Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C(N)=O)c1ccccc1CCc1nc(Nc2cnn(C3CCNCC3)c2)ncc1Cl
InChiKey
FYMHFFRHIPSDGQ-UHFFFAOYSA-N
Route Signature
9a6a4d31ecd0bcdd00671e3a6e682a49612d132934ca7a731f6383ffe9d49311
Synthesis route with 7 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_3d5b40c48f823687ed0bdf05",
"signature": "9a6a4d31ecd0bcdd00671e3a6e682a49612d132934ca7a731f6383ffe9d49311",
"contentHash": "c19a6e71a070a989a1af2bc9f6e1e78e4aeea6c7a09ca47ae92e0326c42df2c8",
"length": 7,
"isConvergent": false
},
"target": {
"id": "sa_744ad5f9ea18611660d99c6a",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-01718",
"moleculeId": "sa_7d6bcd638faef8c40a948baf",
"smiles": "CC(C(N)=O)c1ccccc1CCc1nc(Nc2cnn(C3CCNCC3)c2)ncc1Cl",
"routeLength": 7,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_7d6bcd638faef8c40a948baf",
"inchikey": "FYMHFFRHIPSDGQ-UHFFFAOYSA-N",
"smiles": "CC(C(N)=O)c1ccccc1CCc1nc(Nc2cnn(C3CCNCC3)c2)ncc1Cl"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "14492",
"routeId": "sa_3d5b40c48f823687ed0bdf05",
"moleculeId": "sa_7d6bcd638faef8c40a948baf",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_7d6bcd638faef8c40a948baf",
"inchikey": "FYMHFFRHIPSDGQ-UHFFFAOYSA-N",
"smiles": "CC(C(N)=O)c1ccccc1CCc1nc(Nc2cnn(C3CCNCC3)c2)ncc1Cl"
},
"smiles": "CC(C(N)=O)c1ccccc1CCc1nc(Nc2cnn(C3CCNCC3)c2)ncc1Cl",
"reactionStepId": "sa_da39fefc571f64a770d61dc4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09238644B2;0902;1718053\",\"rsmi\":\"CC(C)(C)OC(=O)[N:20]1[CH2:19][CH2:18][CH:17]([n:16]2[cH:15][c:14]([NH:13][c:12]3[n:11][c:10]([CH2:9][CH2:8][c:7]4[c:6]([CH:2]([CH3:1])[C:3]([NH2:4])=[O:5])[cH:32][cH:31][cH:30][cH:29]4)[c:27]([Cl:28])[cH:26][n:25]3)[cH:24][n:23]2)[CH2:22][CH2:21]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][CH:2]([C:3]([NH2:4])=[O:5])[c:6]1[c:7]([CH2:8][CH2:9][c:10]2[n:11][c:12]([NH:13][c:14]3[cH:15][n:16]([CH:17]4[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]4)[n:23][cH:24]3)[n:25][cH:26][c:27]2[Cl:28])[cH:29][cH:30][cH:31][cH:32]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:20]1[CH2:19][CH2:18][CH:17]([n:16]2[cH:15][c:14]([NH:13][c:12]3[n:11][c:10]([CH2:9][CH2:8][c:7]4[c:6]([CH:2]([CH3:1])[C:3]([NH2:4])=[O:5])[cH:32][cH:31][cH:30][cH:29]4)[c:27]([Cl:28])[cH:26][n:25]3)[cH:24][n:23]2)[CH2:22][CH2:21]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][CH:2]([C:3]([NH2:4])=[O:5])[c:6]1[c:7]([CH2:8][CH2:9][c:10]2[n:11][c:12]([NH:13][c:14]3[cH:15][n:16]([CH:17]4[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]4)[n:23][cH:24]3)[n:25][cH:26][c:27]2[Cl:28])[cH:29][cH:30][cH:31][cH:32]1\"}",
"reactionStep": {
"id": "sa_da39fefc571f64a770d61dc4",
"reactionHash": "a3dc1989bbba713f82ccdc98262364fc04f25b4df278f88e5434a4e6893c8e5b"
},
"children": [
{
"id": "14493",
"routeId": "sa_3d5b40c48f823687ed0bdf05",
"moleculeId": "sa_bd6866d6eb870ba36776dc36",
"parentId": "14492",
"isLeaf": false,
"molecule": {
"id": "sa_bd6866d6eb870ba36776dc36",
"inchikey": "SSYSBPKMRWYZEJ-UHFFFAOYSA-N",
"smiles": "CC(C(N)=O)c1ccccc1CCc1nc(Nc2cnn(C3CCN(C(=O)OC(C)(C)C)CC3)c2)ncc1Cl"
},
"smiles": "CC(C(N)=O)c1ccccc1CCc1nc(Nc2cnn(C3CCN(C(=O)OC(C)(C)C)CC3)c2)ncc1Cl",
"reactionStepId": "sa_37839b67a6ba80efcfaf7b9a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09238644B2;0901;1718052\",\"rsmi\":\"Cl[c:12]1[n:11][c:10]([CH2:9][CH2:8][c:7]2[c:6]([CH:2]([CH3:1])[C:3]([NH2:4])=[O:5])[cH:39][cH:38][cH:37][cH:36]2)[c:34]([Cl:35])[cH:33][n:32]1.[NH2:13][c:14]1[cH:15][n:16]([CH:17]2[CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]2)[n:30][cH:31]1>CC(=O)O.CCCCO>[CH3:1][CH:2]([C:3]([NH2:4])=[O:5])[c:6]1[c:7]([CH2:8][CH2:9][c:10]2[n:11][c:12]([NH:13][c:14]3[cH:15][n:16]([CH:17]4[CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]4)[n:30][cH:31]3)[n:32][cH:33][c:34]2[Cl:35])[cH:36][cH:37][cH:38][cH:39]1\"},\"mapped_reaction_smiles\":\"Cl[c:12]1[n:11][c:10]([CH2:9][CH2:8][c:7]2[c:6]([CH:2]([CH3:1])[C:3]([NH2:4])=[O:5])[cH:39][cH:38][cH:37][cH:36]2)[c:34]([Cl:35])[cH:33][n:32]1.[NH2:13][c:14]1[cH:15][n:16]([CH:17]2[CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]2)[n:30][cH:31]1>CC(=O)O.CCCCO>[CH3:1][CH:2]([C:3]([NH2:4])=[O:5])[c:6]1[c:7]([CH2:8][CH2:9][c:10]2[n:11][c:12]([NH:13][c:14]3[cH:15][n:16]([CH:17]4[CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]4)[n:30][cH:31]3)[n:32][cH:33][c:34]2[Cl:35])[cH:36][cH:37][cH:38][cH:39]1\"}",
"reactionStep": {
"id": "sa_37839b67a6ba80efcfaf7b9a",
"reactionHash": "31ca87f86baabe4b390a1b5414186b25de269a60993bb307297fc3f780bc7871"
},
"children": [
{
"id": "14494",
"routeId": "sa_3d5b40c48f823687ed0bdf05",
"moleculeId": "sa_664fe85bcca3cfe4618cee64",
"parentId": "14493",
"isLeaf": true,
"molecule": {
"id": "sa_664fe85bcca3cfe4618cee64",
"inchikey": "TVJWTRPGFVNAJI-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(n2cc(N)cn2)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(n2cc(N)cn2)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14495",
"routeId": "sa_3d5b40c48f823687ed0bdf05",
"moleculeId": "sa_5768fa54462ffedfc91f512e",
"parentId": "14493",
"isLeaf": false,
"molecule": {
"id": "sa_5768fa54462ffedfc91f512e",
"inchikey": "YWVFNEJAHCAGQD-UHFFFAOYSA-N",
"smiles": "CC(C(N)=O)c1ccccc1CCc1nc(Cl)ncc1Cl"
},
"smiles": "CC(C(N)=O)c1ccccc1CCc1nc(Cl)ncc1Cl",
"reactionStepId": "sa_18803138369a1912d378d465",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09238644B2;0883;1718043\",\"rsmi\":\"[CH3:1][CH:2]([C:3]([NH2:4])=[O:5])[c:6]1[c:7]([C:8]#[C:9][c:10]2[n:11][c:12]([Cl:13])[n:14][cH:15][c:16]2[Cl:17])[cH:18][cH:19][cH:20][cH:21]1>CCOC(C)=O.CN(C)C=O.CO.O=[Pt]>[CH3:1][CH:2]([C:3]([NH2:4])=[O:5])[c:6]1[c:7]([CH2:8][CH2:9][c:10]2[n:11][c:12]([Cl:13])[n:14][cH:15][c:16]2[Cl:17])[cH:18][cH:19][cH:20][cH:21]1\"},\"mapped_reaction_smiles\":\"[CH3:1][CH:2]([C:3]([NH2:4])=[O:5])[c:6]1[c:7]([C:8]#[C:9][c:10]2[n:11][c:12]([Cl:13])[n:14][cH:15][c:16]2[Cl:17])[cH:18][cH:19][cH:20][cH:21]1>CCOC(C)=O.CN(C)C=O.CO.O=[Pt]>[CH3:1][CH:2]([C:3]([NH2:4])=[O:5])[c:6]1[c:7]([CH2:8][CH2:9][c:10]2[n:11][c:12]([Cl:13])[n:14][cH:15][c:16]2[Cl:17])[cH:18][cH:19][cH:20][cH:21]1\"}",
"reactionStep": {
"id": "sa_18803138369a1912d378d465",
"reactionHash": "93ca3b4b8232f9f4d50ef7c39d0c4ece87284d24fa84c3c6ef8561674402300b"
},
"children": [
{
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"routeId": "sa_3d5b40c48f823687ed0bdf05",
"moleculeId": "sa_2ccad580377e3fe9d9599150",
"parentId": "14495",
"isLeaf": false,
"molecule": {
"id": "sa_2ccad580377e3fe9d9599150",
"inchikey": "LLVNGDVNBLJHHE-UHFFFAOYSA-N",
"smiles": "CC(C(N)=O)c1ccccc1C#Cc1nc(Cl)ncc1Cl"
},
"smiles": "CC(C(N)=O)c1ccccc1C#Cc1nc(Cl)ncc1Cl",
"reactionStepId": "sa_574a632b4230cf401854205c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09238644B2;0882;1718042\",\"rsmi\":\"Cl[c:10]1[n:11][c:12]([Cl:13])[n:14][cH:15][c:16]1[Cl:17].[CH3:1][CH:2]([C:3]([NH2:4])=[O:5])[c:6]1[c:7]([C:8]#[CH:9])[cH:18][cH:19][cH:20][cH:21]1>C1COCCO1.CCN(CC)CC.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.[Cu]I>[CH3:1][CH:2]([C:3]([NH2:4])=[O:5])[c:6]1[c:7]([C:8]#[C:9][c:10]2[n:11][c:12]([Cl:13])[n:14][cH:15][c:16]2[Cl:17])[cH:18][cH:19][cH:20][cH:21]1\"},\"mapped_reaction_smiles\":\"Cl[c:10]1[n:11][c:12]([Cl:13])[n:14][cH:15][c:16]1[Cl:17].[CH3:1][CH:2]([C:3]([NH2:4])=[O:5])[c:6]1[c:7]([C:8]#[CH:9])[cH:18][cH:19][cH:20][cH:21]1>C1COCCO1.CCN(CC)CC.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.[Cu]I>[CH3:1][CH:2]([C:3]([NH2:4])=[O:5])[c:6]1[c:7]([C:8]#[C:9][c:10]2[n:11][c:12]([Cl:13])[n:14][cH:15][c:16]2[Cl:17])[cH:18][cH:19][cH:20][cH:21]1\"}",
"reactionStep": {
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"reactionHash": "76cb8a1601da1b1e29304b05b643345a5aabb80a7ace03301ec2cac89817848d"
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"children": [
{
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"routeId": "sa_3d5b40c48f823687ed0bdf05",
"moleculeId": "sa_fde86ac4eaa353047ff34d33",
"parentId": "14496",
"isLeaf": true,
"molecule": {
"id": "sa_fde86ac4eaa353047ff34d33",
"inchikey": "GIKMWFAAEIACRF-UHFFFAOYSA-N",
"smiles": "Clc1ncc(Cl)c(Cl)n1"
},
"smiles": "Clc1ncc(Cl)c(Cl)n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14498",
"routeId": "sa_3d5b40c48f823687ed0bdf05",
"moleculeId": "sa_0d6b298d8e7ad1b87226c088",
"parentId": "14496",
"isLeaf": false,
"molecule": {
"id": "sa_0d6b298d8e7ad1b87226c088",
"inchikey": "MPTDKCBUARYSSY-UHFFFAOYSA-N",
"smiles": "C#Cc1ccccc1C(C)C(N)=O"
},
"smiles": "C#Cc1ccccc1C(C)C(N)=O",
"reactionStepId": "sa_ddfa64721be1659280777819",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09238644B2;0776;1717985\",\"rsmi\":\"C[Si](C)(C)[C:1]#[C:2][c:3]1[c:4]([CH:5]([CH3:6])[C:7]([NH2:8])=[O:9])[cH:10][cH:11][cH:12][cH:13]1>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.O=C(O)O.F.[Na+]>[CH:1]#[C:2][c:3]1[c:4]([CH:5]([CH3:6])[C:7]([NH2:8])=[O:9])[cH:10][cH:11][cH:12][cH:13]1\"},\"mapped_reaction_smiles\":\"C[Si](C)(C)[C:1]#[C:2][c:3]1[c:4]([CH:5]([CH3:6])[C:7]([NH2:8])=[O:9])[cH:10][cH:11][cH:12][cH:13]1>C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.O=C(O)O.F.[Na+]>[CH:1]#[C:2][c:3]1[c:4]([CH:5]([CH3:6])[C:7]([NH2:8])=[O:9])[cH:10][cH:11][cH:12][cH:13]1\"}",
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"children": [
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"molecule": {
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"smiles": "CC(C(N)=O)c1ccccc1C#C[Si](C)(C)C"
},
"smiles": "CC(C(N)=O)c1ccccc1C#C[Si](C)(C)C",
"reactionStepId": "sa_167de347f892032b1ed3f5bf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09238644B2;0775;1717984\",\"rsmi\":\"I[c:7]1[c:6]([CH:2]([CH3:1])[C:3]([NH2:4])=[O:5])[cH:17][cH:16][cH:15][cH:14]1.[CH:8]#[C:9][Si:10]([CH3:11])([CH3:12])[CH3:13]>CC(C)(C)P(C(C)(C)C)C(C)(C)C.CN(C)C=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.F[B-](F)(F)F.[Cu]I>[CH3:1][CH:2]([C:3]([NH2:4])=[O:5])[c:6]1[c:7]([C:8]#[C:9][Si:10]([CH3:11])([CH3:12])[CH3:13])[cH:14][cH:15][cH:16][cH:17]1\"},\"mapped_reaction_smiles\":\"I[c:7]1[c:6]([CH:2]([CH3:1])[C:3]([NH2:4])=[O:5])[cH:17][cH:16][cH:15][cH:14]1.[CH:8]#[C:9][Si:10]([CH3:11])([CH3:12])[CH3:13]>CC(C)(C)P(C(C)(C)C)C(C)(C)C.CN(C)C=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.F[B-](F)(F)F.[Cu]I>[CH3:1][CH:2]([C:3]([NH2:4])=[O:5])[c:6]1[c:7]([C:8]#[C:9][Si:10]([CH3:11])([CH3:12])[CH3:13])[cH:14][cH:15][cH:16][cH:17]1\"}",
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},
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{
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},
"smiles": "CC(C(N)=O)c1ccccc1I",
"reactionStepId": "sa_32807c2fdd3548b8b6cf2f05",
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"metadata": "{\"annotations\":{\"ID\":\"US09238644B2;0770;1717981\",\"rsmi\":\"O[C:3]([CH:2]([CH3:1])[c:6]1[c:7]([I:8])[cH:9][cH:10][cH:11][cH:12]1)=[O:5].[NH3:4]>C1CCOC1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.Cl.O=C(O)O.On1nnc2ccccc21.N>[CH3:1][CH:2]([C:3]([NH2:4])=[O:5])[c:6]1[c:7]([I:8])[cH:9][cH:10][cH:11][cH:12]1\"},\"mapped_reaction_smiles\":\"O[C:3]([CH:2]([CH3:1])[c:6]1[c:7]([I:8])[cH:9][cH:10][cH:11][cH:12]1)=[O:5].[NH3:4]>C1CCOC1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.Cl.O=C(O)O.On1nnc2ccccc21.N>[CH3:1][CH:2]([C:3]([NH2:4])=[O:5])[c:6]1[c:7]([I:8])[cH:9][cH:10][cH:11][cH:12]1\"}",
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"children": [
{
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"parentId": "14501",
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"molecule": {
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"smiles": "CC(C(=O)O)c1ccccc1I"
},
"smiles": "CC(C(=O)O)c1ccccc1I",
"reactionStepId": null,
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},
{
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