Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(=O)NC1CCN(Cc2ccc(CCn3ccc(OCc4ccccc4F)cc3=O)cc2)CC1
InChiKey
AFWNMTQTWDSAPP-UHFFFAOYSA-N
Route Signature
d1d74fd8b4cca64f4a06b6b13859273f4520e5cf831fb9847a2904f3e5ad2db7
Synthesis route with 7 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_05133ab5b95e03773f842af9",
"signature": "d1d74fd8b4cca64f4a06b6b13859273f4520e5cf831fb9847a2904f3e5ad2db7",
"contentHash": "5678e5126dbfc359d3e95a16b698cd78bb5906918103ecd17f6caa3ae61091c9",
"length": 7,
"isConvergent": false
},
"target": {
"id": "sa_25f77ddabf6f4f6e190f933b",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00317",
"moleculeId": "sa_f6b90a421e5855af7ffe78d0",
"smiles": "CC(=O)NC1CCN(Cc2ccc(CCn3ccc(OCc4ccccc4F)cc3=O)cc2)CC1",
"routeLength": 7,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_f6b90a421e5855af7ffe78d0",
"inchikey": "AFWNMTQTWDSAPP-UHFFFAOYSA-N",
"smiles": "CC(=O)NC1CCN(Cc2ccc(CCn3ccc(OCc4ccccc4F)cc3=O)cc2)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13022",
"routeId": "sa_05133ab5b95e03773f842af9",
"moleculeId": "sa_f6b90a421e5855af7ffe78d0",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_f6b90a421e5855af7ffe78d0",
"inchikey": "AFWNMTQTWDSAPP-UHFFFAOYSA-N",
"smiles": "CC(=O)NC1CCN(Cc2ccc(CCn3ccc(OCc4ccccc4F)cc3=O)cc2)CC1"
},
"smiles": "CC(=O)NC1CCN(Cc2ccc(CCn3ccc(OCc4ccccc4F)cc3=O)cc2)CC1",
"reactionStepId": "sa_cdb33e1b8ee8cedf350ae79d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080255083A1;0820;617709\",\"rsmi\":\"Br[CH2:9][c:10]1[cH:11][cH:12][c:13]([CH2:14][CH2:15][n:16]2[cH:17][cH:18][c:19]([O:20][CH2:21][c:22]3[c:23]([F:24])[cH:25][cH:26][cH:27][cH:28]3)[cH:29][c:30]2=[O:31])[cH:32][cH:33]1.[CH3:1][C:2](=[O:3])[NH:4][CH:5]1[CH2:6][CH2:7][NH:8][CH2:34][CH2:35]1>CCN(C(C)C)C(C)C>[CH3:1][C:2](=[O:3])[NH:4][CH:5]1[CH2:6][CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][c:13]([CH2:14][CH2:15][n:16]3[cH:17][cH:18][c:19]([O:20][CH2:21][c:22]4[c:23]([F:24])[cH:25][cH:26][cH:27][cH:28]4)[cH:29][c:30]3=[O:31])[cH:32][cH:33]2)[CH2:34][CH2:35]1\"},\"mapped_reaction_smiles\":\"Br[CH2:9][c:10]1[cH:11][cH:12][c:13]([CH2:14][CH2:15][n:16]2[cH:17][cH:18][c:19]([O:20][CH2:21][c:22]3[c:23]([F:24])[cH:25][cH:26][cH:27][cH:28]3)[cH:29][c:30]2=[O:31])[cH:32][cH:33]1.[CH3:1][C:2](=[O:3])[NH:4][CH:5]1[CH2:6][CH2:7][NH:8][CH2:34][CH2:35]1>CCN(C(C)C)C(C)C>[CH3:1][C:2](=[O:3])[NH:4][CH:5]1[CH2:6][CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][c:13]([CH2:14][CH2:15][n:16]3[cH:17][cH:18][c:19]([O:20][CH2:21][c:22]4[c:23]([F:24])[cH:25][cH:26][cH:27][cH:28]4)[cH:29][c:30]3=[O:31])[cH:32][cH:33]2)[CH2:34][CH2:35]1\"}",
"reactionStep": {
"id": "sa_cdb33e1b8ee8cedf350ae79d",
"reactionHash": "3be60f6a8da817a0f31737c2a8bd89c96c3ec66378a90cf599183836c17e0b6b"
},
"children": [
{
"id": "13023",
"routeId": "sa_05133ab5b95e03773f842af9",
"moleculeId": "sa_fb12f89a5a992fc2291bf927",
"parentId": "13022",
"isLeaf": false,
"molecule": {
"id": "sa_fb12f89a5a992fc2291bf927",
"inchikey": "DLQBOBNBBUIFRX-UHFFFAOYSA-N",
"smiles": "O=c1cc(OCc2ccccc2F)ccn1CCc1ccc(CBr)cc1"
},
"smiles": "O=c1cc(OCc2ccccc2F)ccn1CCc1ccc(CBr)cc1",
"reactionStepId": "sa_b4b832ee6fd852cfa3b32a2c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080255083A1;0811;617707\",\"rsmi\":\"BrP(Br)[Br:24].O[CH2:23][c:22]1[cH:21][cH:20][c:19]([CH2:18][CH2:17][n:16]2[c:2](=[O:1])[cH:3][c:4]([O:5][CH2:6][c:7]3[c:8]([F:9])[cH:10][cH:11][cH:12][cH:13]3)[cH:14][cH:15]2)[cH:26][cH:25]1>ClCCl.O=C(O)O.[Na+]>[O:1]=[c:2]1[cH:3][c:4]([O:5][CH2:6][c:7]2[c:8]([F:9])[cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][n:16]1[CH2:17][CH2:18][c:19]1[cH:20][cH:21][c:22]([CH2:23][Br:24])[cH:25][cH:26]1\"},\"mapped_reaction_smiles\":\"BrP(Br)[Br:24].O[CH2:23][c:22]1[cH:21][cH:20][c:19]([CH2:18][CH2:17][n:16]2[c:2](=[O:1])[cH:3][c:4]([O:5][CH2:6][c:7]3[c:8]([F:9])[cH:10][cH:11][cH:12][cH:13]3)[cH:14][cH:15]2)[cH:26][cH:25]1>ClCCl.O=C(O)O.[Na+]>[O:1]=[c:2]1[cH:3][c:4]([O:5][CH2:6][c:7]2[c:8]([F:9])[cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][n:16]1[CH2:17][CH2:18][c:19]1[cH:20][cH:21][c:22]([CH2:23][Br:24])[cH:25][cH:26]1\"}",
"reactionStep": {
"id": "sa_b4b832ee6fd852cfa3b32a2c",
"reactionHash": "9387c07fd7ec1f9cc3e9478aee57908d22eb570a533c44b7468f05c25c6b0d01"
},
"children": [
{
"id": "13024",
"routeId": "sa_05133ab5b95e03773f842af9",
"moleculeId": "sa_053c67ae4f7ad2829bc57fa8",
"parentId": "13023",
"isLeaf": false,
"molecule": {
"id": "sa_053c67ae4f7ad2829bc57fa8",
"inchikey": "DRLPSZQZWRFLJG-UHFFFAOYSA-N",
"smiles": "O=c1cc(OCc2ccccc2F)ccn1CCc1ccc(CO)cc1"
},
"smiles": "O=c1cc(OCc2ccccc2F)ccn1CCc1ccc(CO)cc1",
"reactionStepId": "sa_8bd5fc325dd05d2c25e4439a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080255083A1;0807;617706\",\"rsmi\":\"Br[CH2:6][c:7]1[c:8]([F:9])[cH:10][cH:11][cH:12][cH:13]1.[O:1]=[c:2]1[cH:3][c:4]([OH:5])[cH:14][cH:15][n:16]1[CH2:17][CH2:18][c:19]1[cH:20][cH:21][c:22]([CH2:23][OH:24])[cH:25][cH:26]1>CCOC(C)=O.CN(C)C=O.O=C(O)O.[K+].[K+]>[O:1]=[c:2]1[cH:3][c:4]([O:5][CH2:6][c:7]2[c:8]([F:9])[cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][n:16]1[CH2:17][CH2:18][c:19]1[cH:20][cH:21][c:22]([CH2:23][OH:24])[cH:25][cH:26]1\"},\"mapped_reaction_smiles\":\"Br[CH2:6][c:7]1[c:8]([F:9])[cH:10][cH:11][cH:12][cH:13]1.[O:1]=[c:2]1[cH:3][c:4]([OH:5])[cH:14][cH:15][n:16]1[CH2:17][CH2:18][c:19]1[cH:20][cH:21][c:22]([CH2:23][OH:24])[cH:25][cH:26]1>CCOC(C)=O.CN(C)C=O.O=C(O)O.[K+].[K+]>[O:1]=[c:2]1[cH:3][c:4]([O:5][CH2:6][c:7]2[c:8]([F:9])[cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15][n:16]1[CH2:17][CH2:18][c:19]1[cH:20][cH:21][c:22]([CH2:23][OH:24])[cH:25][cH:26]1\"}",
"reactionStep": {
"id": "sa_8bd5fc325dd05d2c25e4439a",
"reactionHash": "2f73ad70860c054b38a455107ea7fbb9aac6773782aa6accc3f940e5c1b57a06"
},
"children": [
{
"id": "13025",
"routeId": "sa_05133ab5b95e03773f842af9",
"moleculeId": "sa_65aaabb3a8336f19f5a65089",
"parentId": "13024",
"isLeaf": false,
"molecule": {
"id": "sa_65aaabb3a8336f19f5a65089",
"inchikey": "BHQWYUJRSPZJQB-UHFFFAOYSA-N",
"smiles": "O=c1cc(O)ccn1CCc1ccc(CO)cc1"
},
"smiles": "O=c1cc(O)ccn1CCc1ccc(CO)cc1",
"reactionStepId": "sa_b2043de32da63e05950c8a7a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080255083A1;0339;617616\",\"rsmi\":\"c1ccc(C[O:5][c:4]2[cH:3][c:2](=[O:1])[n:8]([CH2:9][CH2:10][c:11]3[cH:12][cH:13][c:14]([CH2:15][OH:16])[cH:17][cH:18]3)[cH:7][cH:6]2)cc1>CO.[Rh]>[O:1]=[c:2]1[cH:3][c:4]([OH:5])[cH:6][cH:7][n:8]1[CH2:9][CH2:10][c:11]1[cH:12][cH:13][c:14]([CH2:15][OH:16])[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"c1ccc(C[O:5][c:4]2[cH:3][c:2](=[O:1])[n:8]([CH2:9][CH2:10][c:11]3[cH:12][cH:13][c:14]([CH2:15][OH:16])[cH:17][cH:18]3)[cH:7][cH:6]2)cc1>CO.[Rh]>[O:1]=[c:2]1[cH:3][c:4]([OH:5])[cH:6][cH:7][n:8]1[CH2:9][CH2:10][c:11]1[cH:12][cH:13][c:14]([CH2:15][OH:16])[cH:17][cH:18]1\"}",
"reactionStep": {
"id": "sa_b2043de32da63e05950c8a7a",
"reactionHash": "f4a8a0fb667a3d39325db5e9eb41131d7bc361b75d07811fbaab14fc7cf110cf"
},
"children": [
{
"id": "13026",
"routeId": "sa_05133ab5b95e03773f842af9",
"moleculeId": "sa_7060ff2bc56762095ad09b95",
"parentId": "13025",
"isLeaf": false,
"molecule": {
"id": "sa_7060ff2bc56762095ad09b95",
"inchikey": "XQQHHFQRHZLYEO-UHFFFAOYSA-N",
"smiles": "O=c1cc(OCc2ccccc2)ccn1CCc1ccc(CO)cc1"
},
"smiles": "O=c1cc(OCc2ccccc2)ccn1CCc1ccc(CO)cc1",
"reactionStepId": "sa_6656d25e6b3635b0e93dea6b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080255083A1;0335;617615\",\"rsmi\":\"I[CH2:16][CH2:17][c:18]1[cH:19][cH:20][c:21]([CH2:22][OH:23])[cH:24][cH:25]1.[O:1]=[c:2]1[cH:3][c:4]([O:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14][nH:15]1>CN(C)C=O.O=C(O)O.[Cs+].[Cs+]>[O:1]=[c:2]1[cH:3][c:4]([O:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14][n:15]1[CH2:16][CH2:17][c:18]1[cH:19][cH:20][c:21]([CH2:22][OH:23])[cH:24][cH:25]1\"},\"mapped_reaction_smiles\":\"I[CH2:16][CH2:17][c:18]1[cH:19][cH:20][c:21]([CH2:22][OH:23])[cH:24][cH:25]1.[O:1]=[c:2]1[cH:3][c:4]([O:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14][nH:15]1>CN(C)C=O.O=C(O)O.[Cs+].[Cs+]>[O:1]=[c:2]1[cH:3][c:4]([O:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14][n:15]1[CH2:16][CH2:17][c:18]1[cH:19][cH:20][c:21]([CH2:22][OH:23])[cH:24][cH:25]1\"}",
"reactionStep": {
"id": "sa_6656d25e6b3635b0e93dea6b",
"reactionHash": "2a12ed451b6862f6a7052dc36a43a42ee0ecea3f68d8550ed9bc4928c5bebbe0"
},
"children": [
{
"id": "13027",
"routeId": "sa_05133ab5b95e03773f842af9",
"moleculeId": "sa_646d8e2b53b86812a7a0fb9e",
"parentId": "13026",
"isLeaf": true,
"molecule": {
"id": "sa_646d8e2b53b86812a7a0fb9e",
"inchikey": "DOVNUEPFPBWTSV-UHFFFAOYSA-N",
"smiles": "Oc1cc(OCc2ccccc2)ccn1"
},
"smiles": "O=c1cc(OCc2ccccc2)cc[nH]1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13028",
"routeId": "sa_05133ab5b95e03773f842af9",
"moleculeId": "sa_a19399b6886617e7c591c8df",
"parentId": "13026",
"isLeaf": false,
"molecule": {
"id": "sa_a19399b6886617e7c591c8df",
"inchikey": "GUTFFCAOICXFLO-UHFFFAOYSA-N",
"smiles": "OCc1ccc(CCI)cc1"
},
"smiles": "OCc1ccc(CCI)cc1",
"reactionStepId": "sa_53149454115e77297ea828db",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080255083A1;0331;617614\",\"rsmi\":\"Cl[CH2:8][CH2:7][c:6]1[cH:5][cH:4][c:3]([CH2:2][OH:1])[cH:11][cH:10]1.[IH:9]>CC(C)=O.[Na+]>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][I:9])[cH:10][cH:11]1\"},\"mapped_reaction_smiles\":\"Cl[CH2:8][CH2:7][c:6]1[cH:5][cH:4][c:3]([CH2:2][OH:1])[cH:11][cH:10]1.[IH:9]>CC(C)=O.[Na+]>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][I:9])[cH:10][cH:11]1\"}",
"reactionStep": {
"id": "sa_53149454115e77297ea828db",
"reactionHash": "55472c08139095b84ec7a44965053356a146d43aa790621b34380368295e0894"
},
"children": [
{
"id": "13029",
"routeId": "sa_05133ab5b95e03773f842af9",
"moleculeId": "sa_bc906e425e53d363266dfe60",
"parentId": "13028",
"isLeaf": true,
"molecule": {
"id": "sa_bc906e425e53d363266dfe60",
"inchikey": "XMBWDFGMSWQBCA-UHFFFAOYSA-N",
"smiles": "I"
},
"smiles": "I",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13030",
"routeId": "sa_05133ab5b95e03773f842af9",
"moleculeId": "sa_168816ca59d6bc00db504e5e",
"parentId": "13028",
"isLeaf": false,
"molecule": {
"id": "sa_168816ca59d6bc00db504e5e",
"inchikey": "ZHFUXJOYEQQEIJ-UHFFFAOYSA-N",
"smiles": "OCc1ccc(CCCl)cc1"
},
"smiles": "OCc1ccc(CCCl)cc1",
"reactionStepId": "sa_1d48927de7c9e9d57d20979b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20080255083A1;0327;617613\",\"rsmi\":\"O[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][Cl:9])[cH:10][cH:11]1>C1CCOC1.O=C(n1ccnc1)n1ccnc1.B.[Na+]>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][Cl:9])[cH:10][cH:11]1\"},\"mapped_reaction_smiles\":\"O[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][Cl:9])[cH:10][cH:11]1>C1CCOC1.O=C(n1ccnc1)n1ccnc1.B.[Na+]>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][Cl:9])[cH:10][cH:11]1\"}",
"reactionStep": {
"id": "sa_1d48927de7c9e9d57d20979b",
"reactionHash": "9f2d2b562e94cbb5165d17ef197fedbb61c7dd4f4476c010f334fab284398d18"
},
"children": [
{
"id": "13031",
"routeId": "sa_05133ab5b95e03773f842af9",
"moleculeId": "sa_bc6e3ab4853523bfc15a4bee",
"parentId": "13030",
"isLeaf": true,
"molecule": {
"id": "sa_bc6e3ab4853523bfc15a4bee",
"inchikey": "OOAPBGPLZAFZSO-UHFFFAOYSA-N",
"smiles": "O=C(O)c1ccc(CCCl)cc1"
},
"smiles": "O=C(O)c1ccc(CCCl)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
},
{
"id": "13032",
"routeId": "sa_05133ab5b95e03773f842af9",
"moleculeId": "sa_d7d6edf8bc01e4fe7142d706",
"parentId": "13024",
"isLeaf": true,
"molecule": {
"id": "sa_d7d6edf8bc01e4fe7142d706",
"inchikey": "FFWQLZFIMNTUCZ-UHFFFAOYSA-N",
"smiles": "Fc1ccccc1CBr"
},
"smiles": "Fc1ccccc1CBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "13033",
"routeId": "sa_05133ab5b95e03773f842af9",
"moleculeId": "sa_dffdccbce5a44ffb8b04e1d2",
"parentId": "13023",
"isLeaf": true,
"molecule": {
"id": "sa_dffdccbce5a44ffb8b04e1d2",
"inchikey": "IPNPIHIZVLFAFP-UHFFFAOYSA-N",
"smiles": "BrP(Br)Br"
},
"smiles": "BrP(Br)Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "13034",
"routeId": "sa_05133ab5b95e03773f842af9",
"moleculeId": "sa_9cb8d1e0db3f4217f8010dae",
"parentId": "13022",
"isLeaf": true,
"molecule": {
"id": "sa_9cb8d1e0db3f4217f8010dae",
"inchikey": "YLWUSMHZABTZGP-UHFFFAOYSA-N",
"smiles": "CC(O)=NC1CCNCC1"
},
"smiles": "CC(=O)NC1CCNCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}