Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCc1cc2c(Br)cnnc2cc1OC
InChiKey
NHWQMPNVRMZWDG-UHFFFAOYSA-N
Route Signature
5c3221f46cb17d60f2de77c3cb4f5342ece594d3e285a6b14ebd0d1e68a9b9fe
Synthesis route with 9 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_2f1195bea1f8cb4b9235cd0d",
"signature": "5c3221f46cb17d60f2de77c3cb4f5342ece594d3e285a6b14ebd0d1e68a9b9fe",
"contentHash": "16aafbc20ea5f08e261fd399d89c4cc40b2d11509144ae33cbce971b1fed5b09",
"length": 9,
"isConvergent": false
},
"target": {
"id": "sa_4d97cf23db6d40fff2e19803",
"benchmarkSetId": "a82783729b577c36f2e09a2b6fdd55ae9542aed5546571d67ef9cb74dc21f70a",
"targetId": "n5-00007",
"moleculeId": "sa_f7e5bff6a917a92c80981d0d",
"smiles": "CCc1cc2c(Br)cnnc2cc1OC",
"routeLength": 9,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_f7e5bff6a917a92c80981d0d",
"inchikey": "NHWQMPNVRMZWDG-UHFFFAOYSA-N",
"smiles": "CCc1cc2c(Br)cnnc2cc1OC"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "17252",
"routeId": "sa_2f1195bea1f8cb4b9235cd0d",
"moleculeId": "sa_f7e5bff6a917a92c80981d0d",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_f7e5bff6a917a92c80981d0d",
"inchikey": "NHWQMPNVRMZWDG-UHFFFAOYSA-N",
"smiles": "CCc1cc2c(Br)cnnc2cc1OC"
},
"smiles": "CCc1cc2c(Br)cnnc2cc1OC",
"reactionStepId": "sa_dae0bafe289ed96b02b875b2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090099175A1;0249;690163\",\"rsmi\":\"O=P(Br)(Br)[Br:13].O[c:12]1[cH:11][n:10][n:9][c:8]2[cH:7][c:4]([O:5][CH3:6])[c:3]([CH2:2][CH3:1])[cH:15][c:14]21>CC#N.O=C(O)O.[Na+]>[CH3:1][CH2:2][c:3]1[c:4]([O:5][CH3:6])[cH:7][c:8]2[n:9][n:10][cH:11][c:12]([Br:13])[c:14]2[cH:15]1\"},\"mapped_reaction_smiles\":\"O=P(Br)(Br)[Br:13].O[c:12]1[cH:11][n:10][n:9][c:8]2[cH:7][c:4]([O:5][CH3:6])[c:3]([CH2:2][CH3:1])[cH:15][c:14]21>CC#N.O=C(O)O.[Na+]>[CH3:1][CH2:2][c:3]1[c:4]([O:5][CH3:6])[cH:7][c:8]2[n:9][n:10][cH:11][c:12]([Br:13])[c:14]2[cH:15]1\"}",
"reactionStep": {
"id": "sa_dae0bafe289ed96b02b875b2",
"reactionHash": "badd597a3a733dbfbaad173bf94acd4620f67bd385383a0e14ce866420156625"
},
"children": [
{
"id": "17253",
"routeId": "sa_2f1195bea1f8cb4b9235cd0d",
"moleculeId": "sa_1ba3f225da8b42cd763dacb2",
"parentId": "17252",
"isLeaf": false,
"molecule": {
"id": "sa_1ba3f225da8b42cd763dacb2",
"inchikey": "SBUFHPGHGUSAQO-UHFFFAOYSA-N",
"smiles": "CCc1cc2c(O)cnnc2cc1OC"
},
"smiles": "CCc1cc2c(O)cnnc2cc1OC",
"reactionStepId": "sa_9877f42f0c3fd2d5c353288e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090099175A1;0248;690162\",\"rsmi\":\"O=[N:10]O.[CH3:1][CH2:2][c:3]1[c:4]([O:5][CH3:6])[cH:7][c:8]([NH2:9])[c:14]([C:12]([CH3:11])=[O:13])[cH:15]1>Cl.O.O=C(O)O.[Na+].[Na+]>[CH3:1][CH2:2][c:3]1[c:4]([O:5][CH3:6])[cH:7][c:8]2[n:9][n:10][cH:11][c:12]([OH:13])[c:14]2[cH:15]1\"},\"mapped_reaction_smiles\":\"O=[N:10]O.[CH3:1][CH2:2][c:3]1[c:4]([O:5][CH3:6])[cH:7][c:8]([NH2:9])[c:14]([C:12]([CH3:11])=[O:13])[cH:15]1>Cl.O.O=C(O)O.[Na+].[Na+]>[CH3:1][CH2:2][c:3]1[c:4]([O:5][CH3:6])[cH:7][c:8]2[n:9][n:10][cH:11][c:12]([OH:13])[c:14]2[cH:15]1\"}",
"reactionStep": {
"id": "sa_9877f42f0c3fd2d5c353288e",
"reactionHash": "a5b4d4e9d6005cc5edeb458d2072088a01e993d5d7be257c362fb29dae0187b7"
},
"children": [
{
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"routeId": "sa_2f1195bea1f8cb4b9235cd0d",
"moleculeId": "sa_81c0446884d57a7253ff6b54",
"parentId": "17253",
"isLeaf": true,
"molecule": {
"id": "sa_81c0446884d57a7253ff6b54",
"inchikey": "IOVCWXUNBOPUCH-UHFFFAOYSA-N",
"smiles": "[O-]N=[OH+]"
},
"smiles": "O=NO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "17255",
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"moleculeId": "sa_14b3b2b611f9d7f74c6ef5ae",
"parentId": "17253",
"isLeaf": false,
"molecule": {
"id": "sa_14b3b2b611f9d7f74c6ef5ae",
"inchikey": "LSMXGHGQJXRGKN-UHFFFAOYSA-N",
"smiles": "CCc1cc(C(C)=O)c(N)cc1OC"
},
"smiles": "CCc1cc(C(C)=O)c(N)cc1OC",
"reactionStepId": "sa_613f1fb46460810b227843cf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090099175A1;0247;690161\",\"rsmi\":\"CC(=O)[NH:10][c:9]1[c:5]([C:6]([CH3:7])=[O:8])[cH:4][c:3]([CH2:2][CH3:1])[c:12]([O:13][CH3:14])[cH:11]1>C1COCCO1.Cl>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[c:9]([NH2:10])[cH:11][c:12]1[O:13][CH3:14]\"},\"mapped_reaction_smiles\":\"CC(=O)[NH:10][c:9]1[c:5]([C:6]([CH3:7])=[O:8])[cH:4][c:3]([CH2:2][CH3:1])[c:12]([O:13][CH3:14])[cH:11]1>C1COCCO1.Cl>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[c:9]([NH2:10])[cH:11][c:12]1[O:13][CH3:14]\"}",
"reactionStep": {
"id": "sa_613f1fb46460810b227843cf",
"reactionHash": "5600ec917a61e54b7805cfafc39d9ef2c2aa56c9ae1a7e1373734ad083e07efa"
},
"children": [
{
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"moleculeId": "sa_5aa54807531e08be4c57fbbf",
"parentId": "17255",
"isLeaf": false,
"molecule": {
"id": "sa_5aa54807531e08be4c57fbbf",
"inchikey": "KNXJFPZMONJYGC-UHFFFAOYSA-N",
"smiles": "CCc1cc(C(C)=O)c(NC(C)=O)cc1OC"
},
"smiles": "CCc1cc(C(C)=O)c(NC(C)=O)cc1OC",
"reactionStepId": "sa_be93e3a06486f322ec735d07",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090099175A1;0246;690160\",\"rsmi\":\"Cl[C:6]([CH3:7])=[O:8].[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:9]([NH:10][C:11]([CH3:12])=[O:13])[cH:14][c:15]1[O:16][CH3:17]>ClCCl.[Al+3].Cl.Cl.Cl>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[c:9]([NH:10][C:11]([CH3:12])=[O:13])[cH:14][c:15]1[O:16][CH3:17]\"},\"mapped_reaction_smiles\":\"Cl[C:6]([CH3:7])=[O:8].[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:9]([NH:10][C:11]([CH3:12])=[O:13])[cH:14][c:15]1[O:16][CH3:17]>ClCCl.[Al+3].Cl.Cl.Cl>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[c:9]([NH:10][C:11]([CH3:12])=[O:13])[cH:14][c:15]1[O:16][CH3:17]\"}",
"reactionStep": {
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"reactionHash": "ea51bf9bd83f95acd6a7ccf6b55c59058da1e70c9f06d8648ced18f34450dff9"
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"children": [
{
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"moleculeId": "sa_b81cfd4dc89f2437b9878309",
"parentId": "17256",
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"molecule": {
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"inchikey": "RBEWGAODJKBQGP-UHFFFAOYSA-N",
"smiles": "CCc1ccc(NC(C)=O)cc1OC"
},
"smiles": "CCc1ccc(NC(C)=O)cc1OC",
"reactionStepId": "sa_c0b0a5d8aac633e037d40cc1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090099175A1;0245;690159\",\"rsmi\":\"Cl[C:10]([CH3:11])=[O:12].[CH3:1][CH2:2][c:3]1[c:4]([O:5][CH3:6])[cH:7][c:8]([NH2:9])[cH:13][cH:14]1>CCN(CC)CC.ClCCl>[CH3:1][CH2:2][c:3]1[c:4]([O:5][CH3:6])[cH:7][c:8]([NH:9][C:10]([CH3:11])=[O:12])[cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"Cl[C:10]([CH3:11])=[O:12].[CH3:1][CH2:2][c:3]1[c:4]([O:5][CH3:6])[cH:7][c:8]([NH2:9])[cH:13][cH:14]1>CCN(CC)CC.ClCCl>[CH3:1][CH2:2][c:3]1[c:4]([O:5][CH3:6])[cH:7][c:8]([NH:9][C:10]([CH3:11])=[O:12])[cH:13][cH:14]1\"}",
"reactionStep": {
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"children": [
{
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"molecule": {
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"smiles": "CCc1ccc(N)cc1OC"
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"smiles": "CCc1ccc(N)cc1OC",
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"metadata": "{\"annotations\":{\"ID\":\"US20090099175A1;0244;690158\",\"rsmi\":\"O=[N+:9]([O-])[c:8]1[cH:7][c:4]([O:5][CH3:6])[c:3]([CH2:2][CH3:1])[cH:11][cH:10]1>CC(=O)O.CCO.O.Cl.N.[Zn]>[CH3:1][CH2:2][c:3]1[c:4]([O:5][CH3:6])[cH:7][c:8]([NH2:9])[cH:10][cH:11]1\"},\"mapped_reaction_smiles\":\"O=[N+:9]([O-])[c:8]1[cH:7][c:4]([O:5][CH3:6])[c:3]([CH2:2][CH3:1])[cH:11][cH:10]1>CC(=O)O.CCO.O.Cl.N.[Zn]>[CH3:1][CH2:2][c:3]1[c:4]([O:5][CH3:6])[cH:7][c:8]([NH2:9])[cH:10][cH:11]1\"}",
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"smiles": "CCc1ccc([N+](=O)[O-])cc1OC",
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"metadata": "{\"annotations\":{\"ID\":\"US20090099175A1;0243;690157\",\"rsmi\":\"I[CH3:6].[CH3:1][CH2:2][c:3]1[c:4]([OH:5])[cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13]1>CC(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][c:3]1[c:4]([O:5][CH3:6])[cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13]1\"},\"mapped_reaction_smiles\":\"I[CH3:6].[CH3:1][CH2:2][c:3]1[c:4]([OH:5])[cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13]1>CC(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][c:3]1[c:4]([O:5][CH3:6])[cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][cH:13]1\"}",
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"molecule": {
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"metadata": "{\"annotations\":{\"ID\":\"US20090099175A1;0242;690156\",\"rsmi\":\"N[c:4]1[c:3]([CH2:2][CH3:1])[cH:12][cH:11][c:7]([N+:8](=[O:9])[O-:10])[cH:6]1.ON=[O:5]>O.O=S(=O)(O)O.[Na+]>[CH3:1][CH2:2][c:3]1[c:4]([OH:5])[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12]1\"},\"mapped_reaction_smiles\":\"N[c:4]1[c:3]([CH2:2][CH3:1])[cH:12][cH:11][c:7]([N+:8](=[O:9])[O-:10])[cH:6]1.ON=[O:5]>O.O=S(=O)(O)O.[Na+]>[CH3:1][CH2:2][c:3]1[c:4]([OH:5])[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12]1\"}",
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"molecule": {
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{
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"smiles": "CCc1ccc([N+](=O)[O-])cc1N",
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"metadata": "{\"annotations\":{\"ID\":\"US20090099175A1;0241;690155\",\"rsmi\":\"O=[N+:5]([O-])[c:4]1[c:3]([CH2:2][CH3:1])[cH:12][cH:11][c:7]([N+:8](=[O:9])[O-:10])[cH:6]1>CC(=O)O.[Fe]>[CH3:1][CH2:2][c:3]1[c:4]([NH2:5])[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12]1\"},\"mapped_reaction_smiles\":\"O=[N+:5]([O-])[c:4]1[c:3]([CH2:2][CH3:1])[cH:12][cH:11][c:7]([N+:8](=[O:9])[O-:10])[cH:6]1>CC(=O)O.[Fe]>[CH3:1][CH2:2][c:3]1[c:4]([NH2:5])[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][cH:12]1\"}",
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{
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"molecule": {
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"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
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"smiles": "CI",
"reactionStepId": null,
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}
]
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]
},
{
"id": "17265",
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"molecule": {
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"inchikey": "WETWJCDKMRHUPV-UHFFFAOYSA-N",
"smiles": "CC(=O)Cl"
},
"smiles": "CC(=O)Cl",
"reactionStepId": null,
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"children": []
}
]
},
{
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"molecule": {
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"smiles": "CC(=O)Cl"
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},
{
"id": "17267",
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"parentId": "17252",
"isLeaf": true,
"molecule": {
"id": "sa_a1b49eb944a62e16d1beafca",
"inchikey": "UXCDUFKZSUBXGM-UHFFFAOYSA-N",
"smiles": "O=P(Br)(Br)Br"
},
"smiles": "O=P(Br)(Br)Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}