Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN(C)CCNc1ccc(Nc2c(C(=O)C3CC3)cnc3ccc(-c4cc(F)c(O)c(Cl)c4)cc23)cn1
InChiKey
LHVJVPSGSVDRBP-UHFFFAOYSA-N
Route Signature
865638c933f4ca09bb76dfaf994131719d61f15e7d7ca4d0df160b6f33370e6a
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_a6052128c1071e143a15aee3",
"signature": "865638c933f4ca09bb76dfaf994131719d61f15e7d7ca4d0df160b6f33370e6a",
"contentHash": "5128f62f635fd700f1adc75199c1622a414f81af409c204685dac39c3e7e350c",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_4b293535b1003de247efdc8d",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01136",
"moleculeId": "sa_903df57e982fe0390dc98c03",
"smiles": "CN(C)CCNc1ccc(Nc2c(C(=O)C3CC3)cnc3ccc(-c4cc(F)c(O)c(Cl)c4)cc23)cn1",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_903df57e982fe0390dc98c03",
"inchikey": "LHVJVPSGSVDRBP-UHFFFAOYSA-N",
"smiles": "CN(C)CCNc1ccc(Nc2c(C(=O)C3CC3)cnc3ccc(-c4cc(F)c(O)c(Cl)c4)cc23)cn1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9960",
"routeId": "sa_a6052128c1071e143a15aee3",
"moleculeId": "sa_903df57e982fe0390dc98c03",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_903df57e982fe0390dc98c03",
"inchikey": "LHVJVPSGSVDRBP-UHFFFAOYSA-N",
"smiles": "CN(C)CCNc1ccc(Nc2c(C(=O)C3CC3)cnc3ccc(-c4cc(F)c(O)c(Cl)c4)cc23)cn1"
},
"smiles": "CN(C)CCNc1ccc(Nc2c(C(=O)C3CC3)cnc3ccc(-c4cc(F)c(O)c(Cl)c4)cc23)cn1",
"reactionStepId": "sa_b95eae42f03423184e425145",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09120749B2;1876;1661018\",\"rsmi\":\"Br[c:24]1[cH:23][cH:22][c:21]2[n:20][cH:19][c:13]([C:14](=[O:15])[CH:16]3[CH2:17][CH2:18]3)[c:12]([NH:11][c:10]3[cH:9][cH:8][c:7]([NH:6][CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[n:37][cH:36]3)[c:35]2[cH:34]1.CC1(C)OB([c:25]2[cH:26][c:27]([Cl:28])[c:29]([OH:30])[c:31]([F:32])[cH:33]2)OC1(C)C>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH:6][c:7]1[cH:8][cH:9][c:10]([NH:11][c:12]2[c:13]([C:14](=[O:15])[CH:16]3[CH2:17][CH2:18]3)[cH:19][n:20][c:21]3[cH:22][cH:23][c:24](-[c:25]4[cH:26][c:27]([Cl:28])[c:29]([OH:30])[c:31]([F:32])[cH:33]4)[cH:34][c:35]23)[cH:36][n:37]1\"},\"mapped_reaction_smiles\":\"Br[c:24]1[cH:23][cH:22][c:21]2[n:20][cH:19][c:13]([C:14](=[O:15])[CH:16]3[CH2:17][CH2:18]3)[c:12]([NH:11][c:10]3[cH:9][cH:8][c:7]([NH:6][CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[n:37][cH:36]3)[c:35]2[cH:34]1.CC1(C)OB([c:25]2[cH:26][c:27]([Cl:28])[c:29]([OH:30])[c:31]([F:32])[cH:33]2)OC1(C)C>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH:6][c:7]1[cH:8][cH:9][c:10]([NH:11][c:12]2[c:13]([C:14](=[O:15])[CH:16]3[CH2:17][CH2:18]3)[cH:19][n:20][c:21]3[cH:22][cH:23][c:24](-[c:25]4[cH:26][c:27]([Cl:28])[c:29]([OH:30])[c:31]([F:32])[cH:33]4)[cH:34][c:35]23)[cH:36][n:37]1\"}",
"reactionStep": {
"id": "sa_b95eae42f03423184e425145",
"reactionHash": "21eeb513910528f9583b2a2cfbccf8d11d930368a8ca33bc861e66a5aae639fe"
},
"children": [
{
"id": "9961",
"routeId": "sa_a6052128c1071e143a15aee3",
"moleculeId": "sa_095ff5b6c57e954f2a86ebe0",
"parentId": "9960",
"isLeaf": false,
"molecule": {
"id": "sa_095ff5b6c57e954f2a86ebe0",
"inchikey": "CEBBVCKDURRDBD-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2cc(F)c(O)c(Cl)c2)OC1(C)C"
},
"smiles": "CC1(C)OB(c2cc(F)c(O)c(Cl)c2)OC1(C)C",
"reactionStepId": "sa_e038f446060c2beb55ee1190",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09120749B2;1573;1660784\",\"rsmi\":\"Br[c:6]1[cH:7][c:8]([Cl:9])[c:10]([OH:11])[c:12]([F:13])[cH:14]1.CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:16]([CH3:17])([CH3:18])[O:15]2)OC1(C)C>>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][c:8]([Cl:9])[c:10]([OH:11])[c:12]([F:13])[cH:14]2)[O:15][C:16]1([CH3:17])[CH3:18]\"},\"mapped_reaction_smiles\":\"Br[c:6]1[cH:7][c:8]([Cl:9])[c:10]([OH:11])[c:12]([F:13])[cH:14]1.CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:16]([CH3:17])([CH3:18])[O:15]2)OC1(C)C>>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][c:8]([Cl:9])[c:10]([OH:11])[c:12]([F:13])[cH:14]2)[O:15][C:16]1([CH3:17])[CH3:18]\"}",
"reactionStep": {
"id": "sa_e038f446060c2beb55ee1190",
"reactionHash": "9fc687c6ecdf0aaab1735f185845e24a3b9ebdda4ca91aa565f21a4f99f71275"
},
"children": [
{
"id": "9962",
"routeId": "sa_a6052128c1071e143a15aee3",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "9961",
"isLeaf": true,
"molecule": {
"id": "sa_e6c301388ac142801d4af5a2",
"inchikey": "IPWKHHSGDUIRAH-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C"
},
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9963",
"routeId": "sa_a6052128c1071e143a15aee3",
"moleculeId": "sa_3a826975ad0458a2936a42bb",
"parentId": "9961",
"isLeaf": true,
"molecule": {
"id": "sa_3a826975ad0458a2936a42bb",
"inchikey": "QEYONPKSDTUPAX-UHFFFAOYSA-N",
"smiles": "Oc1c(F)cc(Br)cc1Cl"
},
"smiles": "Oc1c(F)cc(Br)cc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "9964",
"routeId": "sa_a6052128c1071e143a15aee3",
"moleculeId": "sa_c38ca57d6681e0fac5103e76",
"parentId": "9960",
"isLeaf": false,
"molecule": {
"id": "sa_c38ca57d6681e0fac5103e76",
"inchikey": "ZYNHMERNZXQKKH-UHFFFAOYSA-N",
"smiles": "CN(C)CCNc1ccc(Nc2c(C(=O)C3CC3)cnc3ccc(Br)cc23)cn1"
},
"smiles": "CN(C)CCNc1ccc(Nc2c(C(=O)C3CC3)cnc3ccc(Br)cc23)cn1",
"reactionStepId": "sa_519a52479562601ba4d84ba9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09120749B2;1518;1660730\",\"rsmi\":\"Cl[c:12]1[c:13]([C:14](=[O:15])[CH:16]2[CH2:17][CH2:18]2)[cH:19][n:20][c:21]2[cH:22][cH:23][c:24]([Br:25])[cH:26][c:27]12.[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH:6][c:7]1[cH:8][cH:9][c:10]([NH2:11])[cH:28][n:29]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH:6][c:7]1[cH:8][cH:9][c:10]([NH:11][c:12]2[c:13]([C:14](=[O:15])[CH:16]3[CH2:17][CH2:18]3)[cH:19][n:20][c:21]3[cH:22][cH:23][c:24]([Br:25])[cH:26][c:27]23)[cH:28][n:29]1\"},\"mapped_reaction_smiles\":\"Cl[c:12]1[c:13]([C:14](=[O:15])[CH:16]2[CH2:17][CH2:18]2)[cH:19][n:20][c:21]2[cH:22][cH:23][c:24]([Br:25])[cH:26][c:27]12.[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH:6][c:7]1[cH:8][cH:9][c:10]([NH2:11])[cH:28][n:29]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH:6][c:7]1[cH:8][cH:9][c:10]([NH:11][c:12]2[c:13]([C:14](=[O:15])[CH:16]3[CH2:17][CH2:18]3)[cH:19][n:20][c:21]3[cH:22][cH:23][c:24]([Br:25])[cH:26][c:27]23)[cH:28][n:29]1\"}",
"reactionStep": {
"id": "sa_519a52479562601ba4d84ba9",
"reactionHash": "18b7f5ff63aec8b667468b151580d0e56710a58640a7578c722dde6415da76a4"
},
"children": [
{
"id": "9965",
"routeId": "sa_a6052128c1071e143a15aee3",
"moleculeId": "sa_3d802d4b22c8f0244dc70e57",
"parentId": "9964",
"isLeaf": false,
"molecule": {
"id": "sa_3d802d4b22c8f0244dc70e57",
"inchikey": "AASLFZACKQKOAQ-UHFFFAOYSA-N",
"smiles": "CN(C)CCNc1ccc(N)cn1"
},
"smiles": "CN(C)CCNc1ccc(N)cn1",
"reactionStepId": "sa_2459cae5ddb7686ce3723b53",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09120749B2;1497;1660713\",\"rsmi\":\"O=[N+:11]([O-])[c:10]1[cH:9][n:8][c:7](Cl)[cH:13][cH:12]1.[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH2:6]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH:6][c:7]1[n:8][cH:9][c:10]([NH2:11])[cH:12][cH:13]1\"},\"mapped_reaction_smiles\":\"O=[N+:11]([O-])[c:10]1[cH:9][n:8][c:7](Cl)[cH:13][cH:12]1.[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH2:6]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH:6][c:7]1[n:8][cH:9][c:10]([NH2:11])[cH:12][cH:13]1\"}",
"reactionStep": {
"id": "sa_2459cae5ddb7686ce3723b53",
"reactionHash": "95c22c1e2a53fff800a1b22f0daeecb40c63474ea22a4bd1c64bfb5c6a3d9795"
},
"children": [
{
"id": "9966",
"routeId": "sa_a6052128c1071e143a15aee3",
"moleculeId": "sa_d7d7d7f9de574373042b07fa",
"parentId": "9965",
"isLeaf": true,
"molecule": {
"id": "sa_d7d7d7f9de574373042b07fa",
"inchikey": "BAZVFQBTJPBRTJ-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccc(Cl)nc1"
},
"smiles": "O=[N+]([O-])c1ccc(Cl)nc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9967",
"routeId": "sa_a6052128c1071e143a15aee3",
"moleculeId": "sa_f26b74c4ec28c4c03fe2dbe3",
"parentId": "9965",
"isLeaf": true,
"molecule": {
"id": "sa_f26b74c4ec28c4c03fe2dbe3",
"inchikey": "DILRJUIACXKSQE-UHFFFAOYSA-N",
"smiles": "CN(C)CCN"
},
"smiles": "CN(C)CCN",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "9968",
"routeId": "sa_a6052128c1071e143a15aee3",
"moleculeId": "sa_694d1c0999722415bfea5cd4",
"parentId": "9964",
"isLeaf": false,
"molecule": {
"id": "sa_694d1c0999722415bfea5cd4",
"inchikey": "SKMHXQZCLNKWIE-UHFFFAOYSA-N",
"smiles": "O=C(c1cnc2ccc(Br)cc2c1Cl)C1CC1"
},
"smiles": "O=C(c1cnc2ccc(Br)cc2c1Cl)C1CC1",
"reactionStepId": "sa_1e4ad053684bebfaa2d06d26",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09120749B2;1341;1660605\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:5].O[c:4]1[c:3]([C:2](=[O:1])[CH:15]2[CH2:16][CH2:17]2)[cH:14][n:13][c:12]2[c:6]1[cH:7][c:8]([Br:9])[cH:10][cH:11]2>>[O:1]=[C:2]([c:3]1[c:4]([Cl:5])[c:6]2[cH:7][c:8]([Br:9])[cH:10][cH:11][c:12]2[n:13][cH:14]1)[CH:15]1[CH2:16][CH2:17]1\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:5].O[c:4]1[c:3]([C:2](=[O:1])[CH:15]2[CH2:16][CH2:17]2)[cH:14][n:13][c:12]2[c:6]1[cH:7][c:8]([Br:9])[cH:10][cH:11]2>>[O:1]=[C:2]([c:3]1[c:4]([Cl:5])[c:6]2[cH:7][c:8]([Br:9])[cH:10][cH:11][c:12]2[n:13][cH:14]1)[CH:15]1[CH2:16][CH2:17]1\"}",
"reactionStep": {
"id": "sa_1e4ad053684bebfaa2d06d26",
"reactionHash": "4a12395483b1e7bbfada77b88b03a7c977ed6151f53bebfa34ffae1624eed5f4"
},
"children": [
{
"id": "9969",
"routeId": "sa_a6052128c1071e143a15aee3",
"moleculeId": "sa_bd9d9fa67d12b04e3c6586b3",
"parentId": "9968",
"isLeaf": true,
"molecule": {
"id": "sa_bd9d9fa67d12b04e3c6586b3",
"inchikey": "MJQSRPAZUHCLKN-UHFFFAOYSA-N",
"smiles": "O=C(c1cnc2ccc(Br)cc2c1O)C1CC1"
},
"smiles": "O=C(c1cnc2ccc(Br)cc2c1O)C1CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9970",
"routeId": "sa_a6052128c1071e143a15aee3",
"moleculeId": "sa_312a7cd3d48a055e9bc98180",
"parentId": "9968",
"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": []
}
]
}
]
}
]
}
}