Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cn1cnc2c(Nc3cccc(Cl)c3)ncc(C(=O)N3CCOCC3)c21
InChiKey
SWIFPNWCWUGFKO-UHFFFAOYSA-N
Route Signature
9c9eba6278a7854d96b99e876015b794811cf648f023d33506b4aba7030ed0f8
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_c74d285e1fbd32a40baaf5a2",
"signature": "9c9eba6278a7854d96b99e876015b794811cf648f023d33506b4aba7030ed0f8",
"contentHash": "f3e2fb4cae42d5932098a0196de24b3b36c5e216babecb5cf165ed78f5f89e30",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_59f02b5d1517e46f30568afc",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-01354",
"moleculeId": "sa_d2793a5282f8555ff7bf11f5",
"smiles": "Cn1cnc2c(Nc3cccc(Cl)c3)ncc(C(=O)N3CCOCC3)c21",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_d2793a5282f8555ff7bf11f5",
"inchikey": "SWIFPNWCWUGFKO-UHFFFAOYSA-N",
"smiles": "Cn1cnc2c(Nc3cccc(Cl)c3)ncc(C(=O)N3CCOCC3)c21"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "5503",
"routeId": "sa_c74d285e1fbd32a40baaf5a2",
"moleculeId": "sa_d2793a5282f8555ff7bf11f5",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_d2793a5282f8555ff7bf11f5",
"inchikey": "SWIFPNWCWUGFKO-UHFFFAOYSA-N",
"smiles": "Cn1cnc2c(Nc3cccc(Cl)c3)ncc(C(=O)N3CCOCC3)c21"
},
"smiles": "Cn1cnc2c(Nc3cccc(Cl)c3)ncc(C(=O)N3CCOCC3)c21",
"reactionStepId": "sa_0edf94844aa1be5455369303",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080221097A1;0326;609277\",\"rsmi\":\"O[C:8]([c:7]1[c:6]2[n:2]([CH3:1])[cH:3][n:4][c:5]2[c:18]([NH:19][c:20]2[cH:21][c:22]([Cl:23])[cH:24][cH:25][cH:26]2)[n:17][cH:16]1)=[O:9].[NH:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O.CO.Cl.ClCCl.F[PH](F)(F)(F)(F)F>[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]1[c:7]([C:8](=[O:9])[N:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1)[cH:16][n:17][c:18]2[NH:19][c:20]1[cH:21][c:22]([Cl:23])[cH:24][cH:25][cH:26]1\"},\"mapped_reaction_smiles\":\"O[C:8]([c:7]1[c:6]2[n:2]([CH3:1])[cH:3][n:4][c:5]2[c:18]([NH:19][c:20]2[cH:21][c:22]([Cl:23])[cH:24][cH:25][cH:26]2)[n:17][cH:16]1)=[O:9].[NH:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2ccccc21)=[N+](C)C.CN(C)C=O.CO.Cl.ClCCl.F[PH](F)(F)(F)(F)F>[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]1[c:7]([C:8](=[O:9])[N:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1)[cH:16][n:17][c:18]2[NH:19][c:20]1[cH:21][c:22]([Cl:23])[cH:24][cH:25][cH:26]1\"}",
"reactionStep": {
"id": "sa_0edf94844aa1be5455369303",
"reactionHash": "1a1be7cbd08e68d71f6bf077036cf08c62be71ab3fcbea428007dcba42c7e000"
},
"children": [
{
"id": "5504",
"routeId": "sa_c74d285e1fbd32a40baaf5a2",
"moleculeId": "sa_a2e86ca3b2155634a69c543b",
"parentId": "5503",
"isLeaf": false,
"molecule": {
"id": "sa_a2e86ca3b2155634a69c543b",
"inchikey": "WRTRHXNRUOIPRM-UHFFFAOYSA-N",
"smiles": "Cn1cnc2c(Nc3cccc(Cl)c3)ncc(C(=O)O)c21"
},
"smiles": "Cn1cnc2c(Nc3cccc(Cl)c3)ncc(C(=O)O)c21",
"reactionStepId": "sa_77da3b3e72bad3e49760eb30",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080221097A1;0286;609267\",\"rsmi\":\"CC[O:10][C:8]([c:7]1[c:6]2[n:2]([CH3:1])[cH:3][n:4][c:5]2[c:13]([NH:14][c:15]2[cH:16][c:17]([Cl:18])[cH:19][cH:20][cH:21]2)[n:12][cH:11]1)=[O:9]>CCO.Cl.O.[Na+].O>[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]1[c:7]([C:8](=[O:9])[OH:10])[cH:11][n:12][c:13]2[NH:14][c:15]1[cH:16][c:17]([Cl:18])[cH:19][cH:20][cH:21]1\"},\"mapped_reaction_smiles\":\"CC[O:10][C:8]([c:7]1[c:6]2[n:2]([CH3:1])[cH:3][n:4][c:5]2[c:13]([NH:14][c:15]2[cH:16][c:17]([Cl:18])[cH:19][cH:20][cH:21]2)[n:12][cH:11]1)=[O:9]>CCO.Cl.O.[Na+].O>[CH3:1][n:2]1[cH:3][n:4][c:5]2[c:6]1[c:7]([C:8](=[O:9])[OH:10])[cH:11][n:12][c:13]2[NH:14][c:15]1[cH:16][c:17]([Cl:18])[cH:19][cH:20][cH:21]1\"}",
"reactionStep": {
"id": "sa_77da3b3e72bad3e49760eb30",
"reactionHash": "f8e04269580a9be630ea46a7ce7aa44e2efe76bd4cbc2efaf2bf2fe13101f5cc"
},
"children": [
{
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"routeId": "sa_c74d285e1fbd32a40baaf5a2",
"moleculeId": "sa_174be9cb21f5d3ecc02fe515",
"parentId": "5504",
"isLeaf": false,
"molecule": {
"id": "sa_174be9cb21f5d3ecc02fe515",
"inchikey": "PZRNOMNTAQONKW-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cnc(Nc2cccc(Cl)c2)c2ncn(C)c12"
},
"smiles": "CCOC(=O)c1cnc(Nc2cccc(Cl)c2)c2ncn(C)c12",
"reactionStepId": "sa_c53bef773b0b2d4a139296de",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080221097A1;0278;609265\",\"rsmi\":\"Cl[c:9]1[n:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:19]2[c:18]1[n:23][cH:22][n:20]2[CH3:21].[NH2:10][c:11]1[cH:12][c:13]([Cl:14])[cH:15][cH:16][cH:17]1>C1COCCO1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH:10][c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][cH:17]2)[c:18]2[c:19]1[n:20]([CH3:21])[cH:22][n:23]2\"},\"mapped_reaction_smiles\":\"Cl[c:9]1[n:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:19]2[c:18]1[n:23][cH:22][n:20]2[CH3:21].[NH2:10][c:11]1[cH:12][c:13]([Cl:14])[cH:15][cH:16][cH:17]1>C1COCCO1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([NH:10][c:11]2[cH:12][c:13]([Cl:14])[cH:15][cH:16][cH:17]2)[c:18]2[c:19]1[n:20]([CH3:21])[cH:22][n:23]2\"}",
"reactionStep": {
"id": "sa_c53bef773b0b2d4a139296de",
"reactionHash": "7e27ceb40a4d70f9bf540c528755c17666fa133e89a6fe2a192f43f17a25f5ea"
},
"children": [
{
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"routeId": "sa_c74d285e1fbd32a40baaf5a2",
"moleculeId": "sa_7f956797e753f661a58a3af6",
"parentId": "5505",
"isLeaf": false,
"molecule": {
"id": "sa_7f956797e753f661a58a3af6",
"inchikey": "PGMRNWAAHFDBRJ-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cnc(Cl)c2ncn(C)c12"
},
"smiles": "CCOC(=O)c1cnc(Cl)c2ncn(C)c12",
"reactionStepId": "sa_697ffe3a10e772f68c2390d6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080221097A1;0262;609260\",\"rsmi\":\"CCO[CH:15](OCC)OCC.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([Cl:10])[c:11]([NH2:16])[c:12]1[NH:13][CH3:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([Cl:10])[c:11]2[c:12]1[n:13]([CH3:14])[cH:15][n:16]2\"},\"mapped_reaction_smiles\":\"CCO[CH:15](OCC)OCC.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([Cl:10])[c:11]([NH2:16])[c:12]1[NH:13][CH3:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([Cl:10])[c:11]2[c:12]1[n:13]([CH3:14])[cH:15][n:16]2\"}",
"reactionStep": {
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"reactionHash": "a02915d532c323d28769888ce6375dfa894ed904b33eceb7a17de3846b6dd48a"
},
"children": [
{
"id": "5507",
"routeId": "sa_c74d285e1fbd32a40baaf5a2",
"moleculeId": "sa_dc98236d967ab0cdbd0fcd04",
"parentId": "5506",
"isLeaf": true,
"molecule": {
"id": "sa_dc98236d967ab0cdbd0fcd04",
"inchikey": "GKASDNZWUGIAMG-UHFFFAOYSA-N",
"smiles": "CCOC(OCC)OCC"
},
"smiles": "CCOC(OCC)OCC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5508",
"routeId": "sa_c74d285e1fbd32a40baaf5a2",
"moleculeId": "sa_7570c1eb10195b42417d700e",
"parentId": "5506",
"isLeaf": false,
"molecule": {
"id": "sa_7570c1eb10195b42417d700e",
"inchikey": "LNJFEZBSTJTQOB-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cnc(Cl)c(N)c1NC"
},
"smiles": "CCOC(=O)c1cnc(Cl)c(N)c1NC",
"reactionStepId": "sa_bd8e850c94053fa5a9d45aaa",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080221097A1;0258;609258\",\"rsmi\":\"O=[N+:11]([O-])[c:10]1[c:7]([NH:8][CH3:9])[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:15][n:14][c:12]1[Cl:13]>CCCCCC.CCO.[Ni]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([NH:8][CH3:9])[c:10]([NH2:11])[c:12]([Cl:13])[n:14][cH:15]1\"},\"mapped_reaction_smiles\":\"O=[N+:11]([O-])[c:10]1[c:7]([NH:8][CH3:9])[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:15][n:14][c:12]1[Cl:13]>CCCCCC.CCO.[Ni]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([NH:8][CH3:9])[c:10]([NH2:11])[c:12]([Cl:13])[n:14][cH:15]1\"}",
"reactionStep": {
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"children": [
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"routeId": "sa_c74d285e1fbd32a40baaf5a2",
"moleculeId": "sa_6216e48f0c41ad87c4d7d889",
"parentId": "5508",
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"molecule": {
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"inchikey": "ZSKQGDAGYNBORF-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cnc(Cl)c([N+](=O)[O-])c1NC"
},
"smiles": "CCOC(=O)c1cnc(Cl)c([N+](=O)[O-])c1NC",
"reactionStepId": "sa_91a4f8d7c33f5eb544185daa",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080221097A1;0253;609256\",\"rsmi\":\"Cl[c:7]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:17][n:16][c:14]([Cl:15])[c:10]1[N+:11](=[O:12])[O-:13].[NH2:8][CH3:9]>CCN(CC)CC.CCO>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([NH:8][CH3:9])[c:10]([N+:11](=[O:12])[O-:13])[c:14]([Cl:15])[n:16][cH:17]1\"},\"mapped_reaction_smiles\":\"Cl[c:7]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:17][n:16][c:14]([Cl:15])[c:10]1[N+:11](=[O:12])[O-:13].[NH2:8][CH3:9]>CCN(CC)CC.CCO>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([NH:8][CH3:9])[c:10]([N+:11](=[O:12])[O-:13])[c:14]([Cl:15])[n:16][cH:17]1\"}",
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"children": [
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"parentId": "5509",
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"molecule": {
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"inchikey": "BAVYZALUXZFZLV-UHFFFAOYSA-N",
"smiles": "CN"
},
"smiles": "CN",
"reactionStepId": null,
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"metadata": null,
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{
"id": "5511",
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"molecule": {
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"inchikey": "VMNMZVKEDHEOEJ-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cnc(Cl)c([N+](=O)[O-])c1Cl"
},
"smiles": "CCOC(=O)c1cnc(Cl)c([N+](=O)[O-])c1Cl",
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}
]
},
{
"id": "5512",
"routeId": "sa_c74d285e1fbd32a40baaf5a2",
"moleculeId": "sa_71a94b96aaf33e48d671bf46",
"parentId": "5505",
"isLeaf": true,
"molecule": {
"id": "sa_71a94b96aaf33e48d671bf46",
"inchikey": "PNPCRKVUWYDDST-UHFFFAOYSA-N",
"smiles": "Nc1cccc(Cl)c1"
},
"smiles": "Nc1cccc(Cl)c1",
"reactionStepId": null,
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}
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},
{
"id": "5513",
"routeId": "sa_c74d285e1fbd32a40baaf5a2",
"moleculeId": "sa_39d71c291f7fdf13918cc969",
"parentId": "5503",
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"molecule": {
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"inchikey": "YNAVUWVOSKDBBP-UHFFFAOYSA-N",
"smiles": "C1COCCN1"
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"smiles": "C1COCCN1",
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]
}
}