Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
NCCn1cnc2cc(C(=O)N3CCCC4CCCCC43)ccc21
InChiKey
AHHYMVYSVJIGKV-UHFFFAOYSA-N
Route Signature
16de10faf1cd9b2fa3adfb696b9d4ce9ebc9e96ed1799a4caf1e4a5c3f146774
Synthesis route with 8 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_993b406c1963c803aecc9bfe",
"signature": "16de10faf1cd9b2fa3adfb696b9d4ce9ebc9e96ed1799a4caf1e4a5c3f146774",
"contentHash": "6230178ce45c60cb39c82bb66ca60ecd5bd173a2531f84da09c97700145a601c",
"length": 8,
"isConvergent": false
},
"target": {
"id": "sa_fba12284be27135767d16d73",
"benchmarkSetId": "a82783729b577c36f2e09a2b6fdd55ae9542aed5546571d67ef9cb74dc21f70a",
"targetId": "n5-00087",
"moleculeId": "sa_2b647c5ce0ca158b2e3f5fbd",
"smiles": "NCCn1cnc2cc(C(=O)N3CCCC4CCCCC43)ccc21",
"routeLength": 8,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_2b647c5ce0ca158b2e3f5fbd",
"inchikey": "AHHYMVYSVJIGKV-UHFFFAOYSA-N",
"smiles": "NCCn1cnc2cc(C(=O)N3CCCC4CCCCC43)ccc21"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "17627",
"routeId": "sa_993b406c1963c803aecc9bfe",
"moleculeId": "sa_2b647c5ce0ca158b2e3f5fbd",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_2b647c5ce0ca158b2e3f5fbd",
"inchikey": "AHHYMVYSVJIGKV-UHFFFAOYSA-N",
"smiles": "NCCn1cnc2cc(C(=O)N3CCCC4CCCCC43)ccc21"
},
"smiles": "NCCn1cnc2cc(C(=O)N3CCCC4CCCCC43)ccc21",
"reactionStepId": "sa_2364e5ec321742dc2336c412",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090118259A1;0756;699533\",\"rsmi\":\"[N-]=[N+]=[N:1][CH2:2][CH2:3][n:4]1[cH:5][n:6][c:7]2[c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[N:14]1[CH2:15][CH2:16][CH2:17][CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH:23]13)[cH:24]2>CO.[Pd]>[NH2:1][CH2:2][CH2:3][n:4]1[cH:5][n:6][c:7]2[c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[N:14]1[CH2:15][CH2:16][CH2:17][CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH:23]13)[cH:24]2\"},\"mapped_reaction_smiles\":\"[N-]=[N+]=[N:1][CH2:2][CH2:3][n:4]1[cH:5][n:6][c:7]2[c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[N:14]1[CH2:15][CH2:16][CH2:17][CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH:23]13)[cH:24]2>CO.[Pd]>[NH2:1][CH2:2][CH2:3][n:4]1[cH:5][n:6][c:7]2[c:8]1[cH:9][cH:10][c:11]([C:12](=[O:13])[N:14]1[CH2:15][CH2:16][CH2:17][CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH:23]13)[cH:24]2\"}",
"reactionStep": {
"id": "sa_2364e5ec321742dc2336c412",
"reactionHash": "f36d335d5255f29f093e6e7e636a1e37cd2d3978875f32f45dfd1c1c0f99ae4e"
},
"children": [
{
"id": "17628",
"routeId": "sa_993b406c1963c803aecc9bfe",
"moleculeId": "sa_5ea7c145d189005a3ede7d49",
"parentId": "17627",
"isLeaf": false,
"molecule": {
"id": "sa_5ea7c145d189005a3ede7d49",
"inchikey": "WYRDKABWOWFSIJ-UHFFFAOYSA-N",
"smiles": "[N-]=[N+]=NCCn1cnc2cc(C(=O)N3CCCC4CCCCC43)ccc21"
},
"smiles": "[N-]=[N+]=NCCn1cnc2cc(C(=O)N3CCCC4CCCCC43)ccc21",
"reactionStepId": "sa_7dd05187bfeb545fca306002",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090118259A1;0755;699532\",\"rsmi\":\"O[C:14]([c:13]1[cH:12][cH:11][c:10]2[n:6]([CH2:5][CH2:4][N:3]=[N+:2]=[N-:1])[cH:7][n:8][c:9]2[cH:26]1)=[O:15].[NH:16]1[CH2:17][CH2:18][CH2:19][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH:25]12>CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.On1nnc2ccccc21>[N-:1]=[N+:2]=[N:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[N:16]1[CH2:17][CH2:18][CH2:19][CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH:25]13)[cH:26]2\"},\"mapped_reaction_smiles\":\"O[C:14]([c:13]1[cH:12][cH:11][c:10]2[n:6]([CH2:5][CH2:4][N:3]=[N+:2]=[N-:1])[cH:7][n:8][c:9]2[cH:26]1)=[O:15].[NH:16]1[CH2:17][CH2:18][CH2:19][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH:25]12>CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CN(C)C=O.Cl.On1nnc2ccccc21>[N-:1]=[N+:2]=[N:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[N:16]1[CH2:17][CH2:18][CH2:19][CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH:25]13)[cH:26]2\"}",
"reactionStep": {
"id": "sa_7dd05187bfeb545fca306002",
"reactionHash": "543e2b6ead60a2734ebeae54e2d3fd773a05455a64434474576605522c9ce692"
},
"children": [
{
"id": "17629",
"routeId": "sa_993b406c1963c803aecc9bfe",
"moleculeId": "sa_af753bf71cdcec76d022dc29",
"parentId": "17628",
"isLeaf": false,
"molecule": {
"id": "sa_af753bf71cdcec76d022dc29",
"inchikey": "PAYGRNBJULMCAD-UHFFFAOYSA-N",
"smiles": "[N-]=[N+]=NCCn1cnc2cc(C(=O)O)ccc21"
},
"smiles": "[N-]=[N+]=NCCn1cnc2cc(C(=O)O)ccc21",
"reactionStepId": "sa_1154ad3853c887e8319e1447",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090118259A1;0748;699528\",\"rsmi\":\"C[O:16][C:14]([c:13]1[cH:12][cH:11][c:10]2[n:6]([CH2:5][CH2:4][N:3]=[N+:2]=[N-:1])[cH:7][n:8][c:9]2[cH:17]1)=[O:15]>C1CCOC1.O.[Li+].O>[N-:1]=[N+:2]=[N:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[OH:16])[cH:17]2\"},\"mapped_reaction_smiles\":\"C[O:16][C:14]([c:13]1[cH:12][cH:11][c:10]2[n:6]([CH2:5][CH2:4][N:3]=[N+:2]=[N-:1])[cH:7][n:8][c:9]2[cH:17]1)=[O:15]>C1CCOC1.O.[Li+].O>[N-:1]=[N+:2]=[N:3][CH2:4][CH2:5][n:6]1[cH:7][n:8][c:9]2[c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[OH:16])[cH:17]2\"}",
"reactionStep": {
"id": "sa_1154ad3853c887e8319e1447",
"reactionHash": "f8aa6435bb4f0b0efd5faf2ad94fcc4d951e1c4e01ee7ff5583b4780d3c9b525"
},
"children": [
{
"id": "17630",
"routeId": "sa_993b406c1963c803aecc9bfe",
"moleculeId": "sa_14dabe97540fe940a144e805",
"parentId": "17629",
"isLeaf": false,
"molecule": {
"id": "sa_14dabe97540fe940a144e805",
"inchikey": "BYFGQFFOHZCHBZ-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc2c(c1)ncn2CCN=[N+]=[N-]"
},
"smiles": "COC(=O)c1ccc2c(c1)ncn2CCN=[N+]=[N-]",
"reactionStepId": "sa_98edd03882eb47ce88d927a4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090118259A1;0747;699527\",\"rsmi\":\"Cl[CH2:13][CH2:12][n:11]1[c:8]2[c:7]([cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:10][cH:9]2)[n:18][cH:17]1.[N-:14]=[N+:15]=[N-:16]>CS(C)=O.[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([cH:9][cH:10]1)[n:11]([CH2:12][CH2:13][N:14]=[N+:15]=[N-:16])[cH:17][n:18]2\"},\"mapped_reaction_smiles\":\"Cl[CH2:13][CH2:12][n:11]1[c:8]2[c:7]([cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:10][cH:9]2)[n:18][cH:17]1.[N-:14]=[N+:15]=[N-:16]>CS(C)=O.[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([cH:9][cH:10]1)[n:11]([CH2:12][CH2:13][N:14]=[N+:15]=[N-:16])[cH:17][n:18]2\"}",
"reactionStep": {
"id": "sa_98edd03882eb47ce88d927a4",
"reactionHash": "d50bf38350a87ba4d92de076ac48f5228be49b7d03d0ac5901c3550c35a7c603"
},
"children": [
{
"id": "17631",
"routeId": "sa_993b406c1963c803aecc9bfe",
"moleculeId": "sa_50a8f83dd89c267fbada1205",
"parentId": "17630",
"isLeaf": true,
"molecule": {
"id": "sa_50a8f83dd89c267fbada1205",
"inchikey": "IVRMZWNICZWHMI-UHFFFAOYSA-N",
"smiles": "[N]N=[N-]"
},
"smiles": "[N-]=[N+]=[N-]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "17632",
"routeId": "sa_993b406c1963c803aecc9bfe",
"moleculeId": "sa_9ce7818f97fd6af99c5a41d3",
"parentId": "17630",
"isLeaf": false,
"molecule": {
"id": "sa_9ce7818f97fd6af99c5a41d3",
"inchikey": "KTIHDHTYGWLKTQ-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc2c(c1)ncn2CCCl"
},
"smiles": "COC(=O)c1ccc2c(c1)ncn2CCCl",
"reactionStepId": "sa_683bc658424744538fd30655",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090118259A1;0746;699526\",\"rsmi\":\"O=[CH:15]O.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:16])[c:8]([NH:11][CH2:12][CH2:13][Cl:14])[cH:9][cH:10]1>O=C(O)O.[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([cH:9][cH:10]1)[n:11]([CH2:12][CH2:13][Cl:14])[cH:15][n:16]2\"},\"mapped_reaction_smiles\":\"O=[CH:15]O.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:16])[c:8]([NH:11][CH2:12][CH2:13][Cl:14])[cH:9][cH:10]1>O=C(O)O.[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([cH:9][cH:10]1)[n:11]([CH2:12][CH2:13][Cl:14])[cH:15][n:16]2\"}",
"reactionStep": {
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"children": [
{
"id": "17633",
"routeId": "sa_993b406c1963c803aecc9bfe",
"moleculeId": "sa_3bff5ea8042027b95a7e61c6",
"parentId": "17632",
"isLeaf": true,
"molecule": {
"id": "sa_3bff5ea8042027b95a7e61c6",
"inchikey": "BDAGIHXWWSANSR-UHFFFAOYSA-N",
"smiles": "O=CO"
},
"smiles": "O=CO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "17634",
"routeId": "sa_993b406c1963c803aecc9bfe",
"moleculeId": "sa_7cbb90a364ed5239af4ffe56",
"parentId": "17632",
"isLeaf": false,
"molecule": {
"id": "sa_7cbb90a364ed5239af4ffe56",
"inchikey": "MIAZJBIKGQZNFY-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(NCCCl)c(N)c1"
},
"smiles": "COC(=O)c1ccc(NCCCl)c(N)c1",
"reactionStepId": "sa_10a02ece69bcf50a07dd80c7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090118259A1;0745;699525\",\"rsmi\":\"O=[N+:8]([O-])[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:15][cH:14][c:9]1[NH:10][CH2:11][CH2:12][Cl:13]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[c:9]([NH:10][CH2:11][CH2:12][Cl:13])[cH:14][cH:15]1\"},\"mapped_reaction_smiles\":\"O=[N+:8]([O-])[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:15][cH:14][c:9]1[NH:10][CH2:11][CH2:12][Cl:13]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[c:9]([NH:10][CH2:11][CH2:12][Cl:13])[cH:14][cH:15]1\"}",
"reactionStep": {
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"children": [
{
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"molecule": {
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"inchikey": "DZAHTXIZTUIMNI-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(NCCCl)c([N+](=O)[O-])c1"
},
"smiles": "COC(=O)c1ccc(NCCCl)c([N+](=O)[O-])c1",
"reactionStepId": "sa_4eff67a037b9d1420800b045",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090118259A1;0744;699524\",\"rsmi\":\"F[c:11]1[c:7]([N+:8](=[O:9])[O-:10])[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:17][cH:16]1.[NH2:12][CH2:13][CH2:14][Cl:15]>CN(C)C=O.Cl.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]([NH:12][CH2:13][CH2:14][Cl:15])[cH:16][cH:17]1\"},\"mapped_reaction_smiles\":\"F[c:11]1[c:7]([N+:8](=[O:9])[O-:10])[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:17][cH:16]1.[NH2:12][CH2:13][CH2:14][Cl:15]>CN(C)C=O.Cl.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]([NH:12][CH2:13][CH2:14][Cl:15])[cH:16][cH:17]1\"}",
"reactionStep": {
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"children": [
{
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"molecule": {
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"smiles": "COC(=O)c1ccc(F)c([N+](=O)[O-])c1",
"reactionStepId": "sa_82362ac2c0c151e8d31bbcb2",
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"metadata": "{\"annotations\":{\"ID\":\"US20090118259A1;0743;699523\",\"rsmi\":\"I[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]([F:12])[cH:13][cH:14]1>CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]([F:12])[cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"I[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]([F:12])[cH:13][cH:14]1>CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([N+:8](=[O:9])[O-:10])[c:11]([F:12])[cH:13][cH:14]1\"}",
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"children": [
{
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"isLeaf": true,
"molecule": {
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"inchikey": "BOJWTAQWPVBIPG-UHFFFAOYSA-N",
"smiles": "O=C(O)c1ccc(F)c([N+](=O)[O-])c1"
},
"smiles": "O=C(O)c1ccc(F)c([N+](=O)[O-])c1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "17638",
"routeId": "sa_993b406c1963c803aecc9bfe",
"moleculeId": "sa_82fdccf7d1cc329c9db73f21",
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"molecule": {
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"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
},
"smiles": "CI",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
},
{
"id": "17639",
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"moleculeId": "sa_6c1ab7f5b259f4d917e2193a",
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"molecule": {
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"inchikey": "VKPPFDPXZWFDFA-UHFFFAOYSA-N",
"smiles": "NCCCl"
},
"smiles": "NCCCl",
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"template": null,
"metadata": null,
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}
]
}
]
}
]
}
]
}
]
},
{
"id": "17640",
"routeId": "sa_993b406c1963c803aecc9bfe",
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"parentId": "17628",
"isLeaf": true,
"molecule": {
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