Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1cnn(C)c1-c1cc(C(=O)N[C@@H](Cc2cccc(F)c2)CN2C(=O)c3ccccc3C2=O)sc1Cl
InChiKey
AEZCNFAGFSDRNO-SFHVURJKSA-N
Route Signature
71e3818f678954114a3b6f507cf498db08df13b1b937d8e32eaeedfa8a9eb360
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_af9d399db39728f1ff23e494",
"signature": "71e3818f678954114a3b6f507cf498db08df13b1b937d8e32eaeedfa8a9eb360",
"contentHash": "6b142cfd2dcf0d24192e6f01900ee59c53fc95ede02aaf379601905597d662ac",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_8e713ba33efbe47f2d38cb55",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01258",
"moleculeId": "sa_e00419830ab16d5a581936f1",
"smiles": "Cc1cnn(C)c1-c1cc(C(=O)N[C@@H](Cc2cccc(F)c2)CN2C(=O)c3ccccc3C2=O)sc1Cl",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_e00419830ab16d5a581936f1",
"inchikey": "AEZCNFAGFSDRNO-SFHVURJKSA-N",
"smiles": "Cc1cnn(C)c1-c1cc(C(=O)N[C@@H](Cc2cccc(F)c2)CN2C(=O)c3ccccc3C2=O)sc1Cl"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "1378",
"routeId": "sa_af9d399db39728f1ff23e494",
"moleculeId": "sa_e00419830ab16d5a581936f1",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_e00419830ab16d5a581936f1",
"inchikey": "AEZCNFAGFSDRNO-SFHVURJKSA-N",
"smiles": "Cc1cnn(C)c1-c1cc(C(=O)N[C@@H](Cc2cccc(F)c2)CN2C(=O)c3ccccc3C2=O)sc1Cl"
},
"smiles": "Cc1cnn(C)c1-c1cc(C(=O)N[C@@H](Cc2cccc(F)c2)CN2C(=O)c3ccccc3C2=O)sc1Cl",
"reactionStepId": "sa_82a4ea7b1e9276b44c3baecb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150152092A1;1920;1701236\",\"rsmi\":\"O[C:9]([c:8]1[s:7][c:5]([Cl:6])[c:4](-[c:3]2[c:2]([CH3:1])[cH:37][n:36][n:34]2[CH3:35])[cH:33]1)=[O:10].[NH2:11][C@@H:12]([CH2:13][c:14]1[cH:15][c:16]([F:17])[cH:18][cH:19][cH:20]1)[CH2:21][N:22]1[C:23](=[O:24])[c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]2[C:31]1=[O:32]>Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.CCN(C(C)C)C(C)C.ClCCl.F[PH](F)(F)(F)(F)F>[CH3:1][c:2]1[c:3](-[c:4]2[c:5]([Cl:6])[s:7][c:8]([C:9](=[O:10])[NH:11][C@@H:12]([CH2:13][c:14]3[cH:15][c:16]([F:17])[cH:18][cH:19][cH:20]3)[CH2:21][N:22]3[C:23](=[O:24])[c:25]4[cH:26][cH:27][cH:28][cH:29][c:30]4[C:31]3=[O:32])[cH:33]2)[n:34]([CH3:35])[n:36][cH:37]1\"},\"mapped_reaction_smiles\":\"O[C:9]([c:8]1[s:7][c:5]([Cl:6])[c:4](-[c:3]2[c:2]([CH3:1])[cH:37][n:36][n:34]2[CH3:35])[cH:33]1)=[O:10].[NH2:11][C@@H:12]([CH2:13][c:14]1[cH:15][c:16]([F:17])[cH:18][cH:19][cH:20]1)[CH2:21][N:22]1[C:23](=[O:24])[c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]2[C:31]1=[O:32]>Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.CCN(C(C)C)C(C)C.ClCCl.F[PH](F)(F)(F)(F)F>[CH3:1][c:2]1[c:3](-[c:4]2[c:5]([Cl:6])[s:7][c:8]([C:9](=[O:10])[NH:11][C@@H:12]([CH2:13][c:14]3[cH:15][c:16]([F:17])[cH:18][cH:19][cH:20]3)[CH2:21][N:22]3[C:23](=[O:24])[c:25]4[cH:26][cH:27][cH:28][cH:29][c:30]4[C:31]3=[O:32])[cH:33]2)[n:34]([CH3:35])[n:36][cH:37]1\"}",
"reactionStep": {
"id": "sa_82a4ea7b1e9276b44c3baecb",
"reactionHash": "417dc1f285cff9d435951edc88f584c98a14dff73dc1c7c6e6e19687802a847d"
},
"children": [
{
"id": "1379",
"routeId": "sa_af9d399db39728f1ff23e494",
"moleculeId": "sa_ba1654004ce7839457f64467",
"parentId": "1378",
"isLeaf": true,
"molecule": {
"id": "sa_ba1654004ce7839457f64467",
"inchikey": "VMLDWVQVTSBBHQ-ZDUSSCGKSA-N",
"smiles": "N[C@@H](Cc1cccc(F)c1)CN1C(=O)c2ccccc2C1=O"
},
"smiles": "N[C@@H](Cc1cccc(F)c1)CN1C(=O)c2ccccc2C1=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1380",
"routeId": "sa_af9d399db39728f1ff23e494",
"moleculeId": "sa_d81b55b9b3dcb43fdffc1332",
"parentId": "1378",
"isLeaf": false,
"molecule": {
"id": "sa_d81b55b9b3dcb43fdffc1332",
"inchikey": "ZUNSJLVMTGIATE-UHFFFAOYSA-N",
"smiles": "Cc1cnn(C)c1-c1cc(C(=O)O)sc1Cl"
},
"smiles": "Cc1cnn(C)c1-c1cc(C(=O)O)sc1Cl",
"reactionStepId": "sa_3c7a64116ff4c12a0575ff48",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150152092A1;1668;1701186\",\"rsmi\":\"C[O:11][C:9]([c:8]1[s:7][c:5]([Cl:6])[c:4](-[c:3]2[c:2]([CH3:1])[cH:16][n:15][n:13]2[CH3:14])[cH:12]1)=[O:10]>C1CCOC1.[Na+].O>[CH3:1][c:2]1[c:3](-[c:4]2[c:5]([Cl:6])[s:7][c:8]([C:9](=[O:10])[OH:11])[cH:12]2)[n:13]([CH3:14])[n:15][cH:16]1\"},\"mapped_reaction_smiles\":\"C[O:11][C:9]([c:8]1[s:7][c:5]([Cl:6])[c:4](-[c:3]2[c:2]([CH3:1])[cH:16][n:15][n:13]2[CH3:14])[cH:12]1)=[O:10]>C1CCOC1.[Na+].O>[CH3:1][c:2]1[c:3](-[c:4]2[c:5]([Cl:6])[s:7][c:8]([C:9](=[O:10])[OH:11])[cH:12]2)[n:13]([CH3:14])[n:15][cH:16]1\"}",
"reactionStep": {
"id": "sa_3c7a64116ff4c12a0575ff48",
"reactionHash": "c58fb2e66a3e62040bd2b398e95f7da352c380610ea1658c4dcb95cdab35697c"
},
"children": [
{
"id": "1381",
"routeId": "sa_af9d399db39728f1ff23e494",
"moleculeId": "sa_c7a39826ab70d70c3ac7cc0a",
"parentId": "1380",
"isLeaf": false,
"molecule": {
"id": "sa_c7a39826ab70d70c3ac7cc0a",
"inchikey": "VNYLUUGCWVHQHW-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(-c2c(C)cnn2C)c(Cl)s1"
},
"smiles": "COC(=O)c1cc(-c2c(C)cnn2C)c(Cl)s1",
"reactionStepId": "sa_a961fb60490f3e78d90779c7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150152092A1;1666;1701185\",\"rsmi\":\"Br[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[s:17][c:15]1[Cl:16].CC1(C)OB([c:8]2[c:9]([CH3:10])[cH:11][n:12][n:13]2[CH3:14])OC1(C)C>C1COCCO1.CC(C)(C)[PH]([Pd][PH](C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C(C)(C)C)C(C)(C)C.O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[c:9]([CH3:10])[cH:11][n:12][n:13]2[CH3:14])[c:15]([Cl:16])[s:17]1\"},\"mapped_reaction_smiles\":\"Br[c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[s:17][c:15]1[Cl:16].CC1(C)OB([c:8]2[c:9]([CH3:10])[cH:11][n:12][n:13]2[CH3:14])OC1(C)C>C1COCCO1.CC(C)(C)[PH]([Pd][PH](C(C)(C)C)(C(C)(C)C)C(C)(C)C)(C(C)(C)C)C(C)(C)C.O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[c:9]([CH3:10])[cH:11][n:12][n:13]2[CH3:14])[c:15]([Cl:16])[s:17]1\"}",
"reactionStep": {
"id": "sa_a961fb60490f3e78d90779c7",
"reactionHash": "8614ebaa6e3c939547024beeef00a89074008496644c7cf57c82a125f99fd9e8"
},
"children": [
{
"id": "1382",
"routeId": "sa_af9d399db39728f1ff23e494",
"moleculeId": "sa_a9b9d82c541966b3e4b7aab9",
"parentId": "1381",
"isLeaf": false,
"molecule": {
"id": "sa_a9b9d82c541966b3e4b7aab9",
"inchikey": "LVOXXQQWCWKTOM-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(Br)c(Cl)s1"
},
"smiles": "COC(=O)c1cc(Br)c(Cl)s1",
"reactionStepId": "sa_f16f56517c4458027f926d94",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150152092A1;1058;1701000\",\"rsmi\":\"Br[Br:8].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:9]([Cl:10])[s:11]1>ClC(Cl)Cl.[Al+3].Cl.Cl.Cl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Br:8])[c:9]([Cl:10])[s:11]1\"},\"mapped_reaction_smiles\":\"Br[Br:8].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:9]([Cl:10])[s:11]1>ClC(Cl)Cl.[Al+3].Cl.Cl.Cl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Br:8])[c:9]([Cl:10])[s:11]1\"}",
"reactionStep": {
"id": "sa_f16f56517c4458027f926d94",
"reactionHash": "addb6b1810bd2eae3f9484afca4a3dc3e18284a8042bcc8a7b11172d6128994e"
},
"children": [
{
"id": "1383",
"routeId": "sa_af9d399db39728f1ff23e494",
"moleculeId": "sa_24211e89e565c162ea935f73",
"parentId": "1382",
"isLeaf": true,
"molecule": {
"id": "sa_24211e89e565c162ea935f73",
"inchikey": "GDTBXPJZTBHREO-UHFFFAOYSA-N",
"smiles": "BrBr"
},
"smiles": "BrBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1384",
"routeId": "sa_af9d399db39728f1ff23e494",
"moleculeId": "sa_665695acbcf86e717cd20eaa",
"parentId": "1382",
"isLeaf": false,
"molecule": {
"id": "sa_665695acbcf86e717cd20eaa",
"inchikey": "SQVGSFPLDUMEDG-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(Cl)s1"
},
"smiles": "COC(=O)c1ccc(Cl)s1",
"reactionStepId": "sa_5588632383ecda22347889d3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150152092A1;0759;1700945\",\"rsmi\":\"O[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([Cl:9])[s:10]1.[CH3:1][OH:2]>O=S(=O)(O)O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([Cl:9])[s:10]1\"},\"mapped_reaction_smiles\":\"O[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([Cl:9])[s:10]1.[CH3:1][OH:2]>O=S(=O)(O)O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([Cl:9])[s:10]1\"}",
"reactionStep": {
"id": "sa_5588632383ecda22347889d3",
"reactionHash": "87bd14ff182cfba8e44496d6545c374f46fc04e52d1ac3060cadd5faedcac087"
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"children": [
{
"id": "1385",
"routeId": "sa_af9d399db39728f1ff23e494",
"moleculeId": "sa_061a3efbe4d30c2cc87d48e7",
"parentId": "1384",
"isLeaf": true,
"molecule": {
"id": "sa_061a3efbe4d30c2cc87d48e7",
"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
"smiles": "CO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1386",
"routeId": "sa_af9d399db39728f1ff23e494",
"moleculeId": "sa_2d03bbc0e5221b59c85749a8",
"parentId": "1384",
"isLeaf": true,
"molecule": {
"id": "sa_2d03bbc0e5221b59c85749a8",
"inchikey": "QZLSBOVWPHXCLT-UHFFFAOYSA-N",
"smiles": "O=C(O)c1ccc(Cl)s1"
},
"smiles": "O=C(O)c1ccc(Cl)s1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
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}
]
}
]
},
{
"id": "1387",
"routeId": "sa_af9d399db39728f1ff23e494",
"moleculeId": "sa_2f68826be482af2b35a59914",
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"molecule": {
"id": "sa_2f68826be482af2b35a59914",
"inchikey": "NOZSCXDKBYFTBH-UHFFFAOYSA-N",
"smiles": "Cc1cnn(C)c1B1OC(C)(C)C(C)(C)O1"
},
"smiles": "Cc1cnn(C)c1B1OC(C)(C)C(C)(C)O1",
"reactionStepId": "sa_4db35629482177a31ca12ec3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150152092A1;0682;1700936\",\"rsmi\":\"CC(C)O[B:4]1[O:5][C:6]([CH3:7])([CH3:8])[C:9]([CH3:10])([CH3:11])[O:12]1.[CH3:1][c:2]1[cH:3][n:13]([CH3:14])[n:15][cH:16]1>C1CCOC1.Cl.[Li]CCCC.N>[CH3:1][c:2]1[c:3]([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:9]([CH3:10])([CH3:11])[O:12]2)[n:13]([CH3:14])[n:15][cH:16]1\"},\"mapped_reaction_smiles\":\"CC(C)O[B:4]1[O:5][C:6]([CH3:7])([CH3:8])[C:9]([CH3:10])([CH3:11])[O:12]1.[CH3:1][c:2]1[cH:3][n:13]([CH3:14])[n:15][cH:16]1>C1CCOC1.Cl.[Li]CCCC.N>[CH3:1][c:2]1[c:3]([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:9]([CH3:10])([CH3:11])[O:12]2)[n:13]([CH3:14])[n:15][cH:16]1\"}",
"reactionStep": {
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"reactionHash": "30c3bb5d3076f043be9b398becfbc06a2dd92f03aede2b92f94ad8bec50bdd64"
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"children": [
{
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"moleculeId": "sa_b6e2297b6c44b134993b2a34",
"parentId": "1387",
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"molecule": {
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"inchikey": "MRWWWZLJWNIEEJ-UHFFFAOYSA-N",
"smiles": "CC(C)OB1OC(C)(C)C(C)(C)O1"
},
"smiles": "CC(C)OB1OC(C)(C)C(C)(C)O1",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "1389",
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"molecule": {
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"inchikey": "SZQCPPRPWDXLMM-UHFFFAOYSA-N",
"smiles": "Cc1cnn(C)c1"
},
"smiles": "Cc1cnn(C)c1",
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}
]
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]
}
]
}
]
}
}