Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(=O)c1cccc(Cc2nc(C(=O)Cl)co2)c1
InChiKey
VIKLWERJWBOSGY-UHFFFAOYSA-N
Route Signature
b1683d6142fdbed7029f49f0f8f56e2ab0cb61c9340e77328aff09f315b71f7c
Synthesis route with 7 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_dfb98317b939bae6f9ce0578",
"signature": "b1683d6142fdbed7029f49f0f8f56e2ab0cb61c9340e77328aff09f315b71f7c",
"contentHash": "cc7e665a69c95f78e6fa68c26a18e9ded3f34b460b9e6e20853bf3047fb26f57",
"length": 7,
"isConvergent": false
},
"target": {
"id": "sa_999d481602c2a50a262f87cd",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-02218",
"moleculeId": "sa_c4276834aa87bb45259edd91",
"smiles": "CC(=O)c1cccc(Cc2nc(C(=O)Cl)co2)c1",
"routeLength": 7,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_c4276834aa87bb45259edd91",
"inchikey": "VIKLWERJWBOSGY-UHFFFAOYSA-N",
"smiles": "CC(=O)c1cccc(Cc2nc(C(=O)Cl)co2)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "14686",
"routeId": "sa_dfb98317b939bae6f9ce0578",
"moleculeId": "sa_c4276834aa87bb45259edd91",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_c4276834aa87bb45259edd91",
"inchikey": "VIKLWERJWBOSGY-UHFFFAOYSA-N",
"smiles": "CC(=O)c1cccc(Cc2nc(C(=O)Cl)co2)c1"
},
"smiles": "CC(=O)c1cccc(Cc2nc(C(=O)Cl)co2)c1",
"reactionStepId": "sa_ad8f9704bf8e3cd4749670ef",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120115916A1;0550;1212349\",\"rsmi\":\"O=C(Cl)C(=O)[Cl:15].O[C:13]([c:12]1[n:11][c:10]([CH2:9][c:8]2[cH:7][cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:18]2)[o:17][cH:16]1)=[O:14]>CN(C)C=O.Cc1ccccc1.N#N>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][c:10]2[n:11][c:12]([C:13](=[O:14])[Cl:15])[cH:16][o:17]2)[cH:18]1\"},\"mapped_reaction_smiles\":\"O=C(Cl)C(=O)[Cl:15].O[C:13]([c:12]1[n:11][c:10]([CH2:9][c:8]2[cH:7][cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:18]2)[o:17][cH:16]1)=[O:14]>CN(C)C=O.Cc1ccccc1.N#N>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][c:10]2[n:11][c:12]([C:13](=[O:14])[Cl:15])[cH:16][o:17]2)[cH:18]1\"}",
"reactionStep": {
"id": "sa_ad8f9704bf8e3cd4749670ef",
"reactionHash": "99e7a9ca1b63be417624917ea21f82f468da6a1c488c6d53eab2fe7bddf76807"
},
"children": [
{
"id": "14687",
"routeId": "sa_dfb98317b939bae6f9ce0578",
"moleculeId": "sa_83e7d4ec882b44062b48ca58",
"parentId": "14686",
"isLeaf": true,
"molecule": {
"id": "sa_83e7d4ec882b44062b48ca58",
"inchikey": "CTSLXHKWHWQRSH-UHFFFAOYSA-N",
"smiles": "O=C(Cl)C(=O)Cl"
},
"smiles": "O=C(Cl)C(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14688",
"routeId": "sa_dfb98317b939bae6f9ce0578",
"moleculeId": "sa_6586d2ea20497c817798c213",
"parentId": "14686",
"isLeaf": false,
"molecule": {
"id": "sa_6586d2ea20497c817798c213",
"inchikey": "NPUKZWXWSNELQC-UHFFFAOYSA-N",
"smiles": "CC(=O)c1cccc(Cc2nc(C(=O)O)co2)c1"
},
"smiles": "CC(=O)c1cccc(Cc2nc(C(=O)O)co2)c1",
"reactionStepId": "sa_4d1e9078883cf8003e9acbed",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120115916A1;0549;1212348\",\"rsmi\":\"C[O:15][C:13]([c:12]1[n:11][c:10]([CH2:9][c:8]2[cH:7][cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:18]2)[o:17][cH:16]1)=[O:14]>C1CCOC1.Cl.N#N.[Na+].O>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][c:10]2[n:11][c:12]([C:13](=[O:14])[OH:15])[cH:16][o:17]2)[cH:18]1\"},\"mapped_reaction_smiles\":\"C[O:15][C:13]([c:12]1[n:11][c:10]([CH2:9][c:8]2[cH:7][cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:18]2)[o:17][cH:16]1)=[O:14]>C1CCOC1.Cl.N#N.[Na+].O>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][c:10]2[n:11][c:12]([C:13](=[O:14])[OH:15])[cH:16][o:17]2)[cH:18]1\"}",
"reactionStep": {
"id": "sa_4d1e9078883cf8003e9acbed",
"reactionHash": "033d2a671983d8d04c217ffe9e20e84c4dec5e3066f3b6df8f05f108c1186ec7"
},
"children": [
{
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"moleculeId": "sa_570344311b6e1f094b0e70b4",
"parentId": "14688",
"isLeaf": false,
"molecule": {
"id": "sa_570344311b6e1f094b0e70b4",
"inchikey": "BJTIMGUBGCLSEP-UHFFFAOYSA-N",
"smiles": "COC(=O)c1coc(Cc2cccc(C(C)=O)c2)n1"
},
"smiles": "COC(=O)c1coc(Cc2cccc(C(C)=O)c2)n1",
"reactionStepId": "sa_83f680f974ed41211945506f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120115916A1;0548;1212347\",\"rsmi\":\"C1C[O:15][C:13]([c:12]2[cH:11][c:10]([CH2:9][c:8]3[o:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[n:19]3)[cH:18][cH:17][cH:16]2)([CH3:14])O1>C1CCOC1.Cl.N#N.O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][o:7][c:8]([CH2:9][c:10]2[cH:11][c:12]([C:13]([CH3:14])=[O:15])[cH:16][cH:17][cH:18]2)[n:19]1\"},\"mapped_reaction_smiles\":\"C1C[O:15][C:13]([c:12]2[cH:11][c:10]([CH2:9][c:8]3[o:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[n:19]3)[cH:18][cH:17][cH:16]2)([CH3:14])O1>C1CCOC1.Cl.N#N.O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][o:7][c:8]([CH2:9][c:10]2[cH:11][c:12]([C:13]([CH3:14])=[O:15])[cH:16][cH:17][cH:18]2)[n:19]1\"}",
"reactionStep": {
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"reactionHash": "af57921277ce61e24d93698f33c9c1bf8398400a2f34a2cd5122fc665933aa56"
},
"children": [
{
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"moleculeId": "sa_ccfe4e685e16cc508e340c38",
"parentId": "14689",
"isLeaf": false,
"molecule": {
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"inchikey": "PZTNCVGZXYYOPY-UHFFFAOYSA-N",
"smiles": "COC(=O)c1coc(Cc2cccc(C3(C)OCCO3)c2)n1"
},
"smiles": "COC(=O)c1coc(Cc2cccc(C3(C)OCCO3)c2)n1",
"reactionStepId": "sa_1fbad8e6c6f7cf81dff82270",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120115916A1;0547;1212346\",\"rsmi\":\"[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][O:7][C:8]([CH2:9][c:10]2[cH:11][c:12]([C:13]3([CH3:14])[O:15][CH2:16][CH2:17][O:18]3)[cH:19][cH:20][cH:21]2)=[N:22]1>Br[Cu]Br.C1CCC2=NCCCN2CC1.C1N2CN3CN1CN(C2)C3.ClCCl.N#N>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][o:7][c:8]([CH2:9][c:10]2[cH:11][c:12]([C:13]3([CH3:14])[O:15][CH2:16][CH2:17][O:18]3)[cH:19][cH:20][cH:21]2)[n:22]1\"},\"mapped_reaction_smiles\":\"[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][O:7][C:8]([CH2:9][c:10]2[cH:11][c:12]([C:13]3([CH3:14])[O:15][CH2:16][CH2:17][O:18]3)[cH:19][cH:20][cH:21]2)=[N:22]1>Br[Cu]Br.C1CCC2=NCCCN2CC1.C1N2CN3CN1CN(C2)C3.ClCCl.N#N>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][o:7][c:8]([CH2:9][c:10]2[cH:11][c:12]([C:13]3([CH3:14])[O:15][CH2:16][CH2:17][O:18]3)[cH:19][cH:20][cH:21]2)[n:22]1\"}",
"reactionStep": {
"id": "sa_1fbad8e6c6f7cf81dff82270",
"reactionHash": "0fd61f49d9aa88407172d8e80a18a9e5121fd683145a4576d8fe61617490f4eb"
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"children": [
{
"id": "14691",
"routeId": "sa_dfb98317b939bae6f9ce0578",
"moleculeId": "sa_60626691a8f3b04f656bb528",
"parentId": "14690",
"isLeaf": false,
"molecule": {
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"inchikey": "XWDJPHIFMMRDQD-UHFFFAOYSA-N",
"smiles": "COC(=O)C1COC(Cc2cccc(C3(C)OCCO3)c2)=N1"
},
"smiles": "COC(=O)C1COC(Cc2cccc(C3(C)OCCO3)c2)=N1",
"reactionStepId": "sa_3fbec38506e57e3ffcbaae5f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120115916A1;0546;1212345\",\"rsmi\":\"O=[C:8]([CH2:9][c:10]1[cH:11][c:12]([C:13]2([CH3:14])[O:15][CH2:16][CH2:17][O:18]2)[cH:19][cH:20][cH:21]1)[NH:22][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][OH:7]>C1CCOC1.CC[N+](CC)(CC)S(=O)(=O)NC(=O)OC.N#N.O>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][O:7][C:8]([CH2:9][c:10]2[cH:11][c:12]([C:13]3([CH3:14])[O:15][CH2:16][CH2:17][O:18]3)[cH:19][cH:20][cH:21]2)=[N:22]1\"},\"mapped_reaction_smiles\":\"O=[C:8]([CH2:9][c:10]1[cH:11][c:12]([C:13]2([CH3:14])[O:15][CH2:16][CH2:17][O:18]2)[cH:19][cH:20][cH:21]1)[NH:22][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][OH:7]>C1CCOC1.CC[N+](CC)(CC)S(=O)(=O)NC(=O)OC.N#N.O>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][O:7][C:8]([CH2:9][c:10]2[cH:11][c:12]([C:13]3([CH3:14])[O:15][CH2:16][CH2:17][O:18]3)[cH:19][cH:20][cH:21]2)=[N:22]1\"}",
"reactionStep": {
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"children": [
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"moleculeId": "sa_eca4187ac04da9ec0cbe6091",
"parentId": "14691",
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"molecule": {
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"inchikey": "YJLYYZGGDAZTHQ-UHFFFAOYSA-N",
"smiles": "COC(=O)C(CO)NC(=O)Cc1cccc(C2(C)OCCO2)c1"
},
"smiles": "COC(=O)C(CO)NC(=O)Cc1cccc(C2(C)OCCO2)c1",
"reactionStepId": "sa_3791138398988a186395c2b2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120115916A1;0545;1212344\",\"rsmi\":\"O[C:9](=[O:10])[CH2:11][c:12]1[cH:13][c:14]([C:15]2([CH3:16])[O:17][CH2:18][CH2:19][O:20]2)[cH:21][cH:22][cH:23]1.[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][OH:7])[NH2:8]>CCN(C(C)C)C(C)C.CN(C)c1ccncc1.Cl.ClCCCl.ClCCl.N#N.O.On1nnc2ccccc21>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][OH:7])[NH:8][C:9](=[O:10])[CH2:11][c:12]1[cH:13][c:14]([C:15]2([CH3:16])[O:17][CH2:18][CH2:19][O:20]2)[cH:21][cH:22][cH:23]1\"},\"mapped_reaction_smiles\":\"O[C:9](=[O:10])[CH2:11][c:12]1[cH:13][c:14]([C:15]2([CH3:16])[O:17][CH2:18][CH2:19][O:20]2)[cH:21][cH:22][cH:23]1.[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][OH:7])[NH2:8]>CCN(C(C)C)C(C)C.CN(C)c1ccncc1.Cl.ClCCCl.ClCCl.N#N.O.On1nnc2ccccc21>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][OH:7])[NH:8][C:9](=[O:10])[CH2:11][c:12]1[cH:13][c:14]([C:15]2([CH3:16])[O:17][CH2:18][CH2:19][O:20]2)[cH:21][cH:22][cH:23]1\"}",
"reactionStep": {
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"children": [
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"moleculeId": "sa_1cd45175baf9efd209de8dd6",
"parentId": "14692",
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"molecule": {
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"inchikey": "ANSUDRATXSJBLY-VKHMYHEASA-N",
"smiles": "COC(=O)[C@@H](N)CO"
},
"smiles": "COC(=O)[C@@H](N)CO",
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{
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"molecule": {
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"inchikey": "TXDSUNHRSGBANR-UHFFFAOYSA-N",
"smiles": "CC1(c2cccc(CC(=O)O)c2)OCCO1"
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"smiles": "CC1(c2cccc(CC(=O)O)c2)OCCO1",
"reactionStepId": "sa_450e29ad59893f2fa6dd9bbc",
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"metadata": "{\"annotations\":{\"ID\":\"US20120115916A1;0542;1212341\",\"rsmi\":\"CC[O:11][C:9]([CH2:8][c:7]1[cH:6][cH:5][cH:4][c:3]([C:2]2([CH3:1])[O:13][CH2:14][CH2:15][O:16]2)[cH:12]1)=[O:10]>C1CCOC1.Cl.N#N.[Na+].O>[CH3:1][C:2]1([c:3]2[cH:4][cH:5][cH:6][c:7]([CH2:8][C:9](=[O:10])[OH:11])[cH:12]2)[O:13][CH2:14][CH2:15][O:16]1\"},\"mapped_reaction_smiles\":\"CC[O:11][C:9]([CH2:8][c:7]1[cH:6][cH:5][cH:4][c:3]([C:2]2([CH3:1])[O:13][CH2:14][CH2:15][O:16]2)[cH:12]1)=[O:10]>C1CCOC1.Cl.N#N.[Na+].O>[CH3:1][C:2]1([c:3]2[cH:4][cH:5][cH:6][c:7]([CH2:8][C:9](=[O:10])[OH:11])[cH:12]2)[O:13][CH2:14][CH2:15][O:16]1\"}",
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},
"smiles": "CCOC(=O)Cc1cccc(C2(C)OCCO2)c1",
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]
}
]
}
}