Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCn1ncc2c(NC3CC3)c(C3=NOC4(CCCCC4)C3)cnc21
InChiKey
HTBLBHHGZZBQSS-UHFFFAOYSA-N
Route Signature
3c41d2a82eb5abebd621022c9fb5b8906fefe6f44a3d8c3ed3639b782a61866f
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_582d463fa8bc7f468650557a",
"signature": "3c41d2a82eb5abebd621022c9fb5b8906fefe6f44a3d8c3ed3639b782a61866f",
"contentHash": "57abef42de480d2b83b774e8aab9d63be419244e6e835ae7897e7b0b8631aa94",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_86b6fb7d89ed4e2a8f0ef1b9",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00975",
"moleculeId": "sa_091c6e6498d62782bbfcee1d",
"smiles": "CCn1ncc2c(NC3CC3)c(C3=NOC4(CCCCC4)C3)cnc21",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_091c6e6498d62782bbfcee1d",
"inchikey": "HTBLBHHGZZBQSS-UHFFFAOYSA-N",
"smiles": "CCn1ncc2c(NC3CC3)c(C3=NOC4(CCCCC4)C3)cnc21"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "5182",
"routeId": "sa_582d463fa8bc7f468650557a",
"moleculeId": "sa_091c6e6498d62782bbfcee1d",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_091c6e6498d62782bbfcee1d",
"inchikey": "HTBLBHHGZZBQSS-UHFFFAOYSA-N",
"smiles": "CCn1ncc2c(NC3CC3)c(C3=NOC4(CCCCC4)C3)cnc21"
},
"smiles": "CCn1ncc2c(NC3CC3)c(C3=NOC4(CCCCC4)C3)cnc21",
"reactionStepId": "sa_4658fda931bd6c5c72b5895c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100022571A1;0109;827832\",\"rsmi\":\"[C:14]1(=[CH2:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1.[CH3:1][CH2:2][n:3]1[n:4][cH:5][c:6]2[c:7]1[n:8][cH:9][c:10]([CH:11]=[N:12][OH:13])[c:21]2[NH:22][CH:23]1[CH2:24][CH2:25]1>C1CCOC1.[Na+].OCl>[CH3:1][CH2:2][n:3]1[n:4][cH:5][c:6]2[c:7]1[n:8][cH:9][c:10]([C:11]1=[N:12][O:13][C:14]3([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]3)[CH2:20]1)[c:21]2[NH:22][CH:23]1[CH2:24][CH2:25]1\"},\"mapped_reaction_smiles\":\"[C:14]1(=[CH2:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1.[CH3:1][CH2:2][n:3]1[n:4][cH:5][c:6]2[c:7]1[n:8][cH:9][c:10]([CH:11]=[N:12][OH:13])[c:21]2[NH:22][CH:23]1[CH2:24][CH2:25]1>C1CCOC1.[Na+].OCl>[CH3:1][CH2:2][n:3]1[n:4][cH:5][c:6]2[c:7]1[n:8][cH:9][c:10]([C:11]1=[N:12][O:13][C:14]3([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]3)[CH2:20]1)[c:21]2[NH:22][CH:23]1[CH2:24][CH2:25]1\"}",
"reactionStep": {
"id": "sa_4658fda931bd6c5c72b5895c",
"reactionHash": "1b995a451d102abb41633022401e3ae77cfbd20e7957eae10e934308c6c39bbd"
},
"children": [
{
"id": "5183",
"routeId": "sa_582d463fa8bc7f468650557a",
"moleculeId": "sa_dc77427d19fc0c0dafa3ff89",
"parentId": "5182",
"isLeaf": false,
"molecule": {
"id": "sa_dc77427d19fc0c0dafa3ff89",
"inchikey": "HBWKCUWXXHRWAO-UHFFFAOYSA-N",
"smiles": "CCn1ncc2c(NC3CC3)c(C=NO)cnc21"
},
"smiles": "CCn1ncc2c(NC3CC3)c(C=NO)cnc21",
"reactionStepId": "sa_3d6330440dd1fbee34e676aa",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100022571A1;0104;827831\",\"rsmi\":\"O=[CH:13][c:12]1[c:7]([NH:8][CH:9]2[CH2:10][CH2:11]2)[c:6]2[cH:5][n:4][n:3]([CH2:2][CH3:1])[c:18]2[n:17][cH:16]1.[NH2:14][OH:15]>CC(=O)O.CCO.Cl.[Na+]>[CH3:1][CH2:2][n:3]1[n:4][cH:5][c:6]2[c:7]([NH:8][CH:9]3[CH2:10][CH2:11]3)[c:12]([CH:13]=[N:14][OH:15])[cH:16][n:17][c:18]12\"},\"mapped_reaction_smiles\":\"O=[CH:13][c:12]1[c:7]([NH:8][CH:9]2[CH2:10][CH2:11]2)[c:6]2[cH:5][n:4][n:3]([CH2:2][CH3:1])[c:18]2[n:17][cH:16]1.[NH2:14][OH:15]>CC(=O)O.CCO.Cl.[Na+]>[CH3:1][CH2:2][n:3]1[n:4][cH:5][c:6]2[c:7]([NH:8][CH:9]3[CH2:10][CH2:11]3)[c:12]([CH:13]=[N:14][OH:15])[cH:16][n:17][c:18]12\"}",
"reactionStep": {
"id": "sa_3d6330440dd1fbee34e676aa",
"reactionHash": "854038524e4a623452018db6c3b6bea7c092383c631009fb4804af150dfe5572"
},
"children": [
{
"id": "5184",
"routeId": "sa_582d463fa8bc7f468650557a",
"moleculeId": "sa_04a18e3f07bde82ca29399ee",
"parentId": "5183",
"isLeaf": true,
"molecule": {
"id": "sa_04a18e3f07bde82ca29399ee",
"inchikey": "AVXURJPOCDRRFD-UHFFFAOYSA-N",
"smiles": "NO"
},
"smiles": "NO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5185",
"routeId": "sa_582d463fa8bc7f468650557a",
"moleculeId": "sa_a777f21414c40a79c16e49e2",
"parentId": "5183",
"isLeaf": false,
"molecule": {
"id": "sa_a777f21414c40a79c16e49e2",
"inchikey": "KAFIDEYOEYNCFW-UHFFFAOYSA-N",
"smiles": "CCn1ncc2c(NC3CC3)c(C=O)cnc21"
},
"smiles": "CCn1ncc2c(NC3CC3)c(C=O)cnc21",
"reactionStepId": "sa_4def4379a09cdec46fb4104d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100022571A1;0099;827830\",\"rsmi\":\"CON(C)[C:13]([c:12]1[c:7]([NH:8][CH:9]2[CH2:10][CH2:11]2)[c:6]2[cH:5][n:4][n:3]([CH2:2][CH3:1])[c:17]2[n:16][cH:15]1)=[O:14]>COCCO[AlH]OCCOC.Cc1ccccc1.O=C(O)CC(O)(CC(=O)O)C(=O)O.[Na+]>[CH3:1][CH2:2][n:3]1[n:4][cH:5][c:6]2[c:7]([NH:8][CH:9]3[CH2:10][CH2:11]3)[c:12]([CH:13]=[O:14])[cH:15][n:16][c:17]12\"},\"mapped_reaction_smiles\":\"CON(C)[C:13]([c:12]1[c:7]([NH:8][CH:9]2[CH2:10][CH2:11]2)[c:6]2[cH:5][n:4][n:3]([CH2:2][CH3:1])[c:17]2[n:16][cH:15]1)=[O:14]>COCCO[AlH]OCCOC.Cc1ccccc1.O=C(O)CC(O)(CC(=O)O)C(=O)O.[Na+]>[CH3:1][CH2:2][n:3]1[n:4][cH:5][c:6]2[c:7]([NH:8][CH:9]3[CH2:10][CH2:11]3)[c:12]([CH:13]=[O:14])[cH:15][n:16][c:17]12\"}",
"reactionStep": {
"id": "sa_4def4379a09cdec46fb4104d",
"reactionHash": "17a0002a363cf270458a83e44681d0e0897c420415a88021205adf80e4b43560"
},
"children": [
{
"id": "5186",
"routeId": "sa_582d463fa8bc7f468650557a",
"moleculeId": "sa_580d1cd022e96a6607175114",
"parentId": "5185",
"isLeaf": false,
"molecule": {
"id": "sa_580d1cd022e96a6607175114",
"inchikey": "RNYKJZDYJNBQKR-UHFFFAOYSA-N",
"smiles": "CCn1ncc2c(NC3CC3)c(C(=O)N(C)OC)cnc21"
},
"smiles": "CCn1ncc2c(NC3CC3)c(C(=O)N(C)OC)cnc21",
"reactionStepId": "sa_a77f90dae16a1acfbcbbf3f2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100022571A1;0094;827829\",\"rsmi\":\"O[C:13]([c:12]1[c:7]([NH:8][CH:9]2[CH2:10][CH2:11]2)[c:6]2[cH:5][n:4][n:3]([CH2:2][CH3:1])[c:21]2[n:20][cH:19]1)=[O:14].[NH:15]([CH3:16])[O:17][CH3:18]>CCN=C=NCCCN(C)C.CN(C)C=O.CN1CCOCC1.Cl.Cl.O.Oc1cccc2[nH]nnc12>[CH3:1][CH2:2][n:3]1[n:4][cH:5][c:6]2[c:7]([NH:8][CH:9]3[CH2:10][CH2:11]3)[c:12]([C:13](=[O:14])[N:15]([CH3:16])[O:17][CH3:18])[cH:19][n:20][c:21]12\"},\"mapped_reaction_smiles\":\"O[C:13]([c:12]1[c:7]([NH:8][CH:9]2[CH2:10][CH2:11]2)[c:6]2[cH:5][n:4][n:3]([CH2:2][CH3:1])[c:21]2[n:20][cH:19]1)=[O:14].[NH:15]([CH3:16])[O:17][CH3:18]>CCN=C=NCCCN(C)C.CN(C)C=O.CN1CCOCC1.Cl.Cl.O.Oc1cccc2[nH]nnc12>[CH3:1][CH2:2][n:3]1[n:4][cH:5][c:6]2[c:7]([NH:8][CH:9]3[CH2:10][CH2:11]3)[c:12]([C:13](=[O:14])[N:15]([CH3:16])[O:17][CH3:18])[cH:19][n:20][c:21]12\"}",
"reactionStep": {
"id": "sa_a77f90dae16a1acfbcbbf3f2",
"reactionHash": "c448b30612e3cef753c29ba317c1cdc4326a92b5ea46c038d7104dbcc0767584"
},
"children": [
{
"id": "5187",
"routeId": "sa_582d463fa8bc7f468650557a",
"moleculeId": "sa_28811014447e7b2f3cc61067",
"parentId": "5186",
"isLeaf": false,
"molecule": {
"id": "sa_28811014447e7b2f3cc61067",
"inchikey": "GWFMYGFZLDQWHP-UHFFFAOYSA-N",
"smiles": "CCn1ncc2c(NC3CC3)c(C(=O)O)cnc21"
},
"smiles": "CCn1ncc2c(NC3CC3)c(C(=O)O)cnc21",
"reactionStepId": "sa_417491f01b37221f421a8d00",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100022571A1;0089;827828\",\"rsmi\":\"CC[O:15][C:13]([c:12]1[c:7]([NH:8][CH:9]2[CH2:10][CH2:11]2)[c:6]2[cH:5][n:4][n:3]([CH2:2][CH3:1])[c:18]2[n:17][cH:16]1)=[O:14]>CCO.O.[Na+].O>[CH3:1][CH2:2][n:3]1[n:4][cH:5][c:6]2[c:7]([NH:8][CH:9]3[CH2:10][CH2:11]3)[c:12]([C:13](=[O:14])[OH:15])[cH:16][n:17][c:18]12\"},\"mapped_reaction_smiles\":\"CC[O:15][C:13]([c:12]1[c:7]([NH:8][CH:9]2[CH2:10][CH2:11]2)[c:6]2[cH:5][n:4][n:3]([CH2:2][CH3:1])[c:18]2[n:17][cH:16]1)=[O:14]>CCO.O.[Na+].O>[CH3:1][CH2:2][n:3]1[n:4][cH:5][c:6]2[c:7]([NH:8][CH:9]3[CH2:10][CH2:11]3)[c:12]([C:13](=[O:14])[OH:15])[cH:16][n:17][c:18]12\"}",
"reactionStep": {
"id": "sa_417491f01b37221f421a8d00",
"reactionHash": "f382a64cf503a71a2786927b0e12390d2c3f6361692e15049331bcf73b8f306a"
},
"children": [
{
"id": "5188",
"routeId": "sa_582d463fa8bc7f468650557a",
"moleculeId": "sa_f3e57438e6122fd60c2cf4f8",
"parentId": "5187",
"isLeaf": false,
"molecule": {
"id": "sa_f3e57438e6122fd60c2cf4f8",
"inchikey": "BGAIHLXXDKWJJX-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cnc2c(cnn2CC)c1NC1CC1"
},
"smiles": "CCOC(=O)c1cnc2c(cnn2CC)c1NC1CC1",
"reactionStepId": "sa_39b172fe0f9918d08ad5aa06",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100022571A1;0084;827827\",\"rsmi\":\"Cl[c:11]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][n:8][c:9]2[c:10]1[cH:16][n:17][n:18]2[CH2:19][CH3:20].[NH2:12][CH:13]1[CH2:14][CH2:15]1>CC#N>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]2[c:10]([c:11]1[NH:12][CH:13]1[CH2:14][CH2:15]1)[cH:16][n:17][n:18]2[CH2:19][CH3:20]\"},\"mapped_reaction_smiles\":\"Cl[c:11]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][n:8][c:9]2[c:10]1[cH:16][n:17][n:18]2[CH2:19][CH3:20].[NH2:12][CH:13]1[CH2:14][CH2:15]1>CC#N>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]2[c:10]([c:11]1[NH:12][CH:13]1[CH2:14][CH2:15]1)[cH:16][n:17][n:18]2[CH2:19][CH3:20]\"}",
"reactionStep": {
"id": "sa_39b172fe0f9918d08ad5aa06",
"reactionHash": "b3939ee9a2fe52cd4021ade1f49f4ae07c593f25cf0c951a4948964e8639f212"
},
"children": [
{
"id": "5189",
"routeId": "sa_582d463fa8bc7f468650557a",
"moleculeId": "sa_f7b02628c6b00fb9d50a0f6c",
"parentId": "5188",
"isLeaf": true,
"molecule": {
"id": "sa_f7b02628c6b00fb9d50a0f6c",
"inchikey": "HTJDQJBWANPRPF-UHFFFAOYSA-N",
"smiles": "NC1CC1"
},
"smiles": "NC1CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "5190",
"routeId": "sa_582d463fa8bc7f468650557a",
"moleculeId": "sa_0a1e857817c1e327da5a6a09",
"parentId": "5188",
"isLeaf": true,
"molecule": {
"id": "sa_0a1e857817c1e327da5a6a09",
"inchikey": "RCQMGWFLFNPCJC-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cnc2c(cnn2CC)c1Cl"
},
"smiles": "CCOC(=O)c1cnc2c(cnn2CC)c1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "5191",
"routeId": "sa_582d463fa8bc7f468650557a",
"moleculeId": "sa_93e456f7e04541ecb6ebcb69",
"parentId": "5186",
"isLeaf": true,
"molecule": {
"id": "sa_93e456f7e04541ecb6ebcb69",
"inchikey": "KRKPYFLIYNGWTE-UHFFFAOYSA-N",
"smiles": "CNOC"
},
"smiles": "CNOC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "5192",
"routeId": "sa_582d463fa8bc7f468650557a",
"moleculeId": "sa_0bc4c2f52541b7ae32807d5d",
"parentId": "5182",
"isLeaf": true,
"molecule": {
"id": "sa_0bc4c2f52541b7ae32807d5d",
"inchikey": "YULMNMJFAZWLLN-UHFFFAOYSA-N",
"smiles": "C=C1CCCCC1"
},
"smiles": "C=C1CCCCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}