Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1ccc(C2=C(c3ccc(OCc4nc5ccccn5c4Cl)cc3)C(=O)C(C)(C)O2)cc1
InChiKey
YMEOBDUNHNWSDE-UHFFFAOYSA-N
Route Signature
f5a20c87c48b071e7859c4a13dddefe5ef84a3e3397f3c4e9cfc65d8e0297704
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_98b0503787ed41cc89bac9e2",
"signature": "f5a20c87c48b071e7859c4a13dddefe5ef84a3e3397f3c4e9cfc65d8e0297704",
"contentHash": "8b9745bfbf15fe23a6ac02ee21ba75ae0e790a15322fe9be892adb89b4ec0521",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_2d5edfea27868c014dc2bd8f",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-05062",
"moleculeId": "sa_5b38d168f18f92afe8a99e30",
"smiles": "COc1ccc(C2=C(c3ccc(OCc4nc5ccccn5c4Cl)cc3)C(=O)C(C)(C)O2)cc1",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_5b38d168f18f92afe8a99e30",
"inchikey": "YMEOBDUNHNWSDE-UHFFFAOYSA-N",
"smiles": "COc1ccc(C2=C(c3ccc(OCc4nc5ccccn5c4Cl)cc3)C(=O)C(C)(C)O2)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "11345",
"routeId": "sa_98b0503787ed41cc89bac9e2",
"moleculeId": "sa_5b38d168f18f92afe8a99e30",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_5b38d168f18f92afe8a99e30",
"inchikey": "YMEOBDUNHNWSDE-UHFFFAOYSA-N",
"smiles": "COc1ccc(C2=C(c3ccc(OCc4nc5ccccn5c4Cl)cc3)C(=O)C(C)(C)O2)cc1"
},
"smiles": "COc1ccc(C2=C(c3ccc(OCc4nc5ccccn5c4Cl)cc3)C(=O)C(C)(C)O2)cc1",
"reactionStepId": "sa_82181597d2473ec21c19e9f3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150322069A1;0273;1782727\",\"rsmi\":\"Cl[CH2:14][c:15]1[c:16]([Cl:17])[n:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[n:24]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2=[C:8]([c:9]3[cH:10][cH:11][c:12]([OH:13])[cH:25][cH:26]3)[C:27](=[O:28])[C:29]([CH3:30])([CH3:31])[O:32]2)[cH:33][cH:34]1>CN(C)C=O.O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2=[C:8]([c:9]3[cH:10][cH:11][c:12]([O:13][CH2:14][c:15]4[c:16]([Cl:17])[n:18]5[cH:19][cH:20][cH:21][cH:22][c:23]5[n:24]4)[cH:25][cH:26]3)[C:27](=[O:28])[C:29]([CH3:30])([CH3:31])[O:32]2)[cH:33][cH:34]1\"},\"mapped_reaction_smiles\":\"Cl[CH2:14][c:15]1[c:16]([Cl:17])[n:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[n:24]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2=[C:8]([c:9]3[cH:10][cH:11][c:12]([OH:13])[cH:25][cH:26]3)[C:27](=[O:28])[C:29]([CH3:30])([CH3:31])[O:32]2)[cH:33][cH:34]1>CN(C)C=O.O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2=[C:8]([c:9]3[cH:10][cH:11][c:12]([O:13][CH2:14][c:15]4[c:16]([Cl:17])[n:18]5[cH:19][cH:20][cH:21][cH:22][c:23]5[n:24]4)[cH:25][cH:26]3)[C:27](=[O:28])[C:29]([CH3:30])([CH3:31])[O:32]2)[cH:33][cH:34]1\"}",
"reactionStep": {
"id": "sa_82181597d2473ec21c19e9f3",
"reactionHash": "7e403d6b4cb66e15f7c71756d182280483651d003407258b601b98d8cc601d7b"
},
"children": [
{
"id": "11346",
"routeId": "sa_98b0503787ed41cc89bac9e2",
"moleculeId": "sa_a5b69b86049f06b8780c1aaf",
"parentId": "11345",
"isLeaf": false,
"molecule": {
"id": "sa_a5b69b86049f06b8780c1aaf",
"inchikey": "LLZWLTNRVWSERT-UHFFFAOYSA-N",
"smiles": "ClCc1nc2ccccn2c1Cl"
},
"smiles": "ClCc1nc2ccccn2c1Cl",
"reactionStepId": "sa_c0b83282f9c72779aec1a3c3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150322069A1;0271;1782726\",\"rsmi\":\"O=C1CCC(=O)N1[Cl:5].[Cl:1][CH2:2][c:3]1[cH:4][n:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12]1>ClCCl>[Cl:1][CH2:2][c:3]1[c:4]([Cl:5])[n:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12]1\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Cl:5].[Cl:1][CH2:2][c:3]1[cH:4][n:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12]1>ClCCl>[Cl:1][CH2:2][c:3]1[c:4]([Cl:5])[n:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12]1\"}",
"reactionStep": {
"id": "sa_c0b83282f9c72779aec1a3c3",
"reactionHash": "22bc498b623ae27732de49e490a625dd3afbb03fb1a53de0c2aa3328a45b3a21"
},
"children": [
{
"id": "11347",
"routeId": "sa_98b0503787ed41cc89bac9e2",
"moleculeId": "sa_a576f9b9a2caa305053d217d",
"parentId": "11346",
"isLeaf": true,
"molecule": {
"id": "sa_a576f9b9a2caa305053d217d",
"inchikey": "JRNVZBWKYDBUCA-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Cl"
},
"smiles": "O=C1CCC(=O)N1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11348",
"routeId": "sa_98b0503787ed41cc89bac9e2",
"moleculeId": "sa_ca9645603641aec360a41e71",
"parentId": "11346",
"isLeaf": false,
"molecule": {
"id": "sa_ca9645603641aec360a41e71",
"inchikey": "LBCREEUWXFNSAC-UHFFFAOYSA-N",
"smiles": "ClCc1cn2ccccc2n1"
},
"smiles": "ClCc1cn2ccccc2n1",
"reactionStepId": "sa_ace5e348a02f257563ee3bf1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150322069A1;0237;1782711\",\"rsmi\":\"O=[C:3]([CH2:2][Cl:1])[CH2:4]Cl.[n:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[NH2:11]>CC#N>[Cl:1][CH2:2][c:3]1[cH:4][n:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[n:11]1\"},\"mapped_reaction_smiles\":\"O=[C:3]([CH2:2][Cl:1])[CH2:4]Cl.[n:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[NH2:11]>CC#N>[Cl:1][CH2:2][c:3]1[cH:4][n:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[n:11]1\"}",
"reactionStep": {
"id": "sa_ace5e348a02f257563ee3bf1",
"reactionHash": "087294e473671d77785a78d28f9e7c51b52b79fc3fa1cc65f70d66b3c0a77dc7"
},
"children": [
{
"id": "11349",
"routeId": "sa_98b0503787ed41cc89bac9e2",
"moleculeId": "sa_9d881fcfb8e5da75f7e5b12a",
"parentId": "11348",
"isLeaf": true,
"molecule": {
"id": "sa_9d881fcfb8e5da75f7e5b12a",
"inchikey": "ICSNLGPSRYBMBD-UHFFFAOYSA-N",
"smiles": "Nc1ccccn1"
},
"smiles": "Nc1ccccn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11350",
"routeId": "sa_98b0503787ed41cc89bac9e2",
"moleculeId": "sa_1813f853c602aa1908730623",
"parentId": "11348",
"isLeaf": true,
"molecule": {
"id": "sa_1813f853c602aa1908730623",
"inchikey": "SUNMBRGCANLOEG-UHFFFAOYSA-N",
"smiles": "O=C(CCl)CCl"
},
"smiles": "O=C(CCl)CCl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "11351",
"routeId": "sa_98b0503787ed41cc89bac9e2",
"moleculeId": "sa_f3390a9f90ff98d256afd0c2",
"parentId": "11345",
"isLeaf": false,
"molecule": {
"id": "sa_f3390a9f90ff98d256afd0c2",
"inchikey": "LMXYGAVAHBJETI-UHFFFAOYSA-N",
"smiles": "COc1ccc(C2=C(c3ccc(O)cc3)C(=O)C(C)(C)O2)cc1"
},
"smiles": "COc1ccc(C2=C(c3ccc(O)cc3)C(=O)C(C)(C)O2)cc1",
"reactionStepId": "sa_73a97699a1d58fdd84c2e825",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150322069A1;0199;1782693\",\"rsmi\":\"c1ccc(C[O:13][c:12]2[cH:11][cH:10][c:9]([C:8]3=[C:7]([c:6]4[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:23][cH:22]4)[O:21][C:18]([CH3:19])([CH3:20])[C:16]3=[O:17])[cH:15][cH:14]2)cc1>CO.[H][H].[Pd]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2=[C:8]([c:9]3[cH:10][cH:11][c:12]([OH:13])[cH:14][cH:15]3)[C:16](=[O:17])[C:18]([CH3:19])([CH3:20])[O:21]2)[cH:22][cH:23]1\"},\"mapped_reaction_smiles\":\"c1ccc(C[O:13][c:12]2[cH:11][cH:10][c:9]([C:8]3=[C:7]([c:6]4[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:23][cH:22]4)[O:21][C:18]([CH3:19])([CH3:20])[C:16]3=[O:17])[cH:15][cH:14]2)cc1>CO.[H][H].[Pd]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]2=[C:8]([c:9]3[cH:10][cH:11][c:12]([OH:13])[cH:14][cH:15]3)[C:16](=[O:17])[C:18]([CH3:19])([CH3:20])[O:21]2)[cH:22][cH:23]1\"}",
"reactionStep": {
"id": "sa_73a97699a1d58fdd84c2e825",
"reactionHash": "81231a99dca0586bf5b43d0a05ebc2c1d2c02746bd10bd4632ff37941a500ba5"
},
"children": [
{
"id": "11352",
"routeId": "sa_98b0503787ed41cc89bac9e2",
"moleculeId": "sa_c5fd2f76ed89e3337e4a36ee",
"parentId": "11351",
"isLeaf": true,
"molecule": {
"id": "sa_c5fd2f76ed89e3337e4a36ee",
"inchikey": "QFMSFXLFIITTAT-UHFFFAOYSA-N",
"smiles": "COc1ccc(C2=C(c3ccc(OCc4ccccc4)cc3)C(=O)C(C)(C)O2)cc1"
},
"smiles": "COc1ccc(C2=C(c3ccc(OCc4ccccc4)cc3)C(=O)C(C)(C)O2)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}