Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COCCn1c(-c2ccc(C(C)C)cc2)nc2c(-c3ccccc3)ccc(OC)c21
InChiKey
WMEGNZJQCNDVNQ-UHFFFAOYSA-N
Route Signature
74784e8f2b98133c854304001ff6ebeb22096ab54d275ecd399b9dd3bc91994d
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_b26da39b6d5712a3e90a3cd9",
"signature": "74784e8f2b98133c854304001ff6ebeb22096ab54d275ecd399b9dd3bc91994d",
"contentHash": "99f90889a480d1bf6b507f02c44d07ef85c3d8b1c6c83c0d21d1980ef6f4f02d",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_9ccd4c2ca897ef61475ebe4f",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00580",
"moleculeId": "sa_c36b2123f0cec54eb1de04a0",
"smiles": "COCCn1c(-c2ccc(C(C)C)cc2)nc2c(-c3ccccc3)ccc(OC)c21",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_c36b2123f0cec54eb1de04a0",
"inchikey": "WMEGNZJQCNDVNQ-UHFFFAOYSA-N",
"smiles": "COCCn1c(-c2ccc(C(C)C)cc2)nc2c(-c3ccccc3)ccc(OC)c21"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13519",
"routeId": "sa_b26da39b6d5712a3e90a3cd9",
"moleculeId": "sa_c36b2123f0cec54eb1de04a0",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_c36b2123f0cec54eb1de04a0",
"inchikey": "WMEGNZJQCNDVNQ-UHFFFAOYSA-N",
"smiles": "COCCn1c(-c2ccc(C(C)C)cc2)nc2c(-c3ccccc3)ccc(OC)c21"
},
"smiles": "COCCn1c(-c2ccc(C(C)C)cc2)nc2c(-c3ccccc3)ccc(OC)c21",
"reactionStepId": "sa_a51b874d98c3ab1d13598ace",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08030497B2;0292;1118024\",\"rsmi\":\"Br[c:24]1[c:17]2[n:16][c:6](-[c:7]3[cH:8][cH:9][c:10]([CH:11]([CH3:12])[CH3:13])[cH:14][cH:15]3)[n:5]([CH2:4][CH2:3][O:2][CH3:1])[c:18]2[c:19]([O:20][CH3:21])[cH:22][cH:23]1.OB(O)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>Cc1ccccc1.O.O=C(O)O.[Na+].[Na+].[Pd].c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][CH2:3][CH2:4][n:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([CH:11]([CH3:12])[CH3:13])[cH:14][cH:15]2)[n:16][c:17]2[c:18]1[c:19]([O:20][CH3:21])[cH:22][cH:23][c:24]2-[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"Br[c:24]1[c:17]2[n:16][c:6](-[c:7]3[cH:8][cH:9][c:10]([CH:11]([CH3:12])[CH3:13])[cH:14][cH:15]3)[n:5]([CH2:4][CH2:3][O:2][CH3:1])[c:18]2[c:19]([O:20][CH3:21])[cH:22][cH:23]1.OB(O)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>Cc1ccccc1.O.O=C(O)O.[Na+].[Na+].[Pd].c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][CH2:3][CH2:4][n:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([CH:11]([CH3:12])[CH3:13])[cH:14][cH:15]2)[n:16][c:17]2[c:18]1[c:19]([O:20][CH3:21])[cH:22][cH:23][c:24]2-[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1\"}",
"reactionStep": {
"id": "sa_a51b874d98c3ab1d13598ace",
"reactionHash": "7b7648d8338f13633b2b324eaf07b9457f985f2aaa5bb9a2865faab9034f3177"
},
"children": [
{
"id": "13520",
"routeId": "sa_b26da39b6d5712a3e90a3cd9",
"moleculeId": "sa_05364e99571ecb363666a42f",
"parentId": "13519",
"isLeaf": true,
"molecule": {
"id": "sa_05364e99571ecb363666a42f",
"inchikey": "HXITXNWTGFUOAU-UHFFFAOYSA-N",
"smiles": "OB(O)c1ccccc1"
},
"smiles": "OB(O)c1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13521",
"routeId": "sa_b26da39b6d5712a3e90a3cd9",
"moleculeId": "sa_d5f710cfb0211b4589ff6657",
"parentId": "13519",
"isLeaf": false,
"molecule": {
"id": "sa_d5f710cfb0211b4589ff6657",
"inchikey": "MUNWQWHRPBVEMS-UHFFFAOYSA-N",
"smiles": "COCCn1c(-c2ccc(C(C)C)cc2)nc2c(Br)ccc(OC)c21"
},
"smiles": "COCCn1c(-c2ccc(C(C)C)cc2)nc2c(Br)ccc(OC)c21",
"reactionStepId": "sa_6971dfc92d5d7f62ed2284dd",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08030497B2;0234;1118015\",\"rsmi\":\"Br[CH2:4][CH2:3][O:2][CH3:1].[nH:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([CH:11]([CH3:12])[CH3:13])[cH:14][cH:15]2)[n:16][c:17]2[c:18]1[c:19]([O:20][CH3:21])[cH:22][cH:23][c:24]2[Br:25]>CN(C)C=O.O.[HH].[Na+]>[CH3:1][O:2][CH2:3][CH2:4][n:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([CH:11]([CH3:12])[CH3:13])[cH:14][cH:15]2)[n:16][c:17]2[c:18]1[c:19]([O:20][CH3:21])[cH:22][cH:23][c:24]2[Br:25]\"},\"mapped_reaction_smiles\":\"Br[CH2:4][CH2:3][O:2][CH3:1].[nH:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([CH:11]([CH3:12])[CH3:13])[cH:14][cH:15]2)[n:16][c:17]2[c:18]1[c:19]([O:20][CH3:21])[cH:22][cH:23][c:24]2[Br:25]>CN(C)C=O.O.[HH].[Na+]>[CH3:1][O:2][CH2:3][CH2:4][n:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([CH:11]([CH3:12])[CH3:13])[cH:14][cH:15]2)[n:16][c:17]2[c:18]1[c:19]([O:20][CH3:21])[cH:22][cH:23][c:24]2[Br:25]\"}",
"reactionStep": {
"id": "sa_6971dfc92d5d7f62ed2284dd",
"reactionHash": "5c27f4c99eda944757505eb29b884b4c214856cbeb28032abcd07c0ac4d6e171"
},
"children": [
{
"id": "13522",
"routeId": "sa_b26da39b6d5712a3e90a3cd9",
"moleculeId": "sa_fed6d6d1430d2a29d4b1fcf0",
"parentId": "13521",
"isLeaf": false,
"molecule": {
"id": "sa_fed6d6d1430d2a29d4b1fcf0",
"inchikey": "WFKFLPVFEYSZSK-UHFFFAOYSA-N",
"smiles": "COc1ccc(Br)c2nc(-c3ccc(C(C)C)cc3)[nH]c12"
},
"smiles": "COc1ccc(Br)c2nc(-c3ccc(C(C)C)cc3)[nH]c12",
"reactionStepId": "sa_4a891b6dbc33b6640b1139f0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08030497B2;0239;1118016\",\"rsmi\":\"O=[C:11]([NH:10][c:9]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([Br:7])[c:8]1[NH2:21])[c:12]1[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]1>CC(=O)O.CCOC(C)=O>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[c:8]2[c:9]1[nH:10][c:11](-[c:12]1[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]1)[n:21]2\"},\"mapped_reaction_smiles\":\"O=[C:11]([NH:10][c:9]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([Br:7])[c:8]1[NH2:21])[c:12]1[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]1>CC(=O)O.CCOC(C)=O>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[c:8]2[c:9]1[nH:10][c:11](-[c:12]1[cH:13][cH:14][c:15]([CH:16]([CH3:17])[CH3:18])[cH:19][cH:20]1)[n:21]2\"}",
"reactionStep": {
"id": "sa_4a891b6dbc33b6640b1139f0",
"reactionHash": "472bd6cd81fe4c60acb8378f0b3fe3e355eafffcacfad76575d02c584529f07c"
},
"children": [
{
"id": "13523",
"routeId": "sa_b26da39b6d5712a3e90a3cd9",
"moleculeId": "sa_6b7f0c30cdf7e752d13dfe65",
"parentId": "13522",
"isLeaf": false,
"molecule": {
"id": "sa_6b7f0c30cdf7e752d13dfe65",
"inchikey": "DNIAPRIUEZFZCJ-UHFFFAOYSA-N",
"smiles": "COc1ccc(Br)c(N)c1NC(=O)c1ccc(C(C)C)cc1"
},
"smiles": "COc1ccc(Br)c(N)c1NC(=O)c1ccc(C(C)C)cc1",
"reactionStepId": "sa_63ebfb884ad53302a5968fe0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08030497B2;0241;1118017\",\"rsmi\":\"O[C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([CH:18]([CH3:19])[CH3:20])[cH:21][cH:22]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[c:8]([NH2:9])[c:10]1[NH2:11]>CN(C)c1ccncc1.ClCCCl.ClCCl>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[c:8]([NH2:9])[c:10]1[NH:11][C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([CH:18]([CH3:19])[CH3:20])[cH:21][cH:22]1\"},\"mapped_reaction_smiles\":\"O[C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([CH:18]([CH3:19])[CH3:20])[cH:21][cH:22]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[c:8]([NH2:9])[c:10]1[NH2:11]>CN(C)c1ccncc1.ClCCCl.ClCCl>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[c:8]([NH2:9])[c:10]1[NH:11][C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([CH:18]([CH3:19])[CH3:20])[cH:21][cH:22]1\"}",
"reactionStep": {
"id": "sa_63ebfb884ad53302a5968fe0",
"reactionHash": "1d8b6ac048d60fa666d657f763e4f6ca96f11b7a522d16379c78aecd1c0fd374"
},
"children": [
{
"id": "13524",
"routeId": "sa_b26da39b6d5712a3e90a3cd9",
"moleculeId": "sa_ac98809dbe3ca8df535ea3b4",
"parentId": "13523",
"isLeaf": true,
"molecule": {
"id": "sa_ac98809dbe3ca8df535ea3b4",
"inchikey": "CKMXAIVXVKGGFM-UHFFFAOYSA-N",
"smiles": "CC(C)c1ccc(C(=O)O)cc1"
},
"smiles": "CC(C)c1ccc(C(=O)O)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13525",
"routeId": "sa_b26da39b6d5712a3e90a3cd9",
"moleculeId": "sa_b9e997f7fbde25a93fa14104",
"parentId": "13523",
"isLeaf": false,
"molecule": {
"id": "sa_b9e997f7fbde25a93fa14104",
"inchikey": "HTNRRCCXOPNUDZ-UHFFFAOYSA-N",
"smiles": "COc1ccc(Br)c(N)c1N"
},
"smiles": "COc1ccc(Br)c(N)c1N",
"reactionStepId": "sa_11a32261b42922796bae57f3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08030497B2;0243;1118018\",\"rsmi\":\"O=[N+:5]([O-])[c:4]1[c:3]([O:2][CH3:1])[cH:11][cH:10][c:8]([Br:9])[c:6]1[N+:7](=O)[O-]>C1CCOC1.[Ni]>[CH3:1][O:2][c:3]1[c:4]([NH2:5])[c:6]([NH2:7])[c:8]([Br:9])[cH:10][cH:11]1\"},\"mapped_reaction_smiles\":\"O=[N+:5]([O-])[c:4]1[c:3]([O:2][CH3:1])[cH:11][cH:10][c:8]([Br:9])[c:6]1[N+:7](=O)[O-]>C1CCOC1.[Ni]>[CH3:1][O:2][c:3]1[c:4]([NH2:5])[c:6]([NH2:7])[c:8]([Br:9])[cH:10][cH:11]1\"}",
"reactionStep": {
"id": "sa_11a32261b42922796bae57f3",
"reactionHash": "e2276b4d7ac76080f38c575d12793ac00eb29022807271adf997b8589d6c7b58"
},
"children": [
{
"id": "13526",
"routeId": "sa_b26da39b6d5712a3e90a3cd9",
"moleculeId": "sa_c91f14e156177203699f9021",
"parentId": "13525",
"isLeaf": false,
"molecule": {
"id": "sa_c91f14e156177203699f9021",
"inchikey": "XFWBPNPOHJWYAY-UHFFFAOYSA-N",
"smiles": "COc1ccc(Br)c([N+](=O)[O-])c1[N+](=O)[O-]"
},
"smiles": "COc1ccc(Br)c([N+](=O)[O-])c1[N+](=O)[O-]",
"reactionStepId": "sa_870da64c4e095e61d615fc89",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08030497B2;0245;1118019\",\"rsmi\":\"O[N+:5](=[O:6])[O-:7].[CH3:1][O:2][c:3]1[cH:4][c:8]([N+:9](=[O:10])[O-:11])[c:12]([Br:13])[cH:14][cH:15]1>O=S(=O)(O)O>[CH3:1][O:2][c:3]1[c:4]([N+:5](=[O:6])[O-:7])[c:8]([N+:9](=[O:10])[O-:11])[c:12]([Br:13])[cH:14][cH:15]1\"},\"mapped_reaction_smiles\":\"O[N+:5](=[O:6])[O-:7].[CH3:1][O:2][c:3]1[cH:4][c:8]([N+:9](=[O:10])[O-:11])[c:12]([Br:13])[cH:14][cH:15]1>O=S(=O)(O)O>[CH3:1][O:2][c:3]1[c:4]([N+:5](=[O:6])[O-:7])[c:8]([N+:9](=[O:10])[O-:11])[c:12]([Br:13])[cH:14][cH:15]1\"}",
"reactionStep": {
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"reactionHash": "f16a314f553a2acd9ec3e741948b906cccc9198826fd77acd67f3a9af46d0ab6"
},
"children": [
{
"id": "13527",
"routeId": "sa_b26da39b6d5712a3e90a3cd9",
"moleculeId": "sa_edac0a7fd043198784a28dd9",
"parentId": "13526",
"isLeaf": true,
"molecule": {
"id": "sa_edac0a7fd043198784a28dd9",
"inchikey": "GRYLNZFGIOXLOG-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])O"
},
"smiles": "O=[N+]([O-])O",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "13528",
"routeId": "sa_b26da39b6d5712a3e90a3cd9",
"moleculeId": "sa_82bd2dcfa91ea4dd20774046",
"parentId": "13526",
"isLeaf": true,
"molecule": {
"id": "sa_82bd2dcfa91ea4dd20774046",
"inchikey": "KCOBIBRGPCFIGF-UHFFFAOYSA-N",
"smiles": "COc1ccc(Br)c([N+](=O)[O-])c1"
},
"smiles": "COc1ccc(Br)c([N+](=O)[O-])c1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
]
}
]
},
{
"id": "13529",
"routeId": "sa_b26da39b6d5712a3e90a3cd9",
"moleculeId": "sa_1d500dd023c3a4d81d60b398",
"parentId": "13521",
"isLeaf": true,
"molecule": {
"id": "sa_1d500dd023c3a4d81d60b398",
"inchikey": "YZUPZGFPHUVJKC-UHFFFAOYSA-N",
"smiles": "COCCBr"
},
"smiles": "COCCBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}