Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCCNc1nc(Nc2ccc(C#N)cc2)ncc1C#CCCCNC(=O)[C@H](C)NC
InChiKey
DGLMYFFRWCTQFI-KRWDZBQOSA-N
Route Signature
4ec45d1edfb172e96abe90cbcab6a34785fbccb620d7cb251fc9c76b6124aab8
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_fdc74c8a6d8855a9fb111cf6",
"signature": "4ec45d1edfb172e96abe90cbcab6a34785fbccb620d7cb251fc9c76b6124aab8",
"contentHash": "d64bd24a7aba4edb43d3af121c4c4ff10f638abd2a87b051134fba0523960715",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_0767865d466662d2fbbb6943",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-01402",
"moleculeId": "sa_7eae0a8eb5c74dd2a708cee7",
"smiles": "CCCNc1nc(Nc2ccc(C#N)cc2)ncc1C#CCCCNC(=O)[C@H](C)NC",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_7eae0a8eb5c74dd2a708cee7",
"inchikey": "DGLMYFFRWCTQFI-KRWDZBQOSA-N",
"smiles": "CCCNc1nc(Nc2ccc(C#N)cc2)ncc1C#CCCCNC(=O)[C@H](C)NC"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "5523",
"routeId": "sa_fdc74c8a6d8855a9fb111cf6",
"moleculeId": "sa_7eae0a8eb5c74dd2a708cee7",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_7eae0a8eb5c74dd2a708cee7",
"inchikey": "DGLMYFFRWCTQFI-KRWDZBQOSA-N",
"smiles": "CCCNc1nc(Nc2ccc(C#N)cc2)ncc1C#CCCCNC(=O)[C@H](C)NC"
},
"smiles": "CCCNc1nc(Nc2ccc(C#N)cc2)ncc1C#CCCCNC(=O)[C@H](C)NC",
"reactionStepId": "sa_fc76b6f50bee0b5a5293f6fb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160229812A1;0200;1917775\",\"rsmi\":\"CC(C)(C)OC(=O)[N:30]([C@H:28]([C:26]([NH:25][CH2:24][CH2:23][CH2:22][C:21]#[C:20][c:19]1[c:5]([NH:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18]1)=[O:27])[CH3:29])[CH3:31]>C1COCCO1.Cl>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18][c:19]1[C:20]#[C:21][CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:27])[C@H:28]([CH3:29])[NH:30][CH3:31]\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:30]([C@H:28]([C:26]([NH:25][CH2:24][CH2:23][CH2:22][C:21]#[C:20][c:19]1[c:5]([NH:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18]1)=[O:27])[CH3:29])[CH3:31]>C1COCCO1.Cl>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18][c:19]1[C:20]#[C:21][CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:27])[C@H:28]([CH3:29])[NH:30][CH3:31]\"}",
"reactionStep": {
"id": "sa_fc76b6f50bee0b5a5293f6fb",
"reactionHash": "059f62cc187a2b63b61b0306a50ae3a873fea2a04f2e6355f4f396e1ea519aa8"
},
"children": [
{
"id": "5524",
"routeId": "sa_fdc74c8a6d8855a9fb111cf6",
"moleculeId": "sa_ce84639af502358d0ae64fca",
"parentId": "5523",
"isLeaf": false,
"molecule": {
"id": "sa_ce84639af502358d0ae64fca",
"inchikey": "ZFTRTVXDTWGDKN-FQEVSTJZSA-N",
"smiles": "CCCNc1nc(Nc2ccc(C#N)cc2)ncc1C#CCCCNC(=O)[C@H](C)N(C)C(=O)OC(C)(C)C"
},
"smiles": "CCCNc1nc(Nc2ccc(C#N)cc2)ncc1C#CCCCNC(=O)[C@H](C)N(C)C(=O)OC(C)(C)C",
"reactionStepId": "sa_60a482d836fc65b9f5fda9a1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160229812A1;0196;1917774\",\"rsmi\":\"O[C:26](=[O:27])[C@H:28]([CH3:29])[N:30]([CH3:31])[C:32](=[O:33])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38].[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18][c:19]1[C:20]#[C:21][CH2:22][CH2:23][CH2:24][NH2:25]>CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CCOC(C)=O.CN(C)C=O.Cl.O.O=C(O)O.On1nnc2ccccc21.[Na+]>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18][c:19]1[C:20]#[C:21][CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:27])[C@H:28]([CH3:29])[N:30]([CH3:31])[C:32](=[O:33])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38]\"},\"mapped_reaction_smiles\":\"O[C:26](=[O:27])[C@H:28]([CH3:29])[N:30]([CH3:31])[C:32](=[O:33])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38].[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18][c:19]1[C:20]#[C:21][CH2:22][CH2:23][CH2:24][NH2:25]>CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CCOC(C)=O.CN(C)C=O.Cl.O.O=C(O)O.On1nnc2ccccc21.[Na+]>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18][c:19]1[C:20]#[C:21][CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:27])[C@H:28]([CH3:29])[N:30]([CH3:31])[C:32](=[O:33])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38]\"}",
"reactionStep": {
"id": "sa_60a482d836fc65b9f5fda9a1",
"reactionHash": "597aa464a09d43a93380a48068201a6ef1a139ccfb452ad2de74b035c2a273c8"
},
"children": [
{
"id": "5525",
"routeId": "sa_fdc74c8a6d8855a9fb111cf6",
"moleculeId": "sa_eaa5182a2ec38e310a9465a4",
"parentId": "5524",
"isLeaf": false,
"molecule": {
"id": "sa_eaa5182a2ec38e310a9465a4",
"inchikey": "DAVLPFVSYZLUBE-UHFFFAOYSA-N",
"smiles": "CCCNc1nc(Nc2ccc(C#N)cc2)ncc1C#CCCCN"
},
"smiles": "CCCNc1nc(Nc2ccc(C#N)cc2)ncc1C#CCCCN",
"reactionStepId": "sa_a56f40e007b50a0bad3af63e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160229812A1;0194;1917773\",\"rsmi\":\"O=C1c2ccccc2C(=O)[N:25]1[CH2:24][CH2:23][CH2:22][C:21]#[C:20][c:19]1[c:5]([NH:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18]1>C1CCOC1.CCO.Cl.NN.O>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18][c:19]1[C:20]#[C:21][CH2:22][CH2:23][CH2:24][NH2:25]\"},\"mapped_reaction_smiles\":\"O=C1c2ccccc2C(=O)[N:25]1[CH2:24][CH2:23][CH2:22][C:21]#[C:20][c:19]1[c:5]([NH:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18]1>C1CCOC1.CCO.Cl.NN.O>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18][c:19]1[C:20]#[C:21][CH2:22][CH2:23][CH2:24][NH2:25]\"}",
"reactionStep": {
"id": "sa_a56f40e007b50a0bad3af63e",
"reactionHash": "487baf8aa3a834136e1d38b64e409a6581bc82684d7f8d5724cb86f87083925e"
},
"children": [
{
"id": "5526",
"routeId": "sa_fdc74c8a6d8855a9fb111cf6",
"moleculeId": "sa_67586b4846c2b309ad8a8f67",
"parentId": "5525",
"isLeaf": false,
"molecule": {
"id": "sa_67586b4846c2b309ad8a8f67",
"inchikey": "QQNUCXMDQWGLSZ-UHFFFAOYSA-N",
"smiles": "CCCNc1nc(Nc2ccc(C#N)cc2)ncc1C#CCCCN1C(=O)c2ccccc2C1=O"
},
"smiles": "CCCNc1nc(Nc2ccc(C#N)cc2)ncc1C#CCCCN1C(=O)c2ccccc2C1=O",
"reactionStepId": "sa_7224211c6ded3cacb506117b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160229812A1;0192;1917772\",\"rsmi\":\"I[c:19]1[c:5]([NH:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18]1.[CH:20]#[C:21][CH2:22][CH2:23][CH2:24][N:25]1[C:26](=[O:27])[c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]2[C:34]1=[O:35]>CCN(CC)CC.CN(C)C=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.[Cu]I>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18][c:19]1[C:20]#[C:21][CH2:22][CH2:23][CH2:24][N:25]1[C:26](=[O:27])[c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]2[C:34]1=[O:35]\"},\"mapped_reaction_smiles\":\"I[c:19]1[c:5]([NH:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18]1.[CH:20]#[C:21][CH2:22][CH2:23][CH2:24][N:25]1[C:26](=[O:27])[c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]2[C:34]1=[O:35]>CCN(CC)CC.CN(C)C=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.[Cu]I>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18][c:19]1[C:20]#[C:21][CH2:22][CH2:23][CH2:24][N:25]1[C:26](=[O:27])[c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]2[C:34]1=[O:35]\"}",
"reactionStep": {
"id": "sa_7224211c6ded3cacb506117b",
"reactionHash": "f5638db066088f8aa7e884a9b4d6d209dc453951f6cb7215acaee6ec35b30785"
},
"children": [
{
"id": "5527",
"routeId": "sa_fdc74c8a6d8855a9fb111cf6",
"moleculeId": "sa_0c4ab06c21361f8762832f27",
"parentId": "5526",
"isLeaf": false,
"molecule": {
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"inchikey": "OGLSMCALEDMRET-UHFFFAOYSA-N",
"smiles": "CCCNc1nc(Nc2ccc(C#N)cc2)ncc1I"
},
"smiles": "CCCNc1nc(Nc2ccc(C#N)cc2)ncc1I",
"reactionStepId": "sa_80fc23b7cdfbbc9c78c9cd24",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160229812A1;0188;1917771\",\"rsmi\":\"Cl[c:7]1[n:6][c:5]([NH:4][CH2:3][CH2:2][CH3:1])[c:19]([I:20])[cH:18][n:17]1.[NH2:8][c:9]1[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]1>CC1(C)C2CC[C@@]1(CS(=O)(=O)O)C(=O)C2.CN1CCCC1=O.O=C(O)O.[Na+]>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18][c:19]1[I:20]\"},\"mapped_reaction_smiles\":\"Cl[c:7]1[n:6][c:5]([NH:4][CH2:3][CH2:2][CH3:1])[c:19]([I:20])[cH:18][n:17]1.[NH2:8][c:9]1[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]1>CC1(C)C2CC[C@@]1(CS(=O)(=O)O)C(=O)C2.CN1CCCC1=O.O=C(O)O.[Na+]>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][cH:16]2)[n:17][cH:18][c:19]1[I:20]\"}",
"reactionStep": {
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"reactionHash": "e34aabbe8d58a959c13efdbf2296dadc65e551bb2fa37b42ed70eb83c1a97586"
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"children": [
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"moleculeId": "sa_279f234d53f139eefab8131d",
"parentId": "5527",
"isLeaf": false,
"molecule": {
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"inchikey": "XRSARAODXOVBTQ-UHFFFAOYSA-N",
"smiles": "CCCNc1nc(Cl)ncc1I"
},
"smiles": "CCCNc1nc(Cl)ncc1I",
"reactionStepId": "sa_661eeb679957e61c88959fd2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160229812A1;0186;1917770\",\"rsmi\":\"Cl[c:5]1[n:6][c:7]([Cl:8])[n:9][cH:10][c:11]1[I:12].[CH3:1][CH2:2][CH2:3][NH2:4]>C1CCOC1.CCN(C(C)C)C(C)C.CCOC(C)=O.O>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([Cl:8])[n:9][cH:10][c:11]1[I:12]\"},\"mapped_reaction_smiles\":\"Cl[c:5]1[n:6][c:7]([Cl:8])[n:9][cH:10][c:11]1[I:12].[CH3:1][CH2:2][CH2:3][NH2:4]>C1CCOC1.CCN(C(C)C)C(C)C.CCOC(C)=O.O>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[n:6][c:7]([Cl:8])[n:9][cH:10][c:11]1[I:12]\"}",
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"children": [
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"molecule": {
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"smiles": "Clc1ncc(I)c(Cl)n1"
},
"smiles": "Clc1ncc(I)c(Cl)n1",
"reactionStepId": null,
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{
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"inchikey": "WGYKZJWCGVVSQN-UHFFFAOYSA-N",
"smiles": "CCCN"
},
"smiles": "CCCN",
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}
]
},
{
"id": "5531",
"routeId": "sa_fdc74c8a6d8855a9fb111cf6",
"moleculeId": "sa_c3882a108ddf2796416c408b",
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"molecule": {
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"inchikey": "YBAZINRZQSAIAY-UHFFFAOYSA-N",
"smiles": "N#Cc1ccc(N)cc1"
},
"smiles": "N#Cc1ccc(N)cc1",
"reactionStepId": null,
"template": null,
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}
]
},
{
"id": "5532",
"routeId": "sa_fdc74c8a6d8855a9fb111cf6",
"moleculeId": "sa_ee0cc7f5ee97af0549974a6b",
"parentId": "5526",
"isLeaf": true,
"molecule": {
"id": "sa_ee0cc7f5ee97af0549974a6b",
"inchikey": "YNZIPXLLPFYDGM-UHFFFAOYSA-N",
"smiles": "C#CCCCN1C(=O)c2ccccc2C1=O"
},
"smiles": "C#CCCCN1C(=O)c2ccccc2C1=O",
"reactionStepId": null,
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}
]
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]
},
{
"id": "5533",
"routeId": "sa_fdc74c8a6d8855a9fb111cf6",
"moleculeId": "sa_ccc6f054ecf44216796be8ea",
"parentId": "5524",
"isLeaf": true,
"molecule": {
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"inchikey": "VLHQXRIIQSTJCQ-LURJTMIESA-N",
"smiles": "C[C@@H](C(=O)O)N(C)C(=O)OC(C)(C)C"
},
"smiles": "C[C@@H](C(=O)O)N(C)C(=O)OC(C)(C)C",
"reactionStepId": null,
"template": null,
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}
]
}
]
}
}