Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1cc([N+](=O)[O-])c(OC(C)C)cc1C1=CCC(N(C)C)CC1
InChiKey
QPIVINFQUAIASJ-UHFFFAOYSA-N
Route Signature
959d4b5abe6feb269f1625a68b273a32bc67415c820f01dce6cb515d9beeede4
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_061062cc24a84a37dd5b6b4e",
"signature": "959d4b5abe6feb269f1625a68b273a32bc67415c820f01dce6cb515d9beeede4",
"contentHash": "639e93b07352cc3428c7324bcc93deaf84c373fef9adcbea17bae1d43cb10cf0",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_2d277723785695fd416864f7",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00132",
"moleculeId": "sa_1145343873f456acd2eb1a8c",
"smiles": "Cc1cc([N+](=O)[O-])c(OC(C)C)cc1C1=CCC(N(C)C)CC1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_1145343873f456acd2eb1a8c",
"inchikey": "QPIVINFQUAIASJ-UHFFFAOYSA-N",
"smiles": "Cc1cc([N+](=O)[O-])c(OC(C)C)cc1C1=CCC(N(C)C)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 3
},
"rootNode": {
"id": "3473",
"routeId": "sa_061062cc24a84a37dd5b6b4e",
"moleculeId": "sa_1145343873f456acd2eb1a8c",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_1145343873f456acd2eb1a8c",
"inchikey": "QPIVINFQUAIASJ-UHFFFAOYSA-N",
"smiles": "Cc1cc([N+](=O)[O-])c(OC(C)C)cc1C1=CCC(N(C)C)CC1"
},
"smiles": "Cc1cc([N+](=O)[O-])c(OC(C)C)cc1C1=CCC(N(C)C)CC1",
"reactionStepId": "sa_9a583ff5ea298faa7b298ed5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150105390A1;0313;1678127\",\"rsmi\":\"O=[C:7]1[CH2:6][CH:5]=[C:4]([c:3]2[c:2]([CH3:1])[cH:23][c:19]([N+:20](=[O:21])[O-:22])[c:14]([O:15][CH:16]([CH3:17])[CH3:18])[cH:13]2)[CH2:12][CH2:11]1.[NH:8]([CH3:9])[CH3:10]>CC(=O)O.CC(=O)OB(OC(C)=O)OC(C)=O.CO.ClCCl.[Na+]>[CH3:1][c:2]1[c:3]([C:4]2=[CH:5][CH2:6][CH:7]([N:8]([CH3:9])[CH3:10])[CH2:11][CH2:12]2)[cH:13][c:14]([O:15][CH:16]([CH3:17])[CH3:18])[c:19]([N+:20](=[O:21])[O-:22])[cH:23]1\"},\"mapped_reaction_smiles\":\"O=[C:7]1[CH2:6][CH:5]=[C:4]([c:3]2[c:2]([CH3:1])[cH:23][c:19]([N+:20](=[O:21])[O-:22])[c:14]([O:15][CH:16]([CH3:17])[CH3:18])[cH:13]2)[CH2:12][CH2:11]1.[NH:8]([CH3:9])[CH3:10]>CC(=O)O.CC(=O)OB(OC(C)=O)OC(C)=O.CO.ClCCl.[Na+]>[CH3:1][c:2]1[c:3]([C:4]2=[CH:5][CH2:6][CH:7]([N:8]([CH3:9])[CH3:10])[CH2:11][CH2:12]2)[cH:13][c:14]([O:15][CH:16]([CH3:17])[CH3:18])[c:19]([N+:20](=[O:21])[O-:22])[cH:23]1\"}",
"reactionStep": {
"id": "sa_9a583ff5ea298faa7b298ed5",
"reactionHash": "5e45218db9ba803e57bd71b512ce3039556cca71ec4288375f02cb9198c1f6dc"
},
"children": [
{
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"moleculeId": "sa_b7ed42d9f953d77bdbb42e5d",
"parentId": "3473",
"isLeaf": false,
"molecule": {
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"inchikey": "NTJCGBIVWNNDBD-UHFFFAOYSA-N",
"smiles": "Cc1cc([N+](=O)[O-])c(OC(C)C)cc1C1=CCC(=O)CC1"
},
"smiles": "Cc1cc([N+](=O)[O-])c(OC(C)C)cc1C1=CCC(=O)CC1",
"reactionStepId": "sa_00d11a7d7b442722ad4f7599",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150105390A1;0311;1678126\",\"rsmi\":\"C1C[O:8][C:7]2(O1)[CH2:6][CH:5]=[C:4]([c:3]1[c:2]([CH3:1])[cH:21][c:17]([N+:18](=[O:19])[O-:20])[c:12]([O:13][CH:14]([CH3:15])[CH3:16])[cH:11]1)[CH2:10][CH2:9]2>CCCCCC.CCOC(C)=O.ClCCl.O=C(O)C(F)(F)F>[CH3:1][c:2]1[c:3]([C:4]2=[CH:5][CH2:6][C:7](=[O:8])[CH2:9][CH2:10]2)[cH:11][c:12]([O:13][CH:14]([CH3:15])[CH3:16])[c:17]([N+:18](=[O:19])[O-:20])[cH:21]1\"},\"mapped_reaction_smiles\":\"C1C[O:8][C:7]2(O1)[CH2:6][CH:5]=[C:4]([c:3]1[c:2]([CH3:1])[cH:21][c:17]([N+:18](=[O:19])[O-:20])[c:12]([O:13][CH:14]([CH3:15])[CH3:16])[cH:11]1)[CH2:10][CH2:9]2>CCCCCC.CCOC(C)=O.ClCCl.O=C(O)C(F)(F)F>[CH3:1][c:2]1[c:3]([C:4]2=[CH:5][CH2:6][C:7](=[O:8])[CH2:9][CH2:10]2)[cH:11][c:12]([O:13][CH:14]([CH3:15])[CH3:16])[c:17]([N+:18](=[O:19])[O-:20])[cH:21]1\"}",
"reactionStep": {
"id": "sa_00d11a7d7b442722ad4f7599",
"reactionHash": "90d73d11f94199f4dd801f34ec7ce7905e273c1b60b0859665a083b3e90056d2"
},
"children": [
{
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"moleculeId": "sa_71f7f41874047ddf14b60ff6",
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"isLeaf": false,
"molecule": {
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"inchikey": "OFNHAUQUQYSACN-UHFFFAOYSA-N",
"smiles": "Cc1cc([N+](=O)[O-])c(OC(C)C)cc1C1=CCC2(CC1)OCCO2"
},
"smiles": "Cc1cc([N+](=O)[O-])c(OC(C)C)cc1C1=CCC2(CC1)OCCO2",
"reactionStepId": "sa_eef5ac77cad8ddc41efe30a6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150105390A1;0309;1678125\",\"rsmi\":\"CC1(C)OB([c:3]2[c:2]([CH3:1])[cH:24][c:20]([N+:21](=[O:22])[O-:23])[c:15]([O:16][CH:17]([CH3:18])[CH3:19])[cH:14]2)OC1(C)C.O=S(=O)(O[C:4]1=[CH:5][CH2:6][C:7]2([CH2:8][CH2:9]1)[O:10][CH2:11][CH2:12][O:13]2)C(F)(F)F>C1CCOC1.CCCCCC.CCOC(C)=O.O.O=P(O)(O)O.[K+].[K+].[K+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][c:2]1[c:3]([C:4]2=[CH:5][CH2:6][C:7]3([CH2:8][CH2:9]2)[O:10][CH2:11][CH2:12][O:13]3)[cH:14][c:15]([O:16][CH:17]([CH3:18])[CH3:19])[c:20]([N+:21](=[O:22])[O-:23])[cH:24]1\"},\"mapped_reaction_smiles\":\"CC1(C)OB([c:3]2[c:2]([CH3:1])[cH:24][c:20]([N+:21](=[O:22])[O-:23])[c:15]([O:16][CH:17]([CH3:18])[CH3:19])[cH:14]2)OC1(C)C.O=S(=O)(O[C:4]1=[CH:5][CH2:6][C:7]2([CH2:8][CH2:9]1)[O:10][CH2:11][CH2:12][O:13]2)C(F)(F)F>C1CCOC1.CCCCCC.CCOC(C)=O.O.O=P(O)(O)O.[K+].[K+].[K+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][c:2]1[c:3]([C:4]2=[CH:5][CH2:6][C:7]3([CH2:8][CH2:9]2)[O:10][CH2:11][CH2:12][O:13]3)[cH:14][c:15]([O:16][CH:17]([CH3:18])[CH3:19])[c:20]([N+:21](=[O:22])[O-:23])[cH:24]1\"}",
"reactionStep": {
"id": "sa_eef5ac77cad8ddc41efe30a6",
"reactionHash": "1bec4052f7a0a46f73d06c7b1271d6ae2ca4bed5d083ac6b9961bb838f003065"
},
"children": [
{
"id": "3476",
"routeId": "sa_061062cc24a84a37dd5b6b4e",
"moleculeId": "sa_8a222a28e22e567b57b7e0e6",
"parentId": "3475",
"isLeaf": true,
"molecule": {
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"inchikey": "NOLMGELTBIIGOL-UHFFFAOYSA-N",
"smiles": "O=S(=O)(OC1=CCC2(CC1)OCCO2)C(F)(F)F"
},
"smiles": "O=S(=O)(OC1=CCC2(CC1)OCCO2)C(F)(F)F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3477",
"routeId": "sa_061062cc24a84a37dd5b6b4e",
"moleculeId": "sa_1ac6ca777e2d92f186689b38",
"parentId": "3475",
"isLeaf": false,
"molecule": {
"id": "sa_1ac6ca777e2d92f186689b38",
"inchikey": "YMBCAHKUERVDCC-UHFFFAOYSA-N",
"smiles": "Cc1cc([N+](=O)[O-])c(OC(C)C)cc1B1OC(C)(C)C(C)(C)O1"
},
"smiles": "Cc1cc([N+](=O)[O-])c(OC(C)C)cc1B1OC(C)(C)C(C)(C)O1",
"reactionStepId": "sa_b32ff192b1f25b230d07f465",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150105390A1;0221;1678094\",\"rsmi\":\"CC1(C)OB([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:9]([CH3:10])([CH3:11])[O:12]2)OC1(C)C.Cl[c:3]1[c:2]([CH3:1])[cH:23][c:19]([N+:20](=[O:21])[O-:22])[c:14]([O:15][CH:16]([CH3:17])[CH3:18])[cH:13]1>C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1COCCO1.CC(=O)O.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[K+].[Pd].[Pd]>[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)[cH:13][c:14]([O:15][CH:16]([CH3:17])[CH3:18])[c:19]([N+:20](=[O:21])[O-:22])[cH:23]1\"},\"mapped_reaction_smiles\":\"CC1(C)OB([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:9]([CH3:10])([CH3:11])[O:12]2)OC1(C)C.Cl[c:3]1[c:2]([CH3:1])[cH:23][c:19]([N+:20](=[O:21])[O-:22])[c:14]([O:15][CH:16]([CH3:17])[CH3:18])[cH:13]1>C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1COCCO1.CC(=O)O.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[K+].[Pd].[Pd]>[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)[cH:13][c:14]([O:15][CH:16]([CH3:17])[CH3:18])[c:19]([N+:20](=[O:21])[O-:22])[cH:23]1\"}",
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"children": [
{
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"routeId": "sa_061062cc24a84a37dd5b6b4e",
"moleculeId": "sa_f0d3a928bea93e571cecba2e",
"parentId": "3477",
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"molecule": {
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"inchikey": "BXIHEXKVDALKGM-UHFFFAOYSA-N",
"smiles": "Cc1cc([N+](=O)[O-])c(OC(C)C)cc1Cl"
},
"smiles": "Cc1cc([N+](=O)[O-])c(OC(C)C)cc1Cl",
"reactionStepId": "sa_73de1229a3f4c67f4b67c9f1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150105390A1;0219;1678093\",\"rsmi\":\"F[c:6]1[cH:5][c:3]([Cl:4])[c:2]([CH3:1])[cH:15][c:11]1[N+:12](=[O:13])[O-:14].[OH:7][CH:8]([CH3:9])[CH3:10]>O=C(O)O.[Cs+].[Cs+]>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([O:7][CH:8]([CH3:9])[CH3:10])[c:11]([N+:12](=[O:13])[O-:14])[cH:15]1\"},\"mapped_reaction_smiles\":\"F[c:6]1[cH:5][c:3]([Cl:4])[c:2]([CH3:1])[cH:15][c:11]1[N+:12](=[O:13])[O-:14].[OH:7][CH:8]([CH3:9])[CH3:10]>O=C(O)O.[Cs+].[Cs+]>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([O:7][CH:8]([CH3:9])[CH3:10])[c:11]([N+:12](=[O:13])[O-:14])[cH:15]1\"}",
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"molecule": {
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"smiles": "CC(C)O"
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{
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"molecule": {
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"inchikey": "YXVJHZWHPLOEAP-UHFFFAOYSA-N",
"smiles": "Cc1cc([N+](=O)[O-])c(F)cc1Cl"
},
"smiles": "Cc1cc([N+](=O)[O-])c(F)cc1Cl",
"reactionStepId": "sa_b9ea664ad9f7740dff513392",
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"metadata": "{\"annotations\":{\"ID\":\"US20150105390A1;0217;1678092\",\"rsmi\":\"[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([F:7])[cH:8][cH:12]1.O[N+:9](=[O:10])[O-:11]>O=S(=O)(O)O.[K+]>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([F:7])[c:8]([N+:9](=[O:10])[O-:11])[cH:12]1\"},\"mapped_reaction_smiles\":\"[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([F:7])[cH:8][cH:12]1.O[N+:9](=[O:10])[O-:11]>O=S(=O)(O)O.[K+]>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([F:7])[c:8]([N+:9](=[O:10])[O-:11])[cH:12]1\"}",
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{
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{
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},
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C",
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]
},
{
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"molecule": {
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"smiles": "CNC"
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}
]
}
}