Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1cccc(Cl)c1Nc1nc2cc(C(=O)Nc3ccc(C(F)(F)F)cn3)c3c(c2[nH]1)CC(C)(C)O3
InChiKey
CMVCWCYAFXJCSR-UHFFFAOYSA-N
Route Signature
15a94b79f6f9b14d7b8e1e34aa2acca7d013bf43926802ec31ff3b771d5db863
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_7baae34f4b582e77bc71e94e",
"signature": "15a94b79f6f9b14d7b8e1e34aa2acca7d013bf43926802ec31ff3b771d5db863",
"contentHash": "6f20b9a59d57a94b1c13069bb8bfb14cd55c8537a186485a11d811b6a21faa12",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_f73c85261125a7127c284746",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-06415",
"moleculeId": "sa_44f762a0b8c4c0954f364c97",
"smiles": "Cc1cccc(Cl)c1Nc1nc2cc(C(=O)Nc3ccc(C(F)(F)F)cn3)c3c(c2[nH]1)CC(C)(C)O3",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_44f762a0b8c4c0954f364c97",
"inchikey": "CMVCWCYAFXJCSR-UHFFFAOYSA-N",
"smiles": "Cc1cccc(Cl)c1Nc1nc2cc(C(=O)Nc3ccc(C(F)(F)F)cn3)c3c(c2[nH]1)CC(C)(C)O3"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "11576",
"routeId": "sa_7baae34f4b582e77bc71e94e",
"moleculeId": "sa_44f762a0b8c4c0954f364c97",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_44f762a0b8c4c0954f364c97",
"inchikey": "CMVCWCYAFXJCSR-UHFFFAOYSA-N",
"smiles": "Cc1cccc(Cl)c1Nc1nc2cc(C(=O)Nc3ccc(C(F)(F)F)cn3)c3c(c2[nH]1)CC(C)(C)O3"
},
"smiles": "Cc1cccc(Cl)c1Nc1nc2cc(C(=O)Nc3ccc(C(F)(F)F)cn3)c3c(c2[nH]1)CC(C)(C)O3",
"reactionStepId": "sa_fea483e37c9b96ea15c102be",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08519149B2;0700;1360670\",\"rsmi\":\"O[C:23]([c:22]1[c:16]2[c:15]([c:13]3[c:12]([n:11][c:10]([NH:9][c:8]4[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]4[Cl:7])[nH:14]3)[cH:36]1)[CH2:21][C:18]([CH3:19])([CH3:20])[O:17]2)=[O:24].[O-][n+:27]1[c:26]([NH2:25])[cH:35][cH:34][c:29]([C:30]([F:31])([F:32])[F:33])[cH:28]1>CC(=O)O.CCN(C(C)C)C(C)C.CCOC(=O)C(C#N)=NOC(N1CCOCC1)=[N+](C)C.F[PH](F)(F)(F)(F)F.[Fe]>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([Cl:7])[c:8]1[NH:9][c:10]1[n:11][c:12]2[c:13]([nH:14]1)[c:15]1[c:16]([c:22]([C:23](=[O:24])[NH:25][c:26]3[n:27][cH:28][c:29]([C:30]([F:31])([F:32])[F:33])[cH:34][cH:35]3)[cH:36]2)[O:17][C:18]([CH3:19])([CH3:20])[CH2:21]1\"},\"mapped_reaction_smiles\":\"O[C:23]([c:22]1[c:16]2[c:15]([c:13]3[c:12]([n:11][c:10]([NH:9][c:8]4[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]4[Cl:7])[nH:14]3)[cH:36]1)[CH2:21][C:18]([CH3:19])([CH3:20])[O:17]2)=[O:24].[O-][n+:27]1[c:26]([NH2:25])[cH:35][cH:34][c:29]([C:30]([F:31])([F:32])[F:33])[cH:28]1>CC(=O)O.CCN(C(C)C)C(C)C.CCOC(=O)C(C#N)=NOC(N1CCOCC1)=[N+](C)C.F[PH](F)(F)(F)(F)F.[Fe]>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([Cl:7])[c:8]1[NH:9][c:10]1[n:11][c:12]2[c:13]([nH:14]1)[c:15]1[c:16]([c:22]([C:23](=[O:24])[NH:25][c:26]3[n:27][cH:28][c:29]([C:30]([F:31])([F:32])[F:33])[cH:34][cH:35]3)[cH:36]2)[O:17][C:18]([CH3:19])([CH3:20])[CH2:21]1\"}",
"reactionStep": {
"id": "sa_fea483e37c9b96ea15c102be",
"reactionHash": "9736177f0bf7e34037d5ff4fbf2925b626bd9900e958559bcec88d3868a0b986"
},
"children": [
{
"id": "11577",
"routeId": "sa_7baae34f4b582e77bc71e94e",
"moleculeId": "sa_46fdf5984eba28f7a38a1fb0",
"parentId": "11576",
"isLeaf": false,
"molecule": {
"id": "sa_46fdf5984eba28f7a38a1fb0",
"inchikey": "QWOWYDWXHGFXBF-UHFFFAOYSA-N",
"smiles": "Nc1ccc(C(F)(F)F)c[n+]1[O-]"
},
"smiles": "Nc1ccc(C(F)(F)F)c[n+]1[O-]",
"reactionStepId": "sa_04b85fabcd9066ba692e132b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08519149B2;0368;1360593\",\"rsmi\":\"O[OH:4].[NH2:1][c:2]1[n:3][cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[cH:11][cH:12]1>CC(=O)O>[NH2:1][c:2]1[n+:3]([O-:4])[cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[cH:11][cH:12]1\"},\"mapped_reaction_smiles\":\"O[OH:4].[NH2:1][c:2]1[n:3][cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[cH:11][cH:12]1>CC(=O)O>[NH2:1][c:2]1[n+:3]([O-:4])[cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[cH:11][cH:12]1\"}",
"reactionStep": {
"id": "sa_04b85fabcd9066ba692e132b",
"reactionHash": "3a30e3630670704f3a34b19eb12b827ba1cf54de3b39759432017c2f1687cccd"
},
"children": [
{
"id": "11578",
"routeId": "sa_7baae34f4b582e77bc71e94e",
"moleculeId": "sa_4dba68d938224067da688ab5",
"parentId": "11577",
"isLeaf": true,
"molecule": {
"id": "sa_4dba68d938224067da688ab5",
"inchikey": "MHAJPDPJQMAIIY-UHFFFAOYSA-N",
"smiles": "OO"
},
"smiles": "OO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11579",
"routeId": "sa_7baae34f4b582e77bc71e94e",
"moleculeId": "sa_d480feb50e946b319a2fa04e",
"parentId": "11577",
"isLeaf": true,
"molecule": {
"id": "sa_d480feb50e946b319a2fa04e",
"inchikey": "RSGVKIIEIXOMPY-UHFFFAOYSA-N",
"smiles": "N=c1ccc(C(F)(F)F)c[nH]1"
},
"smiles": "Nc1ccc(C(F)(F)F)cn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "11580",
"routeId": "sa_7baae34f4b582e77bc71e94e",
"moleculeId": "sa_6b9247e47645f1c7303f2878",
"parentId": "11576",
"isLeaf": false,
"molecule": {
"id": "sa_6b9247e47645f1c7303f2878",
"inchikey": "RPWCZMYZZWKOAT-UHFFFAOYSA-N",
"smiles": "Cc1cccc(Cl)c1Nc1nc2cc(C(=O)O)c3c(c2[nH]1)CC(C)(C)O3"
},
"smiles": "Cc1cccc(Cl)c1Nc1nc2cc(C(=O)O)c3c(c2[nH]1)CC(C)(C)O3",
"reactionStepId": "sa_dbec75b63288bef0e51a92c6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08519149B2;0353;1360587\",\"rsmi\":\"C[O:25][C:23]([c:22]1[c:16]2[c:15]([c:13]3[c:12]([n:11][c:10]([NH:9][c:8]4[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]4[Cl:7])[nH:14]3)[cH:26]1)[CH2:21][C:18]([CH3:19])([CH3:20])[O:17]2)=[O:24]>CO.[Na+].O>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([Cl:7])[c:8]1[NH:9][c:10]1[n:11][c:12]2[c:13]([nH:14]1)[c:15]1[c:16]([c:22]([C:23](=[O:24])[OH:25])[cH:26]2)[O:17][C:18]([CH3:19])([CH3:20])[CH2:21]1\"},\"mapped_reaction_smiles\":\"C[O:25][C:23]([c:22]1[c:16]2[c:15]([c:13]3[c:12]([n:11][c:10]([NH:9][c:8]4[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]4[Cl:7])[nH:14]3)[cH:26]1)[CH2:21][C:18]([CH3:19])([CH3:20])[O:17]2)=[O:24]>CO.[Na+].O>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([Cl:7])[c:8]1[NH:9][c:10]1[n:11][c:12]2[c:13]([nH:14]1)[c:15]1[c:16]([c:22]([C:23](=[O:24])[OH:25])[cH:26]2)[O:17][C:18]([CH3:19])([CH3:20])[CH2:21]1\"}",
"reactionStep": {
"id": "sa_dbec75b63288bef0e51a92c6",
"reactionHash": "bc32b92d6dcd73e369e2bc9ff40c2f89553d3c2eff59d53b99d83f3dc44f0d0e"
},
"children": [
{
"id": "11581",
"routeId": "sa_7baae34f4b582e77bc71e94e",
"moleculeId": "sa_408134bc276f110350a9f1e9",
"parentId": "11580",
"isLeaf": false,
"molecule": {
"id": "sa_408134bc276f110350a9f1e9",
"inchikey": "FIWLJGWLFJUYNU-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc2nc(Nc3c(C)cccc3Cl)[nH]c2c2c1OC(C)(C)C2"
},
"smiles": "COC(=O)c1cc2nc(Nc3c(C)cccc3Cl)[nH]c2c2c1OC(C)(C)C2",
"reactionStepId": "sa_add3c9dd1b4c383c3ca17abe",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08519149B2;0352;1360586\",\"rsmi\":\"S=[C:10]=[N:11][c:12]1[c:13]([Cl:14])[cH:15][cH:16][cH:17][c:18]1[CH3:19].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:20])[c:8]([NH2:9])[c:21]2[c:22]1[O:23][C:24]([CH3:25])([CH3:26])[CH2:27]2>CC#N>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([nH:9][c:10]([NH:11][c:12]3[c:13]([Cl:14])[cH:15][cH:16][cH:17][c:18]3[CH3:19])[n:20]2)[c:21]2[c:22]1[O:23][C:24]([CH3:25])([CH3:26])[CH2:27]2\"},\"mapped_reaction_smiles\":\"S=[C:10]=[N:11][c:12]1[c:13]([Cl:14])[cH:15][cH:16][cH:17][c:18]1[CH3:19].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:20])[c:8]([NH2:9])[c:21]2[c:22]1[O:23][C:24]([CH3:25])([CH3:26])[CH2:27]2>CC#N>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([nH:9][c:10]([NH:11][c:12]3[c:13]([Cl:14])[cH:15][cH:16][cH:17][c:18]3[CH3:19])[n:20]2)[c:21]2[c:22]1[O:23][C:24]([CH3:25])([CH3:26])[CH2:27]2\"}",
"reactionStep": {
"id": "sa_add3c9dd1b4c383c3ca17abe",
"reactionHash": "50dba91b63d39464a4b263eac21aed84f212067192fbebc8b4f9a216c7ee1388"
},
"children": [
{
"id": "11582",
"routeId": "sa_7baae34f4b582e77bc71e94e",
"moleculeId": "sa_1f2d8b95efb0d307a943bda3",
"parentId": "11581",
"isLeaf": false,
"molecule": {
"id": "sa_1f2d8b95efb0d307a943bda3",
"inchikey": "MLQPKPCDKLACIG-UHFFFAOYSA-N",
"smiles": "Cc1cccc(Cl)c1N=C=S"
},
"smiles": "Cc1cccc(Cl)c1N=C=S",
"reactionStepId": "sa_e763722e2ee16519810056ad",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08519149B2;0349;1360585\",\"rsmi\":\"Cl[C:10](Cl)=[S:11].[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([Cl:7])[c:8]1[NH2:9]>CCN(C(C)C)C(C)C>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([Cl:7])[c:8]1[N:9]=[C:10]=[S:11]\"},\"mapped_reaction_smiles\":\"Cl[C:10](Cl)=[S:11].[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([Cl:7])[c:8]1[NH2:9]>CCN(C(C)C)C(C)C>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([Cl:7])[c:8]1[N:9]=[C:10]=[S:11]\"}",
"reactionStep": {
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"reactionHash": "be5833d1c58003773930aef56e4761cca66e4914fdf295a4e0ab1333a6aec059"
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"children": [
{
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"routeId": "sa_7baae34f4b582e77bc71e94e",
"moleculeId": "sa_582afd6920320aebd10b7c25",
"parentId": "11582",
"isLeaf": true,
"molecule": {
"id": "sa_582afd6920320aebd10b7c25",
"inchikey": "WFNLHDJJZSJARK-UHFFFAOYSA-N",
"smiles": "Cc1cccc(Cl)c1N"
},
"smiles": "Cc1cccc(Cl)c1N",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "11584",
"routeId": "sa_7baae34f4b582e77bc71e94e",
"moleculeId": "sa_2e3e3991398655b8f7696737",
"parentId": "11582",
"isLeaf": true,
"molecule": {
"id": "sa_2e3e3991398655b8f7696737",
"inchikey": "ZWZVWGITAAIFPS-UHFFFAOYSA-N",
"smiles": "S=C(Cl)Cl"
},
"smiles": "S=C(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "11585",
"routeId": "sa_7baae34f4b582e77bc71e94e",
"moleculeId": "sa_61a80d2badfe825dfc242ef5",
"parentId": "11581",
"isLeaf": true,
"molecule": {
"id": "sa_61a80d2badfe825dfc242ef5",
"inchikey": "XLKHLOHMZQLVPM-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(N)c(N)c2c1OC(C)(C)C2"
},
"smiles": "COC(=O)c1cc(N)c(N)c2c1OC(C)(C)C2",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
]
}
}