Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)N(CCO)C(=O)c1nc2c(s1)CCOc1ccc(-c3cnn(CC(C)(C)O)c3)cc1-2
InChiKey
LPCPOYDDYNIHBV-UHFFFAOYSA-N
Route Signature
3a84a1980fd9b693d8b93708d852d66c495c853e6b503fe4fd17cd8ee961ba84
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_7a5a25cf52eea5d1b464c6af",
"signature": "3a84a1980fd9b693d8b93708d852d66c495c853e6b503fe4fd17cd8ee961ba84",
"contentHash": "eaf6a9f300ede80b96e04a332ed541fc9beb4bb026db3a5c2d2a43beda3b7154",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_6ee85761b65a4c3d48e738a1",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00549",
"moleculeId": "sa_9627a35f0d90df0538952648",
"smiles": "CC(C)N(CCO)C(=O)c1nc2c(s1)CCOc1ccc(-c3cnn(CC(C)(C)O)c3)cc1-2",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_9627a35f0d90df0538952648",
"inchikey": "LPCPOYDDYNIHBV-UHFFFAOYSA-N",
"smiles": "CC(C)N(CCO)C(=O)c1nc2c(s1)CCOc1ccc(-c3cnn(CC(C)(C)O)c3)cc1-2"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "904",
"routeId": "sa_7a5a25cf52eea5d1b464c6af",
"moleculeId": "sa_9627a35f0d90df0538952648",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_9627a35f0d90df0538952648",
"inchikey": "LPCPOYDDYNIHBV-UHFFFAOYSA-N",
"smiles": "CC(C)N(CCO)C(=O)c1nc2c(s1)CCOc1ccc(-c3cnn(CC(C)(C)O)c3)cc1-2"
},
"smiles": "CC(C)N(CCO)C(=O)c1nc2c(s1)CCOc1ccc(-c3cnn(CC(C)(C)O)c3)cc1-2",
"reactionStepId": "sa_be603afb4b7550cc0fe82ec3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09175009B2;0762;1687896\",\"rsmi\":\"Br[c:20]1[cH:19][c:18]2[c:17]([cH:32][cH:31]1)[O:16][CH2:15][CH2:14][c:13]1[c:12]-2[n:11][c:10]([C:8]([N:4]([CH:2]([CH3:1])[CH3:3])[CH2:5][CH2:6][OH:7])=[O:9])[s:33]1.CC1(C)OB([c:21]2[cH:22][n:23]([CH2:24][C:25]([CH3:26])([CH3:27])[OH:28])[n:29][cH:30]2)OC1(C)C>>[CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][CH2:6][OH:7])[C:8](=[O:9])[c:10]1[n:11][c:12]2[c:13]([s:33]1)[CH2:14][CH2:15][O:16][c:17]1[c:18]-2[cH:19][c:20](-[c:21]2[cH:22][n:23]([CH2:24][C:25]([CH3:26])([CH3:27])[OH:28])[n:29][cH:30]2)[cH:31][cH:32]1\"},\"mapped_reaction_smiles\":\"Br[c:20]1[cH:19][c:18]2[c:17]([cH:32][cH:31]1)[O:16][CH2:15][CH2:14][c:13]1[c:12]-2[n:11][c:10]([C:8]([N:4]([CH:2]([CH3:1])[CH3:3])[CH2:5][CH2:6][OH:7])=[O:9])[s:33]1.CC1(C)OB([c:21]2[cH:22][n:23]([CH2:24][C:25]([CH3:26])([CH3:27])[OH:28])[n:29][cH:30]2)OC1(C)C>>[CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][CH2:6][OH:7])[C:8](=[O:9])[c:10]1[n:11][c:12]2[c:13]([s:33]1)[CH2:14][CH2:15][O:16][c:17]1[c:18]-2[cH:19][c:20](-[c:21]2[cH:22][n:23]([CH2:24][C:25]([CH3:26])([CH3:27])[OH:28])[n:29][cH:30]2)[cH:31][cH:32]1\"}",
"reactionStep": {
"id": "sa_be603afb4b7550cc0fe82ec3",
"reactionHash": "6f14bf4deb234603a373786a8d609bfc279854fcc69095fbfad9358617476e6e"
},
"children": [
{
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"routeId": "sa_7a5a25cf52eea5d1b464c6af",
"moleculeId": "sa_de1c77efec3e8fa7e146717f",
"parentId": "904",
"isLeaf": false,
"molecule": {
"id": "sa_de1c77efec3e8fa7e146717f",
"inchikey": "GCHUQHKHUFMWDH-UHFFFAOYSA-N",
"smiles": "CC(C)(O)Cn1cc(B2OC(C)(C)C(C)(C)O2)cn1"
},
"smiles": "CC(C)(O)Cn1cc(B2OC(C)(C)C(C)(C)O2)cn1",
"reactionStepId": "sa_c11e9618b37deb6f82420db3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09175009B2;0447;1687660\",\"rsmi\":\"[CH3:1][C:2]1([CH3:3])[O:4][CH2:5]1.[nH: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)[cH:18][n:19]1>O=C(O)O.[Cs+].[Cs+]>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][n: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)[cH:18][n:19]1\"},\"mapped_reaction_smiles\":\"[CH3:1][C:2]1([CH3:3])[O:4][CH2:5]1.[nH: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)[cH:18][n:19]1>O=C(O)O.[Cs+].[Cs+]>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][n: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)[cH:18][n:19]1\"}",
"reactionStep": {
"id": "sa_c11e9618b37deb6f82420db3",
"reactionHash": "26d7613b40fe6bbee19bafd91cb756027e5c92bb9663674e58eadb539e7048d8"
},
"children": [
{
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"moleculeId": "sa_88d0e64f760329d74142aa1b",
"parentId": "905",
"isLeaf": true,
"molecule": {
"id": "sa_88d0e64f760329d74142aa1b",
"inchikey": "GELKGHVAFRCJNA-UHFFFAOYSA-N",
"smiles": "CC1(C)CO1"
},
"smiles": "CC1(C)CO1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "907",
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"moleculeId": "sa_228b9e0da2a721dc2ba56581",
"parentId": "905",
"isLeaf": true,
"molecule": {
"id": "sa_228b9e0da2a721dc2ba56581",
"inchikey": "TVOJIBGZFYMWDT-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2cn[nH]c2)OC1(C)C"
},
"smiles": "CC1(C)OB(c2cn[nH]c2)OC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
},
{
"id": "908",
"routeId": "sa_7a5a25cf52eea5d1b464c6af",
"moleculeId": "sa_29fe0f1c1863a8a7e55c677b",
"parentId": "904",
"isLeaf": false,
"molecule": {
"id": "sa_29fe0f1c1863a8a7e55c677b",
"inchikey": "KBOXSDURYOVNNQ-UHFFFAOYSA-N",
"smiles": "CC(C)N(CCO)C(=O)c1nc2c(s1)CCOc1ccc(Br)cc1-2"
},
"smiles": "CC(C)N(CCO)C(=O)c1nc2c(s1)CCOc1ccc(Br)cc1-2",
"reactionStepId": "sa_1897dfadffa89f37fea37aaf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09175009B2;0335;1687620\",\"rsmi\":\"O[C:8](=[O:9])[c:10]1[n:11][c:12]2[c:13]([s:24]1)[CH2:14][CH2:15][O:16][c:17]1[c:18]-2[cH:19][c:20]([Br:21])[cH:22][cH:23]1.[CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6][OH:7]>CCN(C(C)C)C(C)C.CN(C)C=O>[CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][CH2:6][OH:7])[C:8](=[O:9])[c:10]1[n:11][c:12]2[c:13]([s:24]1)[CH2:14][CH2:15][O:16][c:17]1[c:18]-2[cH:19][c:20]([Br:21])[cH:22][cH:23]1\"},\"mapped_reaction_smiles\":\"O[C:8](=[O:9])[c:10]1[n:11][c:12]2[c:13]([s:24]1)[CH2:14][CH2:15][O:16][c:17]1[c:18]-2[cH:19][c:20]([Br:21])[cH:22][cH:23]1.[CH3:1][CH:2]([CH3:3])[NH:4][CH2:5][CH2:6][OH:7]>CCN(C(C)C)C(C)C.CN(C)C=O>[CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][CH2:6][OH:7])[C:8](=[O:9])[c:10]1[n:11][c:12]2[c:13]([s:24]1)[CH2:14][CH2:15][O:16][c:17]1[c:18]-2[cH:19][c:20]([Br:21])[cH:22][cH:23]1\"}",
"reactionStep": {
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"children": [
{
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"routeId": "sa_7a5a25cf52eea5d1b464c6af",
"moleculeId": "sa_b0d0382755d1beb929ddbf88",
"parentId": "908",
"isLeaf": true,
"molecule": {
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"inchikey": "RILLZYSZSDGYGV-UHFFFAOYSA-N",
"smiles": "CC(C)NCCO"
},
"smiles": "CC(C)NCCO",
"reactionStepId": null,
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},
{
"id": "910",
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"inchikey": "ZVQXFCOOXKLDIH-UHFFFAOYSA-N",
"smiles": "O=C(O)c1nc2c(s1)CCOc1ccc(Br)cc1-2"
},
"smiles": "O=C(O)c1nc2c(s1)CCOc1ccc(Br)cc1-2",
"reactionStepId": "sa_579c09f1f36f5c0fc896edf0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09175009B2;0333;1687619\",\"rsmi\":\"CC[O:3][C:2](=[O:1])[c:4]1[n:5][c:6]2[c:7]([s:18]1)[CH2:8][CH2:9][O:10][c:11]1[c:12]-2[cH:13][c:14]([Br:15])[cH:16][cH:17]1>C1CCOC1.O.[Li+].O>[O:1]=[C:2]([OH:3])[c:4]1[n:5][c:6]2[c:7]([s:18]1)[CH2:8][CH2:9][O:10][c:11]1[c:12]-2[cH:13][c:14]([Br:15])[cH:16][cH:17]1\"},\"mapped_reaction_smiles\":\"CC[O:3][C:2](=[O:1])[c:4]1[n:5][c:6]2[c:7]([s:18]1)[CH2:8][CH2:9][O:10][c:11]1[c:12]-2[cH:13][c:14]([Br:15])[cH:16][cH:17]1>C1CCOC1.O.[Li+].O>[O:1]=[C:2]([OH:3])[c:4]1[n:5][c:6]2[c:7]([s:18]1)[CH2:8][CH2:9][O:10][c:11]1[c:12]-2[cH:13][c:14]([Br:15])[cH:16][cH:17]1\"}",
"reactionStep": {
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"molecule": {
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"smiles": "CCOC(=O)c1nc2c(s1)CCOc1ccc(Br)cc1-2"
},
"smiles": "CCOC(=O)c1nc2c(s1)CCOc1ccc(Br)cc1-2",
"reactionStepId": "sa_0261d12ff92236b4ba11c0ca",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09175009B2;0332;1687618\",\"rsmi\":\"O=[C:8]1[CH:9](Br)[CH2:10][CH2:11][O:12][c:13]2[c:14]1[cH:15][c:16]([Br:17])[cH:18][cH:19]2.[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([NH2:7])=[S:20]>CCO>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]2[c:9]([s:20]1)[CH2:10][CH2:11][O:12][c:13]1[c:14]-2[cH:15][c:16]([Br:17])[cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"O=[C:8]1[CH:9](Br)[CH2:10][CH2:11][O:12][c:13]2[c:14]1[cH:15][c:16]([Br:17])[cH:18][cH:19]2.[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([NH2:7])=[S:20]>CCO>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]2[c:9]([s:20]1)[CH2:10][CH2:11][O:12][c:13]1[c:14]-2[cH:15][c:16]([Br:17])[cH:18][cH:19]1\"}",
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"smiles": "O=C1c2cc(Br)ccc2OCCC1Br",
"reactionStepId": "sa_7bdea88d85225677aa94317a",
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"metadata": "{\"annotations\":{\"ID\":\"US09175009B2;0330;1687617\",\"rsmi\":\"Br[Br:14].[O:1]=[C:2]1[c:3]2[c:4]([cH:5][cH:6][c:7]([Br:8])[cH:9]2)[O:10][CH2:11][CH2:12][CH2:13]1>CCOCC>[O:1]=[C:2]1[c:3]2[c:4]([cH:5][cH:6][c:7]([Br:8])[cH:9]2)[O:10][CH2:11][CH2:12][CH:13]1[Br:14]\"},\"mapped_reaction_smiles\":\"Br[Br:14].[O:1]=[C:2]1[c:3]2[c:4]([cH:5][cH:6][c:7]([Br:8])[cH:9]2)[O:10][CH2:11][CH2:12][CH2:13]1>CCOCC>[O:1]=[C:2]1[c:3]2[c:4]([cH:5][cH:6][c:7]([Br:8])[cH:9]2)[O:10][CH2:11][CH2:12][CH:13]1[Br:14]\"}",
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{
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{
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]
}
}