Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C(=O)O)c1ccc2nc(N)oc2c1
InChiKey
MAVBBKBAVYQRQA-UHFFFAOYSA-N
Route Signature
f99ddb0f4c308348eaf5a30497f73f24e1043acdb91531069ead1900227ceba2
Synthesis route with 8 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_302ac1511b9517d03d7769bb",
"signature": "f99ddb0f4c308348eaf5a30497f73f24e1043acdb91531069ead1900227ceba2",
"contentHash": "f3e444af62aa9935dda6fecc4d260a1c7b59d661f5aebd241f5e11c0d482b033",
"length": 8,
"isConvergent": false
},
"target": {
"id": "sa_317fc1918156edacb1e78bf0",
"benchmarkSetId": "a82783729b577c36f2e09a2b6fdd55ae9542aed5546571d67ef9cb74dc21f70a",
"targetId": "n5-00051",
"moleculeId": "sa_fd02c972e6a055293ea917fd",
"smiles": "CC(C(=O)O)c1ccc2nc(N)oc2c1",
"routeLength": 8,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_fd02c972e6a055293ea917fd",
"inchikey": "MAVBBKBAVYQRQA-UHFFFAOYSA-N",
"smiles": "CC(C(=O)O)c1ccc2nc(N)oc2c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "17490",
"routeId": "sa_302ac1511b9517d03d7769bb",
"moleculeId": "sa_fd02c972e6a055293ea917fd",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_fd02c972e6a055293ea917fd",
"inchikey": "MAVBBKBAVYQRQA-UHFFFAOYSA-N",
"smiles": "CC(C(=O)O)c1ccc2nc(N)oc2c1"
},
"smiles": "CC(C(=O)O)c1ccc2nc(N)oc2c1",
"reactionStepId": "sa_4c1f77a1674ea5975fc8e58d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08785474B2;0856;1487192\",\"rsmi\":\"Br[C:13]#[N:14].[CH3:1][CH:2]([C:3](=[O:4])[OH:5])[c:6]1[cH:7][c:8]([OH:15])[c:9]([NH2:12])[cH:10][cH:11]1>O.[Na+].O>[CH3:1][CH:2]([C:3](=[O:4])[OH:5])[c:6]1[cH:7][c:8]2[c:9]([cH:10][cH:11]1)[n:12][c:13]([NH2:14])[o:15]2\"},\"mapped_reaction_smiles\":\"Br[C:13]#[N:14].[CH3:1][CH:2]([C:3](=[O:4])[OH:5])[c:6]1[cH:7][c:8]([OH:15])[c:9]([NH2:12])[cH:10][cH:11]1>O.[Na+].O>[CH3:1][CH:2]([C:3](=[O:4])[OH:5])[c:6]1[cH:7][c:8]2[c:9]([cH:10][cH:11]1)[n:12][c:13]([NH2:14])[o:15]2\"}",
"reactionStep": {
"id": "sa_4c1f77a1674ea5975fc8e58d",
"reactionHash": "d0ca6b5fec5aed4849da8747ba82331b222d65432419ac26fa62267f1b93d767"
},
"children": [
{
"id": "17491",
"routeId": "sa_302ac1511b9517d03d7769bb",
"moleculeId": "sa_30011d6f02d7317821269823",
"parentId": "17490",
"isLeaf": true,
"molecule": {
"id": "sa_30011d6f02d7317821269823",
"inchikey": "ATDGTVJJHBUTRL-UHFFFAOYSA-N",
"smiles": "N#CBr"
},
"smiles": "N#CBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "17492",
"routeId": "sa_302ac1511b9517d03d7769bb",
"moleculeId": "sa_c34faefb46a13f7b14575590",
"parentId": "17490",
"isLeaf": false,
"molecule": {
"id": "sa_c34faefb46a13f7b14575590",
"inchikey": "ZVBINIQZKBXOHX-UHFFFAOYSA-N",
"smiles": "CC(C(=O)O)c1ccc(N)c(O)c1"
},
"smiles": "CC(C(=O)O)c1ccc(N)c(O)c1",
"reactionStepId": "sa_e3a4070c4b63aad0e49f0cea",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08785474B2;0854;1487191\",\"rsmi\":\"O=[N+:11]([O-])[c:10]1[c:8]([OH:9])[cH:7][c:6]([CH:2]([CH3:1])[C:3](=[O:4])[OH:5])[cH:13][cH:12]1>C1CCOC1.CCO.[Pd]>[CH3:1][CH:2]([C:3](=[O:4])[OH:5])[c:6]1[cH:7][c:8]([OH:9])[c:10]([NH2:11])[cH:12][cH:13]1\"},\"mapped_reaction_smiles\":\"O=[N+:11]([O-])[c:10]1[c:8]([OH:9])[cH:7][c:6]([CH:2]([CH3:1])[C:3](=[O:4])[OH:5])[cH:13][cH:12]1>C1CCOC1.CCO.[Pd]>[CH3:1][CH:2]([C:3](=[O:4])[OH:5])[c:6]1[cH:7][c:8]([OH:9])[c:10]([NH2:11])[cH:12][cH:13]1\"}",
"reactionStep": {
"id": "sa_e3a4070c4b63aad0e49f0cea",
"reactionHash": "07a77538b2002e1c071e44b6c76f2477e5373e93738768097e303ba18ba1381c"
},
"children": [
{
"id": "17493",
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"moleculeId": "sa_38ad8686ad29648a4ef0b89f",
"parentId": "17492",
"isLeaf": false,
"molecule": {
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"inchikey": "GXAUQRYAXGQTDO-UHFFFAOYSA-N",
"smiles": "CC(C(=O)O)c1ccc([N+](=O)[O-])c(O)c1"
},
"smiles": "CC(C(=O)O)c1ccc([N+](=O)[O-])c(O)c1",
"reactionStepId": "sa_89abde1d57435e986dda50f1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08785474B2;0852;1487190\",\"rsmi\":\"CC[O:5][C:3]([CH:2]([CH3:1])[c:6]1[cH:7][c:8]([OH:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15]1)=[O:4]>CC(=O)O.CCO.O.[Na+].O>[CH3:1][CH:2]([C:3](=[O:4])[OH:5])[c:6]1[cH:7][c:8]([OH:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15]1\"},\"mapped_reaction_smiles\":\"CC[O:5][C:3]([CH:2]([CH3:1])[c:6]1[cH:7][c:8]([OH:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15]1)=[O:4]>CC(=O)O.CCO.O.[Na+].O>[CH3:1][CH:2]([C:3](=[O:4])[OH:5])[c:6]1[cH:7][c:8]([OH:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14][cH:15]1\"}",
"reactionStep": {
"id": "sa_89abde1d57435e986dda50f1",
"reactionHash": "c376e75477889b9c9b70b36fc78a76058a19e3b1e4c430b7d0f86ebc684c5c03"
},
"children": [
{
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"routeId": "sa_302ac1511b9517d03d7769bb",
"moleculeId": "sa_adffaca4d2780e1b1856f0d9",
"parentId": "17493",
"isLeaf": false,
"molecule": {
"id": "sa_adffaca4d2780e1b1856f0d9",
"inchikey": "DQRHXOJUFKZUHZ-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C(C)c1ccc([N+](=O)[O-])c(O)c1"
},
"smiles": "CCOC(=O)C(C)c1ccc([N+](=O)[O-])c(O)c1",
"reactionStepId": "sa_7913a5939b12eefc98b0ee5b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08785474B2;0681;1487153\",\"rsmi\":\"O=[N+:13]([OH:14])[O-:15].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[c:8]1[cH:9][c:10]([OH:11])[cH:12][cH:16][cH:17]1>CC(=O)O.O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[c:8]1[cH:9][c:10]([OH:11])[c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]1\"},\"mapped_reaction_smiles\":\"O=[N+:13]([OH:14])[O-:15].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[c:8]1[cH:9][c:10]([OH:11])[cH:12][cH:16][cH:17]1>CC(=O)O.O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[c:8]1[cH:9][c:10]([OH:11])[c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]1\"}",
"reactionStep": {
"id": "sa_7913a5939b12eefc98b0ee5b",
"reactionHash": "8c51e62e26aa4addee62442d8072b338fc089cd598120d1b6e5c498acc9e55b6"
},
"children": [
{
"id": "17495",
"routeId": "sa_302ac1511b9517d03d7769bb",
"moleculeId": "sa_261bf1157e2c64b027d67c98",
"parentId": "17494",
"isLeaf": false,
"molecule": {
"id": "sa_261bf1157e2c64b027d67c98",
"inchikey": "CJTQEHIQEPBAAT-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C(C)c1cccc(O)c1"
},
"smiles": "CCOC(=O)C(C)c1cccc(O)c1",
"reactionStepId": "sa_38e23973620add7b45786ee8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08785474B2;0678;1487152\",\"rsmi\":\"COC[O:11][c:10]1[cH:9][c:8]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:7])[cH:14][cH:13][cH:12]1>ClCCl.O.O=C(O)C(F)(F)F.O=C(O)O.[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[c:8]1[cH:9][c:10]([OH:11])[cH:12][cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"COC[O:11][c:10]1[cH:9][c:8]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:7])[cH:14][cH:13][cH:12]1>ClCCl.O.O=C(O)C(F)(F)F.O=C(O)O.[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[c:8]1[cH:9][c:10]([OH:11])[cH:12][cH:13][cH:14]1\"}",
"reactionStep": {
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"children": [
{
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"molecule": {
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"inchikey": "SUDYIXJYWXHXCK-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C(C)c1cccc(OCOC)c1"
},
"smiles": "CCOC(=O)C(C)c1cccc(OCOC)c1",
"reactionStepId": "sa_bf2f228ea62727c16ceef3a6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08785474B2;0675;1487151\",\"rsmi\":\"I[CH3:7].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:8]1[cH:9][c:10]([O:11][CH2:12][O:13][CH3:14])[cH:15][cH:16][cH:17]1>CN(C)C=O.O.[HH].[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[c:8]1[cH:9][c:10]([O:11][CH2:12][O:13][CH3:14])[cH:15][cH:16][cH:17]1\"},\"mapped_reaction_smiles\":\"I[CH3:7].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:8]1[cH:9][c:10]([O:11][CH2:12][O:13][CH3:14])[cH:15][cH:16][cH:17]1>CN(C)C=O.O.[HH].[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[c:8]1[cH:9][c:10]([O:11][CH2:12][O:13][CH3:14])[cH:15][cH:16][cH:17]1\"}",
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"children": [
{
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"parentId": "17496",
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"molecule": {
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"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
},
"smiles": "CI",
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"template": null,
"metadata": null,
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},
{
"id": "17498",
"routeId": "sa_302ac1511b9517d03d7769bb",
"moleculeId": "sa_653c1f0764132d4a168b99f4",
"parentId": "17496",
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"molecule": {
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"inchikey": "XXMXUSHNMAVZEJ-UHFFFAOYSA-N",
"smiles": "CCOC(=O)Cc1cccc(OCOC)c1"
},
"smiles": "CCOC(=O)Cc1cccc(OCOC)c1",
"reactionStepId": "sa_ab50dca1a8bce35f906acad4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08785474B2;0803;1487175\",\"rsmi\":\"Cl[CH2:11][O:12][CH3:13].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][c:9]([OH:10])[cH:14][cH:15][cH:16]1>C1CCOC1.O.[HH].[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][c:9]([O:10][CH2:11][O:12][CH3:13])[cH:14][cH:15][cH:16]1\"},\"mapped_reaction_smiles\":\"Cl[CH2:11][O:12][CH3:13].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][c:9]([OH:10])[cH:14][cH:15][cH:16]1>C1CCOC1.O.[HH].[Na+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][c:9]([O:10][CH2:11][O:12][CH3:13])[cH:14][cH:15][cH:16]1\"}",
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"children": [
{
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"parentId": "17498",
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"molecule": {
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"inchikey": "NSQBADKMIYCCSC-UHFFFAOYSA-N",
"smiles": "CCOC(=O)Cc1cccc(O)c1"
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"smiles": "CCOC(=O)Cc1cccc(O)c1",
"reactionStepId": "sa_9ef330c392d85b7870dc91a2",
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"metadata": "{\"annotations\":{\"ID\":\"US08785474B2;0842;1487185\",\"rsmi\":\"O[C:4](=[O:5])[CH2:6][c:7]1[cH:8][c:9]([OH:10])[cH:11][cH:12][cH:13]1.[CH3:1][CH2:2][OH:3]>O.O=S(=O)(O)O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][c:9]([OH:10])[cH:11][cH:12][cH:13]1\"},\"mapped_reaction_smiles\":\"O[C:4](=[O:5])[CH2:6][c:7]1[cH:8][c:9]([OH:10])[cH:11][cH:12][cH:13]1.[CH3:1][CH2:2][OH:3]>O.O=S(=O)(O)O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][c:7]1[cH:8][c:9]([OH:10])[cH:11][cH:12][cH:13]1\"}",
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"molecule": {
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"smiles": "O=C(O)Cc1cccc(O)c1"
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{
"id": "17501",
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{
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},
{
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"molecule": {
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"inchikey": "GRYLNZFGIOXLOG-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])O"
},
"smiles": "O=[N+]([O-])O",
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}
]
}
]
}
]
}
]
}
}