Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cc1ccc(C(Nc2c(Nc3cccc4[nH]c(=O)[nH]c34)c(=O)c2=O)C2(C)COC2)o1
InChiKey
HXOLNHWSFJEFLV-UHFFFAOYSA-N
Route Signature
f5545942aedfb2d58657da7c32d6a5f1d4e15a99f94e29fc85c5ebed1a9a09c5
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_f4b26ef21b168195adee9c31",
"signature": "f5545942aedfb2d58657da7c32d6a5f1d4e15a99f94e29fc85c5ebed1a9a09c5",
"contentHash": "f0c76c52d19b663c707178ec43b2ddc34a2af8908d106a9cbfcf5d46c8c5bc21",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_2a757a89dd69bac24da391e2",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-01692",
"moleculeId": "sa_bc0777e4f70de9a4a18a9d7d",
"smiles": "Cc1ccc(C(Nc2c(Nc3cccc4[nH]c(=O)[nH]c34)c(=O)c2=O)C2(C)COC2)o1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_bc0777e4f70de9a4a18a9d7d",
"inchikey": "HXOLNHWSFJEFLV-UHFFFAOYSA-N",
"smiles": "Cc1ccc(C(Nc2c(Nc3cccc4[nH]c(=O)[nH]c34)c(=O)c2=O)C2(C)COC2)o1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "1566",
"routeId": "sa_f4b26ef21b168195adee9c31",
"moleculeId": "sa_bc0777e4f70de9a4a18a9d7d",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_bc0777e4f70de9a4a18a9d7d",
"inchikey": "HXOLNHWSFJEFLV-UHFFFAOYSA-N",
"smiles": "Cc1ccc(C(Nc2c(Nc3cccc4[nH]c(=O)[nH]c34)c(=O)c2=O)C2(C)COC2)o1"
},
"smiles": "Cc1ccc(C(Nc2c(Nc3cccc4[nH]c(=O)[nH]c34)c(=O)c2=O)C2(C)COC2)o1",
"reactionStepId": "sa_f8951e9d7e3b1c0a86bb6a36",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140309208A1;0323;1597319\",\"rsmi\":\"CCO[c:8]1[c:9]([NH:10][c:11]2[cH:12][cH:13][cH:14][c:15]3[c:16]2[nH:17][c:18](=[O:19])[nH:20]3)[c:21](=[O:22])[c:23]1=[O:24].[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([NH2:7])[C:25]2([CH3:26])[CH2:27][O:28][CH2:29]2)[o:30]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([NH:7][c:8]2[c:9]([NH:10][c:11]3[cH:12][cH:13][cH:14][c:15]4[c:16]3[nH:17][c:18](=[O:19])[nH:20]4)[c:21](=[O:22])[c:23]2=[O:24])[C:25]2([CH3:26])[CH2:27][O:28][CH2:29]2)[o:30]1\"},\"mapped_reaction_smiles\":\"CCO[c:8]1[c:9]([NH:10][c:11]2[cH:12][cH:13][cH:14][c:15]3[c:16]2[nH:17][c:18](=[O:19])[nH:20]3)[c:21](=[O:22])[c:23]1=[O:24].[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([NH2:7])[C:25]2([CH3:26])[CH2:27][O:28][CH2:29]2)[o:30]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([NH:7][c:8]2[c:9]([NH:10][c:11]3[cH:12][cH:13][cH:14][c:15]4[c:16]3[nH:17][c:18](=[O:19])[nH:20]4)[c:21](=[O:22])[c:23]2=[O:24])[C:25]2([CH3:26])[CH2:27][O:28][CH2:29]2)[o:30]1\"}",
"reactionStep": {
"id": "sa_f8951e9d7e3b1c0a86bb6a36",
"reactionHash": "18f63c389edd6fe7e7c3667f259b511e0994b3fb475d5f0fffe81480cc5d4495"
},
"children": [
{
"id": "1567",
"routeId": "sa_f4b26ef21b168195adee9c31",
"moleculeId": "sa_7d580fcc7f81cba0a4671923",
"parentId": "1566",
"isLeaf": false,
"molecule": {
"id": "sa_7d580fcc7f81cba0a4671923",
"inchikey": "CTXQEZBZQIPFCQ-UHFFFAOYSA-N",
"smiles": "Cc1ccc(C(N)C2(C)COC2)o1"
},
"smiles": "Cc1ccc(C(N)C2(C)COC2)o1",
"reactionStepId": "sa_830c444c139959f47046a089",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140309208A1;0113;1597267\",\"rsmi\":\"[N-]=[N+]=[N:7][CH:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[o:13]1)[C:8]1([CH3:9])[CH2:10][O:11][CH2:12]1>CCO.[H][H].[Pd]>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([NH2:7])[C:8]2([CH3:9])[CH2:10][O:11][CH2:12]2)[o:13]1\"},\"mapped_reaction_smiles\":\"[N-]=[N+]=[N:7][CH:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[o:13]1)[C:8]1([CH3:9])[CH2:10][O:11][CH2:12]1>CCO.[H][H].[Pd]>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([NH2:7])[C:8]2([CH3:9])[CH2:10][O:11][CH2:12]2)[o:13]1\"}",
"reactionStep": {
"id": "sa_830c444c139959f47046a089",
"reactionHash": "06382b7eda3c265d7f2910bc4a67328ab315c80f3df2596b09d73c9149a78609"
},
"children": [
{
"id": "1568",
"routeId": "sa_f4b26ef21b168195adee9c31",
"moleculeId": "sa_141984040ca78ddce07bb3c3",
"parentId": "1567",
"isLeaf": false,
"molecule": {
"id": "sa_141984040ca78ddce07bb3c3",
"inchikey": "CABJPSKGLCGCMD-UHFFFAOYSA-N",
"smiles": "Cc1ccc(C(N=[N+]=[N-])C2(C)COC2)o1"
},
"smiles": "Cc1ccc(C(N=[N+]=[N-])C2(C)COC2)o1",
"reactionStepId": "sa_cdb36e2bf0ad16d81828b1a9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140309208A1;0112;1597266\",\"rsmi\":\"O=P(c1ccccc1)(c1ccccc1)[N:7]=[N+:8]=[N-:9].O[CH:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[o:15]1)[C:10]1([CH3:11])[CH2:12][O:13][CH2:14]1>C1CCC2=NCCCN2CC1.Cc1ccccc1>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([N:7]=[N+:8]=[N-:9])[C:10]2([CH3:11])[CH2:12][O:13][CH2:14]2)[o:15]1\"},\"mapped_reaction_smiles\":\"O=P(c1ccccc1)(c1ccccc1)[N:7]=[N+:8]=[N-:9].O[CH:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[o:15]1)[C:10]1([CH3:11])[CH2:12][O:13][CH2:14]1>C1CCC2=NCCCN2CC1.Cc1ccccc1>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([N:7]=[N+:8]=[N-:9])[C:10]2([CH3:11])[CH2:12][O:13][CH2:14]2)[o:15]1\"}",
"reactionStep": {
"id": "sa_cdb36e2bf0ad16d81828b1a9",
"reactionHash": "57603a09f0b6b64736a915175c6fc211fe7ea9701c1188aa2bee828924262845"
},
"children": [
{
"id": "1569",
"routeId": "sa_f4b26ef21b168195adee9c31",
"moleculeId": "sa_c5c2874bd69a6887f851d32f",
"parentId": "1568",
"isLeaf": false,
"molecule": {
"id": "sa_c5c2874bd69a6887f851d32f",
"inchikey": "KYSLWRXYVXHRRW-UHFFFAOYSA-N",
"smiles": "Cc1ccc(C(O)C2(C)COC2)o1"
},
"smiles": "Cc1ccc(C(O)C2(C)COC2)o1",
"reactionStepId": "sa_c9e2215c87eae489a4aed4d2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140309208A1;0111;1597265\",\"rsmi\":\"[CH3:1][c:2]1[cH:3][cH:4][cH:5][o:13]1.[CH:6](=[O:7])[C:8]1([CH3:9])[CH2:10][O:11][CH2:12]1>C1CCOC1.CCCCCC.Cl.[Li]CCCC.N>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([OH:7])[C:8]2([CH3:9])[CH2:10][O:11][CH2:12]2)[o:13]1\"},\"mapped_reaction_smiles\":\"[CH3:1][c:2]1[cH:3][cH:4][cH:5][o:13]1.[CH:6](=[O:7])[C:8]1([CH3:9])[CH2:10][O:11][CH2:12]1>C1CCOC1.CCCCCC.Cl.[Li]CCCC.N>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([OH:7])[C:8]2([CH3:9])[CH2:10][O:11][CH2:12]2)[o:13]1\"}",
"reactionStep": {
"id": "sa_c9e2215c87eae489a4aed4d2",
"reactionHash": "e733066bac0282fd34dc7fc3a147ec8d3999971eef36137ff9d0cad3289d56fd"
},
"children": [
{
"id": "1570",
"routeId": "sa_f4b26ef21b168195adee9c31",
"moleculeId": "sa_83cbf99e2ec3871dba6c9920",
"parentId": "1569",
"isLeaf": true,
"molecule": {
"id": "sa_83cbf99e2ec3871dba6c9920",
"inchikey": "DUQGFIKXKISULR-UHFFFAOYSA-N",
"smiles": "CC1(C=O)COC1"
},
"smiles": "CC1(C=O)COC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1571",
"routeId": "sa_f4b26ef21b168195adee9c31",
"moleculeId": "sa_983c3ba740fe1f8fc236f5b8",
"parentId": "1569",
"isLeaf": true,
"molecule": {
"id": "sa_983c3ba740fe1f8fc236f5b8",
"inchikey": "VQKFNUFAXTZWDK-UHFFFAOYSA-N",
"smiles": "Cc1ccco1"
},
"smiles": "Cc1ccco1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "1572",
"routeId": "sa_f4b26ef21b168195adee9c31",
"moleculeId": "sa_b2e7e70131d8726a166b6104",
"parentId": "1568",
"isLeaf": true,
"molecule": {
"id": "sa_b2e7e70131d8726a166b6104",
"inchikey": "MKRTXPORKIRPDG-UHFFFAOYSA-N",
"smiles": "[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1"
},
"smiles": "[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "1573",
"routeId": "sa_f4b26ef21b168195adee9c31",
"moleculeId": "sa_4602ee3240d7f308799be7ef",
"parentId": "1566",
"isLeaf": false,
"molecule": {
"id": "sa_4602ee3240d7f308799be7ef",
"inchikey": "YMXNEIFVIIXJIO-UHFFFAOYSA-N",
"smiles": "CCOc1c(Nc2cccc3[nH]c(=O)[nH]c23)c(=O)c1=O"
},
"smiles": "CCOc1c(Nc2cccc3[nH]c(=O)[nH]c23)c(=O)c1=O",
"reactionStepId": "sa_b4d840059756e1218ba3ed88",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140309208A1;0322;1597318\",\"rsmi\":\"CCO[c:5]1[c:4]([O:3][CH2:2][CH3:1])[c:19](=[O:20])[c:17]1=[O:18].[NH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[nH:13][c:14](=[O:15])[nH:16]2>CCO>[CH3:1][CH2:2][O:3][c:4]1[c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][c:11]3[c:12]2[nH:13][c:14](=[O:15])[nH:16]3)[c:17](=[O:18])[c:19]1=[O:20]\"},\"mapped_reaction_smiles\":\"CCO[c:5]1[c:4]([O:3][CH2:2][CH3:1])[c:19](=[O:20])[c:17]1=[O:18].[NH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[nH:13][c:14](=[O:15])[nH:16]2>CCO>[CH3:1][CH2:2][O:3][c:4]1[c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][c:11]3[c:12]2[nH:13][c:14](=[O:15])[nH:16]3)[c:17](=[O:18])[c:19]1=[O:20]\"}",
"reactionStep": {
"id": "sa_b4d840059756e1218ba3ed88",
"reactionHash": "c850a8317bdf8fd4bfd345d13ee6eb6ce345613b7bd1c7042bad153b6b1a7d21"
},
"children": [
{
"id": "1574",
"routeId": "sa_f4b26ef21b168195adee9c31",
"moleculeId": "sa_efecabbf8c53d24f0535234b",
"parentId": "1573",
"isLeaf": true,
"molecule": {
"id": "sa_efecabbf8c53d24f0535234b",
"inchikey": "BCUSTVNWMJXDSE-UHFFFAOYSA-N",
"smiles": "Nc1cccc2[nH]c(=O)[nH]c12"
},
"smiles": "Nc1cccc2[nH]c(=O)[nH]c12",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1575",
"routeId": "sa_f4b26ef21b168195adee9c31",
"moleculeId": "sa_6b9f1ee7bdbd3d75ae33747f",
"parentId": "1573",
"isLeaf": true,
"molecule": {
"id": "sa_6b9f1ee7bdbd3d75ae33747f",
"inchikey": "DFSFLZCLKYZYRD-UHFFFAOYSA-N",
"smiles": "CCOc1c(OCC)c(=O)c1=O"
},
"smiles": "CCOc1c(OCC)c(=O)c1=O",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
}