Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCn1cnc2c(-c3ccc(F)c(-c4ccc(S(=O)(=O)CC)cc4OC)c3)cnnc21
InChiKey
PTTQXDBPTFOCMT-UHFFFAOYSA-N
Route Signature
097e7c5cea195de63abf8bad1b50b338a08eca7f107252bb0673650a2694f318
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_d065f94c336c490aab04df96",
"signature": "097e7c5cea195de63abf8bad1b50b338a08eca7f107252bb0673650a2694f318",
"contentHash": "3cc776e9d73a6f4c58aac265b5f0a682b451a63b170fe42223fd35d15e662121",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_1d0316c7efc1f0eaaa74d2ef",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01518",
"moleculeId": "sa_1c3577b6c7bd12acdb665ebe",
"smiles": "CCn1cnc2c(-c3ccc(F)c(-c4ccc(S(=O)(=O)CC)cc4OC)c3)cnnc21",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_1c3577b6c7bd12acdb665ebe",
"inchikey": "PTTQXDBPTFOCMT-UHFFFAOYSA-N",
"smiles": "CCn1cnc2c(-c3ccc(F)c(-c4ccc(S(=O)(=O)CC)cc4OC)c3)cnnc21"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10265",
"routeId": "sa_d065f94c336c490aab04df96",
"moleculeId": "sa_1c3577b6c7bd12acdb665ebe",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_1c3577b6c7bd12acdb665ebe",
"inchikey": "PTTQXDBPTFOCMT-UHFFFAOYSA-N",
"smiles": "CCn1cnc2c(-c3ccc(F)c(-c4ccc(S(=O)(=O)CC)cc4OC)c3)cnnc21"
},
"smiles": "CCn1cnc2c(-c3ccc(F)c(-c4ccc(S(=O)(=O)CC)cc4OC)c3)cnnc21",
"reactionStepId": "sa_484c2ab4e0286c126f93991b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140171435A1;0333;1540268\",\"rsmi\":\"CC1(C)OB([c:18]2[c:19]([O:20][CH3:21])[cH:22][c:23]([S:24](=[O:25])(=[O:26])[CH2:27][CH3:28])[cH:29][cH:30]2)OC1(C)C.I[c:17]1[c:15]([F:16])[cH:14][cH:13][c:12](-[c:11]2[c:6]3[n:5][cH:4][n:3]([CH2:2][CH3:1])[c:7]3[n:8][n:9][cH:10]2)[cH:31]1>C1COCCO1.CCOC(C)=O.Cl[Pd]Cl.O.O=C(O)O.[Cs+].[Cs+].[Fe+2]>[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]1[n:8][n:9][cH:10][c:11]2-[c:12]1[cH:13][cH:14][c:15]([F:16])[c:17](-[c:18]2[c:19]([O:20][CH3:21])[cH:22][c:23]([S:24](=[O:25])(=[O:26])[CH2:27][CH3:28])[cH:29][cH:30]2)[cH:31]1\"},\"mapped_reaction_smiles\":\"CC1(C)OB([c:18]2[c:19]([O:20][CH3:21])[cH:22][c:23]([S:24](=[O:25])(=[O:26])[CH2:27][CH3:28])[cH:29][cH:30]2)OC1(C)C.I[c:17]1[c:15]([F:16])[cH:14][cH:13][c:12](-[c:11]2[c:6]3[n:5][cH:4][n:3]([CH2:2][CH3:1])[c:7]3[n:8][n:9][cH:10]2)[cH:31]1>C1COCCO1.CCOC(C)=O.Cl[Pd]Cl.O.O=C(O)O.[Cs+].[Cs+].[Fe+2]>[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]1[n:8][n:9][cH:10][c:11]2-[c:12]1[cH:13][cH:14][c:15]([F:16])[c:17](-[c:18]2[c:19]([O:20][CH3:21])[cH:22][c:23]([S:24](=[O:25])(=[O:26])[CH2:27][CH3:28])[cH:29][cH:30]2)[cH:31]1\"}",
"reactionStep": {
"id": "sa_484c2ab4e0286c126f93991b",
"reactionHash": "9dee84dbe0121b582620753720d66685caa5a481d3653b5c571959d74c746fc4"
},
"children": [
{
"id": "10266",
"routeId": "sa_d065f94c336c490aab04df96",
"moleculeId": "sa_d358c2aea62e9cd844efe32a",
"parentId": "10265",
"isLeaf": false,
"molecule": {
"id": "sa_d358c2aea62e9cd844efe32a",
"inchikey": "MEPLIXQNGWBVBD-UHFFFAOYSA-N",
"smiles": "CCS(=O)(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)c(OC)c1"
},
"smiles": "CCS(=O)(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)c(OC)c1",
"reactionStepId": "sa_5989064325892342b92b8397",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140171435A1;0511;1540301\",\"rsmi\":\"Br[c:11]1[c:8]([O:9][CH3:10])[cH:7][c:6]([S:3]([CH2:2][CH3:1])(=[O:4])=[O:5])[cH:22][cH:21]1.CC1(C)OB([B:12]2[O:13][C:14]([CH3:15])([CH3:16])[C:17]([CH3:18])([CH3:19])[O:20]2)OC1(C)C>C1COCCO1.CC(=O)O.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][c:8]([O:9][CH3:10])[c:11]([B:12]2[O:13][C:14]([CH3:15])([CH3:16])[C:17]([CH3:18])([CH3:19])[O:20]2)[cH:21][cH:22]1\"},\"mapped_reaction_smiles\":\"Br[c:11]1[c:8]([O:9][CH3:10])[cH:7][c:6]([S:3]([CH2:2][CH3:1])(=[O:4])=[O:5])[cH:22][cH:21]1.CC1(C)OB([B:12]2[O:13][C:14]([CH3:15])([CH3:16])[C:17]([CH3:18])([CH3:19])[O:20]2)OC1(C)C>C1COCCO1.CC(=O)O.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][c:8]([O:9][CH3:10])[c:11]([B:12]2[O:13][C:14]([CH3:15])([CH3:16])[C:17]([CH3:18])([CH3:19])[O:20]2)[cH:21][cH:22]1\"}",
"reactionStep": {
"id": "sa_5989064325892342b92b8397",
"reactionHash": "ef20cfd2d107eebc25fc33afdb174f2ecf545ccd4fb3eafbd28da32edb8ca2f0"
},
"children": [
{
"id": "10267",
"routeId": "sa_d065f94c336c490aab04df96",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "10266",
"isLeaf": true,
"molecule": {
"id": "sa_e6c301388ac142801d4af5a2",
"inchikey": "IPWKHHSGDUIRAH-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C"
},
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10268",
"routeId": "sa_d065f94c336c490aab04df96",
"moleculeId": "sa_e490f5fd63daf55de2c5da52",
"parentId": "10266",
"isLeaf": false,
"molecule": {
"id": "sa_e490f5fd63daf55de2c5da52",
"inchikey": "YXKNZVOMPQWROS-UHFFFAOYSA-N",
"smiles": "CCS(=O)(=O)c1ccc(Br)c(OC)c1"
},
"smiles": "CCS(=O)(=O)c1ccc(Br)c(OC)c1",
"reactionStepId": "sa_527b88b96ee2d12a4416232b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140171435A1;0501;1540298\",\"rsmi\":\"F[c:8]1[cH:7][c:6]([S:3]([CH2:2][CH3:1])(=[O:4])=[O:5])[cH:14][cH:13][c:11]1[Br:12].[OH:9][CH3:10]>CO.O.[Na+]>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][c:8]([O:9][CH3:10])[c:11]([Br:12])[cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"F[c:8]1[cH:7][c:6]([S:3]([CH2:2][CH3:1])(=[O:4])=[O:5])[cH:14][cH:13][c:11]1[Br:12].[OH:9][CH3:10]>CO.O.[Na+]>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][c:8]([O:9][CH3:10])[c:11]([Br:12])[cH:13][cH:14]1\"}",
"reactionStep": {
"id": "sa_527b88b96ee2d12a4416232b",
"reactionHash": "ef25d308ea2de30aeca7e6c0fabef47c28b8acb2489af2114f58b83edd89fccf"
},
"children": [
{
"id": "10269",
"routeId": "sa_d065f94c336c490aab04df96",
"moleculeId": "sa_061a3efbe4d30c2cc87d48e7",
"parentId": "10268",
"isLeaf": true,
"molecule": {
"id": "sa_061a3efbe4d30c2cc87d48e7",
"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
"smiles": "CO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10270",
"routeId": "sa_d065f94c336c490aab04df96",
"moleculeId": "sa_05c7b5b28c63cb1824dc491a",
"parentId": "10268",
"isLeaf": false,
"molecule": {
"id": "sa_05c7b5b28c63cb1824dc491a",
"inchikey": "UCMNEQPCURNDES-UHFFFAOYSA-N",
"smiles": "CCS(=O)(=O)c1ccc(Br)c(F)c1"
},
"smiles": "CCS(=O)(=O)c1ccc(Br)c(F)c1",
"reactionStepId": "sa_5662833cc8f8694dd6c62ba9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140171435A1;0498;1540297\",\"rsmi\":\"Cl[S:3](=[O:4])(=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([Br:11])[cH:12][cH:13]1.I[CH2:2][CH3:1]>C1CCOC1.CC(=O)O.NN.O.[Na+]>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([Br:11])[cH:12][cH:13]1\"},\"mapped_reaction_smiles\":\"Cl[S:3](=[O:4])(=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([Br:11])[cH:12][cH:13]1.I[CH2:2][CH3:1]>C1CCOC1.CC(=O)O.NN.O.[Na+]>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([Br:11])[cH:12][cH:13]1\"}",
"reactionStep": {
"id": "sa_5662833cc8f8694dd6c62ba9",
"reactionHash": "82d6f719fd99b1af71d390a37f97bc1145dff6dc453cffe42ac5b36c523561d8"
},
"children": [
{
"id": "10271",
"routeId": "sa_d065f94c336c490aab04df96",
"moleculeId": "sa_ba4021c610c673105b10b53d",
"parentId": "10270",
"isLeaf": true,
"molecule": {
"id": "sa_ba4021c610c673105b10b53d",
"inchikey": "HVTICUPFWKNHNG-UHFFFAOYSA-N",
"smiles": "CCI"
},
"smiles": "CCI",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10272",
"routeId": "sa_d065f94c336c490aab04df96",
"moleculeId": "sa_d780d640d0a8409a9f76e6cd",
"parentId": "10270",
"isLeaf": true,
"molecule": {
"id": "sa_d780d640d0a8409a9f76e6cd",
"inchikey": "IZCXVIACMHTZNA-UHFFFAOYSA-N",
"smiles": "O=S(=O)(Cl)c1ccc(Br)c(F)c1"
},
"smiles": "O=S(=O)(Cl)c1ccc(Br)c(F)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "10273",
"routeId": "sa_d065f94c336c490aab04df96",
"moleculeId": "sa_656dd7f89236e1a049167993",
"parentId": "10265",
"isLeaf": false,
"molecule": {
"id": "sa_656dd7f89236e1a049167993",
"inchikey": "ZZUINHVSPNVARR-UHFFFAOYSA-N",
"smiles": "CCn1cnc2c(-c3ccc(F)c(I)c3)cnnc21"
},
"smiles": "CCn1cnc2c(-c3ccc(F)c(I)c3)cnnc21",
"reactionStepId": "sa_a80bf5d354eff521fa0f7aae",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140171435A1;0468;1540288\",\"rsmi\":\"CC1(C)C(=O)N([I:15])C(=O)N1I.[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]1[n:8][n:9][cH:10][c:11]2-[c:12]1[cH:13][cH:14][c:16]([F:17])[cH:18][cH:19]1>ClCCl.O=S(=O)(O)O.[Na+].O>[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]1[n:8][n:9][cH:10][c:11]2-[c:12]1[cH:13][c:14]([I:15])[c:16]([F:17])[cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"CC1(C)C(=O)N([I:15])C(=O)N1I.[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]1[n:8][n:9][cH:10][c:11]2-[c:12]1[cH:13][cH:14][c:16]([F:17])[cH:18][cH:19]1>ClCCl.O=S(=O)(O)O.[Na+].O>[CH3:1][CH2:2][n:3]1[cH:4][n:5][c:6]2[c:7]1[n:8][n:9][cH:10][c:11]2-[c:12]1[cH:13][c:14]([I:15])[c:16]([F:17])[cH:18][cH:19]1\"}",
"reactionStep": {
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"reactionHash": "16551f11a6e6f71eaba28f9cfa978e0fc01409276baa966c9a2d2d234a0fabac"
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"children": [
{
"id": "10274",
"routeId": "sa_d065f94c336c490aab04df96",
"moleculeId": "sa_db98fc7145af4bfd7c2c12dd",
"parentId": "10273",
"isLeaf": true,
"molecule": {
"id": "sa_db98fc7145af4bfd7c2c12dd",
"inchikey": "RDZHCKRAHUPIFK-UHFFFAOYSA-N",
"smiles": "CC1(C)C(=O)N(I)C(=O)N1I"
},
"smiles": "CC1(C)C(=O)N(I)C(=O)N1I",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "10275",
"routeId": "sa_d065f94c336c490aab04df96",
"moleculeId": "sa_3f7b7ea9d8294f17d6999433",
"parentId": "10273",
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"molecule": {
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"inchikey": "UVLBGLSQXYKNIX-UHFFFAOYSA-N",
"smiles": "CCn1cnc2c(-c3ccc(F)cc3)cnnc21"
},
"smiles": "CCn1cnc2c(-c3ccc(F)cc3)cnnc21",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
}
}