Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CNc1nc(C(F)(F)F)ccc1-c1cc(CNC(=O)[C@@H]2C[C@@H](F)CN2S(=O)(=O)c2ccc(F)cc2)ccn1
InChiKey
OUIWGZWQOLEJRB-UZLBHIALSA-N
Route Signature
417988f15770a4e56dde7ca22a17e2f32aa2dd285a7452c7370a96f1cbe9443a
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_086d9008225993a6f31b5056",
"signature": "417988f15770a4e56dde7ca22a17e2f32aa2dd285a7452c7370a96f1cbe9443a",
"contentHash": "3e0f3819a8aa211eb035c7188ef88cf7913d29e89b89ba3b589f9848eca52db2",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_358ef749985ff9cef68aed4e",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-01100",
"moleculeId": "sa_95c0f0082e5d8470b50c2ff0",
"smiles": "CNc1nc(C(F)(F)F)ccc1-c1cc(CNC(=O)[C@@H]2C[C@@H](F)CN2S(=O)(=O)c2ccc(F)cc2)ccn1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_95c0f0082e5d8470b50c2ff0",
"inchikey": "OUIWGZWQOLEJRB-UZLBHIALSA-N",
"smiles": "CNc1nc(C(F)(F)F)ccc1-c1cc(CNC(=O)[C@@H]2C[C@@H](F)CN2S(=O)(=O)c2ccc(F)cc2)ccn1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "14070",
"routeId": "sa_086d9008225993a6f31b5056",
"moleculeId": "sa_95c0f0082e5d8470b50c2ff0",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_95c0f0082e5d8470b50c2ff0",
"inchikey": "OUIWGZWQOLEJRB-UZLBHIALSA-N",
"smiles": "CNc1nc(C(F)(F)F)ccc1-c1cc(CNC(=O)[C@@H]2C[C@@H](F)CN2S(=O)(=O)c2ccc(F)cc2)ccn1"
},
"smiles": "CNc1nc(C(F)(F)F)ccc1-c1cc(CNC(=O)[C@@H]2C[C@@H](F)CN2S(=O)(=O)c2ccc(F)cc2)ccn1",
"reactionStepId": "sa_f899871ab5dc880efe94be4f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160221945A1;2225;1916480\",\"rsmi\":\"F[c:3]1[n:4][c:5]([C:6]([F:7])([F:8])[F:9])[cH:10][cH:11][c:12]1-[c:13]1[n:14][cH:15][cH:16][c:17]([CH2:18][NH:19][C:20](=[O:21])[C@@H:22]2[CH2:23][C@@H:24]([F:25])[CH2:26][N:27]2[S:28](=[O:29])(=[O:30])[c:31]2[cH:32][cH:33][c:34]([F:35])[cH:36][cH:37]2)[cH:38]1.[CH3:1][NH2:2]>C1CCOC1.CS(C)=O>[CH3:1][NH:2][c:3]1[n:4][c:5]([C:6]([F:7])([F:8])[F:9])[cH:10][cH:11][c:12]1-[c:13]1[n:14][cH:15][cH:16][c:17]([CH2:18][NH:19][C:20](=[O:21])[C@@H:22]2[CH2:23][C@@H:24]([F:25])[CH2:26][N:27]2[S:28](=[O:29])(=[O:30])[c:31]2[cH:32][cH:33][c:34]([F:35])[cH:36][cH:37]2)[cH:38]1\"},\"mapped_reaction_smiles\":\"F[c:3]1[n:4][c:5]([C:6]([F:7])([F:8])[F:9])[cH:10][cH:11][c:12]1-[c:13]1[n:14][cH:15][cH:16][c:17]([CH2:18][NH:19][C:20](=[O:21])[C@@H:22]2[CH2:23][C@@H:24]([F:25])[CH2:26][N:27]2[S:28](=[O:29])(=[O:30])[c:31]2[cH:32][cH:33][c:34]([F:35])[cH:36][cH:37]2)[cH:38]1.[CH3:1][NH2:2]>C1CCOC1.CS(C)=O>[CH3:1][NH:2][c:3]1[n:4][c:5]([C:6]([F:7])([F:8])[F:9])[cH:10][cH:11][c:12]1-[c:13]1[n:14][cH:15][cH:16][c:17]([CH2:18][NH:19][C:20](=[O:21])[C@@H:22]2[CH2:23][C@@H:24]([F:25])[CH2:26][N:27]2[S:28](=[O:29])(=[O:30])[c:31]2[cH:32][cH:33][c:34]([F:35])[cH:36][cH:37]2)[cH:38]1\"}",
"reactionStep": {
"id": "sa_f899871ab5dc880efe94be4f",
"reactionHash": "171da65f7c61117fd3d92e8d9c3827b6a7a0158837c38c11f5729ba67d6c0af0"
},
"children": [
{
"id": "14071",
"routeId": "sa_086d9008225993a6f31b5056",
"moleculeId": "sa_e00cdbb7fb9d3ecf114a19d3",
"parentId": "14070",
"isLeaf": true,
"molecule": {
"id": "sa_e00cdbb7fb9d3ecf114a19d3",
"inchikey": "BAVYZALUXZFZLV-UHFFFAOYSA-N",
"smiles": "CN"
},
"smiles": "CN",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14072",
"routeId": "sa_086d9008225993a6f31b5056",
"moleculeId": "sa_f52716c51b3f23bf5aa92ad4",
"parentId": "14070",
"isLeaf": false,
"molecule": {
"id": "sa_f52716c51b3f23bf5aa92ad4",
"inchikey": "IXBFKZROCQEAND-BEFAXECRSA-N",
"smiles": "O=C(NCc1ccnc(-c2ccc(C(F)(F)F)nc2F)c1)[C@@H]1C[C@@H](F)CN1S(=O)(=O)c1ccc(F)cc1"
},
"smiles": "O=C(NCc1ccnc(-c2ccc(C(F)(F)F)nc2F)c1)[C@@H]1C[C@@H](F)CN1S(=O)(=O)c1ccc(F)cc1",
"reactionStepId": "sa_69d075c21249df3280071709",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160221945A1;2220;1916478\",\"rsmi\":\"Br[c:7]1[cH:6][c:5]([CH2:4][NH:3][C:2](=[O:1])[C@@H:22]2[CH2:23][C@@H:24]([F:25])[CH2:26][N:27]2[S:28](=[O:29])(=[O:30])[c:31]2[cH:32][cH:33][c:34]([F:35])[cH:36][cH:37]2)[cH:21][cH:20][n:19]1.OB(O)[c:8]1[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[n:16][c:17]1[F:18]>CC#N.Cl[Pd]Cl.O=C(O)O.[Cs+].[Cs+].[Fe+2]>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[n:16][c:17]2[F:18])[n:19][cH:20][cH:21]1)[C@@H:22]1[CH2:23][C@@H:24]([F:25])[CH2:26][N:27]1[S:28](=[O:29])(=[O:30])[c:31]1[cH:32][cH:33][c:34]([F:35])[cH:36][cH:37]1\"},\"mapped_reaction_smiles\":\"Br[c:7]1[cH:6][c:5]([CH2:4][NH:3][C:2](=[O:1])[C@@H:22]2[CH2:23][C@@H:24]([F:25])[CH2:26][N:27]2[S:28](=[O:29])(=[O:30])[c:31]2[cH:32][cH:33][c:34]([F:35])[cH:36][cH:37]2)[cH:21][cH:20][n:19]1.OB(O)[c:8]1[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[n:16][c:17]1[F:18]>CC#N.Cl[Pd]Cl.O=C(O)O.[Cs+].[Cs+].[Fe+2]>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[n:16][c:17]2[F:18])[n:19][cH:20][cH:21]1)[C@@H:22]1[CH2:23][C@@H:24]([F:25])[CH2:26][N:27]1[S:28](=[O:29])(=[O:30])[c:31]1[cH:32][cH:33][c:34]([F:35])[cH:36][cH:37]1\"}",
"reactionStep": {
"id": "sa_69d075c21249df3280071709",
"reactionHash": "92d35cd953103c79e2e2aa921d53994ed0b6cfb0bf21e1acf5905c958622ae28"
},
"children": [
{
"id": "14073",
"routeId": "sa_086d9008225993a6f31b5056",
"moleculeId": "sa_c21eaa7e0cd8dcbaa39fa802",
"parentId": "14072",
"isLeaf": false,
"molecule": {
"id": "sa_c21eaa7e0cd8dcbaa39fa802",
"inchikey": "BAWHCCGAFJHJOB-HIFRSBDPSA-N",
"smiles": "O=C(NCc1ccnc(Br)c1)[C@@H]1C[C@@H](F)CN1S(=O)(=O)c1ccc(F)cc1"
},
"smiles": "O=C(NCc1ccnc(Br)c1)[C@@H]1C[C@@H](F)CN1S(=O)(=O)c1ccc(F)cc1",
"reactionStepId": "sa_8739d33cae889b194e7268db",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160221945A1;2218;1916477\",\"rsmi\":\"Cl[S:18](=[O:19])(=[O:20])[c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]1.[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][c:7]([Br:8])[n:9][cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@@H:14]([F:15])[CH2:16][NH:17]1>CCN(CC)CC.CN(C)C=O.ClCCl>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][c:7]([Br:8])[n:9][cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@@H:14]([F:15])[CH2:16][N:17]1[S:18](=[O:19])(=[O:20])[c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]1\"},\"mapped_reaction_smiles\":\"Cl[S:18](=[O:19])(=[O:20])[c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]1.[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][c:7]([Br:8])[n:9][cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@@H:14]([F:15])[CH2:16][NH:17]1>CCN(CC)CC.CN(C)C=O.ClCCl>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][c:7]([Br:8])[n:9][cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@@H:14]([F:15])[CH2:16][N:17]1[S:18](=[O:19])(=[O:20])[c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]1\"}",
"reactionStep": {
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"reactionHash": "8b997d30e86fe5031c0579ea795f3e45d5139da6b09b50072296479585845f97"
},
"children": [
{
"id": "14074",
"routeId": "sa_086d9008225993a6f31b5056",
"moleculeId": "sa_fc86336e1b262adfba88e57f",
"parentId": "14073",
"isLeaf": true,
"molecule": {
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"inchikey": "BFXHJFKKRGVUMU-UHFFFAOYSA-N",
"smiles": "O=S(=O)(Cl)c1ccc(F)cc1"
},
"smiles": "O=S(=O)(Cl)c1ccc(F)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "14075",
"routeId": "sa_086d9008225993a6f31b5056",
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"isLeaf": false,
"molecule": {
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"inchikey": "OEHCNBGKGUWCBV-BDAKNGLRSA-N",
"smiles": "O=C(NCc1ccnc(Br)c1)[C@@H]1C[C@@H](F)CN1"
},
"smiles": "O=C(NCc1ccnc(Br)c1)[C@@H]1C[C@@H](F)CN1",
"reactionStepId": "sa_3c37394e7ab7b3705a2ecba7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160221945A1;2216;1916476\",\"rsmi\":\"CC(C)(C)OC(=O)[N:17]1[C@H:12]([C:2](=[O:1])[NH:3][CH2:4][c:5]2[cH:6][c:7]([Br:8])[n:9][cH:10][cH:11]2)[CH2:13][C@@H:14]([F:15])[CH2:16]1>ClCCl.O=C(O)C(F)(F)F>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][c:7]([Br:8])[n:9][cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@@H:14]([F:15])[CH2:16][NH:17]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:17]1[C@H:12]([C:2](=[O:1])[NH:3][CH2:4][c:5]2[cH:6][c:7]([Br:8])[n:9][cH:10][cH:11]2)[CH2:13][C@@H:14]([F:15])[CH2:16]1>ClCCl.O=C(O)C(F)(F)F>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][c:7]([Br:8])[n:9][cH:10][cH:11]1)[C@@H:12]1[CH2:13][C@@H:14]([F:15])[CH2:16][NH:17]1\"}",
"reactionStep": {
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"reactionHash": "cbb07ab3b276b58b1abc2fa0671cad699070f366c08ab1cd0191c55168bd06b7"
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"children": [
{
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"molecule": {
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"inchikey": "NVPOOHJRQKPWTJ-NEPJUHHUSA-N",
"smiles": "CC(C)(C)OC(=O)N1C[C@H](F)C[C@H]1C(=O)NCc1ccnc(Br)c1"
},
"smiles": "CC(C)(C)OC(=O)N1C[C@H](F)C[C@H]1C(=O)NCc1ccnc(Br)c1",
"reactionStepId": "sa_5810208b886665fcd9bbd07f",
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"metadata": "{\"annotations\":{\"ID\":\"US20160221945A1;2214;1916475\",\"rsmi\":\"O[C:14]([C@H:13]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][C@H:10]([F:11])[CH2:12]1)=[O:15].[NH2:16][CH2:17][c:18]1[cH:19][c:20]([Br:21])[n:22][cH:23][cH:24]1>CCN(CC)CC.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][C@H:10]([F:11])[CH2:12][C@H:13]1[C:14](=[O:15])[NH:16][CH2:17][c:18]1[cH:19][c:20]([Br:21])[n:22][cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"O[C:14]([C@H:13]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][C@H:10]([F:11])[CH2:12]1)=[O:15].[NH2:16][CH2:17][c:18]1[cH:19][c:20]([Br:21])[n:22][cH:23][cH:24]1>CCN(CC)CC.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][C@H:10]([F:11])[CH2:12][C@H:13]1[C:14](=[O:15])[NH:16][CH2:17][c:18]1[cH:19][c:20]([Br:21])[n:22][cH:23][cH:24]1\"}",
"reactionStep": {
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"reactionHash": "03e43d91c66dda221a124ff11edabf059be844f7666994b7e75a5e139bf17f2f"
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"children": [
{
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"moleculeId": "sa_fa7f2375bc5333b3ff18f719",
"parentId": "14076",
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"molecule": {
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"inchikey": "OEOAEMBKKWPLSZ-UHFFFAOYSA-N",
"smiles": "NCc1ccnc(Br)c1"
},
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{
"id": "14078",
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"smiles": "CC(C)(C)OC(=O)N1C[C@H](F)C[C@H]1C(=O)O",
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}
]
},
{
"id": "14079",
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"molecule": {
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"inchikey": "JLKCXRRPVZUFJB-UHFFFAOYSA-N",
"smiles": "OB(O)c1ccc(C(F)(F)F)nc1F"
},
"smiles": "OB(O)c1ccc(C(F)(F)F)nc1F",
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]
}
]
}
}