All Photos(1)
Synonym(s):
(3R)-Anthracen-9-yl-[3-(morpholine-4-carbonyl)-[1,4′]bipiperidinyl-1′-yl]-methanone hydrochloride, CP 640186 hydrochloride, CP640186 hydrochloride, [(3R)-1′-(9-Anthracenylcarbonyl)[1,4′-bipiperidin]-3-yl]-4-morpholinyl-methanone hydrochloride
Empirical Formula (Hill Notation):
C30H35N3O3 · HCl
CAS Number:
Molecular Weight:
522.08
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77
Recommended Products
Quality Level
Assay
≥95% (HPLC)
form
powder
storage condition
desiccated
color
white to beige
solubility
H2O: 2 mg/mL, clear (warmed)
storage temp.
room temp
SMILES string
O=C(C1=C2C=CC=CC2=CC3=CC=CC=C31)N(CC4)CCC4N5C[C@H](C(N6CCOCC6)=O)CCC5.[H]Cl
InChI
1S/C30H35N3O3.ClH/c34-29(32-16-18-36-19-17-32)24-8-5-13-33(21-24)25-11-14-31(15-12-25)30(35)28-26-9-3-1-6-22(26)20-23-7-2-4-10-27(23)28;/h1-4,6-7,9-10,20,24-25H,5,8,11-19,21H2;1H/t24-;/m1./s1
InChI key
DUBNXJIOBFRASV-GJFSDDNBSA-N
Application
CP-640186 hydrochloride has been used as an allosteric acetyl-CoA carboxylase (ACC) inhibitor (ACCi) for pharmacological inhibition of lipogenesis to determine if fatty acid synthesis is essential for brown adipose tissue (BAT) whitening. It has also been used as an inhibitor of mammalian acetyl-CoA carboxylase (mACC1/2) to study its effect on meropenem potency against the persisters from multiple pathogens, including B. thailandensis, P. aeruginosa, S.Typhimurium, and attenuated Y. pestis.
Biochem/physiol Actions
CP-640186 is a potent and orally active acetyl-CoA carboxylase 1/2 (ACC-alpha/beta, ACC1/2) inhibitor (IC50 ~50 nM) that targets the carboxyltransferase (CT) domain at the ACC dimer interface (via tight interactions with the putative biotin-binding site) in a reversible manner, uncompetitive with respect to ATP, and non-competitive with respect to bicarbonate, acetyl-CoA, and citrate. CP-610431 inhibits fatty acid (FA) synthesis, triglyceride (TG) synthesis, TG and apoB secretion (IC50 = 1.6, 1.8, 3.0, and 5.7 μM, respectively), but not cholesterol synthesis or apoC3 secretion in HepG2 cells (ACC1), as well as stimulates FA oxidation in C2C12 cells (ACC2) and in rat epitrochlearis muscle strips (EC50 = 57 nM and 1.3 μM, respectively). Oral administration is shown to inhibit FA synthesis in rats, CD1 mice, and ob/ob mice (ED50 = 13, 11, and 4 mg/kg, respectively) and stimulate rat whole body FA oxidation (ED50 ∼30 mg/kg) in vivo.
WGK
WGK 3
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Deepa S Valsangkar et al.
Molecular reproduction and development, 82(9), 679-693 (2015-06-05)
In mouse oocytes, meiotic induction by pharmacological activation of PRKA (adenosine monophosphate-activated protein kinase; formerly known as AMPK) or by hormones depends on stimulation of fatty acid oxidation (FAO). PRKA stimulates FAO by phosphorylating and inactivating acetyl CoA carboxylase (ACAC;
P B Patil et al.
Archives of physiology and biochemistry, 113(1), 13-24 (2007-05-25)
There seems to be an association between increased concentrations of malonyl coenzyme A (malonyl CoA) in skeletal muscle and diabetes and/or insulin resistance. The purpose of the current study was to test the hypothesis that treatments designed to manipulate malonyl
Hailong Zhang et al.
Structure (London, England : 1993), 12(9), 1683-1691 (2004-09-03)
Acetyl-coenzyme A carboxylases (ACCs) are important targets for the development of therapeutic agents against obesity, diabetes, and other diseases. CP-640186 is a potent inhibitor of mammalian ACCs and can reduce body weight and improve insulin sensitivity in test animals. It
Daniel Hess et al.
PloS one, 5(6), e11394-e11394 (2010-07-09)
Lung cancer is the most frequent form of cancer. The survival rate for patients with metastatic lung cancer is approximately 5%, hence alternative therapeutic strategies to treat this disease are critically needed. Recent studies suggest that lipid biosynthetic pathways, particularly
Yasunori Nio et al.
Antiviral research, 132, 262-267 (2016-07-10)
Recently, direct antiviral agents against hepatitis C virus (HCV) infection have been developed as highly effective anti-HCV drugs. However, the appearance of resistant viruses against direct anti-viral agents is an unsolved problem. One of the strategies considered to suppress the
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