles\":\"Cl[c:6]1[n:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]1.[CH3:1][c:2]1[cH:3][c:4]([OH:5])[cH:16][c:17]([CH2:18][OH:19])[cH:20]1>CN(C)C=O.O.O=C(O)O.[K+].[K+]>[CH3:1][c:2]1[cH:3][c:4]([O:5][c:6]2[n:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][c:17]([CH2:18][OH:19])[cH:20]1\"}",
"reactionStep": {
"id": "sa_e681030b0d076fa3d8ced98c",
"reactionHash": "4e35d9798145244b881faedc481c6b5b0ca1a2877df568e29a2446014bc94f3e"
},
"children": [
{
"id": "3551",
"routeId": "sa_a6b387f410dea1e49383343d",
"moleculeId": "sa_40e1997a4fa4e986554920e2",
"parentId": "3550",
"isLeaf": true,
"molecule": {
"id": "sa_40e1997a4fa4e986554920e2",
"inchikey": "JFZJMSDDOOAOIV-UHFFFAOYSA-N",
"smiles": "FC(F)(F)c1ccc(Cl)nc1"
},
"smiles": "FC(F)(F)c1ccc(Cl)nc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3552",
"routeId": "sa_a6b387f410dea1e49383343d",
"moleculeId": "sa_72e55d61f02118e5ef726692",
"parentId": "3550",
"isLeaf": true,
"molecule": {
"id": "sa_72e55d61f02118e5ef726692",
"inchikey": "SDJQWNMVKBEBSJ-UHFFFAOYSA-N",
"smiles": "Cc1cc(O)cc(CO)c1"
},
"smiles": "Cc1cc(O)cc(CO)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "3553",
"routeId": "sa_a6b387f410dea1e49383343d",
"moleculeId": "sa_dc8cb1645d1f4dafe3621d07",
"parentId": "3549",
"isLeaf": true,
"molecule": {
"id": "sa_dc8cb1645d1f4dafe3621d07",
"inchikey": "YMWUJEATGCHHMB-UHFFFAOYSA-N",
"smiles": "ClCCl"
},
"smiles": "ClCCl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "3554",
"routeId": "sa_a6b387f410dea1e49383343d",
"moleculeId": "sa_1131b630e013fb58ee26d7cf",
"parentId": "3546",
"isLeaf": true,
"molecule": {
"id": "sa_1131b630e013fb58ee26d7cf",
"inchikey": "VKRKCBWIVLSRBJ-UHFFFAOYSA-N",
"smiles": "O=C1CCC2(CC1)OCCO2"
},
"smiles": "O=C1CCC2(CC1)OCCO2",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "3555",
"routeId": "sa_a6b387f410dea1e49383343d",
"moleculeId": "sa_c9679fdd876f32f86b77fb69",
"parentId": "3544",
"isLeaf": true,
"molecule": {
"id": "sa_c9679fdd876f32f86b77fb69",
"inchikey": "QGZKDVFQNNGYKY-UHFFFAOYSA-N",
"smiles": "N"
},
"smiles": "N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}