Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COc1cc(Oc2ccc(N3CC(OCCOC4CCCCO4)C3)cc2)c([N+](=O)[O-])cn1
InChiKey
TUBNVCLKAPDOLD-UHFFFAOYSA-N
Route Signature
a7947c0cee78770939a80125a606de0919ccfd03f3386d8c452fe9f8d3e1a7fc
Synthesis route with 3 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_549ca115ed2167de33f23c46",
"signature": "a7947c0cee78770939a80125a606de0919ccfd03f3386d8c452fe9f8d3e1a7fc",
"contentHash": "53bfeb37e46d5f2477c8eba053c5f5eb2e2acfbd2c7d110662ae9ca5f9912750",
"length": 3,
"isConvergent": true
},
"target": {
"id": "sa_be247e92268620e8368c8eea",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-05668",
"moleculeId": "sa_eca534bbf3a0fbbf2deb5993",
"smiles": "COc1cc(Oc2ccc(N3CC(OCCOC4CCCCO4)C3)cc2)c([N+](=O)[O-])cn1",
"routeLength": 3,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_eca534bbf3a0fbbf2deb5993",
"inchikey": "TUBNVCLKAPDOLD-UHFFFAOYSA-N",
"smiles": "COc1cc(Oc2ccc(N3CC(OCCOC4CCCCO4)C3)cc2)c([N+](=O)[O-])cn1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "11443",
"routeId": "sa_549ca115ed2167de33f23c46",
"moleculeId": "sa_eca534bbf3a0fbbf2deb5993",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_eca534bbf3a0fbbf2deb5993",
"inchikey": "TUBNVCLKAPDOLD-UHFFFAOYSA-N",
"smiles": "COc1cc(Oc2ccc(N3CC(OCCOC4CCCCO4)C3)cc2)c([N+](=O)[O-])cn1"
},
"smiles": "COc1cc(Oc2ccc(N3CC(OCCOC4CCCCO4)C3)cc2)c([N+](=O)[O-])cn1",
"reactionStepId": "sa_500a61bd2f4c927ced518771",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160207883A1;0706;1908321\",\"rsmi\":\"Cl[c:10]1[c:6]([N+:7](=[O:8])[O-:9])[cH:5][n:4][c:3]([O:2][CH3:1])[cH:32]1.[OH:11][c:12]1[cH:13][cH:14][c:15]([N:16]2[CH2:17][CH:18]([O:19][CH2:20][CH2:21][O:22][CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27][O:28]3)[CH2:29]2)[cH:30][cH:31]1>CN(C)C=O.O=C(O)O.[HH].[Na+].[Na+]>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[c:10]([O:11][c:12]2[cH:13][cH:14][c:15]([N:16]3[CH2:17][CH:18]([O:19][CH2:20][CH2:21][O:22][CH:23]4[CH2:24][CH2:25][CH2:26][CH2:27][O:28]4)[CH2:29]3)[cH:30][cH:31]2)[cH:32]1\"},\"mapped_reaction_smiles\":\"Cl[c:10]1[c:6]([N+:7](=[O:8])[O-:9])[cH:5][n:4][c:3]([O:2][CH3:1])[cH:32]1.[OH:11][c:12]1[cH:13][cH:14][c:15]([N:16]2[CH2:17][CH:18]([O:19][CH2:20][CH2:21][O:22][CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27][O:28]3)[CH2:29]2)[cH:30][cH:31]1>CN(C)C=O.O=C(O)O.[HH].[Na+].[Na+]>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[c:10]([O:11][c:12]2[cH:13][cH:14][c:15]([N:16]3[CH2:17][CH:18]([O:19][CH2:20][CH2:21][O:22][CH:23]4[CH2:24][CH2:25][CH2:26][CH2:27][O:28]4)[CH2:29]3)[cH:30][cH:31]2)[cH:32]1\"}",
"reactionStep": {
"id": "sa_500a61bd2f4c927ced518771",
"reactionHash": "f0a19b960bae6d6b3c023c1972fd3ef909c64019ca589889edc2165007cb90fb"
},
"children": [
{
"id": "11444",
"routeId": "sa_549ca115ed2167de33f23c46",
"moleculeId": "sa_3ff9a5909d4e480ee3326a35",
"parentId": "11443",
"isLeaf": false,
"molecule": {
"id": "sa_3ff9a5909d4e480ee3326a35",
"inchikey": "CZHWJHZGZXCVIQ-UHFFFAOYSA-N",
"smiles": "COc1cc(Cl)c([N+](=O)[O-])cn1"
},
"smiles": "COc1cc(Cl)c([N+](=O)[O-])cn1",
"reactionStepId": "sa_9d133d46a4352d30ca86c735",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160207883A1;0337;1908262\",\"rsmi\":\"I[CH3:1].[OH:2][c:3]1[n:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[c:10]([Cl:11])[cH:12]1>C1CCOC1.O=C(O)O.[Ag+2]>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[c:10]([Cl:11])[cH:12]1\"},\"mapped_reaction_smiles\":\"I[CH3:1].[OH:2][c:3]1[n:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[c:10]([Cl:11])[cH:12]1>C1CCOC1.O=C(O)O.[Ag+2]>[CH3:1][O:2][c:3]1[n:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[c:10]([Cl:11])[cH:12]1\"}",
"reactionStep": {
"id": "sa_9d133d46a4352d30ca86c735",
"reactionHash": "20f5697144a47d625fce81735f47142b6c06997d82ce399a89d6b068dcd061a7"
},
"children": [
{
"id": "11445",
"routeId": "sa_549ca115ed2167de33f23c46",
"moleculeId": "sa_82fdccf7d1cc329c9db73f21",
"parentId": "11444",
"isLeaf": true,
"molecule": {
"id": "sa_82fdccf7d1cc329c9db73f21",
"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
},
"smiles": "CI",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11446",
"routeId": "sa_549ca115ed2167de33f23c46",
"moleculeId": "sa_f991b56beec2a4c78700f85e",
"parentId": "11444",
"isLeaf": true,
"molecule": {
"id": "sa_f991b56beec2a4c78700f85e",
"inchikey": "VZBXTOUZMQUTIQ-UHFFFAOYSA-N",
"smiles": "O=c1cc(Cl)c([N+](=O)[O-])c[nH]1"
},
"smiles": "O=[N+]([O-])c1cnc(O)cc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "11447",
"routeId": "sa_549ca115ed2167de33f23c46",
"moleculeId": "sa_8e5f9be47fbff73e38f5232f",
"parentId": "11443",
"isLeaf": false,
"molecule": {
"id": "sa_8e5f9be47fbff73e38f5232f",
"inchikey": "MGKAXVVAWGIQMT-UHFFFAOYSA-N",
"smiles": "Oc1ccc(N2CC(OCCOC3CCCCO3)C2)cc1"
},
"smiles": "Oc1ccc(N2CC(OCCOC3CCCCO3)C2)cc1",
"reactionStepId": "sa_01a72b7eb88fca19036773c2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160207883A1;0289;1908247\",\"rsmi\":\"CC(C)(C)[Si](C)(C)[O:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH:8]([O:9][CH2:10][CH2:11][O:12][CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17][O:18]3)[CH2:19]2)[cH:20][cH:21]1>C1CCOC1.C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.O.F>[OH:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH:8]([O:9][CH2:10][CH2:11][O:12][CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17][O:18]3)[CH2:19]2)[cH:20][cH:21]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)[Si](C)(C)[O:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH:8]([O:9][CH2:10][CH2:11][O:12][CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17][O:18]3)[CH2:19]2)[cH:20][cH:21]1>C1CCOC1.C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.O.F>[OH:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH:8]([O:9][CH2:10][CH2:11][O:12][CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17][O:18]3)[CH2:19]2)[cH:20][cH:21]1\"}",
"reactionStep": {
"id": "sa_01a72b7eb88fca19036773c2",
"reactionHash": "dc4f5a844683191f51a22221ca6aa313ca86c378223a12473ff7be78141f91fc"
},
"children": [
{
"id": "11448",
"routeId": "sa_549ca115ed2167de33f23c46",
"moleculeId": "sa_4714c1446d95293b1e910ca5",
"parentId": "11447",
"isLeaf": false,
"molecule": {
"id": "sa_4714c1446d95293b1e910ca5",
"inchikey": "PDTYQPNDOYVAKG-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)Oc1ccc(N2CC(OCCOC3CCCCO3)C2)cc1"
},
"smiles": "CC(C)(C)[Si](C)(C)Oc1ccc(N2CC(OCCOC3CCCCO3)C2)cc1",
"reactionStepId": "sa_255c9216744657a66686659a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160207883A1;0286;1908246\",\"rsmi\":\"I[c:12]1[cH:11][cH:10][c:9]([O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[cH:28][cH:27]1.[NH:13]1[CH2:14][CH:15]([O:16][CH2:17][CH2:18][O:19][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][O:25]2)[CH2:26]1>CC(=O)O.CC(=O)O.CC(C)(C)O.Cc1ccccc1.O.[Na+].[Pd+2].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][cH:11][c:12]([N:13]2[CH2:14][CH:15]([O:16][CH2:17][CH2:18][O:19][CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][O:25]3)[CH2:26]2)[cH:27][cH:28]1\"},\"mapped_reaction_smiles\":\"I[c:12]1[cH:11][cH:10][c:9]([O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[cH:28][cH:27]1.[NH:13]1[CH2:14][CH:15]([O:16][CH2:17][CH2:18][O:19][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][O:25]2)[CH2:26]1>CC(=O)O.CC(=O)O.CC(C)(C)O.Cc1ccccc1.O.[Na+].[Pd+2].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][cH:11][c:12]([N:13]2[CH2:14][CH:15]([O:16][CH2:17][CH2:18][O:19][CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][O:25]3)[CH2:26]2)[cH:27][cH:28]1\"}",
"reactionStep": {
"id": "sa_255c9216744657a66686659a",
"reactionHash": "985bb77e9be297df7b06eb4bd48eb92c2679aa631c2ce80c2e7fc35e3c4873c4"
},
"children": [
{
"id": "11449",
"routeId": "sa_549ca115ed2167de33f23c46",
"moleculeId": "sa_358bb64e0b4e062f118e6334",
"parentId": "11448",
"isLeaf": true,
"molecule": {
"id": "sa_358bb64e0b4e062f118e6334",
"inchikey": "FVXATZLWJPLBPP-UHFFFAOYSA-N",
"smiles": "CC(C)(C)[Si](C)(C)Oc1ccc(I)cc1"
},
"smiles": "CC(C)(C)[Si](C)(C)Oc1ccc(I)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "11450",
"routeId": "sa_549ca115ed2167de33f23c46",
"moleculeId": "sa_97350dc50142e210aa0a3876",
"parentId": "11448",
"isLeaf": true,
"molecule": {
"id": "sa_97350dc50142e210aa0a3876",
"inchikey": "GLHWDEDTRKVHPX-UHFFFAOYSA-N",
"smiles": "C1CCC(OCCOC2CNC2)OC1"
},
"smiles": "C1CCC(OCCOC2CNC2)OC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
}