Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN(Cc1ccc(OCC(=O)O)c(-c2ccc(F)c(S(C)(=O)=O)c2)c1)S(=O)(=O)c1ccc(F)cc1
InChiKey
PCWLOIGAZYFKSK-UHFFFAOYSA-N
Route Signature
41efc1d64883bc64f1795891aa4a838a0e731e25dd672b0961a10a3e90921c9e
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_210d91e81f625cabd8dec421",
"signature": "41efc1d64883bc64f1795891aa4a838a0e731e25dd672b0961a10a3e90921c9e",
"contentHash": "82b85a2faec550e7d7a8940b36101cda3975c83ac37651ba0d63d13e9ecae5a5",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_3e7f20390494233e9ece1ce0",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00922",
"moleculeId": "sa_963a1ce21f1b2cd75f6b5676",
"smiles": "CN(Cc1ccc(OCC(=O)O)c(-c2ccc(F)c(S(C)(=O)=O)c2)c1)S(=O)(=O)c1ccc(F)cc1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_963a1ce21f1b2cd75f6b5676",
"inchikey": "PCWLOIGAZYFKSK-UHFFFAOYSA-N",
"smiles": "CN(Cc1ccc(OCC(=O)O)c(-c2ccc(F)c(S(C)(=O)=O)c2)c1)S(=O)(=O)c1ccc(F)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13916",
"routeId": "sa_210d91e81f625cabd8dec421",
"moleculeId": "sa_963a1ce21f1b2cd75f6b5676",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_963a1ce21f1b2cd75f6b5676",
"inchikey": "PCWLOIGAZYFKSK-UHFFFAOYSA-N",
"smiles": "CN(Cc1ccc(OCC(=O)O)c(-c2ccc(F)c(S(C)(=O)=O)c2)c1)S(=O)(=O)c1ccc(F)cc1"
},
"smiles": "CN(Cc1ccc(OCC(=O)O)c(-c2ccc(F)c(S(C)(=O)=O)c2)c1)S(=O)(=O)c1ccc(F)cc1",
"reactionStepId": "sa_265082254ffa1dbc92b088f3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130102609A1;0334;1358907\",\"rsmi\":\"CC(C)(C)[O:23][C:21]([CH2:20][O:19][c:18]1[c:6](-[c:7]2[cH:8][c:9]([S:10]([CH3:11])(=[O:12])=[O:13])[c:14]([F:15])[cH:16][cH:17]2)[cH:5][c:4]([CH2:3][N:2]([CH3:1])[S:26](=[O:27])(=[O:28])[c:29]2[cH:30][cH:31][c:32]([F:33])[cH:34][cH:35]2)[cH:25][cH:24]1)=[O:22]>ClCCl.O=C(O)C(F)(F)F>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:9]([S:10]([CH3:11])(=[O:12])=[O:13])[c:14]([F:15])[cH:16][cH:17]2)[c:18]([O:19][CH2:20][C:21](=[O:22])[OH:23])[cH:24][cH:25]1)[S:26](=[O:27])(=[O:28])[c:29]1[cH:30][cH:31][c:32]([F:33])[cH:34][cH:35]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)[O:23][C:21]([CH2:20][O:19][c:18]1[c:6](-[c:7]2[cH:8][c:9]([S:10]([CH3:11])(=[O:12])=[O:13])[c:14]([F:15])[cH:16][cH:17]2)[cH:5][c:4]([CH2:3][N:2]([CH3:1])[S:26](=[O:27])(=[O:28])[c:29]2[cH:30][cH:31][c:32]([F:33])[cH:34][cH:35]2)[cH:25][cH:24]1)=[O:22]>ClCCl.O=C(O)C(F)(F)F>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:9]([S:10]([CH3:11])(=[O:12])=[O:13])[c:14]([F:15])[cH:16][cH:17]2)[c:18]([O:19][CH2:20][C:21](=[O:22])[OH:23])[cH:24][cH:25]1)[S:26](=[O:27])(=[O:28])[c:29]1[cH:30][cH:31][c:32]([F:33])[cH:34][cH:35]1\"}",
"reactionStep": {
"id": "sa_265082254ffa1dbc92b088f3",
"reactionHash": "7fa942c9b3b270c7b102d860ad2a9d2429d7e3d1149c0bec00c7dc5a81dd9e43"
},
"children": [
{
"id": "13917",
"routeId": "sa_210d91e81f625cabd8dec421",
"moleculeId": "sa_e074ccddbfe88250058683b9",
"parentId": "13916",
"isLeaf": false,
"molecule": {
"id": "sa_e074ccddbfe88250058683b9",
"inchikey": "OOYIXTAEIIQENK-UHFFFAOYSA-N",
"smiles": "CN(Cc1ccc(OCC(=O)OC(C)(C)C)c(-c2ccc(F)c(S(C)(=O)=O)c2)c1)S(=O)(=O)c1ccc(F)cc1"
},
"smiles": "CN(Cc1ccc(OCC(=O)OC(C)(C)C)c(-c2ccc(F)c(S(C)(=O)=O)c2)c1)S(=O)(=O)c1ccc(F)cc1",
"reactionStepId": "sa_291f686ecd4d7fb30baaae99",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130102609A1;0332;1358906\",\"rsmi\":\"Cl[S:30](=[O:31])(=[O:32])[c:33]1[cH:34][cH:35][c:36]([F:37])[cH:38][cH:39]1.[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:9]([S:10]([CH3:11])(=[O:12])=[O:13])[c:14]([F:15])[cH:16][cH:17]2)[c:18]([O:19][CH2:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[cH:28][cH:29]1>CCN(CC)CC.ClCCl>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:9]([S:10]([CH3:11])(=[O:12])=[O:13])[c:14]([F:15])[cH:16][cH:17]2)[c:18]([O:19][CH2:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[cH:28][cH:29]1)[S:30](=[O:31])(=[O:32])[c:33]1[cH:34][cH:35][c:36]([F:37])[cH:38][cH:39]1\"},\"mapped_reaction_smiles\":\"Cl[S:30](=[O:31])(=[O:32])[c:33]1[cH:34][cH:35][c:36]([F:37])[cH:38][cH:39]1.[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:9]([S:10]([CH3:11])(=[O:12])=[O:13])[c:14]([F:15])[cH:16][cH:17]2)[c:18]([O:19][CH2:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[cH:28][cH:29]1>CCN(CC)CC.ClCCl>[CH3:1][N:2]([CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:9]([S:10]([CH3:11])(=[O:12])=[O:13])[c:14]([F:15])[cH:16][cH:17]2)[c:18]([O:19][CH2:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[cH:28][cH:29]1)[S:30](=[O:31])(=[O:32])[c:33]1[cH:34][cH:35][c:36]([F:37])[cH:38][cH:39]1\"}",
"reactionStep": {
"id": "sa_291f686ecd4d7fb30baaae99",
"reactionHash": "17ea91cffc69ccc488751751c39f88419ecf4caf10964f0c509ae765219a5f26"
},
"children": [
{
"id": "13918",
"routeId": "sa_210d91e81f625cabd8dec421",
"moleculeId": "sa_fc86336e1b262adfba88e57f",
"parentId": "13917",
"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": "13919",
"routeId": "sa_210d91e81f625cabd8dec421",
"moleculeId": "sa_2e85be12d424b87cd51402a2",
"parentId": "13917",
"isLeaf": false,
"molecule": {
"id": "sa_2e85be12d424b87cd51402a2",
"inchikey": "XZRFRLHCUWNDMX-UHFFFAOYSA-N",
"smiles": "CNCc1ccc(OCC(=O)OC(C)(C)C)c(-c2ccc(F)c(S(C)(=O)=O)c2)c1"
},
"smiles": "CNCc1ccc(OCC(=O)OC(C)(C)C)c(-c2ccc(F)c(S(C)(=O)=O)c2)c1",
"reactionStepId": "sa_ad102c9a008cd57d04a7cda2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130102609A1;0330;1358905\",\"rsmi\":\"O=[CH:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:9]([S:10]([CH3:11])(=[O:12])=[O:13])[c:14]([F:15])[cH:16][cH:17]2)[c:18]([O:19][CH2:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[cH:28][cH:29]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]([S:10]([CH3:11])(=[O:12])=[O:13])[c:14]([F:15])[cH:16][cH:17]2)[c:18]([O:19][CH2:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[cH:28][cH:29]1\"},\"mapped_reaction_smiles\":\"O=[CH:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:9]([S:10]([CH3:11])(=[O:12])=[O:13])[c:14]([F:15])[cH:16][cH:17]2)[c:18]([O:19][CH2:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[cH:28][cH:29]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]([S:10]([CH3:11])(=[O:12])=[O:13])[c:14]([F:15])[cH:16][cH:17]2)[c:18]([O:19][CH2:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[cH:28][cH:29]1\"}",
"reactionStep": {
"id": "sa_ad102c9a008cd57d04a7cda2",
"reactionHash": "c8946b0ec0ab853868be10083aea24c178c4ff5dade27ba42d0e4b82e452e0d7"
},
"children": [
{
"id": "13920",
"routeId": "sa_210d91e81f625cabd8dec421",
"moleculeId": "sa_e00cdbb7fb9d3ecf114a19d3",
"parentId": "13919",
"isLeaf": true,
"molecule": {
"id": "sa_e00cdbb7fb9d3ecf114a19d3",
"inchikey": "BAVYZALUXZFZLV-UHFFFAOYSA-N",
"smiles": "CN"
},
"smiles": "CN",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13921",
"routeId": "sa_210d91e81f625cabd8dec421",
"moleculeId": "sa_a7c38eff14e3869698a5d96f",
"parentId": "13919",
"isLeaf": false,
"molecule": {
"id": "sa_a7c38eff14e3869698a5d96f",
"inchikey": "JGCVFTOPBCSCET-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)COc1ccc(C=O)cc1-c1ccc(F)c(S(C)(=O)=O)c1"
},
"smiles": "CC(C)(C)OC(=O)COc1ccc(C=O)cc1-c1ccc(F)c(S(C)(=O)=O)c1",
"reactionStepId": "sa_5d206d8c4aceb1193e7f04aa",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130102609A1;0328;1358904\",\"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](-[c:12]2[cH:13][c:14]([S:15]([CH3:16])(=[O:17])=[O:18])[c:19]([F:20])[cH:21][cH:22]2)[cH:23][c:24]([CH:25]=[O:26])[cH:27][cH:28]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](-[c:12]2[cH:13][c:14]([S:15]([CH3:16])(=[O:17])=[O:18])[c:19]([F:20])[cH:21][cH:22]2)[cH:23][c:24]([CH:25]=[O:26])[cH:27][cH:28]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](-[c:12]2[cH:13][c:14]([S:15]([CH3:16])(=[O:17])=[O:18])[c:19]([F:20])[cH:21][cH:22]2)[cH:23][c:24]([CH:25]=[O:26])[cH:27][cH:28]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](-[c:12]2[cH:13][c:14]([S:15]([CH3:16])(=[O:17])=[O:18])[c:19]([F:20])[cH:21][cH:22]2)[cH:23][c:24]([CH:25]=[O:26])[cH:27][cH:28]1\"}",
"reactionStep": {
"id": "sa_5d206d8c4aceb1193e7f04aa",
"reactionHash": "7423a8bd50d185840025fefe842fc3e71178258e50761358946d1cff718f3661"
},
"children": [
{
"id": "13922",
"routeId": "sa_210d91e81f625cabd8dec421",
"moleculeId": "sa_b050ad2816ce9056bc19cbb6",
"parentId": "13921",
"isLeaf": true,
"molecule": {
"id": "sa_b050ad2816ce9056bc19cbb6",
"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": "13923",
"routeId": "sa_210d91e81f625cabd8dec421",
"moleculeId": "sa_4dc571a8f8500a50eb3916b2",
"parentId": "13921",
"isLeaf": false,
"molecule": {
"id": "sa_4dc571a8f8500a50eb3916b2",
"inchikey": "ZWNJUKHXQHTBLW-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)c1cc(-c2cc(C=O)ccc2O)ccc1F"
},
"smiles": "CS(=O)(=O)c1cc(-c2cc(C=O)ccc2O)ccc1F",
"reactionStepId": "sa_4048345da6fafeaf4cc218ef",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130102609A1;0326;1358903\",\"rsmi\":\"C[O:13][c:12]1[c:11](-[c:10]2[cH:9][cH:8][c:6]([F:7])[c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[cH:20]2)[cH:19][c:16]([CH:17]=[O:18])[cH:15][cH:14]1>BrB(Br)Br.CO.ClCCl>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[c:6]([F:7])[cH:8][cH:9][c:10](-[c:11]2[c:12]([OH:13])[cH:14][cH:15][c:16]([CH:17]=[O:18])[cH:19]2)[cH:20]1\"},\"mapped_reaction_smiles\":\"C[O:13][c:12]1[c:11](-[c:10]2[cH:9][cH:8][c:6]([F:7])[c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[cH:20]2)[cH:19][c:16]([CH:17]=[O:18])[cH:15][cH:14]1>BrB(Br)Br.CO.ClCCl>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[c:6]([F:7])[cH:8][cH:9][c:10](-[c:11]2[c:12]([OH:13])[cH:14][cH:15][c:16]([CH:17]=[O:18])[cH:19]2)[cH:20]1\"}",
"reactionStep": {
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"reactionHash": "3beb48eb474c0885dd768c973ba8e3aa777931ee160c70811555f2cbf3d9127d"
},
"children": [
{
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"moleculeId": "sa_9e80dad29cc5149e56ff081e",
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"molecule": {
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"inchikey": "IEUQSUGGKBPLDS-UHFFFAOYSA-N",
"smiles": "COc1ccc(C=O)cc1-c1ccc(F)c(S(C)(=O)=O)c1"
},
"smiles": "COc1ccc(C=O)cc1-c1ccc(F)c(S(C)(=O)=O)c1",
"reactionStepId": "sa_e032c3098c19a5defc1e8d6d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130102609A1;0324;1358902\",\"rsmi\":\"Br[c:5]1[cH:6][c:7]([S:8]([CH3:9])(=[O:10])=[O:11])[c:12]([F:13])[cH:14][cH:15]1.OB(O)[c:4]1[c:3]([O:2][CH3:1])[cH:21][cH:20][c:17]([CH:18]=[O:19])[cH:16]1>C1COCCO1.O.O=C(O)O.[K+].[K+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][c:3]1[c:4](-[c:5]2[cH:6][c:7]([S:8]([CH3:9])(=[O:10])=[O:11])[c:12]([F:13])[cH:14][cH:15]2)[cH:16][c:17]([CH:18]=[O:19])[cH:20][cH:21]1\"},\"mapped_reaction_smiles\":\"Br[c:5]1[cH:6][c:7]([S:8]([CH3:9])(=[O:10])=[O:11])[c:12]([F:13])[cH:14][cH:15]1.OB(O)[c:4]1[c:3]([O:2][CH3:1])[cH:21][cH:20][c:17]([CH:18]=[O:19])[cH:16]1>C1COCCO1.O.O=C(O)O.[K+].[K+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][c:3]1[c:4](-[c:5]2[cH:6][c:7]([S:8]([CH3:9])(=[O:10])=[O:11])[c:12]([F:13])[cH:14][cH:15]2)[cH:16][c:17]([CH:18]=[O:19])[cH:20][cH:21]1\"}",
"reactionStep": {
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"reactionHash": "bf7fb431b6432e7fa6c55d4bf03afe2b17bd03e90d10eee4254fd69b3ca0009b"
},
"children": [
{
"id": "13925",
"routeId": "sa_210d91e81f625cabd8dec421",
"moleculeId": "sa_aaa0e38e95e437a6668c9b19",
"parentId": "13924",
"isLeaf": true,
"molecule": {
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"inchikey": "NKKNXLPHCRLBDY-UHFFFAOYSA-N",
"smiles": "COc1ccc(C=O)cc1B(O)O"
},
"smiles": "COc1ccc(C=O)cc1B(O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "13926",
"routeId": "sa_210d91e81f625cabd8dec421",
"moleculeId": "sa_a191786d710b3aeb6e0ea68d",
"parentId": "13924",
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"molecule": {
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"smiles": "CS(=O)(=O)c1cc(Br)ccc1F"
},
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}
]
}
]
}
]
}
]
}
]
}
]
}
}