Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCOC(=O)/C(F)=C(/C)c1cc2c(cc1OCC)OC(C)(C)C=C2C(C)C
InChiKey
YSLXCWAUZACMKI-XSFVSMFZSA-N
Route Signature
1e5208b1dbe89eee57e6955df793acea5fede2ec77f1bb887b5c139512f87f42
Synthesis route with 7 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_9fcd0b3bc9004b72818c99ed",
"signature": "1e5208b1dbe89eee57e6955df793acea5fede2ec77f1bb887b5c139512f87f42",
"contentHash": "bebf47b6be52995e1cc72672785e7f0f6a5d489eddd1688668c1e815fe95b6b0",
"length": 7,
"isConvergent": false
},
"target": {
"id": "sa_6ffb525c84d6877c53d9b90e",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00219",
"moleculeId": "sa_55fc2a50826c8aa6e75f372f",
"smiles": "CCOC(=O)/C(F)=C(/C)c1cc2c(cc1OCC)OC(C)(C)C=C2C(C)C",
"routeLength": 7,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_55fc2a50826c8aa6e75f372f",
"inchikey": "YSLXCWAUZACMKI-XSFVSMFZSA-N",
"smiles": "CCOC(=O)/C(F)=C(/C)c1cc2c(cc1OCC)OC(C)(C)C=C2C(C)C"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "12863",
"routeId": "sa_9fcd0b3bc9004b72818c99ed",
"moleculeId": "sa_55fc2a50826c8aa6e75f372f",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_55fc2a50826c8aa6e75f372f",
"inchikey": "YSLXCWAUZACMKI-XSFVSMFZSA-N",
"smiles": "CCOC(=O)/C(F)=C(/C)c1cc2c(cc1OCC)OC(C)(C)C=C2C(C)C"
},
"smiles": "CCOC(=O)/C(F)=C(/C)c1cc2c(cc1OCC)OC(C)(C)C=C2C(C)C",
"reactionStepId": "sa_15566f6919bde3213069c21c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050096380A1;0224;248363\",\"rsmi\":\"CCOP(=O)(OCC)[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[F:7].O=[C:8]([CH3:9])[c:10]1[c:11]([O:12][CH2:13][CH3:14])[cH:15][c:16]2[c:26]([cH:27]1)[C:22]([CH:23]([CH3:24])[CH3:25])=[CH:21][C:18]([CH3:19])([CH3:20])[O:17]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])/[C:6]([F:7])=[C:8](/[CH3:9])[c:10]1[c:11]([O:12][CH2:13][CH3:14])[cH:15][c:16]2[c:26]([cH:27]1)[C:22]([CH:23]([CH3:24])[CH3:25])=[CH:21][C:18]([CH3:19])([CH3:20])[O:17]2\"},\"mapped_reaction_smiles\":\"CCOP(=O)(OCC)[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[F:7].O=[C:8]([CH3:9])[c:10]1[c:11]([O:12][CH2:13][CH3:14])[cH:15][c:16]2[c:26]([cH:27]1)[C:22]([CH:23]([CH3:24])[CH3:25])=[CH:21][C:18]([CH3:19])([CH3:20])[O:17]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])/[C:6]([F:7])=[C:8](/[CH3:9])[c:10]1[c:11]([O:12][CH2:13][CH3:14])[cH:15][c:16]2[c:26]([cH:27]1)[C:22]([CH:23]([CH3:24])[CH3:25])=[CH:21][C:18]([CH3:19])([CH3:20])[O:17]2\"}",
"reactionStep": {
"id": "sa_15566f6919bde3213069c21c",
"reactionHash": "bc391b3de443d6910ffd740d755190f354368c6ad0f414490db6a89f22bfe8d7"
},
"children": [
{
"id": "12864",
"routeId": "sa_9fcd0b3bc9004b72818c99ed",
"moleculeId": "sa_d450590ec9f7a0f9393a6975",
"parentId": "12863",
"isLeaf": true,
"molecule": {
"id": "sa_d450590ec9f7a0f9393a6975",
"inchikey": "FVPISMANESAJQZ-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C(F)P(=O)(OCC)OCC"
},
"smiles": "CCOC(=O)C(F)P(=O)(OCC)OCC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12865",
"routeId": "sa_9fcd0b3bc9004b72818c99ed",
"moleculeId": "sa_d02bfabebc3ada4f204fef3c",
"parentId": "12863",
"isLeaf": false,
"molecule": {
"id": "sa_d02bfabebc3ada4f204fef3c",
"inchikey": "LKDBEDDMPXIYQU-UHFFFAOYSA-N",
"smiles": "CCOc1cc2c(cc1C(C)=O)C(C(C)C)=CC(C)(C)O2"
},
"smiles": "CCOc1cc2c(cc1C(C)=O)C(C(C)C)=CC(C)(C)O2",
"reactionStepId": "sa_60c0d2ca1e4b907d83a19213",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050096380A1;0206;248354\",\"rsmi\":\"I[CH2:2][CH3:1].[OH:3][c:4]1[c:5]([C:6]([CH3:7])=[O:8])[cH:9][c:10]2[c:11]([cH:12]1)[O:13][C:14]([CH3:15])([CH3:16])[CH:17]=[C:18]2[CH:19]([CH3:20])[CH3:21]>CC(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][O:3][c:4]1[c:5]([C:6]([CH3:7])=[O:8])[cH:9][c:10]2[c:11]([cH:12]1)[O:13][C:14]([CH3:15])([CH3:16])[CH:17]=[C:18]2[CH:19]([CH3:20])[CH3:21]\"},\"mapped_reaction_smiles\":\"I[CH2:2][CH3:1].[OH:3][c:4]1[c:5]([C:6]([CH3:7])=[O:8])[cH:9][c:10]2[c:11]([cH:12]1)[O:13][C:14]([CH3:15])([CH3:16])[CH:17]=[C:18]2[CH:19]([CH3:20])[CH3:21]>CC(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][O:3][c:4]1[c:5]([C:6]([CH3:7])=[O:8])[cH:9][c:10]2[c:11]([cH:12]1)[O:13][C:14]([CH3:15])([CH3:16])[CH:17]=[C:18]2[CH:19]([CH3:20])[CH3:21]\"}",
"reactionStep": {
"id": "sa_60c0d2ca1e4b907d83a19213",
"reactionHash": "0ffb606d654160ea8424060cac7261923c37ef8a1071815f349d2dbda790bc6b"
},
"children": [
{
"id": "12866",
"routeId": "sa_9fcd0b3bc9004b72818c99ed",
"moleculeId": "sa_24ac4bd2d940c003bc25c0e8",
"parentId": "12865",
"isLeaf": false,
"molecule": {
"id": "sa_24ac4bd2d940c003bc25c0e8",
"inchikey": "HQJVBRPJSVNFLJ-UHFFFAOYSA-N",
"smiles": "CC(=O)c1cc2c(cc1O)OC(C)(C)C=C2C(C)C"
},
"smiles": "CC(=O)c1cc2c(cc1O)OC(C)(C)C=C2C(C)C",
"reactionStepId": "sa_c27b2c481b00bacdeab75ed1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050096380A1;0204;248353\",\"rsmi\":\"C[O:6][c:5]1[c:4]([C:2]([CH3:1])=[O:3])[cH:19][c:18]2[c:8]([cH:7]1)[O:9][C:10]([CH3:11])([CH3:12])[CH:13]=[C:14]2[CH:15]([CH3:16])[CH3:17]>BrB(Br)Br.ClCCl>[CH3:1][C:2](=[O:3])[c:4]1[c:5]([OH:6])[cH:7][c:8]2[c:18]([cH:19]1)[C:14]([CH:15]([CH3:16])[CH3:17])=[CH:13][C:10]([CH3:11])([CH3:12])[O:9]2\"},\"mapped_reaction_smiles\":\"C[O:6][c:5]1[c:4]([C:2]([CH3:1])=[O:3])[cH:19][c:18]2[c:8]([cH:7]1)[O:9][C:10]([CH3:11])([CH3:12])[CH:13]=[C:14]2[CH:15]([CH3:16])[CH3:17]>BrB(Br)Br.ClCCl>[CH3:1][C:2](=[O:3])[c:4]1[c:5]([OH:6])[cH:7][c:8]2[c:18]([cH:19]1)[C:14]([CH:15]([CH3:16])[CH3:17])=[CH:13][C:10]([CH3:11])([CH3:12])[O:9]2\"}",
"reactionStep": {
"id": "sa_c27b2c481b00bacdeab75ed1",
"reactionHash": "56d6d0515bbb910b0a24ba6ef992413d6543076047554e9fa03c61a13a1389e4"
},
"children": [
{
"id": "12867",
"routeId": "sa_9fcd0b3bc9004b72818c99ed",
"moleculeId": "sa_5169254ce485fc1ebc000bcd",
"parentId": "12866",
"isLeaf": false,
"molecule": {
"id": "sa_5169254ce485fc1ebc000bcd",
"inchikey": "CHTKCMLVUQTUME-UHFFFAOYSA-N",
"smiles": "COc1cc2c(cc1C(C)=O)C(C(C)C)=CC(C)(C)O2"
},
"smiles": "COc1cc2c(cc1C(C)=O)C(C(C)C)=CC(C)(C)O2",
"reactionStepId": "sa_4f1bb5336ef91c5b6e17f9c5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050096380A1;0187;248349\",\"rsmi\":\"Br[c:4]1[c:3]([O:2][CH3:1])[cH:11][c:10]2[c:9]([cH:8]1)[C:17]([CH:18]([CH3:19])[CH3:20])=[CH:16][C:13]([CH3:14])([CH3:15])[O:12]2.CCCC[Sn](CCCC)(CCCC)[C:5](=[CH2:6])[O:7]CC>C1CCOC1>[CH3:1][O:2][c:3]1[c:4]([C:5]([CH3:6])=[O:7])[cH:8][c:9]2[c:10]([cH:11]1)[O:12][C:13]([CH3:14])([CH3:15])[CH:16]=[C:17]2[CH:18]([CH3:19])[CH3:20]\"},\"mapped_reaction_smiles\":\"Br[c:4]1[c:3]([O:2][CH3:1])[cH:11][c:10]2[c:9]([cH:8]1)[C:17]([CH:18]([CH3:19])[CH3:20])=[CH:16][C:13]([CH3:14])([CH3:15])[O:12]2.CCCC[Sn](CCCC)(CCCC)[C:5](=[CH2:6])[O:7]CC>C1CCOC1>[CH3:1][O:2][c:3]1[c:4]([C:5]([CH3:6])=[O:7])[cH:8][c:9]2[c:10]([cH:11]1)[O:12][C:13]([CH3:14])([CH3:15])[CH:16]=[C:17]2[CH:18]([CH3:19])[CH3:20]\"}",
"reactionStep": {
"id": "sa_4f1bb5336ef91c5b6e17f9c5",
"reactionHash": "e2010339b0db80e93ee3903b55290c2026a8e36216210b07685b790641084f0a"
},
"children": [
{
"id": "12868",
"routeId": "sa_9fcd0b3bc9004b72818c99ed",
"moleculeId": "sa_1ea9e182d7de920290d9ddd9",
"parentId": "12867",
"isLeaf": true,
"molecule": {
"id": "sa_1ea9e182d7de920290d9ddd9",
"inchikey": "HGXJOXHYPGNVNK-UHFFFAOYSA-N",
"smiles": "C=[C](OCC)[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC"
},
"smiles": "C=[C](OCC)[Sn]([CH2]CCC)([CH2]CCC)[CH2]CCC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12869",
"routeId": "sa_9fcd0b3bc9004b72818c99ed",
"moleculeId": "sa_642b52d19abbd2c3d92a2486",
"parentId": "12867",
"isLeaf": false,
"molecule": {
"id": "sa_642b52d19abbd2c3d92a2486",
"inchikey": "TWCBULNZCXMEOP-UHFFFAOYSA-N",
"smiles": "COc1cc2c(cc1Br)C(C(C)C)=CC(C)(C)O2"
},
"smiles": "COc1cc2c(cc1Br)C(C(C)C)=CC(C)(C)O2",
"reactionStepId": "sa_adcd510b6503e694634d6a6e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050096380A1;0097;248331\",\"rsmi\":\"Cl[Mg][CH:16]([CH3:17])[CH3:18].O=[C:15]1[c:7]2[cH:6][c:4]([Br:5])[c:3]([O:2][CH3:1])[cH:9][c:8]2[O:10][C:11]([CH3:12])([CH3:13])[CH2:14]1>C1CCOC1.Cc1ccc(S(=O)(=O)O)cc1>[CH3:1][O:2][c:3]1[c:4]([Br:5])[cH:6][c:7]2[c:8]([cH:9]1)[O:10][C:11]([CH3:12])([CH3:13])[CH:14]=[C:15]2[CH:16]([CH3:17])[CH3:18]\"},\"mapped_reaction_smiles\":\"Cl[Mg][CH:16]([CH3:17])[CH3:18].O=[C:15]1[c:7]2[cH:6][c:4]([Br:5])[c:3]([O:2][CH3:1])[cH:9][c:8]2[O:10][C:11]([CH3:12])([CH3:13])[CH2:14]1>C1CCOC1.Cc1ccc(S(=O)(=O)O)cc1>[CH3:1][O:2][c:3]1[c:4]([Br:5])[cH:6][c:7]2[c:8]([cH:9]1)[O:10][C:11]([CH3:12])([CH3:13])[CH:14]=[C:15]2[CH:16]([CH3:17])[CH3:18]\"}",
"reactionStep": {
"id": "sa_adcd510b6503e694634d6a6e",
"reactionHash": "1ae8e9b4637862a601752be8d8201da4bafbd9a1d9f610e08a8dab53e5120b11"
},
"children": [
{
"id": "12870",
"routeId": "sa_9fcd0b3bc9004b72818c99ed",
"moleculeId": "sa_638330db227b14d84a4e0168",
"parentId": "12869",
"isLeaf": true,
"molecule": {
"id": "sa_638330db227b14d84a4e0168",
"inchikey": "GPIBKUJXKCEZOH-UHFFFAOYSA-M",
"smiles": "C[CH](C)[Mg][Cl]"
},
"smiles": "C[CH](C)[Mg][Cl]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12871",
"routeId": "sa_9fcd0b3bc9004b72818c99ed",
"moleculeId": "sa_351e61afbeafd61a5e506d98",
"parentId": "12869",
"isLeaf": false,
"molecule": {
"id": "sa_351e61afbeafd61a5e506d98",
"inchikey": "YZIFHMKTHLEZHI-UHFFFAOYSA-N",
"smiles": "COc1cc2c(cc1Br)C(=O)CC(C)(C)O2"
},
"smiles": "COc1cc2c(cc1Br)C(=O)CC(C)(C)O2",
"reactionStepId": "sa_20e7295046f22131712e26f1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050096380A1;0073;248319\",\"rsmi\":\"O=C1CCC(=O)N1[Br:5].[CH3:1][O:2][c:3]1[cH:4][cH:6][c:7]2[c:15]([cH:16]1)[O:14][C:11]([CH3:12])([CH3:13])[CH2:10][C:8]2=[O:9]>CN(C)C=O>[CH3:1][O:2][c:3]1[c:4]([Br:5])[cH:6][c:7]2[c:15]([cH:16]1)[O:14][C:11]([CH3:12])([CH3:13])[CH2:10][C:8]2=[O:9]\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:5].[CH3:1][O:2][c:3]1[cH:4][cH:6][c:7]2[c:15]([cH:16]1)[O:14][C:11]([CH3:12])([CH3:13])[CH2:10][C:8]2=[O:9]>CN(C)C=O>[CH3:1][O:2][c:3]1[c:4]([Br:5])[cH:6][c:7]2[c:15]([cH:16]1)[O:14][C:11]([CH3:12])([CH3:13])[CH2:10][C:8]2=[O:9]\"}",
"reactionStep": {
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"reactionHash": "2f1a7eb054e7fc1b8d20fbf5b2770fe8aa4a3a5b8308d4efbda5e123ba16dab2"
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"children": [
{
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"routeId": "sa_9fcd0b3bc9004b72818c99ed",
"moleculeId": "sa_ccdcf23ac83e7a68bfa4f2e5",
"parentId": "12871",
"isLeaf": true,
"molecule": {
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"inchikey": "PCLIMKBDDGJMGD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Br"
},
"smiles": "O=C1CCC(=O)N1Br",
"reactionStepId": null,
"template": null,
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},
{
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"molecule": {
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"inchikey": "QXKXYXNEOUCMIY-UHFFFAOYSA-N",
"smiles": "COc1ccc2c(c1)OC(C)(C)CC2=O"
},
"smiles": "COc1ccc2c(c1)OC(C)(C)CC2=O",
"reactionStepId": "sa_069b8923202fa7555c168b76",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20050096380A1;0071;248318\",\"rsmi\":\"O[C:7](=[O:8])[CH:9]=[C:10]([CH3:11])[CH3:12].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:14]([OH:13])[cH:15]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:14]([cH:15]1)[O:13][C:10]([CH3:11])([CH3:12])[CH2:9][C:7]2=[O:8]\"},\"mapped_reaction_smiles\":\"O[C:7](=[O:8])[CH:9]=[C:10]([CH3:11])[CH3:12].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:14]([OH:13])[cH:15]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:14]([cH:15]1)[O:13][C:10]([CH3:11])([CH3:12])[CH2:9][C:7]2=[O:8]\"}",
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"children": [
{
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"routeId": "sa_9fcd0b3bc9004b72818c99ed",
"moleculeId": "sa_ee2a07fc317193386474fcf1",
"parentId": "12873",
"isLeaf": true,
"molecule": {
"id": "sa_ee2a07fc317193386474fcf1",
"inchikey": "ASHGTJPOSUFTGB-UHFFFAOYSA-N",
"smiles": "COc1cccc(O)c1"
},
"smiles": "COc1cccc(O)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12875",
"routeId": "sa_9fcd0b3bc9004b72818c99ed",
"moleculeId": "sa_76f4704578410799feacf9b0",
"parentId": "12873",
"isLeaf": true,
"molecule": {
"id": "sa_76f4704578410799feacf9b0",
"inchikey": "YYPNJNDODFVZLE-UHFFFAOYSA-N",
"smiles": "CC(C)=CC(=O)O"
},
"smiles": "CC(C)=CC(=O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
]
},
{
"id": "12876",
"routeId": "sa_9fcd0b3bc9004b72818c99ed",
"moleculeId": "sa_ba4021c610c673105b10b53d",
"parentId": "12865",
"isLeaf": true,
"molecule": {
"id": "sa_ba4021c610c673105b10b53d",
"inchikey": "HVTICUPFWKNHNG-UHFFFAOYSA-N",
"smiles": "CCI"
},
"smiles": "CCI",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}