Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN(Cc1ccc(OCC(=O)OC(C)(C)C)c(-c2cc(F)cc(C#N)c2)c1)S(=O)(=O)c1ccc(F)cc1
InChiKey
SHPUHBUVHXNJFU-UHFFFAOYSA-N
Route Signature
a2bb8ec439c77fcc55c5a6df97afd8a11f744144b4734c223b6351270bb1cb2c
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_24f146fa4796bd558babde1a",
"signature": "a2bb8ec439c77fcc55c5a6df97afd8a11f744144b4734c223b6351270bb1cb2c",
"contentHash": "b539a10bc2322721ea1067b89a93959f8a65472f3202fb72d844412039abe495",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_c02ef6d58139bc84a8bf9ebd",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00706",
"moleculeId": "sa_d8408a72b67766511cc2f737",
"smiles": "CN(Cc1ccc(OCC(=O)OC(C)(C)C)c(-c2cc(F)cc(C#N)c2)c1)S(=O)(=O)c1ccc(F)cc1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_d8408a72b67766511cc2f737",
"inchikey": "SHPUHBUVHXNJFU-UHFFFAOYSA-N",
"smiles": "CN(Cc1ccc(OCC(=O)OC(C)(C)C)c(-c2cc(F)cc(C#N)c2)c1)S(=O)(=O)c1ccc(F)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "1128",
"routeId": "sa_24f146fa4796bd558babde1a",
"moleculeId": "sa_d8408a72b67766511cc2f737",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_d8408a72b67766511cc2f737",
"inchikey": "SHPUHBUVHXNJFU-UHFFFAOYSA-N",
"smiles": "CN(Cc1ccc(OCC(=O)OC(C)(C)C)c(-c2cc(F)cc(C#N)c2)c1)S(=O)(=O)c1ccc(F)cc1"
},
"smiles": "CN(Cc1ccc(OCC(=O)OC(C)(C)C)c(-c2cc(F)cc(C#N)c2)c1)S(=O)(=O)c1ccc(F)cc1",
"reactionStepId": "sa_bbad08e59d8739116d804ed6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130102609A1;0308;1358898\",\"rsmi\":\"Cl[S:28](=[O:29])(=[O:30])[c:31]1[cH:32][cH:33][c:34]([F:35])[cH:36][cH:37]1.[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:9]([C:10]#[N:11])[cH:12][c:13]([F:14])[cH:15]2)[c:16]([O:17][CH2:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[cH:26][cH:27]1>CCN(CC)CC.ClCCl.O>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:9]([C:10]#[N:11])[cH:12][c:13]([F:14])[cH:15]2)[c:16]([O:17][CH2:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[cH:26][cH: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\":\"Cl[S:28](=[O:29])(=[O:30])[c:31]1[cH:32][cH:33][c:34]([F:35])[cH:36][cH:37]1.[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:9]([C:10]#[N:11])[cH:12][c:13]([F:14])[cH:15]2)[c:16]([O:17][CH2:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[cH:26][cH:27]1>CCN(CC)CC.ClCCl.O>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:9]([C:10]#[N:11])[cH:12][c:13]([F:14])[cH:15]2)[c:16]([O:17][CH2:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[cH:26][cH: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_bbad08e59d8739116d804ed6",
"reactionHash": "51bad026ffcad651d52132973d5880744c6148a38a0798f6ad17aa21ed11896c"
},
"children": [
{
"id": "1129",
"routeId": "sa_24f146fa4796bd558babde1a",
"moleculeId": "sa_fc86336e1b262adfba88e57f",
"parentId": "1128",
"isLeaf": true,
"molecule": {
"id": "sa_fc86336e1b262adfba88e57f",
"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,
"reactionStep": null,
"children": []
},
{
"id": "1130",
"routeId": "sa_24f146fa4796bd558babde1a",
"moleculeId": "sa_529dcd44a86f2cc2af76be79",
"parentId": "1128",
"isLeaf": false,
"molecule": {
"id": "sa_529dcd44a86f2cc2af76be79",
"inchikey": "NQFIAYHDSOZTEA-UHFFFAOYSA-N",
"smiles": "CNCc1ccc(OCC(=O)OC(C)(C)C)c(-c2cc(F)cc(C#N)c2)c1"
},
"smiles": "CNCc1ccc(OCC(=O)OC(C)(C)C)c(-c2cc(F)cc(C#N)c2)c1",
"reactionStepId": "sa_ad1e82b2bb136dd1c7e7e543",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130102609A1;0306;1358897\",\"rsmi\":\"O=[CH:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:9]([C:10]#[N:11])[cH:12][c:13]([F:14])[cH:15]2)[c:16]([O:17][CH2:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[cH:26][cH:27]1.[CH3:1][NH2:2]>C1CCOC1.CO.O.B.[Na+]>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:9]([C:10]#[N:11])[cH:12][c:13]([F:14])[cH:15]2)[c:16]([O:17][CH2:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[cH:26][cH:27]1\"},\"mapped_reaction_smiles\":\"O=[CH:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:9]([C:10]#[N:11])[cH:12][c:13]([F:14])[cH:15]2)[c:16]([O:17][CH2:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[cH:26][cH:27]1.[CH3:1][NH2:2]>C1CCOC1.CO.O.B.[Na+]>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:9]([C:10]#[N:11])[cH:12][c:13]([F:14])[cH:15]2)[c:16]([O:17][CH2:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[cH:26][cH:27]1\"}",
"reactionStep": {
"id": "sa_ad1e82b2bb136dd1c7e7e543",
"reactionHash": "ff990e6fbb1678b1c985ca782477c0e866d3a36536c4ec8f2488893c30cbc84f"
},
"children": [
{
"id": "1131",
"routeId": "sa_24f146fa4796bd558babde1a",
"moleculeId": "sa_e00cdbb7fb9d3ecf114a19d3",
"parentId": "1130",
"isLeaf": true,
"molecule": {
"id": "sa_e00cdbb7fb9d3ecf114a19d3",
"inchikey": "BAVYZALUXZFZLV-UHFFFAOYSA-N",
"smiles": "CN"
},
"smiles": "CN",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1132",
"routeId": "sa_24f146fa4796bd558babde1a",
"moleculeId": "sa_172d398b2dd95e8cee7b2b32",
"parentId": "1130",
"isLeaf": false,
"molecule": {
"id": "sa_172d398b2dd95e8cee7b2b32",
"inchikey": "CRVYSIIAFVAGAQ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)COc1ccc(C=O)cc1-c1cc(F)cc(C#N)c1"
},
"smiles": "CC(C)(C)OC(=O)COc1ccc(C=O)cc1-c1cc(F)cc(C#N)c1",
"reactionStepId": "sa_18cef770cd1aeb6323b7e260",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130102609A1;0304;1358896\",\"rsmi\":\"Br[c:11]1[c:10]([O:9][CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:26][cH:25][c:22]([CH:23]=[O:24])[cH:21]1.CC1(C)OB([c:12]2[cH:13][c:14]([C:15]#[N:16])[cH:17][c:18]([F:19])[cH:20]2)OC1(C)C>C1COCCO1.O.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][O:9][c:10]1[c:11](-[c:12]2[cH:13][c:14]([C:15]#[N:16])[cH:17][c:18]([F:19])[cH:20]2)[cH:21][c:22]([CH:23]=[O:24])[cH:25][cH:26]1\"},\"mapped_reaction_smiles\":\"Br[c:11]1[c:10]([O:9][CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:26][cH:25][c:22]([CH:23]=[O:24])[cH:21]1.CC1(C)OB([c:12]2[cH:13][c:14]([C:15]#[N:16])[cH:17][c:18]([F:19])[cH:20]2)OC1(C)C>C1COCCO1.O.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][O:9][c:10]1[c:11](-[c:12]2[cH:13][c:14]([C:15]#[N:16])[cH:17][c:18]([F:19])[cH:20]2)[cH:21][c:22]([CH:23]=[O:24])[cH:25][cH:26]1\"}",
"reactionStep": {
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"reactionHash": "f18b3722f858b3688872d263b59e83679d0f7a70701730554e338302c9f0c4aa"
},
"children": [
{
"id": "1133",
"routeId": "sa_24f146fa4796bd558babde1a",
"moleculeId": "sa_130c451ba05f3f090c95a057",
"parentId": "1132",
"isLeaf": false,
"molecule": {
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"inchikey": "DXIMGGKOTCJKAJ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)COc1ccc(C=O)cc1Br"
},
"smiles": "CC(C)(C)OC(=O)COc1ccc(C=O)cc1Br",
"reactionStepId": "sa_0b6adde9ad94086dc7f2ca30",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130102609A1;0245;1358877\",\"rsmi\":\"Br[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[OH:9][c:10]1[c:11]([Br:12])[cH:13][c:14]([CH:15]=[O:16])[cH:17][cH:18]1>CN(C)C=O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][O:9][c:10]1[c:11]([Br:12])[cH:13][c:14]([CH:15]=[O:16])[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"Br[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[OH:9][c:10]1[c:11]([Br:12])[cH:13][c:14]([CH:15]=[O:16])[cH:17][cH:18]1>CN(C)C=O.O=C(O)O.[Cs+].[Cs+]>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][O:9][c:10]1[c:11]([Br:12])[cH:13][c:14]([CH:15]=[O:16])[cH:17][cH:18]1\"}",
"reactionStep": {
"id": "sa_0b6adde9ad94086dc7f2ca30",
"reactionHash": "38a683ec41a2c2f12f3cb0e9265a3d8c9f6b45ff1de6f5a85194743ff47fbeae"
},
"children": [
{
"id": "1134",
"routeId": "sa_24f146fa4796bd558babde1a",
"moleculeId": "sa_b050ad2816ce9056bc19cbb6",
"parentId": "1133",
"isLeaf": true,
"molecule": {
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"inchikey": "BNWCETAHAJSBFG-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)CBr"
},
"smiles": "CC(C)(C)OC(=O)CBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1135",
"routeId": "sa_24f146fa4796bd558babde1a",
"moleculeId": "sa_39d9b9bc047423add77dfe16",
"parentId": "1133",
"isLeaf": true,
"molecule": {
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"inchikey": "UOTMHAOCAJROQF-UHFFFAOYSA-N",
"smiles": "O=Cc1ccc(O)c(Br)c1"
},
"smiles": "O=Cc1ccc(O)c(Br)c1",
"reactionStepId": null,
"template": null,
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}
]
},
{
"id": "1136",
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"molecule": {
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"inchikey": "WWDTYZLFIFQZDE-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2cc(F)cc(C#N)c2)OC1(C)C"
},
"smiles": "CC1(C)OB(c2cc(F)cc(C#N)c2)OC1(C)C",
"reactionStepId": "sa_2e7252fce6a6b4722af4700b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130102609A1;0301;1358895\",\"rsmi\":\"Br[c:6]1[cH:7][c:8]([C:9]#[N:10])[cH:11][c:12]([F:13])[cH:14]1.CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:16]([CH3:17])([CH3:18])[O:15]2)OC1(C)C>CC(=O)O.CN(C)C=O.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][c:8]([C:9]#[N:10])[cH:11][c:12]([F:13])[cH:14]2)[O:15][C:16]1([CH3:17])[CH3:18]\"},\"mapped_reaction_smiles\":\"Br[c:6]1[cH:7][c:8]([C:9]#[N:10])[cH:11][c:12]([F:13])[cH:14]1.CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:16]([CH3:17])([CH3:18])[O:15]2)OC1(C)C>CC(=O)O.CN(C)C=O.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][c:8]([C:9]#[N:10])[cH:11][c:12]([F:13])[cH:14]2)[O:15][C:16]1([CH3:17])[CH3:18]\"}",
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"children": [
{
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"smiles": "N#Cc1cc(F)cc(Br)c1"
},
"smiles": "N#Cc1cc(F)cc(Br)c1",
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{
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"molecule": {
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"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",
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}
]
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]
}
]
}
]
}
}