Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COCCN1CCN(c2ccc(N3C[C@H](CN=[N+]=[N-])OC3=O)cc2F)CC1=O
InChiKey
BDEHKPIOTSEGFE-ZDUSSCGKSA-N
Route Signature
a1c61fdf06b9ba9781fd30145e2f448725efdecdf4fe30262624afcbf71d5daa
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_15dc2da6596084a43fb13b22",
"signature": "a1c61fdf06b9ba9781fd30145e2f448725efdecdf4fe30262624afcbf71d5daa",
"contentHash": "623750b88eabb59f99a7298fab9566db689b1009239ce269f9e42afa77451781",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_541b5e5cbb92a6d8e8a485b1",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-09631",
"moleculeId": "sa_929fb2eb4bd21e0152f47030",
"smiles": "COCCN1CCN(c2ccc(N3C[C@H](CN=[N+]=[N-])OC3=O)cc2F)CC1=O",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_929fb2eb4bd21e0152f47030",
"inchikey": "BDEHKPIOTSEGFE-ZDUSSCGKSA-N",
"smiles": "COCCN1CCN(c2ccc(N3C[C@H](CN=[N+]=[N-])OC3=O)cc2F)CC1=O"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "16632",
"routeId": "sa_15dc2da6596084a43fb13b22",
"moleculeId": "sa_929fb2eb4bd21e0152f47030",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_929fb2eb4bd21e0152f47030",
"inchikey": "BDEHKPIOTSEGFE-ZDUSSCGKSA-N",
"smiles": "COCCN1CCN(c2ccc(N3C[C@H](CN=[N+]=[N-])OC3=O)cc2F)CC1=O"
},
"smiles": "COCCN1CCN(c2ccc(N3C[C@H](CN=[N+]=[N-])OC3=O)cc2F)CC1=O",
"reactionStepId": "sa_2b725646e2991126d33bb57c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06069145;;473955\",\"rsmi\":\"CS(=O)(=O)O[CH2:17][C@H:16]1[CH2:15][N:14]([c:13]2[cH:12][c:10]([F:11])[c:9]([N:8]3[CH2:7][CH2:6][N:5]([CH2:4][CH2:3][O:2][CH3:1])[C:27](=[O:28])[CH2:26]3)[cH:25][cH:24]2)[C:22](=[O:23])[O:21]1.[N-:18]=[N+:19]=[N-:20]>CN(C)C=O.[Na+]>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[c:10]([F:11])[cH:12][c:13]([N:14]3[CH2:15][C@H:16]([CH2:17][N:18]=[N+:19]=[N-:20])[O:21][C:22]3=[O:23])[cH:24][cH:25]2)[CH2:26][C:27]1=[O:28]\"},\"mapped_reaction_smiles\":\"CS(=O)(=O)O[CH2:17][C@H:16]1[CH2:15][N:14]([c:13]2[cH:12][c:10]([F:11])[c:9]([N:8]3[CH2:7][CH2:6][N:5]([CH2:4][CH2:3][O:2][CH3:1])[C:27](=[O:28])[CH2:26]3)[cH:25][cH:24]2)[C:22](=[O:23])[O:21]1.[N-:18]=[N+:19]=[N-:20]>CN(C)C=O.[Na+]>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[c:10]([F:11])[cH:12][c:13]([N:14]3[CH2:15][C@H:16]([CH2:17][N:18]=[N+:19]=[N-:20])[O:21][C:22]3=[O:23])[cH:24][cH:25]2)[CH2:26][C:27]1=[O:28]\"}",
"reactionStep": {
"id": "sa_2b725646e2991126d33bb57c",
"reactionHash": "6dc970b3af2948c554bb996294d3aa2f8df4135b14c5a6e990648e30517dc505"
},
"children": [
{
"id": "16633",
"routeId": "sa_15dc2da6596084a43fb13b22",
"moleculeId": "sa_50a8f83dd89c267fbada1205",
"parentId": "16632",
"isLeaf": true,
"molecule": {
"id": "sa_50a8f83dd89c267fbada1205",
"inchikey": "IVRMZWNICZWHMI-UHFFFAOYSA-N",
"smiles": "[N]N=[N-]"
},
"smiles": "[N-]=[N+]=[N-]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "16634",
"routeId": "sa_15dc2da6596084a43fb13b22",
"moleculeId": "sa_e92051d25c04c422429f76ad",
"parentId": "16632",
"isLeaf": false,
"molecule": {
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"inchikey": "OMFPYJXQRUFOIQ-CQSZACIVSA-N",
"smiles": "COCCN1CCN(c2ccc(N3C[C@H](COS(C)(=O)=O)OC3=O)cc2F)CC1=O"
},
"smiles": "COCCN1CCN(c2ccc(N3C[C@H](COS(C)(=O)=O)OC3=O)cc2F)CC1=O",
"reactionStepId": "sa_7ad4b5a611f90ba9e593673c",
"template": null,
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"reactionStep": {
"id": "sa_7ad4b5a611f90ba9e593673c",
"reactionHash": "d9ea8d92d1ec43808a8f70cb71aa4b5a1652ac6c99a2d0c5e1b7d4bd7763abf8"
},
"children": [
{
"id": "16635",
"routeId": "sa_15dc2da6596084a43fb13b22",
"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "16634",
"isLeaf": true,
"molecule": {
"id": "sa_d2a31ea58046b00856f61ca5",
"inchikey": "QARBMVPHQWIHKH-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Cl"
},
"smiles": "CS(=O)(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "16636",
"routeId": "sa_15dc2da6596084a43fb13b22",
"moleculeId": "sa_356997477388884cdea6e35c",
"parentId": "16634",
"isLeaf": false,
"molecule": {
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"inchikey": "ZIGBTBXKJLFMNZ-CYBMUJFWSA-N",
"smiles": "COCCN1CCN(c2ccc(N3C[C@H](CO)OC3=O)cc2F)CC1=O"
},
"smiles": "COCCN1CCN(c2ccc(N3C[C@H](CO)OC3=O)cc2F)CC1=O",
"reactionStepId": "sa_02deb0cad5d691708a754732",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06069145;;473953\",\"rsmi\":\"CCCC(=O)[O:18][CH2:17][C@H:16]1[CH2:15][O:19]1.c1ccc(CO[C:20]([NH:14][c:13]2[cH:12][c:10]([F:11])[c:9]([N:8]3[CH2:7][CH2:6][N:5]([CH2:4][CH2:3][O:2][CH3:1])[C:25](=[O:26])[CH2:24]3)[cH:23][cH:22]2)=[O:21])cc1>C1CCOC1.CN1CCCN(C)C1=O.O=C(O)O.[Li]CCCC.[Na+]>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[c:10]([F:11])[cH:12][c:13]([N:14]3[CH2:15][C@H:16]([CH2:17][OH:18])[O:19][C:20]3=[O:21])[cH:22][cH:23]2)[CH2:24][C:25]1=[O:26]\"},\"mapped_reaction_smiles\":\"CCCC(=O)[O:18][CH2:17][C@H:16]1[CH2:15][O:19]1.c1ccc(CO[C:20]([NH:14][c:13]2[cH:12][c:10]([F:11])[c:9]([N:8]3[CH2:7][CH2:6][N:5]([CH2:4][CH2:3][O:2][CH3:1])[C:25](=[O:26])[CH2:24]3)[cH:23][cH:22]2)=[O:21])cc1>C1CCOC1.CN1CCCN(C)C1=O.O=C(O)O.[Li]CCCC.[Na+]>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[c:10]([F:11])[cH:12][c:13]([N:14]3[CH2:15][C@H:16]([CH2:17][OH:18])[O:19][C:20]3=[O:21])[cH:22][cH:23]2)[CH2:24][C:25]1=[O:26]\"}",
"reactionStep": {
"id": "sa_02deb0cad5d691708a754732",
"reactionHash": "655b4a44d5c65d732230d4149423ed2f80177d6a9ea8ac2698227ca515ee0fb2"
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"children": [
{
"id": "16637",
"routeId": "sa_15dc2da6596084a43fb13b22",
"moleculeId": "sa_21b09fad2208acf1341023eb",
"parentId": "16636",
"isLeaf": false,
"molecule": {
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"inchikey": "CSIKIOASIZCGRC-UHFFFAOYSA-N",
"smiles": "COCCN1CCN(c2ccc(NC(=O)OCc3ccccc3)cc2F)CC1=O"
},
"smiles": "COCCN1CCN(c2ccc(NC(=O)OCc3ccccc3)cc2F)CC1=O",
"reactionStepId": "sa_403405eb7b0c27b050d0f564",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06069145;;473952\",\"rsmi\":\"Cl[C:15](=[O:16])[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[c:10]([F:11])[cH:12][c:13]([NH2:14])[cH:25][cH:26]2)[CH2:27][C:28]1=[O:29]>ClCCl.c1ccncc1>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[c:10]([F:11])[cH:12][c:13]([NH:14][C:15](=[O:16])[O:17][CH2:18][c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[cH:25][cH:26]2)[CH2:27][C:28]1=[O:29]\"},\"mapped_reaction_smiles\":\"Cl[C:15](=[O:16])[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[c:10]([F:11])[cH:12][c:13]([NH2:14])[cH:25][cH:26]2)[CH2:27][C:28]1=[O:29]>ClCCl.c1ccncc1>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[c:10]([F:11])[cH:12][c:13]([NH:14][C:15](=[O:16])[O:17][CH2:18][c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[cH:25][cH:26]2)[CH2:27][C:28]1=[O:29]\"}",
"reactionStep": {
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"reactionHash": "c7f425efa244011a51990e1df81e2d18d4719d876da8dceeb99392af2de4cbe5"
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"children": [
{
"id": "16638",
"routeId": "sa_15dc2da6596084a43fb13b22",
"moleculeId": "sa_1514403cfb4a58c3c6f69a71",
"parentId": "16637",
"isLeaf": true,
"molecule": {
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"inchikey": "HSDAJNMJOMSNEV-UHFFFAOYSA-N",
"smiles": "O=C(Cl)OCc1ccccc1"
},
"smiles": "O=C(Cl)OCc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "16639",
"routeId": "sa_15dc2da6596084a43fb13b22",
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"parentId": "16637",
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"molecule": {
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"inchikey": "JYMQRBBXRITBDH-UHFFFAOYSA-N",
"smiles": "COCCN1CCN(c2ccc(N)cc2F)CC1=O"
},
"smiles": "COCCN1CCN(c2ccc(N)cc2F)CC1=O",
"reactionStepId": "sa_3a6ed88a858983d9082d32b9",
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"metadata": "{\"annotations\":{\"ID\":\"US06069145;;473951\",\"rsmi\":\"O=[N+:14]([O-])[c:13]1[cH:12][c:10]([F:11])[c:9]([N:8]2[CH2:7][CH2:6][N:5]([CH2:4][CH2:3][O:2][CH3:1])[C:18](=[O:19])[CH2:17]2)[cH:16][cH:15]1>CCOC(C)=O.CN(C)C=O>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[c:10]([F:11])[cH:12][c:13]([NH2:14])[cH:15][cH:16]2)[CH2:17][C:18]1=[O:19]\"},\"mapped_reaction_smiles\":\"O=[N+:14]([O-])[c:13]1[cH:12][c:10]([F:11])[c:9]([N:8]2[CH2:7][CH2:6][N:5]([CH2:4][CH2:3][O:2][CH3:1])[C:18](=[O:19])[CH2:17]2)[cH:16][cH:15]1>CCOC(C)=O.CN(C)C=O>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[c:10]([F:11])[cH:12][c:13]([NH2:14])[cH:15][cH:16]2)[CH2:17][C:18]1=[O:19]\"}",
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"molecule": {
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"smiles": "COCCN1CCN(c2ccc([N+](=O)[O-])cc2F)CC1=O"
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"smiles": "COCCN1CCN(c2ccc([N+](=O)[O-])cc2F)CC1=O",
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"metadata": "{\"annotations\":{\"ID\":\"US06069145;;473950\",\"rsmi\":\"F[c:9]1[c:10]([F:11])[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]1.[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][NH:8][CH2:19][C:20]1=[O:21]>CC#N.CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C.O=C(O)C(F)(F)F>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[c:10]([F:11])[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]2)[CH2:19][C:20]1=[O:21]\"},\"mapped_reaction_smiles\":\"F[c:9]1[c:10]([F:11])[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]1.[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][NH:8][CH2:19][C:20]1=[O:21]>CC#N.CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C.O=C(O)C(F)(F)F>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[c:10]([F:11])[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18]2)[CH2:19][C:20]1=[O:21]\"}",
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{
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"smiles": "COCCN1CCNCC1=O"
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"smiles": "COCCN1CCNCC1=O",
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]
},
{
"id": "16643",
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"molecule": {
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"inchikey": "YLNSNVGRSIOCEU-ZCFIWIBFSA-N",
"smiles": "CCCC(=O)OC[C@H]1CO1"
},
"smiles": "CCCC(=O)OC[C@H]1CO1",
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]
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]
}
]
}
}