Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
N#Cc1cccc(C2CCc3[nH]c(C(=O)O)cc32)c1
InChiKey
ITCSFUVEBIQHEQ-UHFFFAOYSA-N
Route Signature
a36bd939494fad4e33bcafa5efd066efa8ee9bd62e83099df63f53bd948ea924
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_29a211bed6278821bf6df5fe",
"signature": "a36bd939494fad4e33bcafa5efd066efa8ee9bd62e83099df63f53bd948ea924",
"contentHash": "01b3572a2001ef21354b48f3451cbb63d08feb549c9e0ae87f86462936d3b077",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_a4c5cac571880a5c178b2348",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00521",
"moleculeId": "sa_7b90a9ed881819c666b05f6c",
"smiles": "N#Cc1cccc(C2CCc3[nH]c(C(=O)O)cc32)c1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_7b90a9ed881819c666b05f6c",
"inchikey": "ITCSFUVEBIQHEQ-UHFFFAOYSA-N",
"smiles": "N#Cc1cccc(C2CCc3[nH]c(C(=O)O)cc32)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9553",
"routeId": "sa_29a211bed6278821bf6df5fe",
"moleculeId": "sa_7b90a9ed881819c666b05f6c",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_7b90a9ed881819c666b05f6c",
"inchikey": "ITCSFUVEBIQHEQ-UHFFFAOYSA-N",
"smiles": "N#Cc1cccc(C2CCc3[nH]c(C(=O)O)cc32)c1"
},
"smiles": "N#Cc1cccc(C2CCc3[nH]c(C(=O)O)cc32)c1",
"reactionStepId": "sa_f050e429db30d602da3aa3a8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100029737A1;0621;832649\",\"rsmi\":\"C[O:17][C:15]([c:14]1[cH:13][c:12]2[c:11]([nH:18]1)[CH2:10][CH2:9][CH:8]2[c:7]1[cH:6][cH:5][cH:4][c:3]([C:2]#[N:1])[cH:19]1)=[O:16]>C1CCOC1.CO.[Li+].O>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]2[CH2:9][CH2:10][c:11]3[c:12]2[cH:13][c:14]([C:15](=[O:16])[OH:17])[nH:18]3)[cH:19]1\"},\"mapped_reaction_smiles\":\"C[O:17][C:15]([c:14]1[cH:13][c:12]2[c:11]([nH:18]1)[CH2:10][CH2:9][CH:8]2[c:7]1[cH:6][cH:5][cH:4][c:3]([C:2]#[N:1])[cH:19]1)=[O:16]>C1CCOC1.CO.[Li+].O>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]2[CH2:9][CH2:10][c:11]3[c:12]2[cH:13][c:14]([C:15](=[O:16])[OH:17])[nH:18]3)[cH:19]1\"}",
"reactionStep": {
"id": "sa_f050e429db30d602da3aa3a8",
"reactionHash": "bf5e000e985f882625618b7c5f967a93b23df89923cea2a6db9a1b08ddd7a8ec"
},
"children": [
{
"id": "9554",
"routeId": "sa_29a211bed6278821bf6df5fe",
"moleculeId": "sa_76d57941d976f58c1c3f9889",
"parentId": "9553",
"isLeaf": false,
"molecule": {
"id": "sa_76d57941d976f58c1c3f9889",
"inchikey": "SLJRLRDCOXUSFN-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc2c([nH]1)CCC2c1cccc(C#N)c1"
},
"smiles": "COC(=O)c1cc2c([nH]1)CCC2c1cccc(C#N)c1",
"reactionStepId": "sa_7d25d2680a9a8da7a232e88e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100029737A1;0522;832608\",\"rsmi\":\"Br[c:14]1[cH:13][c:12]([CH:11]2[c:7]3[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[nH:20][c:8]3[CH2:9][CH2:10]2)[cH:19][cH:18][cH:17]1.[CH:15]#[N:16]>CC(=O)N(C)C.O.C#N.[Zn+2].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([nH:20]1)[CH2:9][CH2:10][CH:11]2[c:12]1[cH:13][c:14]([C:15]#[N:16])[cH:17][cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"Br[c:14]1[cH:13][c:12]([CH:11]2[c:7]3[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[nH:20][c:8]3[CH2:9][CH2:10]2)[cH:19][cH:18][cH:17]1.[CH:15]#[N:16]>CC(=O)N(C)C.O.C#N.[Zn+2].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([nH:20]1)[CH2:9][CH2:10][CH:11]2[c:12]1[cH:13][c:14]([C:15]#[N:16])[cH:17][cH:18][cH:19]1\"}",
"reactionStep": {
"id": "sa_7d25d2680a9a8da7a232e88e",
"reactionHash": "d7bd35af734ac7475326e8e15613f02042a11c4d24476ad884f593497e398dd7"
},
"children": [
{
"id": "9555",
"routeId": "sa_29a211bed6278821bf6df5fe",
"moleculeId": "sa_5995aff3aeff665a1f3e984d",
"parentId": "9554",
"isLeaf": true,
"molecule": {
"id": "sa_5995aff3aeff665a1f3e984d",
"inchikey": "LELOWRISYMNNSU-UHFFFAOYSA-N",
"smiles": "C#N"
},
"smiles": "C#N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9556",
"routeId": "sa_29a211bed6278821bf6df5fe",
"moleculeId": "sa_f69e62a4b7db694e0824a4ba",
"parentId": "9554",
"isLeaf": false,
"molecule": {
"id": "sa_f69e62a4b7db694e0824a4ba",
"inchikey": "MRMWECVFAILMID-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc2c([nH]1)CCC2c1cccc(Br)c1"
},
"smiles": "COC(=O)c1cc2c([nH]1)CCC2c1cccc(Br)c1",
"reactionStepId": "sa_546f61dbfd1326e61c8806f7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100029737A1;0518;832604\",\"rsmi\":\"Br[Mg][c:12]1[cH:13][c:14]([Br:15])[cH:16][cH:17][cH:18]1.O=[C:11]1[c:7]2[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[nH:19][c:8]2[CH2:9][CH2:10]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([nH:19]1)[CH2:9][CH2:10][CH:11]2[c:12]1[cH:13][c:14]([Br:15])[cH:16][cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"Br[Mg][c:12]1[cH:13][c:14]([Br:15])[cH:16][cH:17][cH:18]1.O=[C:11]1[c:7]2[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[nH:19][c:8]2[CH2:9][CH2:10]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([nH:19]1)[CH2:9][CH2:10][CH:11]2[c:12]1[cH:13][c:14]([Br:15])[cH:16][cH:17][cH:18]1\"}",
"reactionStep": {
"id": "sa_546f61dbfd1326e61c8806f7",
"reactionHash": "290f09591490beec58c13c6f605d451e63970bce375d41163e4cd16dc8d22937"
},
"children": [
{
"id": "9557",
"routeId": "sa_29a211bed6278821bf6df5fe",
"moleculeId": "sa_d79bcc7ea3ef9890d2752089",
"parentId": "9556",
"isLeaf": false,
"molecule": {
"id": "sa_d79bcc7ea3ef9890d2752089",
"inchikey": "ODRYKCOHHIIRKF-UHFFFAOYSA-M",
"smiles": "[Br][Mg][c]1cccc(Br)c1"
},
"smiles": "[Br][Mg][c]1cccc(Br)c1",
"reactionStepId": "sa_1f585fd131d03b36215ee9f3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100029737A1;0518;832605\",\"rsmi\":\"[Br:1][c:3]1[cH:4][c:5]([Br:6])[cH:7][cH:8][cH:9]1.[Mg:2]>C1CCOC1.COC(=O)c1cc2c([nH]1)CC=C2c1cccc(Br)c1.O=C(O)c1cc2c([nH]1)CCC2CC1CCCCC1>[Br:1][Mg:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][cH:8][cH:9]1\"},\"mapped_reaction_smiles\":\"[Br:1][c:3]1[cH:4][c:5]([Br:6])[cH:7][cH:8][cH:9]1.[Mg:2]>C1CCOC1.COC(=O)c1cc2c([nH]1)CC=C2c1cccc(Br)c1.O=C(O)c1cc2c([nH]1)CCC2CC1CCCCC1>[Br:1][Mg:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][cH:8][cH:9]1\"}",
"reactionStep": {
"id": "sa_1f585fd131d03b36215ee9f3",
"reactionHash": "2b364657fdc5c67b79a3bb68d07bfb9efecd7f0a02a68b4fc7118a0bde3faac2"
},
"children": [
{
"id": "9558",
"routeId": "sa_29a211bed6278821bf6df5fe",
"moleculeId": "sa_e68f3a5b8a7381a36c3b7e54",
"parentId": "9557",
"isLeaf": true,
"molecule": {
"id": "sa_e68f3a5b8a7381a36c3b7e54",
"inchikey": "FYYHWMGAXLPEAU-UHFFFAOYSA-N",
"smiles": "[Mg]"
},
"smiles": "[Mg]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9559",
"routeId": "sa_29a211bed6278821bf6df5fe",
"moleculeId": "sa_9e937317330bfbd672767380",
"parentId": "9557",
"isLeaf": true,
"molecule": {
"id": "sa_9e937317330bfbd672767380",
"inchikey": "JSRLURSZEMLAFO-UHFFFAOYSA-N",
"smiles": "Brc1cccc(Br)c1"
},
"smiles": "Brc1cccc(Br)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "9560",
"routeId": "sa_29a211bed6278821bf6df5fe",
"moleculeId": "sa_aa2e740bfe6badd605cf5c24",
"parentId": "9556",
"isLeaf": false,
"molecule": {
"id": "sa_aa2e740bfe6badd605cf5c24",
"inchikey": "PIGXMHQRVXEDIW-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc2c([nH]1)CCC2=O"
},
"smiles": "COC(=O)c1cc2c([nH]1)CCC2=O",
"reactionStepId": "sa_54f52ec7d28b312cd80f9397",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100029737A1;0374;832555\",\"rsmi\":\"O[C:11]([CH2:10][CH2:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[nH:13]1)=[O:12]>ClCCCl.O.O=C(O)O.[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([nH:13]1)[CH2:9][CH2:10][C:11]2=[O:12]\"},\"mapped_reaction_smiles\":\"O[C:11]([CH2:10][CH2:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[nH:13]1)=[O:12]>ClCCCl.O.O=C(O)O.[Na+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([nH:13]1)[CH2:9][CH2:10][C:11]2=[O:12]\"}",
"reactionStep": {
"id": "sa_54f52ec7d28b312cd80f9397",
"reactionHash": "30cc9e707269c4911332158b9239c471e14ba425e907be010f2a52046633cdc0"
},
"children": [
{
"id": "9561",
"routeId": "sa_29a211bed6278821bf6df5fe",
"moleculeId": "sa_3a0c6ccff06ec08cffc6116c",
"parentId": "9560",
"isLeaf": false,
"molecule": {
"id": "sa_3a0c6ccff06ec08cffc6116c",
"inchikey": "MKIXIQIJLIBXKS-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(CCC(=O)O)[nH]1"
},
"smiles": "COC(=O)c1ccc(CCC(=O)O)[nH]1",
"reactionStepId": "sa_436175a4167aba7994a8ce9f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100029737A1;0373;832554\",\"rsmi\":\"CC(C)(C)[O:13][C:11]([CH2:10][CH2:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[nH:14]1)=[O:12]>Cl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][C:11](=[O:12])[OH:13])[nH:14]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)[O:13][C:11]([CH2:10][CH2:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[nH:14]1)=[O:12]>Cl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][C:11](=[O:12])[OH:13])[nH:14]1\"}",
"reactionStep": {
"id": "sa_436175a4167aba7994a8ce9f",
"reactionHash": "7e95a806f662695628adb61348fcc5c9b517b8fd2167c82137bf09b50f4ed3b1"
},
"children": [
{
"id": "9562",
"routeId": "sa_29a211bed6278821bf6df5fe",
"moleculeId": "sa_796cb16ae5f80eaed79e3937",
"parentId": "9561",
"isLeaf": true,
"molecule": {
"id": "sa_796cb16ae5f80eaed79e3937",
"inchikey": "PNOLZJSZLFUQIS-UHFFFAOYSA-N",
"smiles": "COC(=O)c1ccc(CCC(=O)OC(C)(C)C)[nH]1"
},
"smiles": "COC(=O)c1ccc(CCC(=O)OC(C)(C)C)[nH]1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
]
}
}