Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN(C)C(=O)c1nn(-c2ccnc(N)n2)c2cc(C#CC(C)(O)c3ncccn3)ccc12
InChiKey
DGJAPPBDZCNTGD-UHFFFAOYSA-N
Route Signature
7b551c8fac720994954e131a0ae87641f40c062ef81887b021e4fdf2865ecd7a
Synthesis route with 5 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_26dce89dfb4c69b86dd8fb33",
"signature": "7b551c8fac720994954e131a0ae87641f40c062ef81887b021e4fdf2865ecd7a",
"contentHash": "317aca6b06661210b73411b3784cea83c6b5bfdc33d67d40afb7d3d0e1808bec",
"length": 5,
"isConvergent": false
},
"target": {
"id": "sa_f84bdf86487282bde8130649",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-02034",
"moleculeId": "sa_b10ca6e138bb181183e3a90d",
"smiles": "CN(C)C(=O)c1nn(-c2ccnc(N)n2)c2cc(C#CC(C)(O)c3ncccn3)ccc12",
"routeLength": 5,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_b10ca6e138bb181183e3a90d",
"inchikey": "DGJAPPBDZCNTGD-UHFFFAOYSA-N",
"smiles": "CN(C)C(=O)c1nn(-c2ccnc(N)n2)c2cc(C#CC(C)(O)c3ncccn3)ccc12"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "6136",
"routeId": "sa_26dce89dfb4c69b86dd8fb33",
"moleculeId": "sa_b10ca6e138bb181183e3a90d",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_b10ca6e138bb181183e3a90d",
"inchikey": "DGJAPPBDZCNTGD-UHFFFAOYSA-N",
"smiles": "CN(C)C(=O)c1nn(-c2ccnc(N)n2)c2cc(C#CC(C)(O)c3ncccn3)ccc12"
},
"smiles": "CN(C)C(=O)c1nn(-c2ccnc(N)n2)c2cc(C#CC(C)(O)c3ncccn3)ccc12",
"reactionStepId": "sa_cdd10337bcaa57b86a54e38c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150038460A1;0503;1648389\",\"rsmi\":\"[C:21]([CH3:22])(=[O:23])[c:24]1[n:25][cH:26][cH:27][cH:28][n:29]1.[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[n:7][n:8](-[c:9]2[n:10][c:11]([NH2:12])[n:13][cH:14][cH:15]2)[c:16]2[cH:17][c:18]([C:19]#[CH:20])[cH:30][cH:31][c:32]12>C1CCOC1.CC(C)NC(C)C.[Li+]>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[n:7][n:8](-[c:9]2[n:10][c:11]([NH2:12])[n:13][cH:14][cH:15]2)[c:16]2[cH:17][c:18]([C:19]#[C:20][C:21]([CH3:22])([OH:23])[c:24]3[n:25][cH:26][cH:27][cH:28][n:29]3)[cH:30][cH:31][c:32]12\"},\"mapped_reaction_smiles\":\"[C:21]([CH3:22])(=[O:23])[c:24]1[n:25][cH:26][cH:27][cH:28][n:29]1.[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[n:7][n:8](-[c:9]2[n:10][c:11]([NH2:12])[n:13][cH:14][cH:15]2)[c:16]2[cH:17][c:18]([C:19]#[CH:20])[cH:30][cH:31][c:32]12>C1CCOC1.CC(C)NC(C)C.[Li+]>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[n:7][n:8](-[c:9]2[n:10][c:11]([NH2:12])[n:13][cH:14][cH:15]2)[c:16]2[cH:17][c:18]([C:19]#[C:20][C:21]([CH3:22])([OH:23])[c:24]3[n:25][cH:26][cH:27][cH:28][n:29]3)[cH:30][cH:31][c:32]12\"}",
"reactionStep": {
"id": "sa_cdd10337bcaa57b86a54e38c",
"reactionHash": "6df40cfbe7245f98814dd869eeeedd646e15ebe6d13b8e90ba73f23424ac3a41"
},
"children": [
{
"id": "6137",
"routeId": "sa_26dce89dfb4c69b86dd8fb33",
"moleculeId": "sa_d4184a64839b1666af6cc59e",
"parentId": "6136",
"isLeaf": true,
"molecule": {
"id": "sa_d4184a64839b1666af6cc59e",
"inchikey": "SPZUXKZZYDALEY-UHFFFAOYSA-N",
"smiles": "CC(=O)c1ncccn1"
},
"smiles": "CC(=O)c1ncccn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "6138",
"routeId": "sa_26dce89dfb4c69b86dd8fb33",
"moleculeId": "sa_2588a385960a6effd35e1c4c",
"parentId": "6136",
"isLeaf": false,
"molecule": {
"id": "sa_2588a385960a6effd35e1c4c",
"inchikey": "WRBVRZZAEUYBCX-UHFFFAOYSA-N",
"smiles": "C#Cc1ccc2c(C(=O)N(C)C)nn(-c3ccnc(N)n3)c2c1"
},
"smiles": "C#Cc1ccc2c(C(=O)N(C)C)nn(-c3ccnc(N)n3)c2c1",
"reactionStepId": "sa_b77328e7781fbb3734ae10c1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150038460A1;0502;1648388\",\"rsmi\":\"C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[n:9](-[c:10]1[n:11][c:12]([NH2:13])[n:14][cH:15][cH:16]1)[n:17][c:18]2[C:19](=[O:20])[N:21]([CH3:22])[CH3:23]>CO.ClCCl.O=C(O)O.[K+].[K+]>[CH:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[n:9](-[c:10]1[n:11][c:12]([NH2:13])[n:14][cH:15][cH:16]1)[n:17][c:18]2[C:19](=[O:20])[N:21]([CH3:22])[CH3:23]\"},\"mapped_reaction_smiles\":\"C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[n:9](-[c:10]1[n:11][c:12]([NH2:13])[n:14][cH:15][cH:16]1)[n:17][c:18]2[C:19](=[O:20])[N:21]([CH3:22])[CH3:23]>CO.ClCCl.O=C(O)O.[K+].[K+]>[CH:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[n:9](-[c:10]1[n:11][c:12]([NH2:13])[n:14][cH:15][cH:16]1)[n:17][c:18]2[C:19](=[O:20])[N:21]([CH3:22])[CH3:23]\"}",
"reactionStep": {
"id": "sa_b77328e7781fbb3734ae10c1",
"reactionHash": "fee43773579ff9d55919fb39a1f0a085d873f4d7c2d802849f5cc7de21cd21de"
},
"children": [
{
"id": "6139",
"routeId": "sa_26dce89dfb4c69b86dd8fb33",
"moleculeId": "sa_82793414ffc046fbda24c2de",
"parentId": "6138",
"isLeaf": false,
"molecule": {
"id": "sa_82793414ffc046fbda24c2de",
"inchikey": "QDTXNKKQIMAVAQ-UHFFFAOYSA-N",
"smiles": "CN(C)C(=O)c1nn(-c2ccnc(N)n2)c2cc(C#C[Si](C)(C)C)ccc12"
},
"smiles": "CN(C)C(=O)c1nn(-c2ccnc(N)n2)c2cc(C#C[Si](C)(C)C)ccc12",
"reactionStepId": "sa_e03cb9ef350f2805181f02b9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150038460A1;0500;1648387\",\"rsmi\":\"Br[c:18]1[cH:17][c:16]2[n:8](-[c:9]3[n:10][c:11]([NH2:12])[n:13][cH:14][cH:15]3)[n:7][c:6]([C:4]([N:2]([CH3:1])[CH3:3])=[O:5])[c:27]2[cH:26][cH:25]1.[CH:19]#[C:20][Si:21]([CH3:22])([CH3:23])[CH3:24]>C1CCNCC1.[Cu]I.c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[n:7][n:8](-[c:9]2[n:10][c:11]([NH2:12])[n:13][cH:14][cH:15]2)[c:16]2[cH:17][c:18]([C:19]#[C:20][Si:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][cH:26][c:27]12\"},\"mapped_reaction_smiles\":\"Br[c:18]1[cH:17][c:16]2[n:8](-[c:9]3[n:10][c:11]([NH2:12])[n:13][cH:14][cH:15]3)[n:7][c:6]([C:4]([N:2]([CH3:1])[CH3:3])=[O:5])[c:27]2[cH:26][cH:25]1.[CH:19]#[C:20][Si:21]([CH3:22])([CH3:23])[CH3:24]>C1CCNCC1.[Cu]I.c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[n:7][n:8](-[c:9]2[n:10][c:11]([NH2:12])[n:13][cH:14][cH:15]2)[c:16]2[cH:17][c:18]([C:19]#[C:20][Si:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][cH:26][c:27]12\"}",
"reactionStep": {
"id": "sa_e03cb9ef350f2805181f02b9",
"reactionHash": "dbce7cc415c6b25e6b03403da0bd25ac38c04bd9e6bcc590943bc98e33efb4ea"
},
"children": [
{
"id": "6140",
"routeId": "sa_26dce89dfb4c69b86dd8fb33",
"moleculeId": "sa_95a9277ba0d873f43bb42b7f",
"parentId": "6139",
"isLeaf": true,
"molecule": {
"id": "sa_95a9277ba0d873f43bb42b7f",
"inchikey": "CWMFRHBXRUITQE-UHFFFAOYSA-N",
"smiles": "C#C[Si](C)(C)C"
},
"smiles": "C#C[Si](C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "6141",
"routeId": "sa_26dce89dfb4c69b86dd8fb33",
"moleculeId": "sa_18eb7e577f64d11254b39802",
"parentId": "6139",
"isLeaf": false,
"molecule": {
"id": "sa_18eb7e577f64d11254b39802",
"inchikey": "FBZOJNVZEFKYBG-UHFFFAOYSA-N",
"smiles": "CN(C)C(=O)c1nn(-c2ccnc(N)n2)c2cc(Br)ccc12"
},
"smiles": "CN(C)C(=O)c1nn(-c2ccnc(N)n2)c2cc(Br)ccc12",
"reactionStepId": "sa_0000ca612a5fe16e5c83f3f0",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150038460A1;0415;1648362\",\"rsmi\":\"Cl[c:9]1[n:10][c:11]([NH2:12])[n:13][cH:14][cH:15]1.[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[n:7][nH:8][c:16]2[cH:17][c:18]([Br:19])[cH:20][cH:21][c:22]12>CN(C)C=O.[HH].[Na+]>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[n:7][n:8](-[c:9]2[n:10][c:11]([NH2:12])[n:13][cH:14][cH:15]2)[c:16]2[cH:17][c:18]([Br:19])[cH:20][cH:21][c:22]12\"},\"mapped_reaction_smiles\":\"Cl[c:9]1[n:10][c:11]([NH2:12])[n:13][cH:14][cH:15]1.[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[n:7][nH:8][c:16]2[cH:17][c:18]([Br:19])[cH:20][cH:21][c:22]12>CN(C)C=O.[HH].[Na+]>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[n:7][n:8](-[c:9]2[n:10][c:11]([NH2:12])[n:13][cH:14][cH:15]2)[c:16]2[cH:17][c:18]([Br:19])[cH:20][cH:21][c:22]12\"}",
"reactionStep": {
"id": "sa_0000ca612a5fe16e5c83f3f0",
"reactionHash": "6ea4b72313a001f0f2bc7ece17a60871f212e97dcb1b2b112c6ad4778792fade"
},
"children": [
{
"id": "6142",
"routeId": "sa_26dce89dfb4c69b86dd8fb33",
"moleculeId": "sa_a77e6168296baee1c35685f7",
"parentId": "6141",
"isLeaf": true,
"molecule": {
"id": "sa_a77e6168296baee1c35685f7",
"inchikey": "DBGFGNCFYUNXLD-UHFFFAOYSA-N",
"smiles": "N=c1nc(Cl)cc[nH]1"
},
"smiles": "Nc1nccc(Cl)n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "6143",
"routeId": "sa_26dce89dfb4c69b86dd8fb33",
"moleculeId": "sa_cf018766009d144d2bce7797",
"parentId": "6141",
"isLeaf": false,
"molecule": {
"id": "sa_cf018766009d144d2bce7797",
"inchikey": "JTUXXICJICXQRC-UHFFFAOYSA-N",
"smiles": "CN(C)C(=O)c1n[nH]c2cc(Br)ccc12"
},
"smiles": "CN(C)C(=O)c1n[nH]c2cc(Br)ccc12",
"reactionStepId": "sa_6dfe1fac547f6174fad9f75b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150038460A1;0413;1648361\",\"rsmi\":\"O[C:4](=[O:5])[c:6]1[n:7][nH:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]12.[CH3:1][NH:2][CH3:3]>C1CCOC1.CCN=C=NCCCN(C)C.CN(C)C=O.Cl>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[n:7][nH:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]12\"},\"mapped_reaction_smiles\":\"O[C:4](=[O:5])[c:6]1[n:7][nH:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]12.[CH3:1][NH:2][CH3:3]>C1CCOC1.CCN=C=NCCCN(C)C.CN(C)C=O.Cl>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[n:7][nH:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]12\"}",
"reactionStep": {
"id": "sa_6dfe1fac547f6174fad9f75b",
"reactionHash": "4b6f79361bbb7d38bbac756639660271bd497ae43e77fd0dd61657dd8c79b596"
},
"children": [
{
"id": "6144",
"routeId": "sa_26dce89dfb4c69b86dd8fb33",
"moleculeId": "sa_8359db55bb6baf5878c3d699",
"parentId": "6143",
"isLeaf": true,
"molecule": {
"id": "sa_8359db55bb6baf5878c3d699",
"inchikey": "QDQJIDDXPACPKY-UHFFFAOYSA-N",
"smiles": "O=C(O)c1n[nH]c2cc(Br)ccc12"
},
"smiles": "O=C(O)c1n[nH]c2cc(Br)ccc12",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "6145",
"routeId": "sa_26dce89dfb4c69b86dd8fb33",
"moleculeId": "sa_e2676e5c7c9d7a020ed1780e",
"parentId": "6143",
"isLeaf": true,
"molecule": {
"id": "sa_e2676e5c7c9d7a020ed1780e",
"inchikey": "ROSDSFDQCJNGOL-UHFFFAOYSA-N",
"smiles": "CNC"
},
"smiles": "CNC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
]
}
}