Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC1(C)CC2(CC2)Oc2c(C3CC3)cc(C#Cc3ccc(C(=O)O)c(F)c3)cc21
InChiKey
APJKXYNFLYDWJW-UHFFFAOYSA-N
Route Signature
22a3e93db912b5224b52e1a13f49ff524e65613a77634d335d43778d11d71fd5
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_43ac4f4d095831d73aaee054",
"signature": "22a3e93db912b5224b52e1a13f49ff524e65613a77634d335d43778d11d71fd5",
"contentHash": "15626ffd174110bf3d08248c3094e5212ed25ba637eb748db34bb81602c60341",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_b535586fe10aee56252711d2",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-01008",
"moleculeId": "sa_8c7335baec2972e7110a46b1",
"smiles": "CC1(C)CC2(CC2)Oc2c(C3CC3)cc(C#Cc3ccc(C(=O)O)c(F)c3)cc21",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_8c7335baec2972e7110a46b1",
"inchikey": "APJKXYNFLYDWJW-UHFFFAOYSA-N",
"smiles": "CC1(C)CC2(CC2)Oc2c(C3CC3)cc(C#Cc3ccc(C(=O)O)c(F)c3)cc21"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13972",
"routeId": "sa_43ac4f4d095831d73aaee054",
"moleculeId": "sa_8c7335baec2972e7110a46b1",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_8c7335baec2972e7110a46b1",
"inchikey": "APJKXYNFLYDWJW-UHFFFAOYSA-N",
"smiles": "CC1(C)CC2(CC2)Oc2c(C3CC3)cc(C#Cc3ccc(C(=O)O)c(F)c3)cc21"
},
"smiles": "CC1(C)CC2(CC2)Oc2c(C3CC3)cc(C#Cc3ccc(C(=O)O)c(F)c3)cc21",
"reactionStepId": "sa_6aa7480c111e2352497f4b37",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06855512B2;00714;673297\",\"rsmi\":\"C[O:22][C:20]([c:19]1[c:17]([F:18])[cH:16][c:15]([C:14]#[C:13][c:12]2[cH:11][c:10]3[c:9]([c:26]([CH:27]4[CH2:28][CH2:29]4)[cH:25]2)[O:8][C:5]2([CH2:4][C:2]3([CH3:1])[CH3:3])[CH2:6][CH2:7]2)[cH:24][cH:23]1)=[O:21]>CC#N.CO.O.[Na+].O>[CH3:1][C:2]1([CH3:3])[CH2:4][C:5]2([CH2:6][CH2:7]2)[O:8][c:9]2[c:10]1[cH:11][c:12]([C:13]#[C:14][c:15]1[cH:16][c:17]([F:18])[c:19]([C:20](=[O:21])[OH:22])[cH:23][cH:24]1)[cH:25][c:26]2[CH:27]1[CH2:28][CH2:29]1\"},\"mapped_reaction_smiles\":\"C[O:22][C:20]([c:19]1[c:17]([F:18])[cH:16][c:15]([C:14]#[C:13][c:12]2[cH:11][c:10]3[c:9]([c:26]([CH:27]4[CH2:28][CH2:29]4)[cH:25]2)[O:8][C:5]2([CH2:4][C:2]3([CH3:1])[CH3:3])[CH2:6][CH2:7]2)[cH:24][cH:23]1)=[O:21]>CC#N.CO.O.[Na+].O>[CH3:1][C:2]1([CH3:3])[CH2:4][C:5]2([CH2:6][CH2:7]2)[O:8][c:9]2[c:10]1[cH:11][c:12]([C:13]#[C:14][c:15]1[cH:16][c:17]([F:18])[c:19]([C:20](=[O:21])[OH:22])[cH:23][cH:24]1)[cH:25][c:26]2[CH:27]1[CH2:28][CH2:29]1\"}",
"reactionStep": {
"id": "sa_6aa7480c111e2352497f4b37",
"reactionHash": "3ec6c32cb72327ee57f0d83c9ca715342b1203faaf6dbabc3295a60d79ab0374"
},
"children": [
{
"id": "13973",
"routeId": "sa_43ac4f4d095831d73aaee054",
"moleculeId": "sa_a191a6c286acd021564dd88a",
"parentId": "13972",
"isLeaf": false,
"molecule": {
"id": "sa_a191a6c286acd021564dd88a",
"inchikey": "CSIQFZXLEDQFBQ-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(C#Cc2cc(C3CC3)c3c(c2)C(C)(C)CC2(CC2)O3)cc1F"
},
"smiles": "COC(=O)c1ccc(C#Cc2cc(C3CC3)c3c(c2)C(C)(C)CC2(CC2)O3)cc1F",
"reactionStepId": "sa_575d12100b7769bab48dce64",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06855512B2;00711;673296\",\"rsmi\":\"I[c:9]1[cH:8][c:6]([F:7])[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:30][cH:29]1.[CH:10]#[C:11][c:12]1[cH:13][c:14]2[c:15]([c:24]([CH:25]3[CH2:26][CH2:27]3)[cH:28]1)[O:16][C:17]1([CH2:18][CH2:19]1)[CH2:20][C:21]2([CH3:22])[CH3:23]>C1CCOC1.CCCCCC.CCN(CC)CC.CCOC(C)=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.[Cu]I>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([F:7])[cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][c:14]3[c:15]([c:24]([CH:25]4[CH2:26][CH2:27]4)[cH:28]2)[O:16][C:17]2([CH2:18][CH2:19]2)[CH2:20][C:21]3([CH3:22])[CH3:23])[cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"I[c:9]1[cH:8][c:6]([F:7])[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:30][cH:29]1.[CH:10]#[C:11][c:12]1[cH:13][c:14]2[c:15]([c:24]([CH:25]3[CH2:26][CH2:27]3)[cH:28]1)[O:16][C:17]1([CH2:18][CH2:19]1)[CH2:20][C:21]2([CH3:22])[CH3:23]>C1CCOC1.CCCCCC.CCN(CC)CC.CCOC(C)=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.[Cu]I>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([F:7])[cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][c:14]3[c:15]([c:24]([CH:25]4[CH2:26][CH2:27]4)[cH:28]2)[O:16][C:17]2([CH2:18][CH2:19]2)[CH2:20][C:21]3([CH3:22])[CH3:23])[cH:29][cH:30]1\"}",
"reactionStep": {
"id": "sa_575d12100b7769bab48dce64",
"reactionHash": "e32c7c44e8cff9764b9fa54abbdd79b8f6d5122ed4a4cf02f5fc4483f84ce39d"
},
"children": [
{
"id": "13974",
"routeId": "sa_43ac4f4d095831d73aaee054",
"moleculeId": "sa_26741fed81b22b1a0241aa91",
"parentId": "13973",
"isLeaf": false,
"molecule": {
"id": "sa_26741fed81b22b1a0241aa91",
"inchikey": "FYKUMCVXUUWHDN-UHFFFAOYSA-N",
"smiles": "C#Cc1cc(C2CC2)c2c(c1)C(C)(C)CC1(CC1)O2"
},
"smiles": "C#Cc1cc(C2CC2)c2c(c1)C(C)(C)CC1(CC1)O2",
"reactionStepId": "sa_f2b1b91aba02b2093cd122cd",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06855512B2;00690;673293\",\"rsmi\":\"C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][c:5]2[c:6]([c:15]([CH:16]3[CH2:17][CH2:18]3)[cH:19]1)[O:7][C:8]1([CH2:9][CH2:10]1)[CH2:11][C:12]2([CH3:13])[CH3:14]>CCCCCC.CCOC(C)=O.CO.O=C(O)O.[K+].[K+]>[CH:1]#[C:2][c:3]1[cH:4][c:5]2[c:6]([c:15]([CH:16]3[CH2:17][CH2:18]3)[cH:19]1)[O:7][C:8]1([CH2:9][CH2:10]1)[CH2:11][C:12]2([CH3:13])[CH3:14]\"},\"mapped_reaction_smiles\":\"C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][c:5]2[c:6]([c:15]([CH:16]3[CH2:17][CH2:18]3)[cH:19]1)[O:7][C:8]1([CH2:9][CH2:10]1)[CH2:11][C:12]2([CH3:13])[CH3:14]>CCCCCC.CCOC(C)=O.CO.O=C(O)O.[K+].[K+]>[CH:1]#[C:2][c:3]1[cH:4][c:5]2[c:6]([c:15]([CH:16]3[CH2:17][CH2:18]3)[cH:19]1)[O:7][C:8]1([CH2:9][CH2:10]1)[CH2:11][C:12]2([CH3:13])[CH3:14]\"}",
"reactionStep": {
"id": "sa_f2b1b91aba02b2093cd122cd",
"reactionHash": "a65f7ce0e145bb7de6a441bf9d7ebacb9abb366eb4994052412b07d7b5947a48"
},
"children": [
{
"id": "13975",
"routeId": "sa_43ac4f4d095831d73aaee054",
"moleculeId": "sa_9735749d1ad271421d54dd24",
"parentId": "13974",
"isLeaf": false,
"molecule": {
"id": "sa_9735749d1ad271421d54dd24",
"inchikey": "ILLJGXWZMTYTFE-UHFFFAOYSA-N",
"smiles": "CC1(C)CC2(CC2)Oc2c(C3CC3)cc(C#C[Si](C)(C)C)cc21"
},
"smiles": "CC1(C)CC2(CC2)Oc2c(C3CC3)cc(C#C[Si](C)(C)C)cc21",
"reactionStepId": "sa_cab069d6b76beced07bd6d4c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06855512B2;00687;673292\",\"rsmi\":\"Br[c:12]1[cH:11][c:10]2[c:9]([c:20]([CH:21]3[CH2:22][CH2:23]3)[cH:19]1)[O:8][C:5]1([CH2:4][C:2]2([CH3:1])[CH3:3])[CH2:6][CH2:7]1.[CH:13]#[C:14][Si:15]([CH3:16])([CH3:17])[CH3:18]>C1CCOC1.CCCCCC.CCN(CC)CC.CCOC(C)=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.[Cu]I>[CH3:1][C:2]1([CH3:3])[CH2:4][C:5]2([CH2:6][CH2:7]2)[O:8][c:9]2[c:10]1[cH:11][c:12]([C:13]#[C:14][Si:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][c:20]2[CH:21]1[CH2:22][CH2:23]1\"},\"mapped_reaction_smiles\":\"Br[c:12]1[cH:11][c:10]2[c:9]([c:20]([CH:21]3[CH2:22][CH2:23]3)[cH:19]1)[O:8][C:5]1([CH2:4][C:2]2([CH3:1])[CH3:3])[CH2:6][CH2:7]1.[CH:13]#[C:14][Si:15]([CH3:16])([CH3:17])[CH3:18]>C1CCOC1.CCCCCC.CCN(CC)CC.CCOC(C)=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.[Cu]I>[CH3:1][C:2]1([CH3:3])[CH2:4][C:5]2([CH2:6][CH2:7]2)[O:8][c:9]2[c:10]1[cH:11][c:12]([C:13]#[C:14][Si:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][c:20]2[CH:21]1[CH2:22][CH2:23]1\"}",
"reactionStep": {
"id": "sa_cab069d6b76beced07bd6d4c",
"reactionHash": "9ca5bd33a243b97fd57be8591a46486766ccbf32d6a003d7f93e225a156e9f0f"
},
"children": [
{
"id": "13976",
"routeId": "sa_43ac4f4d095831d73aaee054",
"moleculeId": "sa_95a9277ba0d873f43bb42b7f",
"parentId": "13975",
"isLeaf": true,
"molecule": {
"id": "sa_95a9277ba0d873f43bb42b7f",
"inchikey": "CWMFRHBXRUITQE-UHFFFAOYSA-N",
"smiles": "C#C[Si](C)(C)C"
},
"smiles": "C#C[Si](C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13977",
"routeId": "sa_43ac4f4d095831d73aaee054",
"moleculeId": "sa_5e9c007f6ca369e0acb61dae",
"parentId": "13975",
"isLeaf": false,
"molecule": {
"id": "sa_5e9c007f6ca369e0acb61dae",
"inchikey": "WMFWCNYKBAYFGA-UHFFFAOYSA-N",
"smiles": "CC1(C)CC2(CC2)Oc2c(C3CC3)cc(Br)cc21"
},
"smiles": "CC1(C)CC2(CC2)Oc2c(C3CC3)cc(Br)cc21",
"reactionStepId": "sa_92e29a618f091cb054f5dbba",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06855512B2;00684;673291\",\"rsmi\":\"[CH3:1][C:2]1([CH3:3])[CH2:4][C:5]2([CH2:6][CH2:7]2)[O:8][c:9]2[c:10]1[cH:11][c:12]([Br:13])[cH:14][c:15]2[CH:16]=[CH2:18].[N-]=[N+]=[CH2:17]>CC(=O)O.CC(=O)O.CCCCCC.CCOCC.[Pd+2]>[CH3:1][C:2]1([CH3:3])[CH2:4][C:5]2([CH2:6][CH2:7]2)[O:8][c:9]2[c:10]1[cH:11][c:12]([Br:13])[cH:14][c:15]2[CH:16]1[CH2:17][CH2:18]1\"},\"mapped_reaction_smiles\":\"[CH3:1][C:2]1([CH3:3])[CH2:4][C:5]2([CH2:6][CH2:7]2)[O:8][c:9]2[c:10]1[cH:11][c:12]([Br:13])[cH:14][c:15]2[CH:16]=[CH2:18].[N-]=[N+]=[CH2:17]>CC(=O)O.CC(=O)O.CCCCCC.CCOCC.[Pd+2]>[CH3:1][C:2]1([CH3:3])[CH2:4][C:5]2([CH2:6][CH2:7]2)[O:8][c:9]2[c:10]1[cH:11][c:12]([Br:13])[cH:14][c:15]2[CH:16]1[CH2:17][CH2:18]1\"}",
"reactionStep": {
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"reactionHash": "9ed0ec5c50c410eab51e51eb84c0e976adfa66b2d47303cf9e93866239f13060"
},
"children": [
{
"id": "13978",
"routeId": "sa_43ac4f4d095831d73aaee054",
"moleculeId": "sa_592f3ab152cc3c75c0141516",
"parentId": "13977",
"isLeaf": true,
"molecule": {
"id": "sa_592f3ab152cc3c75c0141516",
"inchikey": "UDSLVHBDCYYVPM-UHFFFAOYSA-N",
"smiles": "C=Cc1cc(Br)cc2c1OC1(CC1)CC2(C)C"
},
"smiles": "C=Cc1cc(Br)cc2c1OC1(CC1)CC2(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13979",
"routeId": "sa_43ac4f4d095831d73aaee054",
"moleculeId": "sa_47ec1e93d8bd2e9f135e0452",
"parentId": "13977",
"isLeaf": true,
"molecule": {
"id": "sa_47ec1e93d8bd2e9f135e0452",
"inchikey": "YXHKONLOYHBTNS-UHFFFAOYSA-N",
"smiles": "C=[N+]=[N-]"
},
"smiles": "C=[N+]=[N-]",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
]
},
{
"id": "13980",
"routeId": "sa_43ac4f4d095831d73aaee054",
"moleculeId": "sa_1e0322e2559c40b360da947f",
"parentId": "13973",
"isLeaf": true,
"molecule": {
"id": "sa_1e0322e2559c40b360da947f",
"inchikey": "SCHHLHKOJRWALP-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(I)cc1F"
},
"smiles": "COC(=O)c1ccc(I)cc1F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}