Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Oc1ccc2nc(-c3ccc(-c4nn[nH]n4)cc3Cl)ccc2c1
InChiKey
YLROCXBICGTVLO-UHFFFAOYSA-N
Route Signature
6d215fc702289082ec94fc9e89a5f373e27bf0e83dafa94ec1048452d6ccbc1a
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_26ebc37c820daf8730770c6a",
"signature": "6d215fc702289082ec94fc9e89a5f373e27bf0e83dafa94ec1048452d6ccbc1a",
"contentHash": "8109f4201ceb17d7a2377ae33920118eed2c3b5f5529fbacb2bda6c850c75950",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_ac6e8600bdee328d8a17180a",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00177",
"moleculeId": "sa_607d7d7458af62473c3b5d28",
"smiles": "Oc1ccc2nc(-c3ccc(-c4nn[nH]n4)cc3Cl)ccc2c1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_607d7d7458af62473c3b5d28",
"inchikey": "YLROCXBICGTVLO-UHFFFAOYSA-N",
"smiles": "Oc1ccc2nc(-c3ccc(-c4nn[nH]n4)cc3Cl)ccc2c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "3601",
"routeId": "sa_26ebc37c820daf8730770c6a",
"moleculeId": "sa_607d7d7458af62473c3b5d28",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_607d7d7458af62473c3b5d28",
"inchikey": "YLROCXBICGTVLO-UHFFFAOYSA-N",
"smiles": "Oc1ccc2nc(-c3ccc(-c4nn[nH]n4)cc3Cl)ccc2c1"
},
"smiles": "Oc1ccc2nc(-c3ccc(-c4nn[nH]n4)cc3Cl)ccc2c1",
"reactionStepId": "sa_0b8b3b7f5cce953db1d4f24d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160067254A1;0314;1848769\",\"rsmi\":\"[N-:15]=[N+:16]=[N-:17].[OH:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7](-[c:8]3[c:9]([Cl:10])[cH:11][c:12]([C:13]#[N:14])[cH:18][cH:19]3)[cH:20][cH:21][c:22]2[cH:23]1>COCCOCCO.Cl.[Li+].[Na+]>[OH:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7](-[c:8]3[c:9]([Cl:10])[cH:11][c:12](-[c:13]4[n:14][nH:15][n:16][n:17]4)[cH:18][cH:19]3)[cH:20][cH:21][c:22]2[cH:23]1\"},\"mapped_reaction_smiles\":\"[N-:15]=[N+:16]=[N-:17].[OH:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7](-[c:8]3[c:9]([Cl:10])[cH:11][c:12]([C:13]#[N:14])[cH:18][cH:19]3)[cH:20][cH:21][c:22]2[cH:23]1>COCCOCCO.Cl.[Li+].[Na+]>[OH:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7](-[c:8]3[c:9]([Cl:10])[cH:11][c:12](-[c:13]4[n:14][nH:15][n:16][n:17]4)[cH:18][cH:19]3)[cH:20][cH:21][c:22]2[cH:23]1\"}",
"reactionStep": {
"id": "sa_0b8b3b7f5cce953db1d4f24d",
"reactionHash": "e7cacc1e088f263c0080d523c2c09f22745083ab4b192359ed0dbeb9bdd37f35"
},
"children": [
{
"id": "3602",
"routeId": "sa_26ebc37c820daf8730770c6a",
"moleculeId": "sa_50a8f83dd89c267fbada1205",
"parentId": "3601",
"isLeaf": true,
"molecule": {
"id": "sa_50a8f83dd89c267fbada1205",
"inchikey": "IVRMZWNICZWHMI-UHFFFAOYSA-N",
"smiles": "[N]N=[N-]"
},
"smiles": "[N-]=[N+]=[N-]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3603",
"routeId": "sa_26ebc37c820daf8730770c6a",
"moleculeId": "sa_bb1f81d56025308f24e52a7a",
"parentId": "3601",
"isLeaf": false,
"molecule": {
"id": "sa_bb1f81d56025308f24e52a7a",
"inchikey": "PJUDFQLNOYQBSN-UHFFFAOYSA-N",
"smiles": "N#Cc1ccc(-c2ccc3cc(O)ccc3n2)c(Cl)c1"
},
"smiles": "N#Cc1ccc(-c2ccc3cc(O)ccc3n2)c(Cl)c1",
"reactionStepId": "sa_b406da3088f9e30727e7242c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160067254A1;0313;1848768\",\"rsmi\":\"O=[C:2]([NH2:1])[c:3]1[cH:4][c:5]([Cl:6])[c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][c:13]([OH:14])[cH:15][c:16]3[cH:17][cH:18]2)[cH:19][cH:20]1>CCN(CC)CC.ClCCl.O.O=C(OC(=O)C(F)(F)F)C(F)(F)F>[N:1]#[C:2][c:3]1[cH:4][c:5]([Cl:6])[c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][c:13]([OH:14])[cH:15][c:16]3[cH:17][cH:18]2)[cH:19][cH:20]1\"},\"mapped_reaction_smiles\":\"O=[C:2]([NH2:1])[c:3]1[cH:4][c:5]([Cl:6])[c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][c:13]([OH:14])[cH:15][c:16]3[cH:17][cH:18]2)[cH:19][cH:20]1>CCN(CC)CC.ClCCl.O.O=C(OC(=O)C(F)(F)F)C(F)(F)F>[N:1]#[C:2][c:3]1[cH:4][c:5]([Cl:6])[c:7](-[c:8]2[n:9][c:10]3[cH:11][cH:12][c:13]([OH:14])[cH:15][c:16]3[cH:17][cH:18]2)[cH:19][cH:20]1\"}",
"reactionStep": {
"id": "sa_b406da3088f9e30727e7242c",
"reactionHash": "40710c4fb71ce5592724169e4e5537256a204d8bc3a53b19e312e0f6be28eab2"
},
"children": [
{
"id": "3604",
"routeId": "sa_26ebc37c820daf8730770c6a",
"moleculeId": "sa_513d86f38bf30358b0d92bb6",
"parentId": "3603",
"isLeaf": false,
"molecule": {
"id": "sa_513d86f38bf30358b0d92bb6",
"inchikey": "AKIMQLBZUGCGON-UHFFFAOYSA-N",
"smiles": "NC(=O)c1ccc(-c2ccc3cc(O)ccc3n2)c(Cl)c1"
},
"smiles": "NC(=O)c1ccc(-c2ccc3cc(O)ccc3n2)c(Cl)c1",
"reactionStepId": "sa_64b783f7bcc73d2ab12e0c83",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160067254A1;0312;1848767\",\"rsmi\":\"O[C:2](=[O:3])[c:4]1[cH:5][c:6]([Cl:7])[c:8](-[c:9]2[n:10][c:11]3[cH:12][cH:13][c:14]([OH:15])[cH:16][c:17]3[cH:18][cH:19]2)[cH:20][cH:21]1.[NH3:1]>Cl.O=S(Cl)Cl.O>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([Cl:7])[c:8](-[c:9]2[n:10][c:11]3[cH:12][cH:13][c:14]([OH:15])[cH:16][c:17]3[cH:18][cH:19]2)[cH:20][cH:21]1\"},\"mapped_reaction_smiles\":\"O[C:2](=[O:3])[c:4]1[cH:5][c:6]([Cl:7])[c:8](-[c:9]2[n:10][c:11]3[cH:12][cH:13][c:14]([OH:15])[cH:16][c:17]3[cH:18][cH:19]2)[cH:20][cH:21]1.[NH3:1]>Cl.O=S(Cl)Cl.O>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([Cl:7])[c:8](-[c:9]2[n:10][c:11]3[cH:12][cH:13][c:14]([OH:15])[cH:16][c:17]3[cH:18][cH:19]2)[cH:20][cH:21]1\"}",
"reactionStep": {
"id": "sa_64b783f7bcc73d2ab12e0c83",
"reactionHash": "16d61c4f2851b90dc9b68d1fb758c027c46c8626c9566c766ac082abf1684076"
},
"children": [
{
"id": "3605",
"routeId": "sa_26ebc37c820daf8730770c6a",
"moleculeId": "sa_1435cb940279eeb0749aceaf",
"parentId": "3604",
"isLeaf": false,
"molecule": {
"id": "sa_1435cb940279eeb0749aceaf",
"inchikey": "BXSZILNGNMDGSL-UHFFFAOYSA-N",
"smiles": "O=C(O)c1ccc(-c2ccc3cc(O)ccc3n2)c(Cl)c1"
},
"smiles": "O=C(O)c1ccc(-c2ccc3cc(O)ccc3n2)c(Cl)c1",
"reactionStepId": "sa_8eda8f03eb587be2e817bcc1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160067254A1;0269;1848754\",\"rsmi\":\"C[O:15][c:14]1[cH:13][cH:12][c:11]2[n:10][c:9](-[c:8]3[c:6]([Cl:7])[cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:21][cH:20]3)[cH:19][cH:18][c:17]2[cH:16]1>ClCCl.[Al+3].Cl.Cl.Cl>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([Cl:7])[c:8](-[c:9]2[n:10][c:11]3[cH:12][cH:13][c:14]([OH:15])[cH:16][c:17]3[cH:18][cH:19]2)[cH:20][cH:21]1\"},\"mapped_reaction_smiles\":\"C[O:15][c:14]1[cH:13][cH:12][c:11]2[n:10][c:9](-[c:8]3[c:6]([Cl:7])[cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:21][cH:20]3)[cH:19][cH:18][c:17]2[cH:16]1>ClCCl.[Al+3].Cl.Cl.Cl>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([Cl:7])[c:8](-[c:9]2[n:10][c:11]3[cH:12][cH:13][c:14]([OH:15])[cH:16][c:17]3[cH:18][cH:19]2)[cH:20][cH:21]1\"}",
"reactionStep": {
"id": "sa_8eda8f03eb587be2e817bcc1",
"reactionHash": "e5a4eeb6a43ff20eb98941d4833893cd3c0bd61b8ea399c81f6e58273d61f491"
},
"children": [
{
"id": "3606",
"routeId": "sa_26ebc37c820daf8730770c6a",
"moleculeId": "sa_bcdbda9c028d449b8a9ad33d",
"parentId": "3605",
"isLeaf": false,
"molecule": {
"id": "sa_bcdbda9c028d449b8a9ad33d",
"inchikey": "PVOWBMUBLVXXQF-UHFFFAOYSA-N",
"smiles": "COc1ccc2nc(-c3ccc(C(=O)O)cc3Cl)ccc2c1"
},
"smiles": "COc1ccc2nc(-c3ccc(C(=O)O)cc3Cl)ccc2c1",
"reactionStepId": "sa_97d60ee2b41b2db1a7f70a38",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160067254A1;0268;1848753\",\"rsmi\":\"Cl[c:8]1[n:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:22][c:21]2[cH:20][cH:19]1.OB(O)[c:9]1[c:10]([Cl:11])[cH:12][c:13]([C:14](=[O:15])[OH:16])[cH:17][cH:18]1>CCOC(C)=O.COCCOCCO.Cl[Pd]Cl.O.O=C(O)O.[Fe+2].[K+].[K+]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][c:8](-[c:9]3[c:10]([Cl:11])[cH:12][c:13]([C:14](=[O:15])[OH:16])[cH:17][cH:18]3)[cH:19][cH:20][c:21]2[cH:22]1\"},\"mapped_reaction_smiles\":\"Cl[c:8]1[n:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:22][c:21]2[cH:20][cH:19]1.OB(O)[c:9]1[c:10]([Cl:11])[cH:12][c:13]([C:14](=[O:15])[OH:16])[cH:17][cH:18]1>CCOC(C)=O.COCCOCCO.Cl[Pd]Cl.O.O=C(O)O.[Fe+2].[K+].[K+]>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][c:8](-[c:9]3[c:10]([Cl:11])[cH:12][c:13]([C:14](=[O:15])[OH:16])[cH:17][cH:18]3)[cH:19][cH:20][c:21]2[cH:22]1\"}",
"reactionStep": {
"id": "sa_97d60ee2b41b2db1a7f70a38",
"reactionHash": "508bfed27f46961297fd628dd8051ecaa8b5cf1985982b978928a205139223c5"
},
"children": [
{
"id": "3607",
"routeId": "sa_26ebc37c820daf8730770c6a",
"moleculeId": "sa_f1b2156397423fac3897e5d5",
"parentId": "3606",
"isLeaf": true,
"molecule": {
"id": "sa_f1b2156397423fac3897e5d5",
"inchikey": "FYDHSNLXZRGWFU-UHFFFAOYSA-N",
"smiles": "O=C(O)c1ccc(B(O)O)c(Cl)c1"
},
"smiles": "O=C(O)c1ccc(B(O)O)c(Cl)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3608",
"routeId": "sa_26ebc37c820daf8730770c6a",
"moleculeId": "sa_86b72aaca3749ce987a9d529",
"parentId": "3606",
"isLeaf": false,
"molecule": {
"id": "sa_86b72aaca3749ce987a9d529",
"inchikey": "ZFEJTYQUWRVCFW-UHFFFAOYSA-N",
"smiles": "COc1ccc2nc(Cl)ccc2c1"
},
"smiles": "COc1ccc2nc(Cl)ccc2c1",
"reactionStepId": "sa_89625e74edaf8d96327ee40b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160067254A1;0475;1848821\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:9].O[c:8]1[n:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:13][c:12]2[cH:11][cH:10]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][c:8]([Cl:9])[cH:10][cH:11][c:12]2[cH:13]1\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:9].O[c:8]1[n:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:13][c:12]2[cH:11][cH:10]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7][c:8]([Cl:9])[cH:10][cH:11][c:12]2[cH:13]1\"}",
"reactionStep": {
"id": "sa_89625e74edaf8d96327ee40b",
"reactionHash": "1d789ebe27306e95541b1f0db50360f72281fa629a2a76346930e52158a05833"
},
"children": [
{
"id": "3609",
"routeId": "sa_26ebc37c820daf8730770c6a",
"moleculeId": "sa_9daf6b6a5cc386d0dcbc2cb2",
"parentId": "3608",
"isLeaf": true,
"molecule": {
"id": "sa_9daf6b6a5cc386d0dcbc2cb2",
"inchikey": "MLHXCMWXUMCLNK-UHFFFAOYSA-N",
"smiles": "COc1ccc2[nH]c(=O)ccc2c1"
},
"smiles": "COc1ccc2nc(O)ccc2c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3610",
"routeId": "sa_26ebc37c820daf8730770c6a",
"moleculeId": "sa_312a7cd3d48a055e9bc98180",
"parentId": "3608",
"isLeaf": true,
"molecule": {
"id": "sa_312a7cd3d48a055e9bc98180",
"inchikey": "XHXFXVLFKHQFAL-UHFFFAOYSA-N",
"smiles": "O=P(Cl)(Cl)Cl"
},
"smiles": "O=P(Cl)(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "3611",
"routeId": "sa_26ebc37c820daf8730770c6a",
"moleculeId": "sa_c9679fdd876f32f86b77fb69",
"parentId": "3604",
"isLeaf": true,
"molecule": {
"id": "sa_c9679fdd876f32f86b77fb69",
"inchikey": "QGZKDVFQNNGYKY-UHFFFAOYSA-N",
"smiles": "N"
},
"smiles": "N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
}