Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1cc(Nc2cc(C(F)(F)F)ccn2)nc(-c2cnc(C3(O)CCc4cc(C(=O)O)ccc43)s2)c1
InChiKey
AYTXEKRLUZLIRO-UHFFFAOYSA-N
Route Signature
fe99b5b19af432df52287df6b746d576d89506aa5785b05a08d773180ea021bc
Synthesis route with 4 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_575beecdabe38786f817fa9f",
"signature": "fe99b5b19af432df52287df6b746d576d89506aa5785b05a08d773180ea021bc",
"contentHash": "4324cdcd4682e7f2f45d683e57594b6a271b4eefffdf8b186613cf5fe941512b",
"length": 4,
"isConvergent": false
},
"target": {
"id": "sa_31e5aa046ddf2dc1a3694eff",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-02375",
"moleculeId": "sa_c6bba77edf8baf6e0a7b5d5a",
"smiles": "Cc1cc(Nc2cc(C(F)(F)F)ccn2)nc(-c2cnc(C3(O)CCc4cc(C(=O)O)ccc43)s2)c1",
"routeLength": 4,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_c6bba77edf8baf6e0a7b5d5a",
"inchikey": "AYTXEKRLUZLIRO-UHFFFAOYSA-N",
"smiles": "Cc1cc(Nc2cc(C(F)(F)F)ccn2)nc(-c2cnc(C3(O)CCc4cc(C(=O)O)ccc43)s2)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "14778",
"routeId": "sa_575beecdabe38786f817fa9f",
"moleculeId": "sa_c6bba77edf8baf6e0a7b5d5a",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_c6bba77edf8baf6e0a7b5d5a",
"inchikey": "AYTXEKRLUZLIRO-UHFFFAOYSA-N",
"smiles": "Cc1cc(Nc2cc(C(F)(F)F)ccn2)nc(-c2cnc(C3(O)CCc4cc(C(=O)O)ccc43)s2)c1"
},
"smiles": "Cc1cc(Nc2cc(C(F)(F)F)ccn2)nc(-c2cnc(C3(O)CCc4cc(C(=O)O)ccc43)s2)c1",
"reactionStepId": "sa_b98e1c28a93097c44d124601",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140323440A1;0653;1604458\",\"rsmi\":\"C[O:18][C:16]([c:15]1[cH:14][c:13]2[c:21]([cH:20][cH:19]1)[C:9]([c:8]1[n:7][cH:6][c:5](-[c:4]3[cH:3][c:2]([CH3:1])[cH:36][c:24]([NH:25][c:26]4[n:27][cH:28][cH:29][c:30]([C:31]([F:32])([F:33])[F:34])[cH:35]4)[n:23]3)[s:22]1)([OH:10])[CH2:11][CH2:12]2)=[O:17]>C1CCOC1.CO.O.[K+].O>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][n:7][c:8]([C:9]3([OH:10])[CH2:11][CH2:12][c:13]4[cH:14][c:15]([C:16](=[O:17])[OH:18])[cH:19][cH:20][c:21]43)[s:22]2)[n:23][c:24]([NH:25][c:26]2[n:27][cH:28][cH:29][c:30]([C:31]([F:32])([F:33])[F:34])[cH:35]2)[cH:36]1\"},\"mapped_reaction_smiles\":\"C[O:18][C:16]([c:15]1[cH:14][c:13]2[c:21]([cH:20][cH:19]1)[C:9]([c:8]1[n:7][cH:6][c:5](-[c:4]3[cH:3][c:2]([CH3:1])[cH:36][c:24]([NH:25][c:26]4[n:27][cH:28][cH:29][c:30]([C:31]([F:32])([F:33])[F:34])[cH:35]4)[n:23]3)[s:22]1)([OH:10])[CH2:11][CH2:12]2)=[O:17]>C1CCOC1.CO.O.[K+].O>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][n:7][c:8]([C:9]3([OH:10])[CH2:11][CH2:12][c:13]4[cH:14][c:15]([C:16](=[O:17])[OH:18])[cH:19][cH:20][c:21]43)[s:22]2)[n:23][c:24]([NH:25][c:26]2[n:27][cH:28][cH:29][c:30]([C:31]([F:32])([F:33])[F:34])[cH:35]2)[cH:36]1\"}",
"reactionStep": {
"id": "sa_b98e1c28a93097c44d124601",
"reactionHash": "3448902267a22e2217d675a5a99feee7e635706c8439a97292a2f7fecb786b0b"
},
"children": [
{
"id": "14779",
"routeId": "sa_575beecdabe38786f817fa9f",
"moleculeId": "sa_d5313a4461cb2f0a509ff971",
"parentId": "14778",
"isLeaf": false,
"molecule": {
"id": "sa_d5313a4461cb2f0a509ff971",
"inchikey": "POSCJFQJRRZETF-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc2c(c1)CCC2(O)c1ncc(-c2cc(C)cc(Nc3cc(C(F)(F)F)ccn3)n2)s1"
},
"smiles": "COC(=O)c1ccc2c(c1)CCC2(O)c1ncc(-c2cc(C)cc(Nc3cc(C(F)(F)F)ccn3)n2)s1",
"reactionStepId": "sa_bf7230424dec418354731f42",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140323440A1;0651;1604457\",\"rsmi\":\"[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH2:11][CH2:12][C:13]2=[O:14].[cH:15]1[n:16][cH:17][c:18](-[c:19]2[n:20][c:21]([NH:22][c:23]3[n:24][cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32]3)[cH:33][c:34]([CH3:35])[cH:36]2)[s:37]1>C1CCOC1.CC(C)NC(C)C.[Li+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH2:11][CH2:12][C:13]2([OH:14])[c:15]1[n:16][cH:17][c:18](-[c:19]2[n:20][c:21]([NH:22][c:23]3[n:24][cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32]3)[cH:33][c:34]([CH3:35])[cH:36]2)[s:37]1\"},\"mapped_reaction_smiles\":\"[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH2:11][CH2:12][C:13]2=[O:14].[cH:15]1[n:16][cH:17][c:18](-[c:19]2[n:20][c:21]([NH:22][c:23]3[n:24][cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32]3)[cH:33][c:34]([CH3:35])[cH:36]2)[s:37]1>C1CCOC1.CC(C)NC(C)C.[Li+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH2:11][CH2:12][C:13]2([OH:14])[c:15]1[n:16][cH:17][c:18](-[c:19]2[n:20][c:21]([NH:22][c:23]3[n:24][cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32]3)[cH:33][c:34]([CH3:35])[cH:36]2)[s:37]1\"}",
"reactionStep": {
"id": "sa_bf7230424dec418354731f42",
"reactionHash": "7344414b9f3eb6dae605e2fd2a39842d738fc32767089b6768977b8eb65d1261"
},
"children": [
{
"id": "14780",
"routeId": "sa_575beecdabe38786f817fa9f",
"moleculeId": "sa_47c3a22ee3fb374f8d5e2767",
"parentId": "14779",
"isLeaf": false,
"molecule": {
"id": "sa_47c3a22ee3fb374f8d5e2767",
"inchikey": "WFRKJXXQHKZGRD-UHFFFAOYSA-N",
"smiles": "Cc1cc(Nc2cc(C(F)(F)F)ccn2)nc(-c2cncs2)c1"
},
"smiles": "Cc1cc(Nc2cc(C(F)(F)F)ccn2)nc(-c2cncs2)c1",
"reactionStepId": "sa_40b978e6202abe58d3185da0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140323440A1;0511;1604432\",\"rsmi\":\"Br[c:17]1[n:16][c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]2)[cH:3][c:2]([CH3:1])[cH:23]1.[cH:18]1[cH:19][n:20][cH:21][s:22]1>C=CC.C=CC.CC(=O)N(C)C.CC(C)(C)C(=O)O.CCCCP(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2.Cl[Pd+].Cl[Pd+].O=C(O)O.[K+].[K+]>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]2)[n:16][c:17](-[c:18]2[cH:19][n:20][cH:21][s:22]2)[cH:23]1\"},\"mapped_reaction_smiles\":\"Br[c:17]1[n:16][c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]2)[cH:3][c:2]([CH3:1])[cH:23]1.[cH:18]1[cH:19][n:20][cH:21][s:22]1>C=CC.C=CC.CC(=O)N(C)C.CC(C)(C)C(=O)O.CCCCP(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2.Cl[Pd+].Cl[Pd+].O=C(O)O.[K+].[K+]>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]2)[n:16][c:17](-[c:18]2[cH:19][n:20][cH:21][s:22]2)[cH:23]1\"}",
"reactionStep": {
"id": "sa_40b978e6202abe58d3185da0",
"reactionHash": "008d97aab76d0464aca30ac48746fe64d9b7629ca7a1ab10ed64d757e3f7bde5"
},
"children": [
{
"id": "14781",
"routeId": "sa_575beecdabe38786f817fa9f",
"moleculeId": "sa_e325279e604501686a682ea7",
"parentId": "14780",
"isLeaf": false,
"molecule": {
"id": "sa_e325279e604501686a682ea7",
"inchikey": "CHUJHHQJUKDECG-UHFFFAOYSA-N",
"smiles": "Cc1cc(Br)nc(Nc2cc(C(F)(F)F)ccn2)c1"
},
"smiles": "Cc1cc(Br)nc(Nc2cc(C(F)(F)F)ccn2)c1",
"reactionStepId": "sa_8ec60aaf94f062da720d0549",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140323440A1;0509;1604431\",\"rsmi\":\"Br[c:4]1[cH:3][c:2]([CH3:1])[cH:19][c:17]([Br:18])[n:16]1.[NH2:5][c:6]1[n:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1>C1COCCO1.CC(C)(C)O.Cl[Pd]Cl.N#N.[Fe+2].[Na+]>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]2)[n:16][c:17]([Br:18])[cH:19]1\"},\"mapped_reaction_smiles\":\"Br[c:4]1[cH:3][c:2]([CH3:1])[cH:19][c:17]([Br:18])[n:16]1.[NH2:5][c:6]1[n:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1>C1COCCO1.CC(C)(C)O.Cl[Pd]Cl.N#N.[Fe+2].[Na+]>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]2)[n:16][c:17]([Br:18])[cH:19]1\"}",
"reactionStep": {
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"reactionHash": "b37306a2491e1944e28066295d5110755d3f499ae2158fc9170b47b25a5be218"
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"children": [
{
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"moleculeId": "sa_885bad841320986f6664ebec",
"parentId": "14781",
"isLeaf": true,
"molecule": {
"id": "sa_885bad841320986f6664ebec",
"inchikey": "OHBIPNNTWKNAGC-UHFFFAOYSA-N",
"smiles": "Cc1cc(Br)nc(Br)c1"
},
"smiles": "Cc1cc(Br)nc(Br)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14783",
"routeId": "sa_575beecdabe38786f817fa9f",
"moleculeId": "sa_7d334454ee15f4780238c103",
"parentId": "14781",
"isLeaf": true,
"molecule": {
"id": "sa_7d334454ee15f4780238c103",
"inchikey": "RWGBXAQMUBGGKQ-UHFFFAOYSA-N",
"smiles": "Nc1cc(C(F)(F)F)ccn1"
},
"smiles": "Nc1cc(C(F)(F)F)ccn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
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}
]
},
{
"id": "14784",
"routeId": "sa_575beecdabe38786f817fa9f",
"moleculeId": "sa_7aa23d9ca8f15319d9e6cd68",
"parentId": "14780",
"isLeaf": true,
"molecule": {
"id": "sa_7aa23d9ca8f15319d9e6cd68",
"inchikey": "FZWLAAWBMGSTSO-UHFFFAOYSA-N",
"smiles": "c1cscn1"
},
"smiles": "c1cscn1",
"reactionStepId": null,
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"children": []
}
]
},
{
"id": "14785",
"routeId": "sa_575beecdabe38786f817fa9f",
"moleculeId": "sa_2502340c7f7e1f1aac9e9cb8",
"parentId": "14779",
"isLeaf": true,
"molecule": {
"id": "sa_2502340c7f7e1f1aac9e9cb8",
"inchikey": "YYKBHCRUMAMBPY-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc2c(c1)CCC2=O"
},
"smiles": "COC(=O)c1ccc2c(c1)CCC2=O",
"reactionStepId": null,
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}
]
}
]
}
}