Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CNC(=O)c1c(-c2ccc(F)cc2)oc2cc(N(CCCO)S(C)(=O)=O)c(Br)cc12
InChiKey
MYVJGEFVKJDAHN-UHFFFAOYSA-N
Route Signature
0eae96baa73fdf901fd9a548ccc7445d08bdb924cb8d5f0b3d7dfcd4fdbcf3a0
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_540c39d066f483eebe5ceaf7",
"signature": "0eae96baa73fdf901fd9a548ccc7445d08bdb924cb8d5f0b3d7dfcd4fdbcf3a0",
"contentHash": "a50448eb2672ecbaef785c83282b5a3021da4c8ecc9f0ccd4154af3f43dd74b8",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_3bced3c4db942efd319a88c4",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-03073",
"moleculeId": "sa_9e4649eb8b5d815d40c661de",
"smiles": "CNC(=O)c1c(-c2ccc(F)cc2)oc2cc(N(CCCO)S(C)(=O)=O)c(Br)cc12",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_9e4649eb8b5d815d40c661de",
"inchikey": "MYVJGEFVKJDAHN-UHFFFAOYSA-N",
"smiles": "CNC(=O)c1c(-c2ccc(F)cc2)oc2cc(N(CCCO)S(C)(=O)=O)c(Br)cc12"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "14975",
"routeId": "sa_540c39d066f483eebe5ceaf7",
"moleculeId": "sa_9e4649eb8b5d815d40c661de",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_9e4649eb8b5d815d40c661de",
"inchikey": "MYVJGEFVKJDAHN-UHFFFAOYSA-N",
"smiles": "CNC(=O)c1c(-c2ccc(F)cc2)oc2cc(N(CCCO)S(C)(=O)=O)c(Br)cc12"
},
"smiles": "CNC(=O)c1c(-c2ccc(F)cc2)oc2cc(N(CCCO)S(C)(=O)=O)c(Br)cc12",
"reactionStepId": "sa_4864fee76b1a1b4b55ca6db2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120328569A1;0740;1314202\",\"rsmi\":\"Br[CH2:22][CH2:23][CH2:24][OH:25].[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[o:14][c:15]2[c:16]1[cH:17][c:18]([Br:19])[c:20]([NH:21][S:26]([CH3:27])(=[O:28])=[O:29])[cH:30]2>CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[o:14][c:15]2[c:16]1[cH:17][c:18]([Br:19])[c:20]([N:21]([CH2:22][CH2:23][CH2:24][OH:25])[S:26]([CH3:27])(=[O:28])=[O:29])[cH:30]2\"},\"mapped_reaction_smiles\":\"Br[CH2:22][CH2:23][CH2:24][OH:25].[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[o:14][c:15]2[c:16]1[cH:17][c:18]([Br:19])[c:20]([NH:21][S:26]([CH3:27])(=[O:28])=[O:29])[cH:30]2>CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[o:14][c:15]2[c:16]1[cH:17][c:18]([Br:19])[c:20]([N:21]([CH2:22][CH2:23][CH2:24][OH:25])[S:26]([CH3:27])(=[O:28])=[O:29])[cH:30]2\"}",
"reactionStep": {
"id": "sa_4864fee76b1a1b4b55ca6db2",
"reactionHash": "54889281c51efb5c40668d67a64f8431b707478ff9ef191f5fead08136c31b04"
},
"children": [
{
"id": "14976",
"routeId": "sa_540c39d066f483eebe5ceaf7",
"moleculeId": "sa_4e0739973446652372900716",
"parentId": "14975",
"isLeaf": true,
"molecule": {
"id": "sa_4e0739973446652372900716",
"inchikey": "RQFUZUMFPRMVDX-UHFFFAOYSA-N",
"smiles": "OCCCBr"
},
"smiles": "OCCCBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14977",
"routeId": "sa_540c39d066f483eebe5ceaf7",
"moleculeId": "sa_a4aa56b6941f8b0ba7c86205",
"parentId": "14975",
"isLeaf": false,
"molecule": {
"id": "sa_a4aa56b6941f8b0ba7c86205",
"inchikey": "WTZOSDMRBIVARH-UHFFFAOYSA-N",
"smiles": "CNC(=O)c1c(-c2ccc(F)cc2)oc2cc(NS(C)(=O)=O)c(Br)cc12"
},
"smiles": "CNC(=O)c1c(-c2ccc(F)cc2)oc2cc(NS(C)(=O)=O)c(Br)cc12",
"reactionStepId": "sa_e0d0c261b333e85495fa77af",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120328569A1;0737;1314201\",\"rsmi\":\"O[C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[o:14][c:15]2[c:16]1[cH:17][c:18]([Br:19])[c:20]([NH:21][S:22]([CH3:23])(=[O:24])=[O:25])[cH:26]2.[CH3:1][NH2:2]>CCN(CC)CC.CCN=C=NCCCN(C)C.CCOC(C)=O.CN(C)C=O.Cl.On1nnc2ccccc21>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[o:14][c:15]2[c:16]1[cH:17][c:18]([Br:19])[c:20]([NH:21][S:22]([CH3:23])(=[O:24])=[O:25])[cH:26]2\"},\"mapped_reaction_smiles\":\"O[C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[o:14][c:15]2[c:16]1[cH:17][c:18]([Br:19])[c:20]([NH:21][S:22]([CH3:23])(=[O:24])=[O:25])[cH:26]2.[CH3:1][NH2:2]>CCN(CC)CC.CCN=C=NCCCN(C)C.CCOC(C)=O.CN(C)C=O.Cl.On1nnc2ccccc21>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[o:14][c:15]2[c:16]1[cH:17][c:18]([Br:19])[c:20]([NH:21][S:22]([CH3:23])(=[O:24])=[O:25])[cH:26]2\"}",
"reactionStep": {
"id": "sa_e0d0c261b333e85495fa77af",
"reactionHash": "34fcf8d263f56e608e0aa3dab81586ed604f1a0ad8b12871254e2d19818daef0"
},
"children": [
{
"id": "14978",
"routeId": "sa_540c39d066f483eebe5ceaf7",
"moleculeId": "sa_e00cdbb7fb9d3ecf114a19d3",
"parentId": "14977",
"isLeaf": true,
"molecule": {
"id": "sa_e00cdbb7fb9d3ecf114a19d3",
"inchikey": "BAVYZALUXZFZLV-UHFFFAOYSA-N",
"smiles": "CN"
},
"smiles": "CN",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14979",
"routeId": "sa_540c39d066f483eebe5ceaf7",
"moleculeId": "sa_491fac78857e7e92149470a1",
"parentId": "14977",
"isLeaf": false,
"molecule": {
"id": "sa_491fac78857e7e92149470a1",
"inchikey": "ZUSGVKWOCGGFKZ-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Nc1cc2oc(-c3ccc(F)cc3)c(C(=O)O)c2cc1Br"
},
"smiles": "CS(=O)(=O)Nc1cc2oc(-c3ccc(F)cc3)c(C(=O)O)c2cc1Br",
"reactionStepId": "sa_6757a77dd499d3416638f2e7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120328569A1;0735;1314200\",\"rsmi\":\"C[O:16][C:14]([c:13]1[c:9]2[c:8]([cH:7][c:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[c:11]([Br:12])[cH:10]2)[o:25][c:17]1-[c:18]1[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]1)=[O:15]>C1COCCO1.Cl.O.O.[Li]O>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][c:8]2[c:9]([cH:10][c:11]1[Br:12])[c:13]([C:14](=[O:15])[OH:16])[c:17](-[c:18]1[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]1)[o:25]2\"},\"mapped_reaction_smiles\":\"C[O:16][C:14]([c:13]1[c:9]2[c:8]([cH:7][c:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[c:11]([Br:12])[cH:10]2)[o:25][c:17]1-[c:18]1[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]1)=[O:15]>C1COCCO1.Cl.O.O.[Li]O>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][c:8]2[c:9]([cH:10][c:11]1[Br:12])[c:13]([C:14](=[O:15])[OH:16])[c:17](-[c:18]1[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]1)[o:25]2\"}",
"reactionStep": {
"id": "sa_6757a77dd499d3416638f2e7",
"reactionHash": "235d9e4c1d0780a6834a1b8659d13a6ffceed0c24f0b5237d6fbf0257dfbf022"
},
"children": [
{
"id": "14980",
"routeId": "sa_540c39d066f483eebe5ceaf7",
"moleculeId": "sa_661d69763c0ff99e617c8a48",
"parentId": "14979",
"isLeaf": false,
"molecule": {
"id": "sa_661d69763c0ff99e617c8a48",
"inchikey": "AJVHBVZWVMQACW-UHFFFAOYSA-N",
"smiles": "COC(=O)c1c(-c2ccc(F)cc2)oc2cc(NS(C)(=O)=O)c(Br)cc12"
},
"smiles": "COC(=O)c1c(-c2ccc(F)cc2)oc2cc(NS(C)(=O)=O)c(Br)cc12",
"reactionStepId": "sa_e5201882acf3fc2924033a4d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120328569A1;0625;1314180\",\"rsmi\":\"Cl[S:22]([CH3:23])(=[O:24])=[O:25].[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[o:14][c:15]2[c:16]1[cH:17][c:18]([Br:19])[c:20]([NH2:21])[cH:26]2>ClCCl.O.c1ccncc1>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[o:14][c:15]2[c:16]1[cH:17][c:18]([Br:19])[c:20]([NH:21][S:22]([CH3:23])(=[O:24])=[O:25])[cH:26]2\"},\"mapped_reaction_smiles\":\"Cl[S:22]([CH3:23])(=[O:24])=[O:25].[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[o:14][c:15]2[c:16]1[cH:17][c:18]([Br:19])[c:20]([NH2:21])[cH:26]2>ClCCl.O.c1ccncc1>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[o:14][c:15]2[c:16]1[cH:17][c:18]([Br:19])[c:20]([NH:21][S:22]([CH3:23])(=[O:24])=[O:25])[cH:26]2\"}",
"reactionStep": {
"id": "sa_e5201882acf3fc2924033a4d",
"reactionHash": "c96ed69584a27bdfb17ed943c7ff95649e0b10509c515d959b20cdb5f5d680c5"
},
"children": [
{
"id": "14981",
"routeId": "sa_540c39d066f483eebe5ceaf7",
"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "14980",
"isLeaf": true,
"molecule": {
"id": "sa_d2a31ea58046b00856f61ca5",
"inchikey": "QARBMVPHQWIHKH-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Cl"
},
"smiles": "CS(=O)(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14982",
"routeId": "sa_540c39d066f483eebe5ceaf7",
"moleculeId": "sa_a71d4c78b1c3cf69346e0d55",
"parentId": "14980",
"isLeaf": false,
"molecule": {
"id": "sa_a71d4c78b1c3cf69346e0d55",
"inchikey": "SWPMAUCXSDOOPO-UHFFFAOYSA-N",
"smiles": "COC(=O)c1c(-c2ccc(F)cc2)oc2cc(N)c(Br)cc12"
},
"smiles": "COC(=O)c1c(-c2ccc(F)cc2)oc2cc(N)c(Br)cc12",
"reactionStepId": "sa_cf9c1dc29e6e86b8076ba5b2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120328569A1;0668;1314190\",\"rsmi\":\"O=[N+:21]([O-])[c:20]1[c:18]([Br:19])[cH:17][c:16]2[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:6](-[c:7]3[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]3)[o:14][c:15]2[cH:22]1>C1CCOC1.CO.O.Cl.[Fe].N>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[o:14][c:15]2[c:16]1[cH:17][c:18]([Br:19])[c:20]([NH2:21])[cH:22]2\"},\"mapped_reaction_smiles\":\"O=[N+:21]([O-])[c:20]1[c:18]([Br:19])[cH:17][c:16]2[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:6](-[c:7]3[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]3)[o:14][c:15]2[cH:22]1>C1CCOC1.CO.O.Cl.[Fe].N>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[o:14][c:15]2[c:16]1[cH:17][c:18]([Br:19])[c:20]([NH2:21])[cH:22]2\"}",
"reactionStep": {
"id": "sa_cf9c1dc29e6e86b8076ba5b2",
"reactionHash": "0504cee675db0535b1ea1639bff1f3a657906ce41a0abbeee2832c2f82ce0e4d"
},
"children": [
{
"id": "14983",
"routeId": "sa_540c39d066f483eebe5ceaf7",
"moleculeId": "sa_d9ac08cae5428adcc6ad5f52",
"parentId": "14982",
"isLeaf": false,
"molecule": {
"id": "sa_d9ac08cae5428adcc6ad5f52",
"inchikey": "UIYDXOGOYHWEKS-UHFFFAOYSA-N",
"smiles": "COC(=O)c1c(-c2ccc(F)cc2)oc2cc([N+](=O)[O-])c(Br)cc12"
},
"smiles": "COC(=O)c1c(-c2ccc(F)cc2)oc2cc([N+](=O)[O-])c(Br)cc12",
"reactionStepId": "sa_4380ede7e5ae2e45b4642e3e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120328569A1;0620;1314179\",\"rsmi\":\"O=[N+:21]([OH:22])[O-:23].[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[o:14][c:15]2[c:16]1[cH:17][c:18]([Br:19])[cH:20][cH:24]2>ClC(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[o:14][c:15]2[c:16]1[cH:17][c:18]([Br:19])[c:20]([N+:21](=[O:22])[O-:23])[cH:24]2\"},\"mapped_reaction_smiles\":\"O=[N+:21]([OH:22])[O-:23].[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[o:14][c:15]2[c:16]1[cH:17][c:18]([Br:19])[cH:20][cH:24]2>ClC(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[o:14][c:15]2[c:16]1[cH:17][c:18]([Br:19])[c:20]([N+:21](=[O:22])[O-:23])[cH:24]2\"}",
"reactionStep": {
"id": "sa_4380ede7e5ae2e45b4642e3e",
"reactionHash": "60b5f2d14434491d10f71ca9c0442f0b5642230096824845dfcc15d096d337b7"
},
"children": [
{
"id": "14984",
"routeId": "sa_540c39d066f483eebe5ceaf7",
"moleculeId": "sa_edac0a7fd043198784a28dd9",
"parentId": "14983",
"isLeaf": true,
"molecule": {
"id": "sa_edac0a7fd043198784a28dd9",
"inchikey": "GRYLNZFGIOXLOG-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])O"
},
"smiles": "O=[N+]([O-])O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14985",
"routeId": "sa_540c39d066f483eebe5ceaf7",
"moleculeId": "sa_fd326c7931bdbaf9a653c24f",
"parentId": "14983",
"isLeaf": true,
"molecule": {
"id": "sa_fd326c7931bdbaf9a653c24f",
"inchikey": "GSBFPXKKYLRXDI-UHFFFAOYSA-N",
"smiles": "COC(=O)c1c(-c2ccc(F)cc2)oc2ccc(Br)cc12"
},
"smiles": "COC(=O)c1c(-c2ccc(F)cc2)oc2ccc(Br)cc12",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
]
}
]
}
}