Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
C[C@H]1COCCN1c1ccnc(-c2ccc(NC(=O)NCCO)cc2)n1
InChiKey
LNQLODSTTNHLQE-ZDUSSCGKSA-N
Route Signature
a766b2c4f3c8e6f5c9964c91eb508521ddeb89e7fd7ce82c77b37d1846a15d0f
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_27bac55a17bba506ab85f7dc",
"signature": "a766b2c4f3c8e6f5c9964c91eb508521ddeb89e7fd7ce82c77b37d1846a15d0f",
"contentHash": "07d4918910333c4cf37ca5cd88dad16dc2a5240b8f065e713a72454bf393464a",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_8068508e19aac05a00001aac",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-01604",
"moleculeId": "sa_7188b83c152dd5097103a4ea",
"smiles": "C[C@H]1COCCN1c1ccnc(-c2ccc(NC(=O)NCCO)cc2)n1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_7188b83c152dd5097103a4ea",
"inchikey": "LNQLODSTTNHLQE-ZDUSSCGKSA-N",
"smiles": "C[C@H]1COCCN1c1ccnc(-c2ccc(NC(=O)NCCO)cc2)n1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "1517",
"routeId": "sa_27bac55a17bba506ab85f7dc",
"moleculeId": "sa_7188b83c152dd5097103a4ea",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_7188b83c152dd5097103a4ea",
"inchikey": "LNQLODSTTNHLQE-ZDUSSCGKSA-N",
"smiles": "C[C@H]1COCCN1c1ccnc(-c2ccc(NC(=O)NCCO)cc2)n1"
},
"smiles": "C[C@H]1COCCN1c1ccnc(-c2ccc(NC(=O)NCCO)cc2)n1",
"reactionStepId": "sa_aa6a2c2e92a622f7fa9956df",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130196982A1;0596;1401322\",\"rsmi\":\"CC1(C)OB([c:11]2[cH:12][cH:13][c:14]([NH:15][C:16](=[O:17])[NH:18][CH2:19][CH2:20][OH:21])[cH:22][cH:23]2)OC1(C)C.Cl[c:10]1[n:9][c:8]([N:7]2[C@@H:2]([CH3:1])[CH2:3][O:4][CH2:5][CH2:6]2)[cH:26][cH:25][n:24]1>>[CH3:1][C@H:2]1[CH2:3][O:4][CH2:5][CH2:6][N:7]1[c:8]1[n:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([NH:15][C:16](=[O:17])[NH:18][CH2:19][CH2:20][OH:21])[cH:22][cH:23]2)[n:24][cH:25][cH:26]1\"},\"mapped_reaction_smiles\":\"CC1(C)OB([c:11]2[cH:12][cH:13][c:14]([NH:15][C:16](=[O:17])[NH:18][CH2:19][CH2:20][OH:21])[cH:22][cH:23]2)OC1(C)C.Cl[c:10]1[n:9][c:8]([N:7]2[C@@H:2]([CH3:1])[CH2:3][O:4][CH2:5][CH2:6]2)[cH:26][cH:25][n:24]1>>[CH3:1][C@H:2]1[CH2:3][O:4][CH2:5][CH2:6][N:7]1[c:8]1[n:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([NH:15][C:16](=[O:17])[NH:18][CH2:19][CH2:20][OH:21])[cH:22][cH:23]2)[n:24][cH:25][cH:26]1\"}",
"reactionStep": {
"id": "sa_aa6a2c2e92a622f7fa9956df",
"reactionHash": "6d2400928e7f46906146f49f473361004804faeb7855049193d91968f4f7acc3"
},
"children": [
{
"id": "1518",
"routeId": "sa_27bac55a17bba506ab85f7dc",
"moleculeId": "sa_981cb6eb8049ca1481d405d7",
"parentId": "1517",
"isLeaf": false,
"molecule": {
"id": "sa_981cb6eb8049ca1481d405d7",
"inchikey": "NOKWPLSCENSNSZ-ZETCQYMHSA-N",
"smiles": "C[C@H]1COCCN1c1ccnc(Cl)n1"
},
"smiles": "C[C@H]1COCCN1c1ccnc(Cl)n1",
"reactionStepId": "sa_251120543ec6d413947c72fb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130196982A1;0287;1401284\",\"rsmi\":\"Cl[c:8]1[n:9][c:10]([Cl:11])[n:12][cH:13][cH:14]1.[CH3:1][C@H:2]1[CH2:3][O:4][CH2:5][CH2:6][NH:7]1>CC(C)O.CCN(C(C)C)C(C)C>[CH3:1][C@H:2]1[CH2:3][O:4][CH2:5][CH2:6][N:7]1[c:8]1[n:9][c:10]([Cl:11])[n:12][cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"Cl[c:8]1[n:9][c:10]([Cl:11])[n:12][cH:13][cH:14]1.[CH3:1][C@H:2]1[CH2:3][O:4][CH2:5][CH2:6][NH:7]1>CC(C)O.CCN(C(C)C)C(C)C>[CH3:1][C@H:2]1[CH2:3][O:4][CH2:5][CH2:6][N:7]1[c:8]1[n:9][c:10]([Cl:11])[n:12][cH:13][cH:14]1\"}",
"reactionStep": {
"id": "sa_251120543ec6d413947c72fb",
"reactionHash": "ab6ce6cca8fe0dd96072c7ac5670ff714f378d3a696be71038f87c97e25092ca"
},
"children": [
{
"id": "1519",
"routeId": "sa_27bac55a17bba506ab85f7dc",
"moleculeId": "sa_aeda22e5315bd455d285f564",
"parentId": "1518",
"isLeaf": true,
"molecule": {
"id": "sa_aeda22e5315bd455d285f564",
"inchikey": "BTTNYQZNBZNDOR-UHFFFAOYSA-N",
"smiles": "Clc1ccnc(Cl)n1"
},
"smiles": "Clc1ccnc(Cl)n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1520",
"routeId": "sa_27bac55a17bba506ab85f7dc",
"moleculeId": "sa_469c1cb13b52d21df345947a",
"parentId": "1518",
"isLeaf": true,
"molecule": {
"id": "sa_469c1cb13b52d21df345947a",
"inchikey": "SFWWGMKXCYLZEG-YFKPBYRVSA-N",
"smiles": "C[C@H]1COCCN1"
},
"smiles": "C[C@H]1COCCN1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "1521",
"routeId": "sa_27bac55a17bba506ab85f7dc",
"moleculeId": "sa_3334c4c61b7ed32feff06526",
"parentId": "1517",
"isLeaf": false,
"molecule": {
"id": "sa_3334c4c61b7ed32feff06526",
"inchikey": "XHHSGLRYKNPDMA-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2ccc(NC(=O)NCCO)cc2)OC1(C)C"
},
"smiles": "CC1(C)OB(c2ccc(NC(=O)NCCO)cc2)OC1(C)C",
"reactionStepId": "sa_bf3d0de3bd69ecf9889f6fb6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130196982A1;0333;1401292\",\"rsmi\":\"[NH2:13][CH2:14][CH2:15][OH:16].c1ccc(O[C:11]([NH:10][c:9]2[cH:8][cH:7][c:6]([B:5]3[O:4][C:2]([CH3:1])([CH3:3])[C:20]([CH3:21])([CH3:22])[O:19]3)[cH:18][cH:17]2)=[O:12])cc1>>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[NH:13][CH2:14][CH2:15][OH:16])[cH:17][cH:18]2)[O:19][C:20]1([CH3:21])[CH3:22]\"},\"mapped_reaction_smiles\":\"[NH2:13][CH2:14][CH2:15][OH:16].c1ccc(O[C:11]([NH:10][c:9]2[cH:8][cH:7][c:6]([B:5]3[O:4][C:2]([CH3:1])([CH3:3])[C:20]([CH3:21])([CH3:22])[O:19]3)[cH:18][cH:17]2)=[O:12])cc1>>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[NH:13][CH2:14][CH2:15][OH:16])[cH:17][cH:18]2)[O:19][C:20]1([CH3:21])[CH3:22]\"}",
"reactionStep": {
"id": "sa_bf3d0de3bd69ecf9889f6fb6",
"reactionHash": "72399ea524cc30b9d859628c84e10ec61083981323e9e6936a97b7463402ec75"
},
"children": [
{
"id": "1522",
"routeId": "sa_27bac55a17bba506ab85f7dc",
"moleculeId": "sa_465b8a07686da20bd4f5a4c0",
"parentId": "1521",
"isLeaf": true,
"molecule": {
"id": "sa_465b8a07686da20bd4f5a4c0",
"inchikey": "HZAXFHJVJLSVMW-UHFFFAOYSA-N",
"smiles": "NCCO"
},
"smiles": "NCCO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1523",
"routeId": "sa_27bac55a17bba506ab85f7dc",
"moleculeId": "sa_039e1f705fdafde5d8a8ea1e",
"parentId": "1521",
"isLeaf": false,
"molecule": {
"id": "sa_039e1f705fdafde5d8a8ea1e",
"inchikey": "JTURKCDVNAXKIF-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2ccc(NC(=O)Oc3ccccc3)cc2)OC1(C)C"
},
"smiles": "CC1(C)OB(c2ccc(NC(=O)Oc3ccccc3)cc2)OC1(C)C",
"reactionStepId": "sa_092ebc15b3a9242914dfffc6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130196982A1;0330;1401291\",\"rsmi\":\"F[c:7]1[c:6]([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:23]([CH3:24])([CH3:25])[O:22]2)[cH:21][cH:20][c:9]([NH:10][C:11](=[O:12])[O:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:8]1>CC1(C)OB(c2ccc(N)cc2)OC1(C)C>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[O:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20][cH:21]2)[O:22][C:23]1([CH3:24])[CH3:25]\"},\"mapped_reaction_smiles\":\"F[c:7]1[c:6]([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:23]([CH3:24])([CH3:25])[O:22]2)[cH:21][cH:20][c:9]([NH:10][C:11](=[O:12])[O:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[cH:8]1>CC1(C)OB(c2ccc(N)cc2)OC1(C)C>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[O:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20][cH:21]2)[O:22][C:23]1([CH3:24])[CH3:25]\"}",
"reactionStep": {
"id": "sa_092ebc15b3a9242914dfffc6",
"reactionHash": "4eedda27ea701a1fc69ee5567ffbae02dc9f4a734f1b930c70cf7965a5de61c5"
},
"children": [
{
"id": "1524",
"routeId": "sa_27bac55a17bba506ab85f7dc",
"moleculeId": "sa_cadce737e10bdfa879d52def",
"parentId": "1523",
"isLeaf": false,
"molecule": {
"id": "sa_cadce737e10bdfa879d52def",
"inchikey": "KELNKADYNHJFRO-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2ccc(NC(=O)Oc3ccccc3)cc2F)OC1(C)C"
},
"smiles": "CC1(C)OB(c2ccc(NC(=O)Oc3ccccc3)cc2F)OC1(C)C",
"reactionStepId": "sa_e6ead33c65cf46e714a96b5e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130196982A1;0315;1401289\",\"rsmi\":\"Cl[C:12](=[O:13])[O:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[c:7]([F:8])[cH:9][c:10]([NH2:11])[cH:21][cH:22]2)[O:23][C:24]1([CH3:25])[CH3:26]>C1CCOC1.O=C(O)O.[Na+]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[c:7]([F:8])[cH:9][c:10]([NH:11][C:12](=[O:13])[O:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][cH:22]2)[O:23][C:24]1([CH3:25])[CH3:26]\"},\"mapped_reaction_smiles\":\"Cl[C:12](=[O:13])[O:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[c:7]([F:8])[cH:9][c:10]([NH2:11])[cH:21][cH:22]2)[O:23][C:24]1([CH3:25])[CH3:26]>C1CCOC1.O=C(O)O.[Na+]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[c:7]([F:8])[cH:9][c:10]([NH:11][C:12](=[O:13])[O:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][cH:22]2)[O:23][C:24]1([CH3:25])[CH3:26]\"}",
"reactionStep": {
"id": "sa_e6ead33c65cf46e714a96b5e",
"reactionHash": "5e0c4e5d27dc6c9c4e2052aacfc38bfee015714ef414b32bd13e2ddcbdbc1fef"
},
"children": [
{
"id": "1525",
"routeId": "sa_27bac55a17bba506ab85f7dc",
"moleculeId": "sa_c3f902b5f9863db0f23f1ee5",
"parentId": "1524",
"isLeaf": true,
"molecule": {
"id": "sa_c3f902b5f9863db0f23f1ee5",
"inchikey": "AHWALFGBDFAJAI-UHFFFAOYSA-N",
"smiles": "O=C(Cl)Oc1ccccc1"
},
"smiles": "O=C(Cl)Oc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1526",
"routeId": "sa_27bac55a17bba506ab85f7dc",
"moleculeId": "sa_d299267ecf7804ed2751e963",
"parentId": "1524",
"isLeaf": true,
"molecule": {
"id": "sa_d299267ecf7804ed2751e963",
"inchikey": "FLMNWVXAEGUVNY-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2ccc(N)cc2F)OC1(C)C"
},
"smiles": "CC1(C)OB(c2ccc(N)cc2F)OC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
}