Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
N#Cc1ccc(N2CCN(C(=O)CCN3CCCC(Cc4ccc5c(c4)OCO5)C3)CC2)cc1F
InChiKey
MSUPVWFNSSKKPH-UHFFFAOYSA-N
Route Signature
12b65165762b7543a32566900402b3a43d524697a79a5303810d08e30d18bb57
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_e73ae01d64b39417eb075c75",
"signature": "12b65165762b7543a32566900402b3a43d524697a79a5303810d08e30d18bb57",
"contentHash": "38ca8aa0740daa02590c5fd4c53ac83ef3b4d376c237e935c0c9595f87358987",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_aa4b6e32b7834106f20175a1",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-02609",
"moleculeId": "sa_fac9db154f4dae3155c5b838",
"smiles": "N#Cc1ccc(N2CCN(C(=O)CCN3CCCC(Cc4ccc5c(c4)OCO5)C3)CC2)cc1F",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_fac9db154f4dae3155c5b838",
"inchikey": "MSUPVWFNSSKKPH-UHFFFAOYSA-N",
"smiles": "N#Cc1ccc(N2CCN(C(=O)CCN3CCCC(Cc4ccc5c(c4)OCO5)C3)CC2)cc1F"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 4
},
"rootNode": {
"id": "2019",
"routeId": "sa_e73ae01d64b39417eb075c75",
"moleculeId": "sa_fac9db154f4dae3155c5b838",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_fac9db154f4dae3155c5b838",
"inchikey": "MSUPVWFNSSKKPH-UHFFFAOYSA-N",
"smiles": "N#Cc1ccc(N2CCN(C(=O)CCN3CCCC(Cc4ccc5c(c4)OCO5)C3)CC2)cc1F"
},
"smiles": "N#Cc1ccc(N2CCN(C(=O)CCN3CCCC(Cc4ccc5c(c4)OCO5)C3)CC2)cc1F",
"reactionStepId": "sa_2f171740d9b0251af9e67665",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080255142A1;0103;618872\",\"rsmi\":\"[N:1]#[C:2][c:3]1[c:4]([F:5])[cH:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([C:12](=[O:13])[CH:14]=[CH2:15])[CH2:32][CH2:33]2)[cH:34][cH:35]1.[NH:16]1[CH2:17][CH2:18][CH2:19][CH:20]([CH2:21][c:22]2[cH:23][c:24]3[c:25]([cH:26][cH:27]2)[O:28][CH2:29][O:30]3)[CH2:31]1>C1CCOC1.CCN(CC)CC.ClCCl>[N:1]#[C:2][c:3]1[c:4]([F:5])[cH:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([C:12](=[O:13])[CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][CH2:19][CH:20]([CH2:21][c:22]4[cH:23][c:24]5[c:25]([cH:26][cH:27]4)[O:28][CH2:29][O:30]5)[CH2:31]3)[CH2:32][CH2:33]2)[cH:34][cH:35]1\"},\"mapped_reaction_smiles\":\"[N:1]#[C:2][c:3]1[c:4]([F:5])[cH:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([C:12](=[O:13])[CH:14]=[CH2:15])[CH2:32][CH2:33]2)[cH:34][cH:35]1.[NH:16]1[CH2:17][CH2:18][CH2:19][CH:20]([CH2:21][c:22]2[cH:23][c:24]3[c:25]([cH:26][cH:27]2)[O:28][CH2:29][O:30]3)[CH2:31]1>C1CCOC1.CCN(CC)CC.ClCCl>[N:1]#[C:2][c:3]1[c:4]([F:5])[cH:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([C:12](=[O:13])[CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][CH2:19][CH:20]([CH2:21][c:22]4[cH:23][c:24]5[c:25]([cH:26][cH:27]4)[O:28][CH2:29][O:30]5)[CH2:31]3)[CH2:32][CH2:33]2)[cH:34][cH:35]1\"}",
"reactionStep": {
"id": "sa_2f171740d9b0251af9e67665",
"reactionHash": "076f5774f56021d82397691c204074f36c4c3febda24994ef5c5678d953569b0"
},
"children": [
{
"id": "2020",
"routeId": "sa_e73ae01d64b39417eb075c75",
"moleculeId": "sa_e8dede44d6acb01621276c16",
"parentId": "2019",
"isLeaf": false,
"molecule": {
"id": "sa_e8dede44d6acb01621276c16",
"inchikey": "IQDQPHCDBCJQQO-UHFFFAOYSA-N",
"smiles": "C=CC(=O)N1CCN(c2ccc(C#N)c(F)c2)CC1"
},
"smiles": "C=CC(=O)N1CCN(c2ccc(C#N)c(F)c2)CC1",
"reactionStepId": "sa_8fc5145468f5554a43fa0680",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080255142A1;0110;618877\",\"rsmi\":\"Cl[C:3]([CH:2]=[CH2:1])=[O:4].[NH:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][c:11]([F:12])[c:13]([C:14]#[N:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1>CCN(CC)CC.ClCCl.O=C(O)O.[Na+].[Na+]>[CH2:1]=[CH:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][c:11]([F:12])[c:13]([C:14]#[N:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1\"},\"mapped_reaction_smiles\":\"Cl[C:3]([CH:2]=[CH2:1])=[O:4].[NH:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][c:11]([F:12])[c:13]([C:14]#[N:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1>CCN(CC)CC.ClCCl.O=C(O)O.[Na+].[Na+]>[CH2:1]=[CH:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][c:11]([F:12])[c:13]([C:14]#[N:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1\"}",
"reactionStep": {
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"reactionHash": "fff57c897ba6fc902a768a1e70c78dbc1f2aeeca6a538dd1408a98d3e2b9ea32"
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"children": [
{
"id": "2021",
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"moleculeId": "sa_7aff6ffb4c9c94ad85aeb0a1",
"parentId": "2020",
"isLeaf": false,
"molecule": {
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"inchikey": "GDWPXCGQYKBZHW-UHFFFAOYSA-N",
"smiles": "N#Cc1ccc(N2CCNCC2)cc1F"
},
"smiles": "N#Cc1ccc(N2CCNCC2)cc1F",
"reactionStepId": "sa_9cc7a573d7b9896d18187023",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080255142A1;0109;618876\",\"rsmi\":\"F[c:7]1[cH:6][c:4]([F:5])[c:3]([C:2]#[N:1])[cH:15][cH:14]1.[NH:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1>CC#N.CCOC(C)=O.O=C(O)O.[K+].[K+]>[N:1]#[C:2][c:3]1[c:4]([F:5])[cH:6][c:7]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[cH:14][cH:15]1\"},\"mapped_reaction_smiles\":\"F[c:7]1[cH:6][c:4]([F:5])[c:3]([C:2]#[N:1])[cH:15][cH:14]1.[NH:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1>CC#N.CCOC(C)=O.O=C(O)O.[K+].[K+]>[N:1]#[C:2][c:3]1[c:4]([F:5])[cH:6][c:7]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[cH:14][cH:15]1\"}",
"reactionStep": {
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"reactionHash": "d029577b05192a77b6ef6882b400b20be2d11f0e030b882b8be6080d42063cc0"
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"children": [
{
"id": "2022",
"routeId": "sa_e73ae01d64b39417eb075c75",
"moleculeId": "sa_330bd414c5d4211e41bcaa1a",
"parentId": "2021",
"isLeaf": true,
"molecule": {
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"inchikey": "GLUUGHFHXGJENI-UHFFFAOYSA-N",
"smiles": "C1CNCCN1"
},
"smiles": "C1CNCCN1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "2023",
"routeId": "sa_e73ae01d64b39417eb075c75",
"moleculeId": "sa_c815b89cc103d7d5c6f6c0fc",
"parentId": "2021",
"isLeaf": true,
"molecule": {
"id": "sa_c815b89cc103d7d5c6f6c0fc",
"inchikey": "LJFDXXUKKMEQKE-UHFFFAOYSA-N",
"smiles": "N#Cc1ccc(F)cc1F"
},
"smiles": "N#Cc1ccc(F)cc1F",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
},
{
"id": "2024",
"routeId": "sa_e73ae01d64b39417eb075c75",
"moleculeId": "sa_0b4e45c0d9e46a5808f6bc17",
"parentId": "2020",
"isLeaf": true,
"molecule": {
"id": "sa_0b4e45c0d9e46a5808f6bc17",
"inchikey": "HFBMWMNUJJDEQZ-UHFFFAOYSA-N",
"smiles": "C=CC(=O)Cl"
},
"smiles": "C=CC(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
},
{
"id": "2025",
"routeId": "sa_e73ae01d64b39417eb075c75",
"moleculeId": "sa_b9903c09a76f47f99d4e8bd4",
"parentId": "2019",
"isLeaf": false,
"molecule": {
"id": "sa_b9903c09a76f47f99d4e8bd4",
"inchikey": "JGIVRLDNRBEOHY-UHFFFAOYSA-N",
"smiles": "c1cc2c(cc1CC1CCCNC1)OCO2"
},
"smiles": "c1cc2c(cc1CC1CCCNC1)OCO2",
"reactionStepId": "sa_a14fc762648ba99124c0635c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080255142A1;0108;618875\",\"rsmi\":\"c1ccc(C[N:12]2[CH2:11][CH2:10][CH2:9][CH:8]([CH2:7][c:6]3[cH:1][cH:2][c:3]4[c:4]([cH:5]3)[O:14][CH2:15][O:16]4)[CH2:13]2)cc1>CO>[cH:1]1[cH:2][c:3]2[c:4]([cH:5][c:6]1[CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][NH:12][CH2:13]1)[O:14][CH2:15][O:16]2\"},\"mapped_reaction_smiles\":\"c1ccc(C[N:12]2[CH2:11][CH2:10][CH2:9][CH:8]([CH2:7][c:6]3[cH:1][cH:2][c:3]4[c:4]([cH:5]3)[O:14][CH2:15][O:16]4)[CH2:13]2)cc1>CO>[cH:1]1[cH:2][c:3]2[c:4]([cH:5][c:6]1[CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][NH:12][CH2:13]1)[O:14][CH2:15][O:16]2\"}",
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"molecule": {
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"smiles": "c1ccc(CN2CCCC(Cc3ccc4c(c3)OCO4)C2)cc1"
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"smiles": "c1ccc(CN2CCCC(Cc3ccc4c(c3)OCO4)C2)cc1",
"reactionStepId": "sa_4f24f8bde57ae37f995fcfa8",
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"metadata": "{\"annotations\":{\"ID\":\"US20080255142A1;0107;618874\",\"rsmi\":\"O=[C:21]1[N:6]([CH2:5][c:4]2[cH:3][cH:2][cH:1][cH:23][cH:22]2)[CH2:7][CH2:8][CH2:9][CH:10]1[CH2:11][c:12]1[cH:13][c:14]2[c:15]([cH:16][cH:17]1)[O:18][CH2:19][O:20]2>C1CCOC1.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][N:6]2[CH2:7][CH2:8][CH2:9][CH:10]([CH2:11][c:12]3[cH:13][c:14]4[c:15]([cH:16][cH:17]3)[O:18][CH2:19][O:20]4)[CH2:21]2)[cH:22][cH:23]1\"},\"mapped_reaction_smiles\":\"O=[C:21]1[N:6]([CH2:5][c:4]2[cH:3][cH:2][cH:1][cH:23][cH:22]2)[CH2:7][CH2:8][CH2:9][CH:10]1[CH2:11][c:12]1[cH:13][c:14]2[c:15]([cH:16][cH:17]1)[O:18][CH2:19][O:20]2>C1CCOC1.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][N:6]2[CH2:7][CH2:8][CH2:9][CH:10]([CH2:11][c:12]3[cH:13][c:14]4[c:15]([cH:16][cH:17]3)[O:18][CH2:19][O:20]4)[CH2:21]2)[cH:22][cH:23]1\"}",
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"molecule": {
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"smiles": "O=C1C(Cc2ccc3c(c2)OCO3)CCCN1Cc1ccccc1"
},
"smiles": "O=C1C(Cc2ccc3c(c2)OCO3)CCCN1Cc1ccccc1",
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"metadata": "{\"annotations\":{\"ID\":\"US20080255142A1;0106;618873\",\"rsmi\":\"Br[CH2:4][c:5]1[cH:6][c:7]2[c:8]([cH:9][cH:10]1)[O:11][CH2:12][O:13]2.[O:1]=[C:2]1[CH2:3][CH2:14][CH2:15][CH2:16][N:17]1[CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>C1CCCCC1.C1CCOC1.Cl.[Li]CCCC.N>[O:1]=[C:2]1[CH:3]([CH2:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10]2)[O:11][CH2:12][O:13]3)[CH2:14][CH2:15][CH2:16][N:17]1[CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"Br[CH2:4][c:5]1[cH:6][c:7]2[c:8]([cH:9][cH:10]1)[O:11][CH2:12][O:13]2.[O:1]=[C:2]1[CH2:3][CH2:14][CH2:15][CH2:16][N:17]1[CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>C1CCCCC1.C1CCOC1.Cl.[Li]CCCC.N>[O:1]=[C:2]1[CH:3]([CH2:4][c:5]2[cH:6][c:7]3[c:8]([cH:9][cH:10]2)[O:11][CH2:12][O:13]3)[CH2:14][CH2:15][CH2:16][N:17]1[CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1\"}",
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"smiles": "O=C1CCCCN1Cc1ccccc1"
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{
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"smiles": "BrCc1ccc2c(c1)OCO2",
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}
}