Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(=O)N1CCC(CNC(=O)Nc2cc(-c3cccs3)ccc2N)CC1
InChiKey
JOQXFAGDBYKLIQ-UHFFFAOYSA-N
Route Signature
74bb552c60f1688668085fc7f2434603040e2db89a41c41aa7201ded0b79567b
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_ec5fd289f67d5ea3ba59379e",
"signature": "74bb552c60f1688668085fc7f2434603040e2db89a41c41aa7201ded0b79567b",
"contentHash": "0f4cc87f92ab31ba677de227c5de4c8e2011f650627e1d1a5ddd1d70419385ba",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_8003a712eda7367f93eab42b",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00751",
"moleculeId": "sa_84d3020d05c891696b08003d",
"smiles": "CC(=O)N1CCC(CNC(=O)Nc2cc(-c3cccs3)ccc2N)CC1",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_84d3020d05c891696b08003d",
"inchikey": "JOQXFAGDBYKLIQ-UHFFFAOYSA-N",
"smiles": "CC(=O)N1CCC(CNC(=O)Nc2cc(-c3cccs3)ccc2N)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13761",
"routeId": "sa_ec5fd289f67d5ea3ba59379e",
"moleculeId": "sa_84d3020d05c891696b08003d",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_84d3020d05c891696b08003d",
"inchikey": "JOQXFAGDBYKLIQ-UHFFFAOYSA-N",
"smiles": "CC(=O)N1CCC(CNC(=O)Nc2cc(-c3cccs3)ccc2N)CC1"
},
"smiles": "CC(=O)N1CCC(CNC(=O)Nc2cc(-c3cccs3)ccc2N)CC1",
"reactionStepId": "sa_20d761415d180accd1195d83",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160251351A1;0527;1927158\",\"rsmi\":\"O=[N+:15]([O-])[c:14]1[c:13]([NH:12][C:10]([NH:9][CH2:8][CH:7]2[CH2:6][CH2:5][N:4]([C:2]([CH3:1])=[O:3])[CH2:26][CH2:25]2)=[O:11])[cH:24][c:18](-[c:19]2[cH:20][cH:21][cH:22][s:23]2)[cH:17][cH:16]1>CO.[Pd]>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][NH:9][C:10](=[O:11])[NH:12][c:13]2[c:14]([NH2:15])[cH:16][cH:17][c:18](-[c:19]3[cH:20][cH:21][cH:22][s:23]3)[cH:24]2)[CH2:25][CH2:26]1\"},\"mapped_reaction_smiles\":\"O=[N+:15]([O-])[c:14]1[c:13]([NH:12][C:10]([NH:9][CH2:8][CH:7]2[CH2:6][CH2:5][N:4]([C:2]([CH3:1])=[O:3])[CH2:26][CH2:25]2)=[O:11])[cH:24][c:18](-[c:19]2[cH:20][cH:21][cH:22][s:23]2)[cH:17][cH:16]1>CO.[Pd]>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][NH:9][C:10](=[O:11])[NH:12][c:13]2[c:14]([NH2:15])[cH:16][cH:17][c:18](-[c:19]3[cH:20][cH:21][cH:22][s:23]3)[cH:24]2)[CH2:25][CH2:26]1\"}",
"reactionStep": {
"id": "sa_20d761415d180accd1195d83",
"reactionHash": "898082c39b312f7dd248e1646fa767d47afae7cc88f076eaa3711cc772784f4a"
},
"children": [
{
"id": "13762",
"routeId": "sa_ec5fd289f67d5ea3ba59379e",
"moleculeId": "sa_bfdc2fb287618b9e4d584067",
"parentId": "13761",
"isLeaf": false,
"molecule": {
"id": "sa_bfdc2fb287618b9e4d584067",
"inchikey": "JMGNATYIQSAGFC-UHFFFAOYSA-N",
"smiles": "CC(=O)N1CCC(CNC(=O)Nc2cc(-c3cccs3)ccc2[N+](=O)[O-])CC1"
},
"smiles": "CC(=O)N1CCC(CNC(=O)Nc2cc(-c3cccs3)ccc2[N+](=O)[O-])CC1",
"reactionStepId": "sa_dedcdc8c0b9b5d78b028b900",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160251351A1;0526;1927157\",\"rsmi\":\"CC(=O)O[C:2]([CH3:1])=[O:3].[NH:4]1[CH2:5][CH2:6][CH:7]([CH2:8][NH:9][C:10](=[O:11])[NH:12][c:13]2[c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19][c:20](-[c:21]3[cH:22][cH:23][cH:24][s:25]3)[cH:26]2)[CH2:27][CH2:28]1>CCN(CC)CC.ClCCl.O>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][NH:9][C:10](=[O:11])[NH:12][c:13]2[c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19][c:20](-[c:21]3[cH:22][cH:23][cH:24][s:25]3)[cH:26]2)[CH2:27][CH2:28]1\"},\"mapped_reaction_smiles\":\"CC(=O)O[C:2]([CH3:1])=[O:3].[NH:4]1[CH2:5][CH2:6][CH:7]([CH2:8][NH:9][C:10](=[O:11])[NH:12][c:13]2[c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19][c:20](-[c:21]3[cH:22][cH:23][cH:24][s:25]3)[cH:26]2)[CH2:27][CH2:28]1>CCN(CC)CC.ClCCl.O>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][NH:9][C:10](=[O:11])[NH:12][c:13]2[c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19][c:20](-[c:21]3[cH:22][cH:23][cH:24][s:25]3)[cH:26]2)[CH2:27][CH2:28]1\"}",
"reactionStep": {
"id": "sa_dedcdc8c0b9b5d78b028b900",
"reactionHash": "ab7716e8a681619520a5b0e4f14e42b50155e535d3cb39297baf6bb8a39a1242"
},
"children": [
{
"id": "13763",
"routeId": "sa_ec5fd289f67d5ea3ba59379e",
"moleculeId": "sa_cbb27f7dbd88dd9070dcbc50",
"parentId": "13762",
"isLeaf": false,
"molecule": {
"id": "sa_cbb27f7dbd88dd9070dcbc50",
"inchikey": "JWHLZNVZWWQIMS-UHFFFAOYSA-N",
"smiles": "O=C(NCC1CCNCC1)Nc1cc(-c2cccs2)ccc1[N+](=O)[O-]"
},
"smiles": "O=C(NCC1CCNCC1)Nc1cc(-c2cccs2)ccc1[N+](=O)[O-]",
"reactionStepId": "sa_d04e1ed7385bcef3cad797be",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160251351A1;0525;1927156\",\"rsmi\":\"CC(C)(C)OC(=O)[N:8]1[CH2:7][CH2:6][CH:5]([CH2:4][NH:3][C:2](=[O:1])[NH:11][c:12]2[c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18][c:19](-[c:20]3[cH:21][cH:22][cH:23][s:24]3)[cH:25]2)[CH2:10][CH2:9]1>ClCCl.O=C(O)C(F)(F)F>[O:1]=[C:2]([NH:3][CH2:4][CH:5]1[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]1)[NH:11][c:12]1[c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18][c:19](-[c:20]2[cH:21][cH:22][cH:23][s:24]2)[cH:25]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:8]1[CH2:7][CH2:6][CH:5]([CH2:4][NH:3][C:2](=[O:1])[NH:11][c:12]2[c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18][c:19](-[c:20]3[cH:21][cH:22][cH:23][s:24]3)[cH:25]2)[CH2:10][CH2:9]1>ClCCl.O=C(O)C(F)(F)F>[O:1]=[C:2]([NH:3][CH2:4][CH:5]1[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]1)[NH:11][c:12]1[c:13]([N+:14](=[O:15])[O-:16])[cH:17][cH:18][c:19](-[c:20]2[cH:21][cH:22][cH:23][s:24]2)[cH:25]1\"}",
"reactionStep": {
"id": "sa_d04e1ed7385bcef3cad797be",
"reactionHash": "3490fdbeb37a8884bfd91923c582e5f6431b3ed4aaaad3b2305d4cbf4a8f2f5c"
},
"children": [
{
"id": "13764",
"routeId": "sa_ec5fd289f67d5ea3ba59379e",
"moleculeId": "sa_bf3559e687aac25489ebc290",
"parentId": "13763",
"isLeaf": false,
"molecule": {
"id": "sa_bf3559e687aac25489ebc290",
"inchikey": "OCHVKVCFVMPLCH-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(CNC(=O)Nc2cc(-c3cccs3)ccc2[N+](=O)[O-])CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(CNC(=O)Nc2cc(-c3cccs3)ccc2[N+](=O)[O-])CC1",
"reactionStepId": "sa_e4c885c5802cd0df2f4a01af",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160251351A1;0524;1927155\",\"rsmi\":\"ClC(Cl)(Cl)O[C:14](OC(Cl)(Cl)Cl)=[O:15].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([CH2:12][NH2:13])[CH2:31][CH2:32]1.[NH2:16][c:17]1[c:18]([N+:19](=[O:20])[O-:21])[cH:22][cH:23][c:24](-[c:25]2[cH:26][cH:27][cH:28][s:29]2)[cH:30]1>ClCCl>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([CH2:12][NH:13][C:14](=[O:15])[NH:16][c:17]2[c:18]([N+:19](=[O:20])[O-:21])[cH:22][cH:23][c:24](-[c:25]3[cH:26][cH:27][cH:28][s:29]3)[cH:30]2)[CH2:31][CH2:32]1\"},\"mapped_reaction_smiles\":\"ClC(Cl)(Cl)O[C:14](OC(Cl)(Cl)Cl)=[O:15].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([CH2:12][NH2:13])[CH2:31][CH2:32]1.[NH2:16][c:17]1[c:18]([N+:19](=[O:20])[O-:21])[cH:22][cH:23][c:24](-[c:25]2[cH:26][cH:27][cH:28][s:29]2)[cH:30]1>ClCCl>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([CH2:12][NH:13][C:14](=[O:15])[NH:16][c:17]2[c:18]([N+:19](=[O:20])[O-:21])[cH:22][cH:23][c:24](-[c:25]3[cH:26][cH:27][cH:28][s:29]3)[cH:30]2)[CH2:31][CH2:32]1\"}",
"reactionStep": {
"id": "sa_e4c885c5802cd0df2f4a01af",
"reactionHash": "e7b6bf487503ed9bd2bf6e270ff0e61db4913da521923ee8d9ad61df78399670"
},
"children": [
{
"id": "13765",
"routeId": "sa_ec5fd289f67d5ea3ba59379e",
"moleculeId": "sa_44fe14a202e3e5e967ef7da1",
"parentId": "13764",
"isLeaf": false,
"molecule": {
"id": "sa_44fe14a202e3e5e967ef7da1",
"inchikey": "AVLRTOLFIYWLBH-UHFFFAOYSA-N",
"smiles": "Nc1cc(-c2cccs2)ccc1[N+](=O)[O-]"
},
"smiles": "Nc1cc(-c2cccs2)ccc1[N+](=O)[O-]",
"reactionStepId": "sa_f8e252fc81246eb92a888027",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160251351A1;0379;1927135\",\"rsmi\":\"Br[c:9]1[cH:8][cH:7][c:3]([N+:4](=[O:5])[O-:6])[c:2]([NH2:1])[cH:15]1.OB(O)[c:10]1[cH:11][cH:12][cH:13][s:14]1>C1CCOC1.CCOC(C)=O.O.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[NH2:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][s:14]2)[cH:15]1\"},\"mapped_reaction_smiles\":\"Br[c:9]1[cH:8][cH:7][c:3]([N+:4](=[O:5])[O-:6])[c:2]([NH2:1])[cH:15]1.OB(O)[c:10]1[cH:11][cH:12][cH:13][s:14]1>C1CCOC1.CCOC(C)=O.O.O=C(O)O.[Na+].[Na+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[NH2:1][c:2]1[c:3]([N+:4](=[O:5])[O-:6])[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][s:14]2)[cH:15]1\"}",
"reactionStep": {
"id": "sa_f8e252fc81246eb92a888027",
"reactionHash": "c8a620ae430166dcd69dcf812bca391a43bd17e42a44f870e509097fc55cee0b"
},
"children": [
{
"id": "13766",
"routeId": "sa_ec5fd289f67d5ea3ba59379e",
"moleculeId": "sa_92a52c99643c24217f6e2bb2",
"parentId": "13765",
"isLeaf": true,
"molecule": {
"id": "sa_92a52c99643c24217f6e2bb2",
"inchikey": "ARYHTUPFQTUBBG-UHFFFAOYSA-N",
"smiles": "OB(O)c1cccs1"
},
"smiles": "OB(O)c1cccs1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13767",
"routeId": "sa_ec5fd289f67d5ea3ba59379e",
"moleculeId": "sa_db04b8b59114a832bbad2ca3",
"parentId": "13765",
"isLeaf": true,
"molecule": {
"id": "sa_db04b8b59114a832bbad2ca3",
"inchikey": "RMIFLIVHJLREFJ-UHFFFAOYSA-N",
"smiles": "Nc1cc(Br)ccc1[N+](=O)[O-]"
},
"smiles": "Nc1cc(Br)ccc1[N+](=O)[O-]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "13768",
"routeId": "sa_ec5fd289f67d5ea3ba59379e",
"moleculeId": "sa_47861c33536e20cf58dfda68",
"parentId": "13764",
"isLeaf": true,
"molecule": {
"id": "sa_47861c33536e20cf58dfda68",
"inchikey": "KLKBCNDBOVRQIJ-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)N1CCC(CN)CC1"
},
"smiles": "CC(C)(C)OC(=O)N1CCC(CN)CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13769",
"routeId": "sa_ec5fd289f67d5ea3ba59379e",
"moleculeId": "sa_229d14c9e484394c3a8786c2",
"parentId": "13764",
"isLeaf": true,
"molecule": {
"id": "sa_229d14c9e484394c3a8786c2",
"inchikey": "UCPYLLCMEDAXFR-UHFFFAOYSA-N",
"smiles": "O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl"
},
"smiles": "O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "13770",
"routeId": "sa_ec5fd289f67d5ea3ba59379e",
"moleculeId": "sa_a7893fcf81826693d9b4bed4",
"parentId": "13762",
"isLeaf": true,
"molecule": {
"id": "sa_a7893fcf81826693d9b4bed4",
"inchikey": "WFDIJRYMOXRFFG-UHFFFAOYSA-N",
"smiles": "CC(=O)OC(C)=O"
},
"smiles": "CC(=O)OC(C)=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}