Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1ncnn1-c1ccc(C(=O)N(C2CC2)C2CCN(c3ncc(Cl)cn3)CC2)cc1
InChiKey
BIUCVWBWAWCQFO-UHFFFAOYSA-N
Route Signature
95eaaa6a8f401271e5d96809fa2389216a7215257055603e0a364a7f621ee8b0
Synthesis route with 4 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_529ef317ec5333305f475d12",
"signature": "95eaaa6a8f401271e5d96809fa2389216a7215257055603e0a364a7f621ee8b0",
"contentHash": "2be2f0a86ab2c9dc2d02742202ba011e62c2dd1944f710c9aa234974b1631c29",
"length": 4,
"isConvergent": false
},
"target": {
"id": "sa_48c369d79ebc2bc9b1865f5b",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-06735",
"moleculeId": "sa_711b1bfc23d8a60054ca2d34",
"smiles": "Cc1ncnn1-c1ccc(C(=O)N(C2CC2)C2CCN(c3ncc(Cl)cn3)CC2)cc1",
"routeLength": 4,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_711b1bfc23d8a60054ca2d34",
"inchikey": "BIUCVWBWAWCQFO-UHFFFAOYSA-N",
"smiles": "Cc1ncnn1-c1ccc(C(=O)N(C2CC2)C2CCN(c3ncc(Cl)cn3)CC2)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "8092",
"routeId": "sa_529ef317ec5333305f475d12",
"moleculeId": "sa_711b1bfc23d8a60054ca2d34",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_711b1bfc23d8a60054ca2d34",
"inchikey": "BIUCVWBWAWCQFO-UHFFFAOYSA-N",
"smiles": "Cc1ncnn1-c1ccc(C(=O)N(C2CC2)C2CCN(c3ncc(Cl)cn3)CC2)cc1"
},
"smiles": "Cc1ncnn1-c1ccc(C(=O)N(C2CC2)C2CCN(c3ncc(Cl)cn3)CC2)cc1",
"reactionStepId": "sa_2462b8e1f6fdbf93091f0a87",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08822471B2;0666;1505652\",\"rsmi\":\"O[C:11]([c:10]1[cH:9][cH:8][c:7](-[n:6]2[c:2]([CH3:1])[n:3][cH:4][n:5]2)[cH:31][cH:30]1)=[O:12].[NH:13]([CH:14]1[CH2:15][CH2:16]1)[CH:17]1[CH2:18][CH2:19][N:20]([c:21]2[n:22][cH:23][c:24]([Cl:25])[cH:26][n:27]2)[CH2:28][CH2:29]1>>[CH3:1][c:2]1[n:3][cH:4][n:5][n:6]1-[c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[N:13]([CH:14]2[CH2:15][CH2:16]2)[CH:17]2[CH2:18][CH2:19][N:20]([c:21]3[n:22][cH:23][c:24]([Cl:25])[cH:26][n:27]3)[CH2:28][CH2:29]2)[cH:30][cH:31]1\"},\"mapped_reaction_smiles\":\"O[C:11]([c:10]1[cH:9][cH:8][c:7](-[n:6]2[c:2]([CH3:1])[n:3][cH:4][n:5]2)[cH:31][cH:30]1)=[O:12].[NH:13]([CH:14]1[CH2:15][CH2:16]1)[CH:17]1[CH2:18][CH2:19][N:20]([c:21]2[n:22][cH:23][c:24]([Cl:25])[cH:26][n:27]2)[CH2:28][CH2:29]1>>[CH3:1][c:2]1[n:3][cH:4][n:5][n:6]1-[c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[N:13]([CH:14]2[CH2:15][CH2:16]2)[CH:17]2[CH2:18][CH2:19][N:20]([c:21]3[n:22][cH:23][c:24]([Cl:25])[cH:26][n:27]3)[CH2:28][CH2:29]2)[cH:30][cH:31]1\"}",
"reactionStep": {
"id": "sa_2462b8e1f6fdbf93091f0a87",
"reactionHash": "48ae2f359978e9cd7855e6ab562ef0d1c808f6b4bee5ac71c637695016ab707c"
},
"children": [
{
"id": "8093",
"routeId": "sa_529ef317ec5333305f475d12",
"moleculeId": "sa_746f20c0f39224f8d2105184",
"parentId": "8092",
"isLeaf": true,
"molecule": {
"id": "sa_746f20c0f39224f8d2105184",
"inchikey": "ATRRAGXPNKDBRA-UHFFFAOYSA-N",
"smiles": "Cc1ncnn1-c1ccc(C(=O)O)cc1"
},
"smiles": "Cc1ncnn1-c1ccc(C(=O)O)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "8094",
"routeId": "sa_529ef317ec5333305f475d12",
"moleculeId": "sa_1425d5f5620e5979b5ad3f1d",
"parentId": "8092",
"isLeaf": false,
"molecule": {
"id": "sa_1425d5f5620e5979b5ad3f1d",
"inchikey": "WJOHVNIWWBHNEN-UHFFFAOYSA-N",
"smiles": "Clc1cnc(N2CCC(NC3CC3)CC2)nc1"
},
"smiles": "Clc1cnc(N2CCC(NC3CC3)CC2)nc1",
"reactionStepId": "sa_314592da1f0937002dc259af",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08822471B2;0427;1505541\",\"rsmi\":\"O=[C:9]1[CH2:8][CH2:7][N:6]([c:5]2[n:4][cH:3][c:2]([Cl:1])[cH:17][n:16]2)[CH2:15][CH2:14]1.[NH2:10][CH:11]1[CH2:12][CH2:13]1>CC(=O)O.CC(=O)OB(OC(C)=O)OC(C)=O.ClCCl.[Na+]>[Cl:1][c:2]1[cH:3][n:4][c:5]([N:6]2[CH2:7][CH2:8][CH:9]([NH:10][CH:11]3[CH2:12][CH2:13]3)[CH2:14][CH2:15]2)[n:16][cH:17]1\"},\"mapped_reaction_smiles\":\"O=[C:9]1[CH2:8][CH2:7][N:6]([c:5]2[n:4][cH:3][c:2]([Cl:1])[cH:17][n:16]2)[CH2:15][CH2:14]1.[NH2:10][CH:11]1[CH2:12][CH2:13]1>CC(=O)O.CC(=O)OB(OC(C)=O)OC(C)=O.ClCCl.[Na+]>[Cl:1][c:2]1[cH:3][n:4][c:5]([N:6]2[CH2:7][CH2:8][CH:9]([NH:10][CH:11]3[CH2:12][CH2:13]3)[CH2:14][CH2:15]2)[n:16][cH:17]1\"}",
"reactionStep": {
"id": "sa_314592da1f0937002dc259af",
"reactionHash": "dee2fdb166e3b2303f06b096b67554806bafe65bce8567ddaf8be7578f64abe6"
},
"children": [
{
"id": "8095",
"routeId": "sa_529ef317ec5333305f475d12",
"moleculeId": "sa_a64528ef45f6f9f3682efae6",
"parentId": "8094",
"isLeaf": false,
"molecule": {
"id": "sa_a64528ef45f6f9f3682efae6",
"inchikey": "FESYZRGQGJLUGE-UHFFFAOYSA-N",
"smiles": "O=C1CCN(c2ncc(Cl)cn2)CC1"
},
"smiles": "O=C1CCN(c2ncc(Cl)cn2)CC1",
"reactionStepId": "sa_1018e32f06dae1e8eb628885",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08822471B2;0421;1505540\",\"rsmi\":\"C1C[O:1][C:2]2(O1)[CH2:3][CH2:4][N:5]([c:6]1[n:7][cH:8][c:9]([Cl:10])[cH:11][n:12]1)[CH2:13][CH2:14]2>Cl.[Na+].O>[O:1]=[C:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][cH:8][c:9]([Cl:10])[cH:11][n:12]2)[CH2:13][CH2:14]1\"},\"mapped_reaction_smiles\":\"C1C[O:1][C:2]2(O1)[CH2:3][CH2:4][N:5]([c:6]1[n:7][cH:8][c:9]([Cl:10])[cH:11][n:12]1)[CH2:13][CH2:14]2>Cl.[Na+].O>[O:1]=[C:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][cH:8][c:9]([Cl:10])[cH:11][n:12]2)[CH2:13][CH2:14]1\"}",
"reactionStep": {
"id": "sa_1018e32f06dae1e8eb628885",
"reactionHash": "3f380e3be453b7246503ca2b00536a391aa6af3d54e98596043d02ecb4a9f7e8"
},
"children": [
{
"id": "8096",
"routeId": "sa_529ef317ec5333305f475d12",
"moleculeId": "sa_ca02cfbbe503e340cb307299",
"parentId": "8095",
"isLeaf": false,
"molecule": {
"id": "sa_ca02cfbbe503e340cb307299",
"inchikey": "UUTBEEDHYGODHX-UHFFFAOYSA-N",
"smiles": "Clc1cnc(N2CCC3(CC2)OCCO3)nc1"
},
"smiles": "Clc1cnc(N2CCC3(CC2)OCCO3)nc1",
"reactionStepId": "sa_47f354feeb798d5eeb269260",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08822471B2;0415;1505537\",\"rsmi\":\"Cl[c:5]1[n:4][cH:3][c:2]([Cl:1])[cH:17][n:16]1.[NH:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[O:12][CH2:13][CH2:14][O:15]2>C1COCCO1.CCN(CC)CC.CN(C)C=O>[Cl:1][c:2]1[cH:3][n:4][c:5]([N:6]2[CH2:7][CH2:8][C:9]3([CH2:10][CH2:11]2)[O:12][CH2:13][CH2:14][O:15]3)[n:16][cH:17]1\"},\"mapped_reaction_smiles\":\"Cl[c:5]1[n:4][cH:3][c:2]([Cl:1])[cH:17][n:16]1.[NH:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[O:12][CH2:13][CH2:14][O:15]2>C1COCCO1.CCN(CC)CC.CN(C)C=O>[Cl:1][c:2]1[cH:3][n:4][c:5]([N:6]2[CH2:7][CH2:8][C:9]3([CH2:10][CH2:11]2)[O:12][CH2:13][CH2:14][O:15]3)[n:16][cH:17]1\"}",
"reactionStep": {
"id": "sa_47f354feeb798d5eeb269260",
"reactionHash": "41196341381b35aa45df69a8228d113099fa00bb296d686eb5699b75d19c5327"
},
"children": [
{
"id": "8097",
"routeId": "sa_529ef317ec5333305f475d12",
"moleculeId": "sa_5aaf794597859c28e22a6d55",
"parentId": "8096",
"isLeaf": true,
"molecule": {
"id": "sa_5aaf794597859c28e22a6d55",
"inchikey": "CEJAHXLRNZJPQH-UHFFFAOYSA-N",
"smiles": "Clc1cnc(Cl)nc1"
},
"smiles": "Clc1cnc(Cl)nc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "8098",
"routeId": "sa_529ef317ec5333305f475d12",
"moleculeId": "sa_6a4cb5a22f72185a4044e056",
"parentId": "8096",
"isLeaf": true,
"molecule": {
"id": "sa_6a4cb5a22f72185a4044e056",
"inchikey": "KPKNTUUIEVXMOH-UHFFFAOYSA-N",
"smiles": "C1CC2(CCN1)OCCO2"
},
"smiles": "C1CC2(CCN1)OCCO2",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "8099",
"routeId": "sa_529ef317ec5333305f475d12",
"moleculeId": "sa_f7b02628c6b00fb9d50a0f6c",
"parentId": "8094",
"isLeaf": true,
"molecule": {
"id": "sa_f7b02628c6b00fb9d50a0f6c",
"inchikey": "HTJDQJBWANPRPF-UHFFFAOYSA-N",
"smiles": "NC1CC1"
},
"smiles": "NC1CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}