Detailed information for compound 163163
Basic information
Technical information
- TDR Targets ID: 163163
- Name: 5-chloro-N-[(2S)-3-(4-fluorophenyl)-1-(4-hydr oxypiperidin-1-yl)-1-oxopropan-2-yl]-1H-indol e-2-carboxamide
- MW: 443.898 | Formula: C23H23ClFN3O3
-
H donors: 3
H acceptors: 3
LogP: 3.78
Rotable bonds: 7
Rule of 5 violations (Lipinski): 1 - SMILES: OC1CCN(CC1)C(=O)[C@@H](NC(=O)c1cc2c([nH]1)ccc(c2)Cl)Cc1ccc(cc1)F
- InChi: 1S/C23H23ClFN3O3/c24-16-3-6-19-15(12-16)13-20(26-19)22(30)27-21(11-14-1-4-17(25)5-2-14)23(31)28-9-7-18(29)8-10-28/h1-6,12-13,18,21,26,29H,7-11H2,(H,27,30)/t21-/m0/s1
- InChiKey: YDCGVASFVACWKF-NRFANRHFSA-N
Network
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Synonyms
- 5-chloro-N-[(1S)-1-[(4-fluorophenyl)methyl]-2-(4-hydroxy-1-piperidyl)-2-oxo-ethyl]-1H-indole-2-carboxamide
- 5-chloro-N-[(1S)-1-[(4-fluorophenyl)methyl]-2-(4-hydroxy-1-piperidinyl)-2-oxoethyl]-1H-indole-2-carboxamide
- 5-chloro-N-[(2S)-3-(4-fluorophenyl)-1-(4-hydroxypiperidin-1-yl)-1-oxo-propan-2-yl]-1H-indole-2-carboxamide
- 5-chloro-N-[(1S)-1-(4-fluorobenzyl)-2-(4-hydroxypiperidino)-2-keto-ethyl]-1H-indole-2-carboxamide
- 5-chloro-N-[(1S)-1-(4-fluorobenzyl)-2-(4-hydroxy-1-piperidyl)-2-keto-ethyl]-1H-indole-2-carboxamide
- 5-CHLORO-1H-INDOLE-2-CARBOXYLIC ACID [1-(4-FLUOROBENZYL)-2-(4-HYDROXYPIPERIDIN-1YL)-2-OXOETHYL]AMIDE
- CHI
Targets
Known targets for this compound
| Species | Target name | Source | Bibliographic reference |
|---|---|---|---|
| Homo sapiens | phosphorylase, glycogen, liver | Starlite/ChEMBL | References |
| Homo sapiens | phosphorylase, glycogen | Starlite/ChEMBL | References |
| Homo sapiens | cytochrome P450, family 51, subfamily A, polypeptide 1 | Starlite/ChEMBL | References |
Predicted pathogen targets for this compound
By orthology
By sequence similarity to non orthologous known druggable targets
No druggable targets predicted by sequence similarity
Obtained from network model
Ranking Plot
Putative Targets List
| Species | Potential target | Raw | Global | Species |
|---|---|---|---|---|
| Trypanosoma brucei | Lanosterol 14-alpha demethylase | 0.0183 | 0.2356 | 1 |
| Echinococcus granulosus | glycogen phosphorylase | 0.0261 | 0.3709 | 0.3709 |
| Trypanosoma cruzi | Lanosterol 14-alpha demethylase | 0.0183 | 0.2356 | 1 |
| Trichomonas vaginalis | glycogen phosphorylase, putative | 0.0261 | 0.3709 | 0.5 |
| Echinococcus multilocularis | neuropeptide receptor | 0.0623 | 1 | 1 |
| Brugia malayi | carbohydrate phosphorylase | 0.0261 | 0.3709 | 1 |
| Trypanosoma cruzi | Lanosterol 14-alpha demethylase | 0.0183 | 0.2356 | 1 |
| Echinococcus multilocularis | G protein coupled receptor 139 | 0.0623 | 1 | 1 |
| Echinococcus multilocularis | Glycosyl transferase, family 35 | 0.0261 | 0.3709 | 0.3709 |
| Schistosoma mansoni | glycogen phosphorylase | 0.0261 | 0.3709 | 0.3709 |
| Schistosoma mansoni | glycogen phosphorylase | 0.0261 | 0.3709 | 0.3709 |
| Loa Loa (eye worm) | hypothetical protein | 0.0179 | 0.2292 | 0.618 |
| Leishmania major | lanosterol 14-alpha-demethylase, putative | 0.0183 | 0.2356 | 1 |
| Echinococcus multilocularis | glycogen phosphorylase | 0.0261 | 0.3709 | 0.3709 |
| Mycobacterium tuberculosis | Cytochrome P450 51 Cyp51 (CYPL1) (P450-L1A1) (sterol 14-alpha demethylase) (lanosterol 14-alpha demethylase) (P450-14DM) | 0.0183 | 0.2356 | 1 |
| Echinococcus granulosus | Glycosyl transferase family 35 | 0.0261 | 0.3709 | 0.3709 |
| Loa Loa (eye worm) | glycogen phosphorylase | 0.0261 | 0.3709 | 1 |
| Giardia lamblia | Glycogen phosphorylase | 0.0261 | 0.3709 | 0.5 |
| Echinococcus granulosus | glycogen phosphorylase | 0.0261 | 0.3709 | 0.3709 |
| Brugia malayi | ERG2 and Sigma1 receptor like protein | 0.0179 | 0.2292 | 0.618 |
| Mycobacterium ulcerans | cytochrome P450 51B1 Cyp51B1 | 0.0183 | 0.2356 | 1 |
| Echinococcus multilocularis | glycogen phosphorylase | 0.0261 | 0.3709 | 0.3709 |
| Chlamydia trachomatis | glycogen phosphorylase | 0.0261 | 0.3709 | 0.5 |
| Entamoeba histolytica | glycogen phosphorylase, putative | 0.0261 | 0.3709 | 1 |
| Onchocerca volvulus | Glycogen phosphorylase homolog | 0.0261 | 0.3709 | 0.5 |
| Schistosoma mansoni | glycogen phosphorylase | 0.0113 | 0.1139 | 0.1139 |
| Trichomonas vaginalis | glycogen phosphorylase, putative | 0.0261 | 0.3709 | 0.5 |
| Entamoeba histolytica | glycogen phosphorylase, putative | 0.0261 | 0.3709 | 1 |
| Schistosoma mansoni | neuropeptide receptor | 0.0623 | 1 | 1 |
Activities
| Activity type | Activity value | Assay description | Source | Reference |
|---|---|---|---|---|
| Activity (functional) | = 20 % | Hypoglycemic activity against C57BL/KsJ db/db mouse assessed as reduction of blood glucose at 50 mg/kg, po after 2 hrs relative to control | ChEMBL. | 18434170 |
| Activity (functional) | = 24 % | Hypoglycemic activity in db/db mouse assessed as reduction of plasma glucose at 30 mg/kg, po after 2 hrs relative to control | ChEMBL. | 18952447 |
| Dose (functional) | = 5 mg kg-1 | Hypoglycemic responses resulting from oral dosing in diabetic ob/ob mice(inactive dose), po | ChEMBL. | 9685232 |
| Dose (functional) | = 5 mg kg-1 | Hypoglycemic responses resulting from oral dosing in diabetic ob/ob mice(inactive dose), po | ChEMBL. | 9685232 |
| Dose (functional) | = 10 mg kg-1 | Hypoglycemic responses resulting from oral dosing in diabetic ob/ob mice(active dose), po | ChEMBL. | 9685232 |
| Dose (functional) | = 10 mg kg-1 | Hypoglycemic responses resulting from oral dosing in diabetic ob/ob mice(active dose), po | ChEMBL. | 9685232 |
| Dose (functional) | = 15 mg kg-1 | Hypoglycemic responses resulting from oral dosing in diabetic ob/ob mice(active dose), po | ChEMBL. | 9685232 |
| Dose (functional) | = 15 mg kg-1 | Hypoglycemic responses resulting from oral dosing in diabetic ob/ob mice(active dose), po | ChEMBL. | 9685232 |
| Dose (functional) | = 25 mg kg-1 | Hypoglycemic responses resulting from oral dosing in diabetic ob/ob mice(active dose), po | ChEMBL. | 9685232 |
| Dose (functional) | = 25 mg kg-1 | Hypoglycemic responses resulting from oral dosing in diabetic ob/ob mice(active dose), po | ChEMBL. | 9685232 |
| Dose (functional) | = 50 mg kg-1 | Hypoglycemic responses resulting from oral dosing in diabetic ob/ob mice(active dose), po | ChEMBL. | 9685232 |
| Dose (functional) | = 50 mg kg-1 | Hypoglycemic responses resulting from oral dosing in diabetic ob/ob mice(active dose), po | ChEMBL. | 9685232 |
| Glucose (functional) | = 24 % | Percent decrease in drug -treated plasma glucose concentration, relative to vehicle treated control diabetic ob/ob mice | ChEMBL. | 9685232 |
| Glucose (functional) | = 24 % | Percent decrease in drug -treated plasma glucose concentration, relative to vehicle treated control diabetic ob/ob mice | ChEMBL. | 9685232 |
| Glucose (functional) | = 26 % | Percent decrease in drug -treated plasma glucose concentration, relative to vehicle treated control diabetic ob/ob mice | ChEMBL. | 9685232 |
| Glucose (functional) | = 26 % | Percent decrease in drug -treated plasma glucose concentration, relative to vehicle treated control diabetic ob/ob mice | ChEMBL. | 9685232 |
| Glucose (functional) | = 44 % | Percent decrease in drug -treated plasma glucose concentration, relative to vehicle treated control diabetic ob/ob mice | ChEMBL. | 9685232 |
| Glucose (functional) | = 44 % | Percent decrease in drug -treated plasma glucose concentration, relative to vehicle treated control diabetic ob/ob mice | ChEMBL. | 9685232 |
| Glucose (functional) | = 45 % | Percent decrease in drug -treated plasma glucose concentration, relative to vehicle treated control diabetic ob/ob mice | ChEMBL. | 9685232 |
| Glucose (functional) | = 45 % | Percent decrease in drug -treated plasma glucose concentration, relative to vehicle treated control diabetic ob/ob mice | ChEMBL. | 9685232 |
| IC50 (binding) | = 205 nM | In vitro inhibitory activity against recombinant human liver glycogen phosphorylase a (rHLGPa) catalyzed release of phosphate from glucose-1-phosphate. | ChEMBL. | 9685232 |
| IC50 (binding) | = 205 nM | In vitro inhibitory activity against recombinant human liver glycogen phosphorylase a (rHLGPa) catalyzed release of phosphate from glucose-1-phosphate. | ChEMBL. | 9685232 |
| IC50 (binding) | = 0.5 uM | Inhibition of Rabbit muscle glycogen phosphorylase B. | ChEMBL. | 15214781 |
| IC50 (binding) | = 0.5 uM | Inhibition of Rabbit muscle glycogen phosphorylase B. | ChEMBL. | 15214781 |
| IC50 (binding) | = 0.92 uM | Inhibition of human liver glycogen phosphorylase a | ChEMBL. | 18434170 |
| IC50 (binding) | = 0.92 uM | Inhibition of active form of human liver glycogen phosphorylase | ChEMBL. | 18952447 |
| IC50 (functional) | = 1.9 uM | Inhibition of forskolin-stimulated glycogenolysis in SK-HEP-1 cells | ChEMBL. | 9685232 |
| IC50 (binding) | = 2.4 uM | In vitro inhibition of pig liver Glycogen phosphorylase A. | ChEMBL. | 15214781 |
| IC50 (binding) | = 2.4 uM | In vitro inhibition of pig liver Glycogen phosphorylase A. | ChEMBL. | 15214781 |
| IC50 (binding) | = 4 uM | Inhibition of human CYP51 expressed in Topp 3 cells by lanosterol demethylase assay | ChEMBL. | 17194716 |
| IC50 (binding) | = 4 uM | Inhibition of human CYP51 expressed in Topp 3 cells by lanosterol demethylase assay | ChEMBL. | 17194716 |
Phenotypes
Whole-cell/tissue/organism interactions
We have no records of whole-cell/tissue assays done with this compound
What does this mean?
Many chemical entities in TDR Targets come from high-throughput screenings with whole cells or tissue samples, and not all assayed compounds have been tested against a single a single target protein, probably because they get ruled out during screening process. Even if these compounds may have not been of interest in the original screening, they may come as interesting leads for other screening assays. Furthermore, we may be able to propose drug-target associations using chemical similarities and network patterns.
Annotated phenotypes:
We have no manually annotated phenotypes for this drug.
What does this mean? / Care to help?
In TDR Targets, information about phenotypes that are caused by
drugs, or by genetic manipulation of cells (e.g. gene knockouts or
knockdowns) is manually curated from the literature. These
descriptions help to describe the potential of the target for drug
development. If no information is available for this gene or if the
information is incomplete, this may mean that i) the papers
containing this information either appeared after the curation
effort for this organism was carried out or they were inadvertently
missed by curators; or that ii) the curation effort for this
organism has not yet started.
In any case, if you have information about papers containing relevant validation data for this target, please log in using your TDR Targets username and password and send them to us using the corresponding form in this page (only visible to registered users) or contact us.
In any case, if you have information about papers containing relevant validation data for this target, please log in using your TDR Targets username and password and send them to us using the corresponding form in this page (only visible to registered users) or contact us.
External resources for this compound
- ChEMBL: CHEMBL99889
- PubChem: 444746
Bibliographic References
5 literature references were collected for this gene.
If you have references for this compound, please enter them in a user comment (below) or Contact us.