Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COC(=O)Cc1ccc(OC)c(-c2ccc(C(F)(F)F)cc2CN(Cc2ccccc2)C(=O)OC)c1
InChiKey
ZGCKGVWSUWDPFV-UHFFFAOYSA-N
Route Signature
ecd71d36848937e8d9687d1f9d6a5f92cba4d73b1a31262c4aa54f4b6b31d0c4
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_454b702a2f19f0d09e1cc5be",
"signature": "ecd71d36848937e8d9687d1f9d6a5f92cba4d73b1a31262c4aa54f4b6b31d0c4",
"contentHash": "d269d0505b7e72cbf4debea0e4b0f51fa279dd058083f010f3127757069c719d",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_fb0db309af874cc01e93bdf7",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-02062",
"moleculeId": "sa_fa9676163efbbb249c78d102",
"smiles": "COC(=O)Cc1ccc(OC)c(-c2ccc(C(F)(F)F)cc2CN(Cc2ccccc2)C(=O)OC)c1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_fa9676163efbbb249c78d102",
"inchikey": "ZGCKGVWSUWDPFV-UHFFFAOYSA-N",
"smiles": "COC(=O)Cc1ccc(OC)c(-c2ccc(C(F)(F)F)cc2CN(Cc2ccccc2)C(=O)OC)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "1707",
"routeId": "sa_454b702a2f19f0d09e1cc5be",
"moleculeId": "sa_fa9676163efbbb249c78d102",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_fa9676163efbbb249c78d102",
"inchikey": "ZGCKGVWSUWDPFV-UHFFFAOYSA-N",
"smiles": "COC(=O)Cc1ccc(OC)c(-c2ccc(C(F)(F)F)cc2CN(Cc2ccccc2)C(=O)OC)c1"
},
"smiles": "COC(=O)Cc1ccc(OC)c(-c2ccc(C(F)(F)F)cc2CN(Cc2ccccc2)C(=O)OC)c1",
"reactionStepId": "sa_3826a96c3aa1ccf75262af2b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130158036A1;0643;1383996\",\"rsmi\":\"Cl[C:24](=[O:25])[O:26][CH3:27].[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH3:11])[c:12](-[c:13]2[c:14]([CH2:15][NH:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[cH:28][c:29]([C:30]([F:31])([F:32])[F:33])[cH:34][cH:35]2)[cH:36]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH3:11])[c:12](-[c:13]2[c:14]([CH2:15][N:16]([CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[C:24](=[O:25])[O:26][CH3:27])[cH:28][c:29]([C:30]([F:31])([F:32])[F:33])[cH:34][cH:35]2)[cH:36]1\"},\"mapped_reaction_smiles\":\"Cl[C:24](=[O:25])[O:26][CH3:27].[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH3:11])[c:12](-[c:13]2[c:14]([CH2:15][NH:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[cH:28][c:29]([C:30]([F:31])([F:32])[F:33])[cH:34][cH:35]2)[cH:36]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH3:11])[c:12](-[c:13]2[c:14]([CH2:15][N:16]([CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[C:24](=[O:25])[O:26][CH3:27])[cH:28][c:29]([C:30]([F:31])([F:32])[F:33])[cH:34][cH:35]2)[cH:36]1\"}",
"reactionStep": {
"id": "sa_3826a96c3aa1ccf75262af2b",
"reactionHash": "4a349912fb3a071172444baf781121cca18accd4a8068f987241cbacc77e4a62"
},
"children": [
{
"id": "1708",
"routeId": "sa_454b702a2f19f0d09e1cc5be",
"moleculeId": "sa_7e9bb8281c6773f7082310c4",
"parentId": "1707",
"isLeaf": false,
"molecule": {
"id": "sa_7e9bb8281c6773f7082310c4",
"inchikey": "GLVNXYQFHPAJFC-UHFFFAOYSA-N",
"smiles": "COC(=O)Cc1ccc(OC)c(-c2ccc(C(F)(F)F)cc2CNCc2ccccc2)c1"
},
"smiles": "COC(=O)Cc1ccc(OC)c(-c2ccc(C(F)(F)F)cc2CNCc2ccccc2)c1",
"reactionStepId": "sa_1f2ad7a53557b18f41145023",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130158036A1;0621;1383984\",\"rsmi\":\"O=[CH:15][c:14]1[c:13](-[c:12]2[c:9]([O:10][CH3:11])[cH:8][cH:7][c:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:32]2)[cH:31][cH:30][c:25]([C:26]([F:27])([F:28])[F:29])[cH:24]1.[NH2:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH3:11])[c:12](-[c:13]2[c:14]([CH2:15][NH:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30][cH:31]2)[cH:32]1\"},\"mapped_reaction_smiles\":\"O=[CH:15][c:14]1[c:13](-[c:12]2[c:9]([O:10][CH3:11])[cH:8][cH:7][c:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:32]2)[cH:31][cH:30][c:25]([C:26]([F:27])([F:28])[F:29])[cH:24]1.[NH2:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH3:11])[c:12](-[c:13]2[c:14]([CH2:15][NH:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30][cH:31]2)[cH:32]1\"}",
"reactionStep": {
"id": "sa_1f2ad7a53557b18f41145023",
"reactionHash": "22d5c7d13b06bf06b245f073636150068214cb65934208ae64561849f03762c2"
},
"children": [
{
"id": "1709",
"routeId": "sa_454b702a2f19f0d09e1cc5be",
"moleculeId": "sa_18dfca5e56313ad58df94490",
"parentId": "1708",
"isLeaf": false,
"molecule": {
"id": "sa_18dfca5e56313ad58df94490",
"inchikey": "LMXMLQBNMPQWSL-UHFFFAOYSA-N",
"smiles": "COC(=O)Cc1ccc(OC)c(-c2ccc(C(F)(F)F)cc2C=O)c1"
},
"smiles": "COC(=O)Cc1ccc(OC)c(-c2ccc(C(F)(F)F)cc2C=O)c1",
"reactionStepId": "sa_feb5b387556ea8598d7fbcd9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130158036A1;0544;1383948\",\"rsmi\":\"Br[c:13]1[c:14]([CH:15]=[O:16])[cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]1.CC1(C)OB([c:12]2[c:9]([O:10][CH3:11])[cH:8][cH:7][c:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:25]2)OC1(C)C>COCCOC.ClCCl.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](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH3:11])[c:12](-[c:13]2[c:14]([CH:15]=[O:16])[cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]2)[cH:25]1\"},\"mapped_reaction_smiles\":\"Br[c:13]1[c:14]([CH:15]=[O:16])[cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]1.CC1(C)OB([c:12]2[c:9]([O:10][CH3:11])[cH:8][cH:7][c:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:25]2)OC1(C)C>COCCOC.ClCCl.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](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH3:11])[c:12](-[c:13]2[c:14]([CH:15]=[O:16])[cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]2)[cH:25]1\"}",
"reactionStep": {
"id": "sa_feb5b387556ea8598d7fbcd9",
"reactionHash": "c1f73d1473293cd0b6ebe551aef18ecd27f6b1bf6eeb2c5c6ee1dd9aebb332d8"
},
"children": [
{
"id": "1710",
"routeId": "sa_454b702a2f19f0d09e1cc5be",
"moleculeId": "sa_a4db0f118136896ca050a03d",
"parentId": "1709",
"isLeaf": false,
"molecule": {
"id": "sa_a4db0f118136896ca050a03d",
"inchikey": "CSOBJYGHQOLWOD-UHFFFAOYSA-N",
"smiles": "O=Cc1cc(C(F)(F)F)ccc1Br"
},
"smiles": "O=Cc1cc(C(F)(F)F)ccc1Br",
"reactionStepId": "sa_3f8f8b39ebda172a1f9f339b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130158036A1;0543;1383947\",\"rsmi\":\"[OH:1][CH2:2][c:3]1[c:4]([Br:5])[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13]1>CC#N.CCC[N+](CCC)(CCC)CCC.C[N+]1([O-])CCOCC1.ClCCl.O=[Ru](=O)(=O)O>[O:1]=[CH:2][c:3]1[c:4]([Br:5])[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13]1\"},\"mapped_reaction_smiles\":\"[OH:1][CH2:2][c:3]1[c:4]([Br:5])[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13]1>CC#N.CCC[N+](CCC)(CCC)CCC.C[N+]1([O-])CCOCC1.ClCCl.O=[Ru](=O)(=O)O>[O:1]=[CH:2][c:3]1[c:4]([Br:5])[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13]1\"}",
"reactionStep": {
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"reactionHash": "32cb24024f081434f9468b38cdf55cb853e6ba7e2815d62035fd979abf6600bf"
},
"children": [
{
"id": "1711",
"routeId": "sa_454b702a2f19f0d09e1cc5be",
"moleculeId": "sa_c9e50e9cd672fbc0dd2a0b68",
"parentId": "1710",
"isLeaf": true,
"molecule": {
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"inchikey": "RXASTJJSPATSHH-UHFFFAOYSA-N",
"smiles": "OCc1cc(C(F)(F)F)ccc1Br"
},
"smiles": "OCc1cc(C(F)(F)F)ccc1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
},
{
"id": "1712",
"routeId": "sa_454b702a2f19f0d09e1cc5be",
"moleculeId": "sa_245e685fcfc6df526784170e",
"parentId": "1709",
"isLeaf": false,
"molecule": {
"id": "sa_245e685fcfc6df526784170e",
"inchikey": "MNYSQPXCOWTNQR-UHFFFAOYSA-N",
"smiles": "COC(=O)Cc1ccc(OC)c(B2OC(C)(C)C(C)(C)O2)c1"
},
"smiles": "COC(=O)Cc1ccc(OC)c(B2OC(C)(C)C(C)(C)O2)c1",
"reactionStepId": "sa_2c7b482b1fbfd0586bc33ad6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130158036A1;0542;1383946\",\"rsmi\":\"Br[c:8]1[cH:7][c:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:22][cH:21][c:18]1[O:19][CH3:20].CC1(C)OB([B:9]2[O:10][C:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[O:17]2)OC1(C)C>CC(=O)O.CN(C)C=O.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][c:8]([B:9]2[O:10][C:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[O:17]2)[c:18]([O:19][CH3:20])[cH:21][cH:22]1\"},\"mapped_reaction_smiles\":\"Br[c:8]1[cH:7][c:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:22][cH:21][c:18]1[O:19][CH3:20].CC1(C)OB([B:9]2[O:10][C:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[O:17]2)OC1(C)C>CC(=O)O.CN(C)C=O.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][c:8]([B:9]2[O:10][C:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[O:17]2)[c:18]([O:19][CH3:20])[cH:21][cH:22]1\"}",
"reactionStep": {
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"reactionHash": "2369934f73c9eed8126da4b24909f91976643a96ed4d2200848621a1100a71cd"
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"children": [
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"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "1712",
"isLeaf": true,
"molecule": {
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"inchikey": "IPWKHHSGDUIRAH-UHFFFAOYSA-N",
"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",
"reactionStepId": null,
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},
{
"id": "1714",
"routeId": "sa_454b702a2f19f0d09e1cc5be",
"moleculeId": "sa_1c97a61d8754c56210c850b4",
"parentId": "1712",
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"molecule": {
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"inchikey": "SJYUPYFKRKUSLL-UHFFFAOYSA-N",
"smiles": "COC(=O)Cc1ccc(OC)c(Br)c1"
},
"smiles": "COC(=O)Cc1ccc(OC)c(Br)c1",
"reactionStepId": "sa_c4d7ad1bb1fbee46ca06018d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130158036A1;0541;1383945\",\"rsmi\":\"O[C:3](=[O:4])[CH2:5][c:6]1[cH:7][c:8]([Br:9])[c:10]([O:11][CH3:12])[cH:13][cH:14]1.[CH3:1][OH:2]>O=S(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][c:8]([Br:9])[c:10]([O:11][CH3:12])[cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"O[C:3](=[O:4])[CH2:5][c:6]1[cH:7][c:8]([Br:9])[c:10]([O:11][CH3:12])[cH:13][cH:14]1.[CH3:1][OH:2]>O=S(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][c:8]([Br:9])[c:10]([O:11][CH3:12])[cH:13][cH:14]1\"}",
"reactionStep": {
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"children": [
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"molecule": {
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"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
"smiles": "CO",
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},
{
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"molecule": {
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"inchikey": "POTVGQUUEQTPNA-UHFFFAOYSA-N",
"smiles": "COc1ccc(CC(=O)O)cc1Br"
},
"smiles": "COc1ccc(CC(=O)O)cc1Br",
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}
]
}
]
}
]
},
{
"id": "1717",
"routeId": "sa_454b702a2f19f0d09e1cc5be",
"moleculeId": "sa_6b16c9b5e9c18df10e07c892",
"parentId": "1708",
"isLeaf": true,
"molecule": {
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"inchikey": "WGQKYBSKWIADBV-UHFFFAOYSA-N",
"smiles": "NCc1ccccc1"
},
"smiles": "NCc1ccccc1",
"reactionStepId": null,
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"children": []
}
]
},
{
"id": "1718",
"routeId": "sa_454b702a2f19f0d09e1cc5be",
"moleculeId": "sa_786c6159be77bb31e43bff8a",
"parentId": "1707",
"isLeaf": true,
"molecule": {
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"inchikey": "XMJHPCRAQCTCFT-UHFFFAOYSA-N",
"smiles": "COC(=O)Cl"
},
"smiles": "COC(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
}