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702680-17-9 molecular structure
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(2R,3S)-3-[(5-chloro-1H-indol-2-yl)formamido]-2-hydroxy-N,N-dimethyl-4-phenylbutanamide

ChemBase ID: 73187
Molecular Formular: C21H22ClN3O3
Molecular Mass: 399.87068
Monoisotopic Mass: 399.13496926
SMILES and InChIs

SMILES:
c1(ccc2c(c1)cc([nH]2)C(=O)N[C@H]([C@H](C(=O)N(C)C)O)Cc1ccccc1)Cl
Canonical SMILES:
Clc1ccc2c(c1)cc([nH]2)C(=O)N[C@H]([C@H](C(=O)N(C)C)O)Cc1ccccc1
InChI:
InChI=1S/C21H22ClN3O3/c1-25(2)21(28)19(26)17(10-13-6-4-3-5-7-13)24-20(27)18-12-14-11-15(22)8-9-16(14)23-18/h3-9,11-12,17,19,23,26H,10H2,1-2H3,(H,24,27)/t17-,19+/m0/s1
InChIKey:
HINJNZFCMLSBCI-PKOBYXMFSA-N

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CBID:73187 http://www.chembase.cn/molecule-73187.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2R,3S)-3-[(5-chloro-1H-indol-2-yl)formamido]-2-hydroxy-N,N-dimethyl-4-phenylbutanamide
IUPAC Traditional name
(2R,3S)-3-[(5-chloro-1H-indol-2-yl)formamido]-2-hydroxy-N,N-dimethyl-4-phenylbutanamide
Synonyms
CP-91149
2-Methyl-2-[3-[(3S)-1-[[4-(1-methylethyl)phenyl]acetyl]-3-piperidinyl]phenoxy]propanoic Acid
CP 775146
(S)-2-[3-[1-[(4-Isopropylphenyl)acetyl]piperidin-3-yl]phenoxy]-2-methylpropionic Acid
PF-06340672
CP-775146
5-Chloro-N-[(1S,2R)-3-(dimethylamino)-2-hydroxy-3-oxo-1-(phenylmethyl)propyl]-1H-indole-2-carboxamide
CP-91149
CAS Number
702680-17-9
186392-40-5
MDL Number
MFCD00954145
PubChem SID
162038107
PubChem CID
9843900

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 9843900 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.074857  H Acceptors
H Donor LogD (pH = 5.5) 2.3835182 
LogD (pH = 7.4) 2.38351  Log P 2.3835185 
Molar Refractivity 108.5775 cm3 Polarizability 42.705753 Å3
Polar Surface Area 85.43 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
DMSO: >20 mg/mL expand Show data source
Methanol expand Show data source
Apperance
Off-White Solid expand Show data source
white to off-white powder expand Show data source
Melting Point
70-76°C expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥98% (HPLC) expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C21H22ClN3O3 expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
Selleck Chemicals - S2717 external link
Research Area
Description Cancer
Biological Activity
Description CP-91149 is a selective glycogen phosphorylase (GP) inhibitor with IC50 of 0.13 μM.
Targets GP
IC50 0.13 μM [1]
In Vitro CP-91149 displays 200-fold higher inhibitory activity against human liver glycogen phosphorylase a (HLGPa) than caffeine (IC50 = 26 μM). CP-91149 (10-100 μM) inhibits glucagon-stimulated glycogenolysis in isolated rat hepatocytes in a dose-dependent manner, and in primary human hepatocytes with IC50 of ~2.1 μM. [1] CP-91149 also potently inhibits the activities of human muscle phosphorylase a and b with IC50 of 0.2 μM and ~0.3 μM, respectively. CP-91149 treatment at 2.5 μM induces inactivation of phosphorylase and sequential activation of glycogen synthase in hepatocytes, and increases glycogen synthesis by 7-fold at 5 mM glucose and by 2-fold at 20 mM glucose. CP-91149 can partially counteract the effects of phosphorylase overexpression. [2] CP-91149 also potently inhibits brain GP with IC50 of 0.5 μM in A549 cells. CP-91149 treatment at 10-30 μM causes significant glycogen accumulation in A549 and HSF55 cells. CP-91149 treatment increases G1-phase cells with a significant reduction of the S-phase population in HSF55 cells, correlated with increased expression of p21 and p27. [3] CP-91149 also promotes the dephosphorylation and activation of GS (glycogen synthase) in non-engineered or GP-overexpressing cultured human muscle cells, but exclusively in glucose-deprived cells. [4]
In Vivo Oral administration of CP-91149 to diabetic ob/ob mice at 25-50 mg/kg causes rapid (3 hours) glucose lowering by 100-120 mg/dl without producing hypoglycemia, resulting from inhibition of glycogenolysis in vivo. CP-91149 treatment does not lower glucose levels in normoglycemic, nondiabetic mice. [1] In the non-fasted Goto-Kakizaki (GK) rats, administration of CP-91149 in combination with CS-917 suppresses hepatic glycogen reduction by CS-917 and decreases plasma glucose more than single administration of CS-917. [5]
Clinical Trials
Features
Combination Therapy
Description HLGPa inhibition by CP-91149 is synergistic with caffeine and theophylline, as caffeine or theophylline increases the potency (IC50) of CP-91149 from 1 μM to 0.14 μM. [1]
Protocol
Kinase Assay [1]
Phosphorylase enzyme assay Human liver glycogen phosphorylase a (HLGPa, 85 ng) activity is measured in the direction of glycogen synthesis by the release of phosphate from glucose-1-phosphate at 22°C in 100 μL of buffer containing 50 mM Hepes (pH 7.2), 100 mM KCl, 2.5 mM EGTA, 2.5 mM MgCl2, 0.5 mM glucose-1-phosphate, and 1 mg/mL glycogen. Phosphate is measured at 620 nm, 20 minutes after the addition of 150 μL of 1 M HCl containing 10 mg/mL ammonium molybdate and 0.38 mg/mL malachite green. Increasing concentrations of CP-91149 are added to the assay in 5 μL of 14% DMSO.
Cell Assay [3]
Cell Lines HSF55 and T98G
Concentrations Dissolved in DMSO, final concentrations ~50 μM
Incubation Time 72 hours
Methods Cells are exposed to various concentrations of CP-91149 for 72hours. Viability is determined with manual cell counts following staining with trypan blue exclusion assay. Cells are fixed with 70% ethanol. DNA is stained with propidium iodide and the intensity of fluorescence is measured using a Becton-Dickinson flow cytometer at 488nm for excitation and at 650nm for emission. The cell cycle profile is analyzed using Modifit’s Sync Wizard.
Animal Study [1]
Animal Models Obese, diabetic male C57BL/6J-Lep(ob/ob) mice and their lean, nondiabetic C57BL/6J-?/+ littermates
Formulation Formulated in vehicle consisting of either 0.25% (wt/vol) methyl cellulose in water or 0.1% Pluronic P105 Block Copolymer Surfactant in 0.1% saline
Doses ~50 mg/kg
Administration Orally
References
[1] Martin WH, et al. Proc Natl Acad Sci U S A, 1998, 95(4), 1776-1781.
[2] Aiston S, et al. J Biol Chem, 2001, 276(26), 23858-23866.
[3] Schnier JB, et al. Biochem Biophys Res Commun, 2003, 309(1), 126-134.
[4] Lerín C, et al. Biochem J, 2004, 378(Pt 3), 1073-1077.
[5] Yoshida T, et al. J Pharmacol Sci, 2011, 115(3), 329-335.
Sigma Aldrich - PZ0104 external link
Biochem/physiol Actions
CP-91149 is a selective glycogen phosphorylase inhibitor.
Legal Information
Sold for research purposes under agreement from Pfizer Inc.
Toronto Research Chemicals - C781355 external link
A potent and selective PPARα agonist. It exhibits hypolipidemic activity in vivo.

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