Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1c(N2CCN(C(=O)COC(C)=O)CC2)cc(Br)cc1C(C)(C)C
InChiKey
HMTKDIMDUAJTBJ-UHFFFAOYSA-N
Route Signature
be9dc128391a153572a4c07a256aed93277230f036324c834e0f922f62c41672
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_91f589982e72a997d344d6cd",
"signature": "be9dc128391a153572a4c07a256aed93277230f036324c834e0f922f62c41672",
"contentHash": "8de179f41ed2fb5624038b45f61c52c0ecf6e9e77dcd1381432ae7272abc9e81",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_e92dec87b9229cc14fe693a7",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00022",
"moleculeId": "sa_1fb430739a4691654b65a09f",
"smiles": "COc1c(N2CCN(C(=O)COC(C)=O)CC2)cc(Br)cc1C(C)(C)C",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_1fb430739a4691654b65a09f",
"inchikey": "HMTKDIMDUAJTBJ-UHFFFAOYSA-N",
"smiles": "COc1c(N2CCN(C(=O)COC(C)=O)CC2)cc(Br)cc1C(C)(C)C"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "3384",
"routeId": "sa_91f589982e72a997d344d6cd",
"moleculeId": "sa_1fb430739a4691654b65a09f",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_1fb430739a4691654b65a09f",
"inchikey": "HMTKDIMDUAJTBJ-UHFFFAOYSA-N",
"smiles": "COc1c(N2CCN(C(=O)COC(C)=O)CC2)cc(Br)cc1C(C)(C)C"
},
"smiles": "COc1c(N2CCN(C(=O)COC(C)=O)CC2)cc(Br)cc1C(C)(C)C",
"reactionStepId": "sa_b961bdb95fc4adfd966dc9cc",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07244730B2;1029;796903\",\"rsmi\":\"Cl[C:9](=[O:10])[CH2:11][O:12][C:13]([CH3:14])=[O:15].[CH3:1][O:2][c:3]1[c:4]([N:5]2[CH2:6][CH2:7][NH:8][CH2:16][CH2:17]2)[cH:18][c:19]([Br:20])[cH:21][c:22]1[C:23]([CH3:24])([CH3:25])[CH3:26]>CCN(CC)CC.ClCCl>[CH3:1][O:2][c:3]1[c:4]([N:5]2[CH2:6][CH2:7][N:8]([C:9](=[O:10])[CH2:11][O:12][C:13]([CH3:14])=[O:15])[CH2:16][CH2:17]2)[cH:18][c:19]([Br:20])[cH:21][c:22]1[C:23]([CH3:24])([CH3:25])[CH3:26]\"},\"mapped_reaction_smiles\":\"Cl[C:9](=[O:10])[CH2:11][O:12][C:13]([CH3:14])=[O:15].[CH3:1][O:2][c:3]1[c:4]([N:5]2[CH2:6][CH2:7][NH:8][CH2:16][CH2:17]2)[cH:18][c:19]([Br:20])[cH:21][c:22]1[C:23]([CH3:24])([CH3:25])[CH3:26]>CCN(CC)CC.ClCCl>[CH3:1][O:2][c:3]1[c:4]([N:5]2[CH2:6][CH2:7][N:8]([C:9](=[O:10])[CH2:11][O:12][C:13]([CH3:14])=[O:15])[CH2:16][CH2:17]2)[cH:18][c:19]([Br:20])[cH:21][c:22]1[C:23]([CH3:24])([CH3:25])[CH3:26]\"}",
"reactionStep": {
"id": "sa_b961bdb95fc4adfd966dc9cc",
"reactionHash": "086719772c050dff03463ff25e2a6899810346bac66fe6913663613200dbf3b6"
},
"children": [
{
"id": "3385",
"routeId": "sa_91f589982e72a997d344d6cd",
"moleculeId": "sa_624328e10bc1a3dc9fb22c9a",
"parentId": "3384",
"isLeaf": true,
"molecule": {
"id": "sa_624328e10bc1a3dc9fb22c9a",
"inchikey": "HZDNNJABYXNPPV-UHFFFAOYSA-N",
"smiles": "CC(=O)OCC(=O)Cl"
},
"smiles": "CC(=O)OCC(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3386",
"routeId": "sa_91f589982e72a997d344d6cd",
"moleculeId": "sa_4d439af51a9144d34037b524",
"parentId": "3384",
"isLeaf": false,
"molecule": {
"id": "sa_4d439af51a9144d34037b524",
"inchikey": "PZBHMBCZYYLQDW-UHFFFAOYSA-N",
"smiles": "COc1c(N2CCNCC2)cc(Br)cc1C(C)(C)C"
},
"smiles": "COc1c(N2CCNCC2)cc(Br)cc1C(C)(C)C",
"reactionStepId": "sa_b03a1ca891eb9859be5a911f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07244730B2;0991;796896\",\"rsmi\":\"Cl[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]Cl.[CH3:1][O:2][c:3]1[c:4]([NH2:5])[cH:11][c:12]([Br:13])[cH:14][c:15]1[C:16]([CH3:17])([CH3:18])[CH3:19]>Cl.Clc1ccccc1Cl.O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][c:3]1[c:4]([N:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]2)[cH:11][c:12]([Br:13])[cH:14][c:15]1[C:16]([CH3:17])([CH3:18])[CH3:19]\"},\"mapped_reaction_smiles\":\"Cl[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]Cl.[CH3:1][O:2][c:3]1[c:4]([NH2:5])[cH:11][c:12]([Br:13])[cH:14][c:15]1[C:16]([CH3:17])([CH3:18])[CH3:19]>Cl.Clc1ccccc1Cl.O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][c:3]1[c:4]([N:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]2)[cH:11][c:12]([Br:13])[cH:14][c:15]1[C:16]([CH3:17])([CH3:18])[CH3:19]\"}",
"reactionStep": {
"id": "sa_b03a1ca891eb9859be5a911f",
"reactionHash": "01af349d7e5094cfc1ba46f6f569c66ba1001fbc228bfa54b17d94c93c05aa2d"
},
"children": [
{
"id": "3387",
"routeId": "sa_91f589982e72a997d344d6cd",
"moleculeId": "sa_99c58a35fb8b96c785748167",
"parentId": "3386",
"isLeaf": false,
"molecule": {
"id": "sa_99c58a35fb8b96c785748167",
"inchikey": "BBHISXFMGAZYHB-UHFFFAOYSA-N",
"smiles": "COc1c(N)cc(Br)cc1C(C)(C)C"
},
"smiles": "COc1c(N)cc(Br)cc1C(C)(C)C",
"reactionStepId": "sa_484a917971d93fb5a6435e9a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07244730B2;0935;796885\",\"rsmi\":\"O=[N+:5]([O-])[c:4]1[c:3]([O:2][CH3:1])[c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[cH:9][c:7]([Br:8])[cH:6]1>CO.O.Cl.[Fe].N>[CH3:1][O:2][c:3]1[c:4]([NH2:5])[cH:6][c:7]([Br:8])[cH:9][c:10]1[C:11]([CH3:12])([CH3:13])[CH3:14]\"},\"mapped_reaction_smiles\":\"O=[N+:5]([O-])[c:4]1[c:3]([O:2][CH3:1])[c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[cH:9][c:7]([Br:8])[cH:6]1>CO.O.Cl.[Fe].N>[CH3:1][O:2][c:3]1[c:4]([NH2:5])[cH:6][c:7]([Br:8])[cH:9][c:10]1[C:11]([CH3:12])([CH3:13])[CH3:14]\"}",
"reactionStep": {
"id": "sa_484a917971d93fb5a6435e9a",
"reactionHash": "73c064b1fd707e89fd036c9eff72fa3d52829c46f3873b6cb7387f12a2225101"
},
"children": [
{
"id": "3388",
"routeId": "sa_91f589982e72a997d344d6cd",
"moleculeId": "sa_928a43daece2b0cd237e5060",
"parentId": "3387",
"isLeaf": false,
"molecule": {
"id": "sa_928a43daece2b0cd237e5060",
"inchikey": "UMZIOALQUPMKRE-UHFFFAOYSA-N",
"smiles": "COc1c([N+](=O)[O-])cc(Br)cc1C(C)(C)C"
},
"smiles": "COc1c([N+](=O)[O-])cc(Br)cc1C(C)(C)C",
"reactionStepId": "sa_eb7de260763b9b454a40a0ff",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07244730B2;0932;796884\",\"rsmi\":\"I[CH3:1].[OH:2][c:3]1[c:4]([C:5]([CH3:6])([CH3:7])[CH3:8])[cH:9][c:10]([Br:11])[cH:12][c:13]1[N+:14](=[O:15])[O-:16]>CCOCC.CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][c:3]1[c:4]([C:5]([CH3:6])([CH3:7])[CH3:8])[cH:9][c:10]([Br:11])[cH:12][c:13]1[N+:14](=[O:15])[O-:16]\"},\"mapped_reaction_smiles\":\"I[CH3:1].[OH:2][c:3]1[c:4]([C:5]([CH3:6])([CH3:7])[CH3:8])[cH:9][c:10]([Br:11])[cH:12][c:13]1[N+:14](=[O:15])[O-:16]>CCOCC.CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][c:3]1[c:4]([C:5]([CH3:6])([CH3:7])[CH3:8])[cH:9][c:10]([Br:11])[cH:12][c:13]1[N+:14](=[O:15])[O-:16]\"}",
"reactionStep": {
"id": "sa_eb7de260763b9b454a40a0ff",
"reactionHash": "a6608e8fa7d267cdc22b6703d4401da9336385c64a7598dcdc13feea6e42dd6b"
},
"children": [
{
"id": "3389",
"routeId": "sa_91f589982e72a997d344d6cd",
"moleculeId": "sa_7b73354bc26b4d2f598aed94",
"parentId": "3388",
"isLeaf": false,
"molecule": {
"id": "sa_7b73354bc26b4d2f598aed94",
"inchikey": "IGYZKUXNIXAGHE-UHFFFAOYSA-N",
"smiles": "CC(C)(C)c1cc(Br)cc([N+](=O)[O-])c1O"
},
"smiles": "CC(C)(C)c1cc(Br)cc([N+](=O)[O-])c1O",
"reactionStepId": "sa_2e767665828c7ad6dc05021d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07244730B2;0929;796883\",\"rsmi\":\"O=[N+:9]([OH:10])[O-:11].[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[c:6]([OH:7])[cH:8][cH:12][c:13]([Br:14])[cH:15]1>CCCCCC.CCOCC>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[c:6]([OH:7])[c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]([Br:14])[cH:15]1\"},\"mapped_reaction_smiles\":\"O=[N+:9]([OH:10])[O-:11].[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[c:6]([OH:7])[cH:8][cH:12][c:13]([Br:14])[cH:15]1>CCCCCC.CCOCC>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[c:6]([OH:7])[c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]([Br:14])[cH:15]1\"}",
"reactionStep": {
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"reactionHash": "ebdb10f5bc790d138abb3f99d3e96993f927c61e4513a4f64c01a7f3c115ac01"
},
"children": [
{
"id": "3390",
"routeId": "sa_91f589982e72a997d344d6cd",
"moleculeId": "sa_edac0a7fd043198784a28dd9",
"parentId": "3389",
"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,
"reactionStep": null,
"children": []
},
{
"id": "3391",
"routeId": "sa_91f589982e72a997d344d6cd",
"moleculeId": "sa_a4da2a1ab8fa805b51dff625",
"parentId": "3389",
"isLeaf": false,
"molecule": {
"id": "sa_a4da2a1ab8fa805b51dff625",
"inchikey": "IKMJSWBFODAWTC-UHFFFAOYSA-N",
"smiles": "CC(C)(C)c1cc(Br)ccc1O"
},
"smiles": "CC(C)(C)c1cc(Br)ccc1O",
"reactionStepId": "sa_f02ee30725d225bc54327fad",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US07244730B2;0926;796882\",\"rsmi\":\"O=C1CCC(=O)N1[Br:11].[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[c:6]([OH:7])[cH:8][cH:9][cH:10][cH:12]1>CC#N.CCOCC>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[c:6]([OH:7])[cH:8][cH:9][c:10]([Br:11])[cH:12]1\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:11].[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[c:6]([OH:7])[cH:8][cH:9][cH:10][cH:12]1>CC#N.CCOCC>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[c:6]([OH:7])[cH:8][cH:9][c:10]([Br:11])[cH:12]1\"}",
"reactionStep": {
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"reactionHash": "030703f8b75a8b252a579e685038b344fd17564308c42a2810584d4e9260f32a"
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"children": [
{
"id": "3392",
"routeId": "sa_91f589982e72a997d344d6cd",
"moleculeId": "sa_ccdcf23ac83e7a68bfa4f2e5",
"parentId": "3391",
"isLeaf": true,
"molecule": {
"id": "sa_ccdcf23ac83e7a68bfa4f2e5",
"inchikey": "PCLIMKBDDGJMGD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Br"
},
"smiles": "O=C1CCC(=O)N1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3393",
"routeId": "sa_91f589982e72a997d344d6cd",
"moleculeId": "sa_c3a85a615a35418d740042ad",
"parentId": "3391",
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"molecule": {
"id": "sa_c3a85a615a35418d740042ad",
"inchikey": "WJQOZHYUIDYNHM-UHFFFAOYSA-N",
"smiles": "CC(C)(C)c1ccccc1O"
},
"smiles": "CC(C)(C)c1ccccc1O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "3394",
"routeId": "sa_91f589982e72a997d344d6cd",
"moleculeId": "sa_82fdccf7d1cc329c9db73f21",
"parentId": "3388",
"isLeaf": true,
"molecule": {
"id": "sa_82fdccf7d1cc329c9db73f21",
"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
},
"smiles": "CI",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "3395",
"routeId": "sa_91f589982e72a997d344d6cd",
"moleculeId": "sa_0ebfe7e2bd313e19743683d0",
"parentId": "3386",
"isLeaf": true,
"molecule": {
"id": "sa_0ebfe7e2bd313e19743683d0",
"inchikey": "TXFLGZOGNOOEFZ-UHFFFAOYSA-N",
"smiles": "ClCCNCCCl"
},
"smiles": "ClCCNCCCl",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
}