Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCOc1cn(C(C)C(=O)Nc2ccc(C(=O)O)cc2)c(=O)cc1-c1cc(Cl)ccc1C#N
InChiKey
MHLRUCJOXJQBOK-UHFFFAOYSA-N
Route Signature
a7dbfbc6b25a77060e94d2e1b99d4898cb2af241d184b3aca01244161eabdae8
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_ac4ea4f5c5fb6133ebc9d965",
"signature": "a7dbfbc6b25a77060e94d2e1b99d4898cb2af241d184b3aca01244161eabdae8",
"contentHash": "76246d87d9f8bfea87abb35f8173d7ba924697531fd5faf8d4985c621eed2e94",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_28c9d04c498eb322b4f37239",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00623",
"moleculeId": "sa_1170f70dfe64eb371a88ffca",
"smiles": "CCOc1cn(C(C)C(=O)Nc2ccc(C(=O)O)cc2)c(=O)cc1-c1cc(Cl)ccc1C#N",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_1170f70dfe64eb371a88ffca",
"inchikey": "MHLRUCJOXJQBOK-UHFFFAOYSA-N",
"smiles": "CCOc1cn(C(C)C(=O)Nc2ccc(C(=O)O)cc2)c(=O)cc1-c1cc(Cl)ccc1C#N"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13624",
"routeId": "sa_ac4ea4f5c5fb6133ebc9d965",
"moleculeId": "sa_1170f70dfe64eb371a88ffca",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_1170f70dfe64eb371a88ffca",
"inchikey": "MHLRUCJOXJQBOK-UHFFFAOYSA-N",
"smiles": "CCOc1cn(C(C)C(=O)Nc2ccc(C(=O)O)cc2)c(=O)cc1-c1cc(Cl)ccc1C#N"
},
"smiles": "CCOc1cn(C(C)C(=O)Nc2ccc(C(=O)O)cc2)c(=O)cc1-c1cc(Cl)ccc1C#N",
"reactionStepId": "sa_0c81fbda99efa63705997979",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160052884A1;2551;1843105\",\"rsmi\":\"CC(C)(C)[O:18][C:16]([c:15]1[cH:14][cH:13][c:12]([NH:11][C:9]([CH:7]([n:6]2[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:24](-[c:25]3[c:26]([C:27]#[N:28])[cH:29][cH:30][c:31]([Cl:32])[cH:33]3)[cH:23][c:21]2=[O:22])[CH3:8])=[O:10])[cH:20][cH:19]1)=[O:17]>O=C(O)C(F)(F)F>[CH3:1][CH2:2][O:3][c:4]1[cH:5][n:6]([CH:7]([CH3:8])[C:9](=[O:10])[NH:11][c:12]2[cH:13][cH:14][c:15]([C:16](=[O:17])[OH:18])[cH:19][cH:20]2)[c:21](=[O:22])[cH:23][c:24]1-[c:25]1[c:26]([C:27]#[N:28])[cH:29][cH:30][c:31]([Cl:32])[cH:33]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)[O:18][C:16]([c:15]1[cH:14][cH:13][c:12]([NH:11][C:9]([CH:7]([n:6]2[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:24](-[c:25]3[c:26]([C:27]#[N:28])[cH:29][cH:30][c:31]([Cl:32])[cH:33]3)[cH:23][c:21]2=[O:22])[CH3:8])=[O:10])[cH:20][cH:19]1)=[O:17]>O=C(O)C(F)(F)F>[CH3:1][CH2:2][O:3][c:4]1[cH:5][n:6]([CH:7]([CH3:8])[C:9](=[O:10])[NH:11][c:12]2[cH:13][cH:14][c:15]([C:16](=[O:17])[OH:18])[cH:19][cH:20]2)[c:21](=[O:22])[cH:23][c:24]1-[c:25]1[c:26]([C:27]#[N:28])[cH:29][cH:30][c:31]([Cl:32])[cH:33]1\"}",
"reactionStep": {
"id": "sa_0c81fbda99efa63705997979",
"reactionHash": "880191a0d36255d86ab0b7f2b947211f1cf180ab3ccf0107c76f2bd8ba442e70"
},
"children": [
{
"id": "13625",
"routeId": "sa_ac4ea4f5c5fb6133ebc9d965",
"moleculeId": "sa_709e307646431e48fe86dc33",
"parentId": "13624",
"isLeaf": false,
"molecule": {
"id": "sa_709e307646431e48fe86dc33",
"inchikey": "XIRZFSOMJJSWAE-UHFFFAOYSA-N",
"smiles": "CCOc1cn(C(C)C(=O)Nc2ccc(C(=O)OC(C)(C)C)cc2)c(=O)cc1-c1cc(Cl)ccc1C#N"
},
"smiles": "CCOc1cn(C(C)C(=O)Nc2ccc(C(=O)OC(C)(C)C)cc2)c(=O)cc1-c1cc(Cl)ccc1C#N",
"reactionStepId": "sa_498c750426f9fc9e532d5b64",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160052884A1;1594;1842913\",\"rsmi\":\"O[C:9]([CH:7]([n:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:28](-[c:29]2[c:30]([C:31]#[N:32])[cH:33][cH:34][c:35]([Cl:36])[cH:37]2)[cH:27][c:25]1=[O:26])[CH3:8])=[O:10].[NH2:11][c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][n:6]([CH:7]([CH3:8])[C:9](=[O:10])[NH:11][c:12]2[cH:13][cH:14][c:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]2)[c:25](=[O:26])[cH:27][c:28]1-[c:29]1[c:30]([C:31]#[N:32])[cH:33][cH:34][c:35]([Cl:36])[cH:37]1\"},\"mapped_reaction_smiles\":\"O[C:9]([CH:7]([n:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:28](-[c:29]2[c:30]([C:31]#[N:32])[cH:33][cH:34][c:35]([Cl:36])[cH:37]2)[cH:27][c:25]1=[O:26])[CH3:8])=[O:10].[NH2:11][c:12]1[cH:13][cH:14][c:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][n:6]([CH:7]([CH3:8])[C:9](=[O:10])[NH:11][c:12]2[cH:13][cH:14][c:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][cH:24]2)[c:25](=[O:26])[cH:27][c:28]1-[c:29]1[c:30]([C:31]#[N:32])[cH:33][cH:34][c:35]([Cl:36])[cH:37]1\"}",
"reactionStep": {
"id": "sa_498c750426f9fc9e532d5b64",
"reactionHash": "b2be2c5223bb07ca97409d8b70e574bdfbe877b71d7c745df40b7ed60c6330e3"
},
"children": [
{
"id": "13626",
"routeId": "sa_ac4ea4f5c5fb6133ebc9d965",
"moleculeId": "sa_601dc9b8552bb1f374acf07a",
"parentId": "13625",
"isLeaf": true,
"molecule": {
"id": "sa_601dc9b8552bb1f374acf07a",
"inchikey": "KYORUZMJUKHKFS-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)c1ccc(N)cc1"
},
"smiles": "CC(C)(C)OC(=O)c1ccc(N)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13627",
"routeId": "sa_ac4ea4f5c5fb6133ebc9d965",
"moleculeId": "sa_2f6e20d96d91c3a48ade01a0",
"parentId": "13625",
"isLeaf": false,
"molecule": {
"id": "sa_2f6e20d96d91c3a48ade01a0",
"inchikey": "WKDLCNWIGMJDOI-UHFFFAOYSA-N",
"smiles": "CCOc1cn(C(C)C(=O)O)c(=O)cc1-c1cc(Cl)ccc1C#N"
},
"smiles": "CCOc1cn(C(C)C(=O)O)c(=O)cc1-c1cc(Cl)ccc1C#N",
"reactionStepId": "sa_4d70770e00544118e13954ec",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160052884A1;1591;1842912\",\"rsmi\":\"Br[CH:7]([CH3:8])[C:9](=[O:10])[OH:11].[CH3:1][CH2:2][O:3][c:4]1[cH:5][nH:6][c:12](=[O:13])[cH:14][c:15]1-[c:16]1[c:17]([C:18]#[N:19])[cH:20][cH:21][c:22]([Cl:23])[cH:24]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][n:6]([CH:7]([CH3:8])[C:9](=[O:10])[OH:11])[c:12](=[O:13])[cH:14][c:15]1-[c:16]1[c:17]([C:18]#[N:19])[cH:20][cH:21][c:22]([Cl:23])[cH:24]1\"},\"mapped_reaction_smiles\":\"Br[CH:7]([CH3:8])[C:9](=[O:10])[OH:11].[CH3:1][CH2:2][O:3][c:4]1[cH:5][nH:6][c:12](=[O:13])[cH:14][c:15]1-[c:16]1[c:17]([C:18]#[N:19])[cH:20][cH:21][c:22]([Cl:23])[cH:24]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][n:6]([CH:7]([CH3:8])[C:9](=[O:10])[OH:11])[c:12](=[O:13])[cH:14][c:15]1-[c:16]1[c:17]([C:18]#[N:19])[cH:20][cH:21][c:22]([Cl:23])[cH:24]1\"}",
"reactionStep": {
"id": "sa_4d70770e00544118e13954ec",
"reactionHash": "2ad2cda1a7259c3572cf5c9c83655f01c085c0bc1e6d6ece7a8a951e53c9c9d8"
},
"children": [
{
"id": "13628",
"routeId": "sa_ac4ea4f5c5fb6133ebc9d965",
"moleculeId": "sa_5c73a94f0118acd71ce91213",
"parentId": "13627",
"isLeaf": true,
"molecule": {
"id": "sa_5c73a94f0118acd71ce91213",
"inchikey": "MONMFXREYOKQTI-UHFFFAOYSA-N",
"smiles": "CC(Br)C(=O)O"
},
"smiles": "CC(Br)C(=O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "13629",
"routeId": "sa_ac4ea4f5c5fb6133ebc9d965",
"moleculeId": "sa_719587980e137e3210171c3f",
"parentId": "13627",
"isLeaf": false,
"molecule": {
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"inchikey": "PXDRSMHRITYVPP-UHFFFAOYSA-N",
"smiles": "CCOc1c[nH]c(=O)cc1-c1cc(Cl)ccc1C#N"
},
"smiles": "CCOc1c[nH]c(=O)cc1-c1cc(Cl)ccc1C#N",
"reactionStepId": "sa_9c2581fba67f3040c9e19b7d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160052884A1;1588;1842911\",\"rsmi\":\"C[O:8][c:7]1[n:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[c:10](-[c:11]2[c:12]([C:13]#[N:14])[cH:15][cH:16][c:17]([Cl:18])[cH:19]2)[cH:9]1>Br.c1ccncc1>[CH3:1][CH2:2][O:3][c:4]1[cH:5][nH:6][c:7](=[O:8])[cH:9][c:10]1-[c:11]1[c:12]([C:13]#[N:14])[cH:15][cH:16][c:17]([Cl:18])[cH:19]1\"},\"mapped_reaction_smiles\":\"C[O:8][c:7]1[n:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[c:10](-[c:11]2[c:12]([C:13]#[N:14])[cH:15][cH:16][c:17]([Cl:18])[cH:19]2)[cH:9]1>Br.c1ccncc1>[CH3:1][CH2:2][O:3][c:4]1[cH:5][nH:6][c:7](=[O:8])[cH:9][c:10]1-[c:11]1[c:12]([C:13]#[N:14])[cH:15][cH:16][c:17]([Cl:18])[cH:19]1\"}",
"reactionStep": {
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"reactionHash": "20eead2638211d1001abee61d86ce2af5c472fe9a14281ed0c070552462ca252"
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"children": [
{
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"moleculeId": "sa_b74c2babc5fa3a2c015c432c",
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"molecule": {
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"smiles": "CCOc1cnc(OC)cc1-c1cc(Cl)ccc1C#N"
},
"smiles": "CCOc1cnc(OC)cc1-c1cc(Cl)ccc1C#N",
"reactionStepId": "sa_a8485298aea37be35f1510a3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160052884A1;1585;1842910\",\"rsmi\":\"I[c:11]1[c:4]([O:3][CH2:2][CH3:1])[cH:5][n:6][c:7]([O:8][CH3:9])[cH:10]1.OB(O)[c:12]1[c:13]([C:14]#[N:15])[cH:16][cH:17][c:18]([Cl:19])[cH:20]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][n:6][c:7]([O:8][CH3:9])[cH:10][c:11]1-[c:12]1[c:13]([C:14]#[N:15])[cH:16][cH:17][c:18]([Cl:19])[cH:20]1\"},\"mapped_reaction_smiles\":\"I[c:11]1[c:4]([O:3][CH2:2][CH3:1])[cH:5][n:6][c:7]([O:8][CH3:9])[cH:10]1.OB(O)[c:12]1[c:13]([C:14]#[N:15])[cH:16][cH:17][c:18]([Cl:19])[cH:20]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][n:6][c:7]([O:8][CH3:9])[cH:10][c:11]1-[c:12]1[c:13]([C:14]#[N:15])[cH:16][cH:17][c:18]([Cl:19])[cH:20]1\"}",
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"metadata": "{\"annotations\":{\"ID\":\"US20160052884A1;1582;1842909\",\"rsmi\":\"I[CH2:2][CH3:1].[OH:3][c:4]1[cH:5][n:6][c:7]([O:8][CH3:9])[cH:10][c:11]1[I:12]>CC(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][O:3][c:4]1[cH:5][n:6][c:7]([O:8][CH3:9])[cH:10][c:11]1[I:12]\"},\"mapped_reaction_smiles\":\"I[CH2:2][CH3:1].[OH:3][c:4]1[cH:5][n:6][c:7]([O:8][CH3:9])[cH:10][c:11]1[I:12]>CC(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][O:3][c:4]1[cH:5][n:6][c:7]([O:8][CH3:9])[cH:10][c:11]1[I:12]\"}",
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{
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{
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}
]
}
}