Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COC(=O)Cc1ccc(C#Cc2cc(OC(C)C)c3c(c2)C(C)(C)CCC3=O)cc1
InChiKey
GBBHOZSTTYVTLQ-UHFFFAOYSA-N
Route Signature
a213c9cdc88299376277019e211245f1bc90e7b73c121dddecb4cc8454487bb0
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_9daaa34749dba8a70beef68f",
"signature": "a213c9cdc88299376277019e211245f1bc90e7b73c121dddecb4cc8454487bb0",
"contentHash": "5aef1f91ca861e454fa94a24b97ff89deeaeca1f0200f119b487901cee1c3e22",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_907ef605738b5f563eabb088",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00135",
"moleculeId": "sa_8f3d940c0ae1437e695657b9",
"smiles": "COC(=O)Cc1ccc(C#Cc2cc(OC(C)C)c3c(c2)C(C)(C)CCC3=O)cc1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_8f3d940c0ae1437e695657b9",
"inchikey": "GBBHOZSTTYVTLQ-UHFFFAOYSA-N",
"smiles": "COC(=O)Cc1ccc(C#Cc2cc(OC(C)C)c3c(c2)C(C)(C)CCC3=O)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "12527",
"routeId": "sa_9daaa34749dba8a70beef68f",
"moleculeId": "sa_8f3d940c0ae1437e695657b9",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_8f3d940c0ae1437e695657b9",
"inchikey": "GBBHOZSTTYVTLQ-UHFFFAOYSA-N",
"smiles": "COC(=O)Cc1ccc(C#Cc2cc(OC(C)C)c3c(c2)C(C)(C)CCC3=O)cc1"
},
"smiles": "COC(=O)Cc1ccc(C#Cc2cc(OC(C)C)c3c(c2)C(C)(C)CCC3=O)cc1",
"reactionStepId": "sa_0044885c2e7d5581127f44f7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07638648B2;0722;947623\",\"rsmi\":\"I[c:9]1[cH:8][cH:7][c:6]([CH2:5][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:23]([O:24][CH:25]([CH3:26])[CH3:27])[cH:28]1)[C:16](=[O:17])[CH2:18][CH2:19][C:20]2([CH3:21])[CH3:22]>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])[CH2:5][c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][c:14]3[c:15]([c:23]([O:24][CH:25]([CH3:26])[CH3:27])[cH:28]2)[C:16](=[O:17])[CH2:18][CH2:19][C:20]3([CH3:21])[CH3:22])[cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"I[c:9]1[cH:8][cH:7][c:6]([CH2:5][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:23]([O:24][CH:25]([CH3:26])[CH3:27])[cH:28]1)[C:16](=[O:17])[CH2:18][CH2:19][C:20]2([CH3:21])[CH3:22]>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])[CH2:5][c:6]1[cH:7][cH:8][c:9]([C:10]#[C:11][c:12]2[cH:13][c:14]3[c:15]([c:23]([O:24][CH:25]([CH3:26])[CH3:27])[cH:28]2)[C:16](=[O:17])[CH2:18][CH2:19][C:20]3([CH3:21])[CH3:22])[cH:29][cH:30]1\"}",
"reactionStep": {
"id": "sa_0044885c2e7d5581127f44f7",
"reactionHash": "f66cab01aec97b9fd12c432148c537a1f58c9409202720082f6036c96449245d"
},
"children": [
{
"id": "12528",
"routeId": "sa_9daaa34749dba8a70beef68f",
"moleculeId": "sa_16b1cc1f5dfccb0d11771eb3",
"parentId": "12527",
"isLeaf": false,
"molecule": {
"id": "sa_16b1cc1f5dfccb0d11771eb3",
"inchikey": "DBRXFZQTXVZBMC-UHFFFAOYSA-N",
"smiles": "C#Cc1cc(OC(C)C)c2c(c1)C(C)(C)CCC2=O"
},
"smiles": "C#Cc1cc(OC(C)C)c2c(c1)C(C)(C)CCC2=O",
"reactionStepId": "sa_46106c4a759d273bf41a085a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07638648B2;0720;947622\",\"rsmi\":\"C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][c:5]([O:6][CH:7]([CH3:8])[CH3:9])[c:10]2[c:18]([cH:19]1)[C:15]([CH3:16])([CH3:17])[CH2:14][CH2:13][C:11]2=[O:12]>CO.O=C(O)O.[K+].[K+]>[CH:1]#[C:2][c:3]1[cH:4][c:5]([O:6][CH:7]([CH3:8])[CH3:9])[c:10]2[c:18]([cH:19]1)[C:15]([CH3:16])([CH3:17])[CH2:14][CH2:13][C:11]2=[O:12]\"},\"mapped_reaction_smiles\":\"C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][c:5]([O:6][CH:7]([CH3:8])[CH3:9])[c:10]2[c:18]([cH:19]1)[C:15]([CH3:16])([CH3:17])[CH2:14][CH2:13][C:11]2=[O:12]>CO.O=C(O)O.[K+].[K+]>[CH:1]#[C:2][c:3]1[cH:4][c:5]([O:6][CH:7]([CH3:8])[CH3:9])[c:10]2[c:18]([cH:19]1)[C:15]([CH3:16])([CH3:17])[CH2:14][CH2:13][C:11]2=[O:12]\"}",
"reactionStep": {
"id": "sa_46106c4a759d273bf41a085a",
"reactionHash": "632ff006b7e2e0ef30fc6769cd858a8bc54994579bd11453b0e1aaac9b39fad0"
},
"children": [
{
"id": "12529",
"routeId": "sa_9daaa34749dba8a70beef68f",
"moleculeId": "sa_c3689d5d28053f43da594db8",
"parentId": "12528",
"isLeaf": false,
"molecule": {
"id": "sa_c3689d5d28053f43da594db8",
"inchikey": "YEXGXMJLMGXNLU-UHFFFAOYSA-N",
"smiles": "CC(C)Oc1cc(C#C[Si](C)(C)C)cc2c1C(=O)CCC2(C)C"
},
"smiles": "CC(C)Oc1cc(C#C[Si](C)(C)C)cc2c1C(=O)CCC2(C)C",
"reactionStepId": "sa_d34fcb0b2a8b813fa5e87585",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07638648B2;0718;947621\",\"rsmi\":\"I[CH:2]([CH3:1])[CH3:3].[OH:4][c:5]1[c:6]2[c:14]([cH:15][c:16]([C:17]#[C:18][Si:19]([CH3:20])([CH3:21])[CH3:22])[cH:23]1)[C:11]([CH3:12])([CH3:13])[CH2:10][CH2:9][C:7]2=[O:8]>CC(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[c:6]2[c:14]([cH:15][c:16]([C:17]#[C:18][Si:19]([CH3:20])([CH3:21])[CH3:22])[cH:23]1)[C:11]([CH3:12])([CH3:13])[CH2:10][CH2:9][C:7]2=[O:8]\"},\"mapped_reaction_smiles\":\"I[CH:2]([CH3:1])[CH3:3].[OH:4][c:5]1[c:6]2[c:14]([cH:15][c:16]([C:17]#[C:18][Si:19]([CH3:20])([CH3:21])[CH3:22])[cH:23]1)[C:11]([CH3:12])([CH3:13])[CH2:10][CH2:9][C:7]2=[O:8]>CC(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[c:6]2[c:14]([cH:15][c:16]([C:17]#[C:18][Si:19]([CH3:20])([CH3:21])[CH3:22])[cH:23]1)[C:11]([CH3:12])([CH3:13])[CH2:10][CH2:9][C:7]2=[O:8]\"}",
"reactionStep": {
"id": "sa_d34fcb0b2a8b813fa5e87585",
"reactionHash": "7b7f6a6af696d083371c8c2d2fd3d570b8bd534e7ffbb3ec37761ecb0ae548fe"
},
"children": [
{
"id": "12530",
"routeId": "sa_9daaa34749dba8a70beef68f",
"moleculeId": "sa_1c18b9a29c101d82cfd154ef",
"parentId": "12529",
"isLeaf": true,
"molecule": {
"id": "sa_1c18b9a29c101d82cfd154ef",
"inchikey": "FMKOJHQHASLBPH-UHFFFAOYSA-N",
"smiles": "CC(C)I"
},
"smiles": "CC(C)I",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12531",
"routeId": "sa_9daaa34749dba8a70beef68f",
"moleculeId": "sa_b271eb565070f8b07af1ecdc",
"parentId": "12529",
"isLeaf": false,
"molecule": {
"id": "sa_b271eb565070f8b07af1ecdc",
"inchikey": "RNTVAPJYIHGXEA-UHFFFAOYSA-N",
"smiles": "CC1(C)CCC(=O)c2c(O)cc(C#C[Si](C)(C)C)cc21"
},
"smiles": "CC1(C)CCC(=O)c2c(O)cc(C#C[Si](C)(C)C)cc21",
"reactionStepId": "sa_72801b62bf500a32df5cf01b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07638648B2;0571;947550\",\"rsmi\":\"Br[c:12]1[cH:11][c:9]([OH:10])[c:8]2[c:20]([cH:19]1)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6]2=[O:7].[CH:13]#[C:14][Si:15]([CH3:16])([CH3:17])[CH3:18]>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][CH2:5][C:6](=[O:7])[c:8]2[c:9]([OH:10])[cH:11][c:12]([C:13]#[C:14][Si:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][c:20]21\"},\"mapped_reaction_smiles\":\"Br[c:12]1[cH:11][c:9]([OH:10])[c:8]2[c:20]([cH:19]1)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6]2=[O:7].[CH:13]#[C:14][Si:15]([CH3:16])([CH3:17])[CH3:18]>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][CH2:5][C:6](=[O:7])[c:8]2[c:9]([OH:10])[cH:11][c:12]([C:13]#[C:14][Si:15]([CH3:16])([CH3:17])[CH3:18])[cH:19][c:20]21\"}",
"reactionStep": {
"id": "sa_72801b62bf500a32df5cf01b",
"reactionHash": "5396d30d07bfa6ed75b8ac7ab58f84677056856e90d3d194d4c9b0ff4db32965"
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"children": [
{
"id": "12532",
"routeId": "sa_9daaa34749dba8a70beef68f",
"moleculeId": "sa_95a9277ba0d873f43bb42b7f",
"parentId": "12531",
"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": "12533",
"routeId": "sa_9daaa34749dba8a70beef68f",
"moleculeId": "sa_aec98dc6fd59d90d5b5af5e5",
"parentId": "12531",
"isLeaf": false,
"molecule": {
"id": "sa_aec98dc6fd59d90d5b5af5e5",
"inchikey": "LCTKBYBCVVBKLG-UHFFFAOYSA-N",
"smiles": "CC1(C)CCC(=O)c2c(O)cc(Br)cc21"
},
"smiles": "CC1(C)CCC(=O)c2c(O)cc(Br)cc21",
"reactionStepId": "sa_2a92dec137710de304e985d6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07638648B2;0569;947549\",\"rsmi\":\"C[O:10][c:9]1[c:8]2[c:15]([cH:14][c:12]([Br:13])[cH:11]1)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6]2=[O:7]>ClCCl.O.[Al+3].Cl.Cl.Cl>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]2[c:9]([OH:10])[cH:11][c:12]([Br:13])[cH:14][c:15]21\"},\"mapped_reaction_smiles\":\"C[O:10][c:9]1[c:8]2[c:15]([cH:14][c:12]([Br:13])[cH:11]1)[C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][C:6]2=[O:7]>ClCCl.O.[Al+3].Cl.Cl.Cl>[CH3:1][C:2]1([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]2[c:9]([OH:10])[cH:11][c:12]([Br:13])[cH:14][c:15]21\"}",
"reactionStep": {
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"reactionHash": "0587277dfae87183afba5dd83cdd1c98ae92aee17218c8187b333ad83401ed85"
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"children": [
{
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"routeId": "sa_9daaa34749dba8a70beef68f",
"moleculeId": "sa_25cf3caa95cf69dc29bbd494",
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"isLeaf": false,
"molecule": {
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"inchikey": "YWTITWZHVYDTNO-UHFFFAOYSA-N",
"smiles": "COc1cc(Br)cc2c1C(=O)CCC2(C)C"
},
"smiles": "COc1cc(Br)cc2c1C(=O)CCC2(C)C",
"reactionStepId": "sa_5ffb3a1398d0c424c56f0958",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07638648B2;0567;947548\",\"rsmi\":\"[CH3:1][O:2][c:3]1[c:4]2[c:12]([cH:13][c:14]([Br:15])[cH:16]1)[C:9]([CH3:10])([CH3:11])[CH2:8][CH2:7][CH2:5]2.[OH2:6]>CC(=O)O.CCCCCC.CCOC(C)=O.[Cr+6].[O-2].[O-2].[O-2]>[CH3:1][O:2][c:3]1[c:4]2[c:12]([cH:13][c:14]([Br:15])[cH:16]1)[C:9]([CH3:10])([CH3:11])[CH2:8][CH2:7][C:5]2=[O:6]\"},\"mapped_reaction_smiles\":\"[CH3:1][O:2][c:3]1[c:4]2[c:12]([cH:13][c:14]([Br:15])[cH:16]1)[C:9]([CH3:10])([CH3:11])[CH2:8][CH2:7][CH2:5]2.[OH2:6]>CC(=O)O.CCCCCC.CCOC(C)=O.[Cr+6].[O-2].[O-2].[O-2]>[CH3:1][O:2][c:3]1[c:4]2[c:12]([cH:13][c:14]([Br:15])[cH:16]1)[C:9]([CH3:10])([CH3:11])[CH2:8][CH2:7][C:5]2=[O:6]\"}",
"reactionStep": {
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"reactionHash": "df45952bd99bbb3181f482c281688f032a64fcd2e3a5d749cd50fb943bdf552a"
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"children": [
{
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"moleculeId": "sa_0fc4a14384b5306fd7ebeb34",
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"molecule": {
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"inchikey": "HECMVQJEBMLRKB-UHFFFAOYSA-N",
"smiles": "COc1cc(Br)cc2c1CCCC2(C)C"
},
"smiles": "COc1cc(Br)cc2c1CCCC2(C)C",
"reactionStepId": null,
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{
"id": "12536",
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"moleculeId": "sa_106b35b8a76bbe73829a0a69",
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"molecule": {
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"inchikey": "XLYOFNOQVPJJNP-UHFFFAOYSA-N",
"smiles": "O"
},
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}
]
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]
}
]
}
]
}
]
},
{
"id": "12537",
"routeId": "sa_9daaa34749dba8a70beef68f",
"moleculeId": "sa_11798855af365800c1e0426f",
"parentId": "12527",
"isLeaf": true,
"molecule": {
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"inchikey": "IYIVBGQBEMSRLO-UHFFFAOYSA-N",
"smiles": "COC(=O)Cc1ccc(I)cc1"
},
"smiles": "COC(=O)Cc1ccc(I)cc1",
"reactionStepId": null,
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"children": []
}
]
}
}