Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COCCOc1cccc(-c2c(C)n[nH]c2N)c1OC
InChiKey
INCROPYQYGOBPG-UHFFFAOYSA-N
Route Signature
c32c2f5c894621fc763abdab0ef7afaaf5f6d46195fdc417a2042655bd25fdbb
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_8eb0adfa6f5a00f115e48b10",
"signature": "c32c2f5c894621fc763abdab0ef7afaaf5f6d46195fdc417a2042655bd25fdbb",
"contentHash": "0d53284a4ef628135037c38c71e508e431572f3ae7c3d55ddc2663f2ccb59cd1",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_e7e940b2f2820249118aebdb",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00442",
"moleculeId": "sa_aba02086fc0490e28be3b3e4",
"smiles": "COCCOc1cccc(-c2c(C)n[nH]c2N)c1OC",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_aba02086fc0490e28be3b3e4",
"inchikey": "INCROPYQYGOBPG-UHFFFAOYSA-N",
"smiles": "COCCOc1cccc(-c2c(C)n[nH]c2N)c1OC"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "4288",
"routeId": "sa_8eb0adfa6f5a00f115e48b10",
"moleculeId": "sa_aba02086fc0490e28be3b3e4",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_aba02086fc0490e28be3b3e4",
"inchikey": "INCROPYQYGOBPG-UHFFFAOYSA-N",
"smiles": "COCCOc1cccc(-c2c(C)n[nH]c2N)c1OC"
},
"smiles": "COCCOc1cccc(-c2c(C)n[nH]c2N)c1OC",
"reactionStepId": "sa_861cdab50e15a7be9b2511ee",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07872014B2;0366;1044660\",\"rsmi\":\"O=[C:16]([CH:11]([c:10]1[cH:9][cH:8][cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[c:18]1[O:19][CH3:20])[C:12]#[N:13])[CH3:17].[NH2:14][NH2:15]>CCO.Cl.Cl.O=C(O)O.[Na+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10](-[c:11]2[c:12]([NH2:13])[nH:14][n:15][c:16]2[CH3:17])[c:18]1[O:19][CH3:20]\"},\"mapped_reaction_smiles\":\"O=[C:16]([CH:11]([c:10]1[cH:9][cH:8][cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[c:18]1[O:19][CH3:20])[C:12]#[N:13])[CH3:17].[NH2:14][NH2:15]>CCO.Cl.Cl.O=C(O)O.[Na+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10](-[c:11]2[c:12]([NH2:13])[nH:14][n:15][c:16]2[CH3:17])[c:18]1[O:19][CH3:20]\"}",
"reactionStep": {
"id": "sa_861cdab50e15a7be9b2511ee",
"reactionHash": "e82dc393eda81d15e2fdb1818ea8038fdb659c0aa8d9efc8baeeaa974facce46"
},
"children": [
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"routeId": "sa_8eb0adfa6f5a00f115e48b10",
"moleculeId": "sa_508aafed68ef7cbf9971bcd9",
"parentId": "4288",
"isLeaf": false,
"molecule": {
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"inchikey": "IJVHNURIIDFPGJ-UHFFFAOYSA-N",
"smiles": "COCCOc1cccc(C(C#N)C(C)=O)c1OC"
},
"smiles": "COCCOc1cccc(C(C#N)C(C)=O)c1OC",
"reactionStepId": "sa_0a1e1172ad351f565ace4205",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07872014B2;0365;1044659\",\"rsmi\":\"CCO[C:14]([CH3:15])=[O:16].[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]([CH2:11][C:12]#[N:13])[c:17]1[O:18][CH3:19]>C1CCOC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]([CH:11]([C:12]#[N:13])[C:14]([CH3:15])=[O:16])[c:17]1[O:18][CH3:19]\"},\"mapped_reaction_smiles\":\"CCO[C:14]([CH3:15])=[O:16].[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]([CH2:11][C:12]#[N:13])[c:17]1[O:18][CH3:19]>C1CCOC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]([CH:11]([C:12]#[N:13])[C:14]([CH3:15])=[O:16])[c:17]1[O:18][CH3:19]\"}",
"reactionStep": {
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"reactionHash": "d0506257a949570bfb588c3d25947e95b3b6780c2fb82b741b5f5a9ad75b2979"
},
"children": [
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"moleculeId": "sa_74318b5ade134733c71a860c",
"parentId": "4289",
"isLeaf": false,
"molecule": {
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"inchikey": "CTBAEBFWWXLTEJ-UHFFFAOYSA-N",
"smiles": "COCCOc1cccc(CC#N)c1OC"
},
"smiles": "COCCOc1cccc(CC#N)c1OC",
"reactionStepId": "sa_f5858c75f32ad87b5031ee9e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07872014B2;0364;1044658\",\"rsmi\":\"Cl[CH2:11][c:10]1[cH:9][cH:8][cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[c:14]1[O:15][CH3:16].[CH:12]#[N:13]>CCOC(C)=O.CN(C)C=O.[K+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]([CH2:11][C:12]#[N:13])[c:14]1[O:15][CH3:16]\"},\"mapped_reaction_smiles\":\"Cl[CH2:11][c:10]1[cH:9][cH:8][cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[c:14]1[O:15][CH3:16].[CH:12]#[N:13]>CCOC(C)=O.CN(C)C=O.[K+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]([CH2:11][C:12]#[N:13])[c:14]1[O:15][CH3:16]\"}",
"reactionStep": {
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"reactionHash": "ffdb306f37f367a5ea752a521194019bda198fb5bf65a6b1a3195c4874360655"
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"children": [
{
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"routeId": "sa_8eb0adfa6f5a00f115e48b10",
"moleculeId": "sa_5995aff3aeff665a1f3e984d",
"parentId": "4290",
"isLeaf": true,
"molecule": {
"id": "sa_5995aff3aeff665a1f3e984d",
"inchikey": "LELOWRISYMNNSU-UHFFFAOYSA-N",
"smiles": "C#N"
},
"smiles": "C#N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4292",
"routeId": "sa_8eb0adfa6f5a00f115e48b10",
"moleculeId": "sa_9f815a486a48c1b1080c1be5",
"parentId": "4290",
"isLeaf": false,
"molecule": {
"id": "sa_9f815a486a48c1b1080c1be5",
"inchikey": "YKCSTBXHUPWAMA-UHFFFAOYSA-N",
"smiles": "COCCOc1cccc(CCl)c1OC"
},
"smiles": "COCCOc1cccc(CCl)c1OC",
"reactionStepId": "sa_9da9a2418bdf0110130f4ead",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07872014B2;0363;1044657\",\"rsmi\":\"O=S(Cl)[Cl:12].O[CH2:11][c:10]1[cH:9][cH:8][cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[c:13]1[O:14][CH3:15]>C1CCOC1.O.c1ccncc1>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]([CH2:11][Cl:12])[c:13]1[O:14][CH3:15]\"},\"mapped_reaction_smiles\":\"O=S(Cl)[Cl:12].O[CH2:11][c:10]1[cH:9][cH:8][cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[c:13]1[O:14][CH3:15]>C1CCOC1.O.c1ccncc1>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]([CH2:11][Cl:12])[c:13]1[O:14][CH3:15]\"}",
"reactionStep": {
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"reactionHash": "14efac37376a3922e92ddec31b460df17fdc0954c1c96c1f569a6aab54340abc"
},
"children": [
{
"id": "4293",
"routeId": "sa_8eb0adfa6f5a00f115e48b10",
"moleculeId": "sa_cd67ce42f230ef1a4063353c",
"parentId": "4292",
"isLeaf": true,
"molecule": {
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"inchikey": "FYSNRJHAOHDILO-UHFFFAOYSA-N",
"smiles": "O=S(Cl)Cl"
},
"smiles": "O=S(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4294",
"routeId": "sa_8eb0adfa6f5a00f115e48b10",
"moleculeId": "sa_bd3ded81659159090cf870c4",
"parentId": "4292",
"isLeaf": false,
"molecule": {
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"inchikey": "YBTTVUQHBHKPIY-UHFFFAOYSA-N",
"smiles": "COCCOc1cccc(CO)c1OC"
},
"smiles": "COCCOc1cccc(CO)c1OC",
"reactionStepId": "sa_55eac7da5edb25a29c507d76",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07872014B2;0362;1044656\",\"rsmi\":\"CO[C:11]([c:10]1[cH:9][cH:8][cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[c:13]1[O:14][CH3:15])=[O:12]>C1CCOC1.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]([CH2:11][OH:12])[c:13]1[O:14][CH3:15]\"},\"mapped_reaction_smiles\":\"CO[C:11]([c:10]1[cH:9][cH:8][cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[c:13]1[O:14][CH3:15])=[O:12]>C1CCOC1.[Al+3].[HH].[HH].[HH].[HH].[Li+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]([CH2:11][OH:12])[c:13]1[O:14][CH3:15]\"}",
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"molecule": {
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"inchikey": "UPKQRQYMJQEJDV-UHFFFAOYSA-N",
"smiles": "COCCOc1cccc(C(=O)OC)c1OC"
},
"smiles": "COCCOc1cccc(C(=O)OC)c1OC",
"reactionStepId": "sa_ed8b654976b403b13e3d4075",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07872014B2;0361;1044655\",\"rsmi\":\"Br[CH2:4][CH2:3][O:2][CH3:1].[OH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH3:14])[c:15]1[O:16][CH3:17]>CC#N.CCOC(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH3:14])[c:15]1[O:16][CH3:17]\"},\"mapped_reaction_smiles\":\"Br[CH2:4][CH2:3][O:2][CH3:1].[OH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH3:14])[c:15]1[O:16][CH3:17]>CC#N.CCOC(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH3:14])[c:15]1[O:16][CH3:17]\"}",
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"children": [
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"routeId": "sa_8eb0adfa6f5a00f115e48b10",
"moleculeId": "sa_d4bc9f5bac09c0a598b0e6a4",
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"molecule": {
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"inchikey": "NKRCBDHKPQKBBU-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cccc(O)c1OC"
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"smiles": "COC(=O)c1cccc(O)c1OC",
"reactionStepId": null,
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{
"id": "4297",
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"molecule": {
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"inchikey": "YZUPZGFPHUVJKC-UHFFFAOYSA-N",
"smiles": "COCCBr"
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"smiles": "COCCBr",
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]
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}
]
}
]
},
{
"id": "4298",
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"molecule": {
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"inchikey": "XEKOWRVHYACXOJ-UHFFFAOYSA-N",
"smiles": "CCOC(C)=O"
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"smiles": "CCOC(C)=O",
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},
{
"id": "4299",
"routeId": "sa_8eb0adfa6f5a00f115e48b10",
"moleculeId": "sa_681b90bfe3789a310096845b",
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"molecule": {
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"inchikey": "OAKJQQAXSVQMHS-UHFFFAOYSA-N",
"smiles": "NN"
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"smiles": "NN",
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]
}
}