Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCS(=O)(=O)NCc1cncc(-c2cc3c(cc2Cl)N(C)C(=O)CC3)c1
InChiKey
AFSUGETVIMCCPK-UHFFFAOYSA-N
Route Signature
aef7f7552b35a34aadd000364e6c8cd4ec3f1cd4e5881492864e12881b190045
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_ac0a41cd7c32d29e56af2cb6",
"signature": "aef7f7552b35a34aadd000364e6c8cd4ec3f1cd4e5881492864e12881b190045",
"contentHash": "160d445e7eefbeeedc370ae9d464b9f32b0e6b10ad06e6cdfad7d27d0b00d5a1",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_e34ecf1deec241f4e688883f",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-02340",
"moleculeId": "sa_3be6dcbaf925ff3a922d2029",
"smiles": "CCS(=O)(=O)NCc1cncc(-c2cc3c(cc2Cl)N(C)C(=O)CC3)c1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_3be6dcbaf925ff3a922d2029",
"inchikey": "AFSUGETVIMCCPK-UHFFFAOYSA-N",
"smiles": "CCS(=O)(=O)NCc1cncc(-c2cc3c(cc2Cl)N(C)C(=O)CC3)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "1896",
"routeId": "sa_ac0a41cd7c32d29e56af2cb6",
"moleculeId": "sa_3be6dcbaf925ff3a922d2029",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_3be6dcbaf925ff3a922d2029",
"inchikey": "AFSUGETVIMCCPK-UHFFFAOYSA-N",
"smiles": "CCS(=O)(=O)NCc1cncc(-c2cc3c(cc2Cl)N(C)C(=O)CC3)c1"
},
"smiles": "CCS(=O)(=O)NCc1cncc(-c2cc3c(cc2Cl)N(C)C(=O)CC3)c1",
"reactionStepId": "sa_b52ee917cf945b43167800d8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130072679A1;0847;1348286\",\"rsmi\":\"Br[c:10]1[cH:9][c:8]([CH2:7][NH:6][S:3]([CH2:2][CH3:1])(=[O:4])=[O:5])[cH:26][n:25][cH:24]1.CC1(C)OB([c:11]2[c:12]([Cl:13])[cH:14][c:15]3[c:16]([cH:17]2)[CH2:18][CH2:19][C:20](=[O:21])[N:22]3[CH3:23])OC1(C)C>CCOC(C)=O.CN(C)C=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O=C(O)O.[Na+].[Na+]>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[NH:6][CH2:7][c:8]1[cH:9][c:10](-[c:11]2[c:12]([Cl:13])[cH:14][c:15]3[c:16]([cH:17]2)[CH2:18][CH2:19][C:20](=[O:21])[N:22]3[CH3:23])[cH:24][n:25][cH:26]1\"},\"mapped_reaction_smiles\":\"Br[c:10]1[cH:9][c:8]([CH2:7][NH:6][S:3]([CH2:2][CH3:1])(=[O:4])=[O:5])[cH:26][n:25][cH:24]1.CC1(C)OB([c:11]2[c:12]([Cl:13])[cH:14][c:15]3[c:16]([cH:17]2)[CH2:18][CH2:19][C:20](=[O:21])[N:22]3[CH3:23])OC1(C)C>CCOC(C)=O.CN(C)C=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O=C(O)O.[Na+].[Na+]>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[NH:6][CH2:7][c:8]1[cH:9][c:10](-[c:11]2[c:12]([Cl:13])[cH:14][c:15]3[c:16]([cH:17]2)[CH2:18][CH2:19][C:20](=[O:21])[N:22]3[CH3:23])[cH:24][n:25][cH:26]1\"}",
"reactionStep": {
"id": "sa_b52ee917cf945b43167800d8",
"reactionHash": "82f38842eb9ea0e062d65a43358a248f2e2b77408416a54711962fcffb1766be"
},
"children": [
{
"id": "1897",
"routeId": "sa_ac0a41cd7c32d29e56af2cb6",
"moleculeId": "sa_30ce1b5dc6ad4cf752f2b09d",
"parentId": "1896",
"isLeaf": false,
"molecule": {
"id": "sa_30ce1b5dc6ad4cf752f2b09d",
"inchikey": "BCDKUDMEVAEYJE-UHFFFAOYSA-N",
"smiles": "CN1C(=O)CCc2cc(B3OC(C)(C)C(C)(C)O3)c(Cl)cc21"
},
"smiles": "CN1C(=O)CCc2cc(B3OC(C)(C)C(C)(C)O3)c(Cl)cc21",
"reactionStepId": "sa_d0672aa54648f9c8fc454616",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130072679A1;0845;1348285\",\"rsmi\":\"Br[c:9]1[cH:8][c:7]2[c:22]([cH:21][c:19]1[Cl:20])[N:2]([CH3:1])[C:3](=[O:4])[CH2:5][CH2:6]2.CC1(C)OB([B:10]2[O:11][C:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[O:18]2)OC1(C)C>C1COCCO1.CC(=O)O.CCOC(C)=O.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][CH2:6][c:7]2[cH:8][c:9]([B:10]3[O:11][C:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[O:18]3)[c:19]([Cl:20])[cH:21][c:22]21\"},\"mapped_reaction_smiles\":\"Br[c:9]1[cH:8][c:7]2[c:22]([cH:21][c:19]1[Cl:20])[N:2]([CH3:1])[C:3](=[O:4])[CH2:5][CH2:6]2.CC1(C)OB([B:10]2[O:11][C:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[O:18]2)OC1(C)C>C1COCCO1.CC(=O)O.CCOC(C)=O.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][CH2:6][c:7]2[cH:8][c:9]([B:10]3[O:11][C:12]([CH3:13])([CH3:14])[C:15]([CH3:16])([CH3:17])[O:18]3)[c:19]([Cl:20])[cH:21][c:22]21\"}",
"reactionStep": {
"id": "sa_d0672aa54648f9c8fc454616",
"reactionHash": "fc2742088cd334a3f7c5bab9d3bd941a0fe319de9df4bae0c7273bf5854f4812"
},
"children": [
{
"id": "1898",
"routeId": "sa_ac0a41cd7c32d29e56af2cb6",
"moleculeId": "sa_9af08ce7cff6eb9f9c6deafb",
"parentId": "1897",
"isLeaf": false,
"molecule": {
"id": "sa_9af08ce7cff6eb9f9c6deafb",
"inchikey": "IFKKHHBIBWEPQF-UHFFFAOYSA-N",
"smiles": "CN1C(=O)CCc2cc(Br)c(Cl)cc21"
},
"smiles": "CN1C(=O)CCc2cc(Br)c(Cl)cc21",
"reactionStepId": "sa_afee028e2b95b181ca98a165",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130072679A1;0843;1348284\",\"rsmi\":\"I[CH3:1].[NH:2]1[C:3](=[O:4])[CH2:5][CH2:6][c:7]2[cH:8][c:9]([Br:10])[c:11]([Cl:12])[cH:13][c:14]21>CC(C)(C)O.CN(C)C=O.O.[K+]>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][CH2:6][c:7]2[cH:8][c:9]([Br:10])[c:11]([Cl:12])[cH:13][c:14]21\"},\"mapped_reaction_smiles\":\"I[CH3:1].[NH:2]1[C:3](=[O:4])[CH2:5][CH2:6][c:7]2[cH:8][c:9]([Br:10])[c:11]([Cl:12])[cH:13][c:14]21>CC(C)(C)O.CN(C)C=O.O.[K+]>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][CH2:6][c:7]2[cH:8][c:9]([Br:10])[c:11]([Cl:12])[cH:13][c:14]21\"}",
"reactionStep": {
"id": "sa_afee028e2b95b181ca98a165",
"reactionHash": "7eac29fa9a36d65d305fdb026fe8c586d48bad6fd249c01b45760d6338b5db87"
},
"children": [
{
"id": "1899",
"routeId": "sa_ac0a41cd7c32d29e56af2cb6",
"moleculeId": "sa_2c1c3ab7275753101c63773a",
"parentId": "1898",
"isLeaf": false,
"molecule": {
"id": "sa_2c1c3ab7275753101c63773a",
"inchikey": "HGGUWHWVJPOCLK-UHFFFAOYSA-N",
"smiles": "O=C1CCc2cc(Br)c(Cl)cc2N1"
},
"smiles": "O=C1CCc2cc(Br)c(Cl)cc2N1",
"reactionStepId": "sa_8f6bbfa65aaea51dead02d18",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130072679A1;0841;1348283\",\"rsmi\":\"Cl[CH2:4][CH2:3][C:2](=[O:1])[NH:13][c:12]1[cH:5][cH:6][c:7]([Br:8])[c:9]([Cl:10])[cH:11]1>[Al+3].Cl.Cl.Cl>[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][c:7]([Br:8])[c:9]([Cl:10])[cH:11][c:12]2[NH:13]1\"},\"mapped_reaction_smiles\":\"Cl[CH2:4][CH2:3][C:2](=[O:1])[NH:13][c:12]1[cH:5][cH:6][c:7]([Br:8])[c:9]([Cl:10])[cH:11]1>[Al+3].Cl.Cl.Cl>[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][c:7]([Br:8])[c:9]([Cl:10])[cH:11][c:12]2[NH:13]1\"}",
"reactionStep": {
"id": "sa_8f6bbfa65aaea51dead02d18",
"reactionHash": "15d9ea25ccd12f2b7be3ea8402cdca24b7d580123eaaea490927f9d36839fde2"
},
"children": [
{
"id": "1900",
"routeId": "sa_ac0a41cd7c32d29e56af2cb6",
"moleculeId": "sa_f49e7cd84411aa07852509f4",
"parentId": "1899",
"isLeaf": false,
"molecule": {
"id": "sa_f49e7cd84411aa07852509f4",
"inchikey": "QOPFKGOBJUYBLM-UHFFFAOYSA-N",
"smiles": "O=C(CCCl)Nc1ccc(Br)c(Cl)c1"
},
"smiles": "O=C(CCCl)Nc1ccc(Br)c(Cl)c1",
"reactionStepId": "sa_d5d2377710dc1af98e9b8790",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130072679A1;0839;1348282\",\"rsmi\":\"Cl[C:2](=[O:1])[CH2:3][CH2:4][Cl:5].[NH2:6][c:7]1[cH:8][c:9]([Cl:10])[c:11]([Br:12])[cH:13][cH:14]1>ClCCCl.c1ccncc1>[O:1]=[C:2]([CH2:3][CH2:4][Cl:5])[NH:6][c:7]1[cH:8][c:9]([Cl:10])[c:11]([Br:12])[cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"Cl[C:2](=[O:1])[CH2:3][CH2:4][Cl:5].[NH2:6][c:7]1[cH:8][c:9]([Cl:10])[c:11]([Br:12])[cH:13][cH:14]1>ClCCCl.c1ccncc1>[O:1]=[C:2]([CH2:3][CH2:4][Cl:5])[NH:6][c:7]1[cH:8][c:9]([Cl:10])[c:11]([Br:12])[cH:13][cH:14]1\"}",
"reactionStep": {
"id": "sa_d5d2377710dc1af98e9b8790",
"reactionHash": "b0c806d431d026c352dfc0bda522f0196b5294b463a2ca1fdfeee0d939b62df5"
},
"children": [
{
"id": "1901",
"routeId": "sa_ac0a41cd7c32d29e56af2cb6",
"moleculeId": "sa_4346d8dfa1e3ce4d5ccbd312",
"parentId": "1900",
"isLeaf": true,
"molecule": {
"id": "sa_4346d8dfa1e3ce4d5ccbd312",
"inchikey": "INUNLMUAPJVRME-UHFFFAOYSA-N",
"smiles": "O=C(Cl)CCCl"
},
"smiles": "O=C(Cl)CCCl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1902",
"routeId": "sa_ac0a41cd7c32d29e56af2cb6",
"moleculeId": "sa_1f16c8fa2ecdd31ce400ccf4",
"parentId": "1900",
"isLeaf": true,
"molecule": {
"id": "sa_1f16c8fa2ecdd31ce400ccf4",
"inchikey": "QLYHPNUFNZJXOQ-UHFFFAOYSA-N",
"smiles": "Nc1ccc(Br)c(Cl)c1"
},
"smiles": "Nc1ccc(Br)c(Cl)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "1903",
"routeId": "sa_ac0a41cd7c32d29e56af2cb6",
"moleculeId": "sa_82fdccf7d1cc329c9db73f21",
"parentId": "1898",
"isLeaf": true,
"molecule": {
"id": "sa_82fdccf7d1cc329c9db73f21",
"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
},
"smiles": "CI",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "1904",
"routeId": "sa_ac0a41cd7c32d29e56af2cb6",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "1897",
"isLeaf": true,
"molecule": {
"id": "sa_e6c301388ac142801d4af5a2",
"inchikey": "IPWKHHSGDUIRAH-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C"
},
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "1905",
"routeId": "sa_ac0a41cd7c32d29e56af2cb6",
"moleculeId": "sa_2440d6b3df902d83619e995a",
"parentId": "1896",
"isLeaf": false,
"molecule": {
"id": "sa_2440d6b3df902d83619e995a",
"inchikey": "PAIFOXAOIFQAFT-UHFFFAOYSA-N",
"smiles": "CCS(=O)(=O)NCc1cncc(Br)c1"
},
"smiles": "CCS(=O)(=O)NCc1cncc(Br)c1",
"reactionStepId": "sa_dfb6bb8c7ab24dedb4c7dad1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130072679A1;0584;1348183\",\"rsmi\":\"O=[CH:7][c:8]1[cH:9][c:10]([Br:11])[cH:12][n:13][cH:14]1.[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[NH2:6]>CC(C)O.CC(C)O.CC(C)O.CC(C)O.CO.Cc1ccccc1.O.B.[Na+].[Ti+4]>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[NH:6][CH2:7][c:8]1[cH:9][c:10]([Br:11])[cH:12][n:13][cH:14]1\"},\"mapped_reaction_smiles\":\"O=[CH:7][c:8]1[cH:9][c:10]([Br:11])[cH:12][n:13][cH:14]1.[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[NH2:6]>CC(C)O.CC(C)O.CC(C)O.CC(C)O.CO.Cc1ccccc1.O.B.[Na+].[Ti+4]>[CH3:1][CH2:2][S:3](=[O:4])(=[O:5])[NH:6][CH2:7][c:8]1[cH:9][c:10]([Br:11])[cH:12][n:13][cH:14]1\"}",
"reactionStep": {
"id": "sa_dfb6bb8c7ab24dedb4c7dad1",
"reactionHash": "54637a5fad1162c52719421a019fe007f04796ba58a4b239d1407e6576378f66"
},
"children": [
{
"id": "1906",
"routeId": "sa_ac0a41cd7c32d29e56af2cb6",
"moleculeId": "sa_3f1c5fe9d7bc7c775bfdb3f2",
"parentId": "1905",
"isLeaf": true,
"molecule": {
"id": "sa_3f1c5fe9d7bc7c775bfdb3f2",
"inchikey": "NGUVGKAEOFPLDT-UHFFFAOYSA-N",
"smiles": "O=Cc1cncc(Br)c1"
},
"smiles": "O=Cc1cncc(Br)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "1907",
"routeId": "sa_ac0a41cd7c32d29e56af2cb6",
"moleculeId": "sa_9dbf1886f94097c58e5a438a",
"parentId": "1905",
"isLeaf": true,
"molecule": {
"id": "sa_9dbf1886f94097c58e5a438a",
"inchikey": "ZCRZCMUDOWDGOB-UHFFFAOYSA-N",
"smiles": "CCS(N)(=O)=O"
},
"smiles": "CCS(N)(=O)=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}