Hyodeoxycholic acid

Names

[ CAS No. ]:
83-49-8

[ Name ]:
Hyodeoxycholic acid

[Synonym ]:
Hyodeoxycholic
MFCD00003681
Iodeoxycholic acid
EINECS 201-483-2
HYODEOXYCHOLANIC ACID
HYODESOXYCHOLIC ACID
HYDROCHOLIC ACID
7-deoxyhyocholicacid
HDCA
Pig deoxybile acid
Hyodeoxycholic acid

Biological Activity

[Description]:

Hyodeoxycholic acid is a secondary bile acid formed in the small intestine by the gut flora, and acts as a TGR5 (GPCR19) agonist, with an EC50 of 31.6 µM in CHO cells.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> GPCR19

Research Areas >> Metabolic Disease

Natural Products >> Steroids

[Target]

Human Endogenous Metabolite

[In Vitro]

Hyodeoxycholic acid is a secondary hydrophilic bile acid formed in the small intestine by the gut flora, and acts as an agonist of TGR5, with an EC50 of 31.6 µM in CHO cells[1]. Hyodeoxycholic acid (50, 100 μM) increases the expression of genes (Abca1, Abcg1, and Apoe) involved in cholesterol efflux in RAW 264.7 cells[2].

[In Vivo]

Hyodeoxycholic acid (HDCA; 1.25% (wt/wt)) obviously decreases fat mass and increases lean mass but does not raise the serum levels of any organ toxicity markers in LDLRKO mice. Hyodeoxycholic acid inhibits atherosclerotic lesion formation in LDLRKO at multiple sites, improves plasma lipoprotein profiles, decreases plasma glucose level and intestinal cholesterol absorption efficiency and increases daily cholesterol excretion through fecal output. Hyodeoxycholic acid also improves HDL function as measured by a cholesterol efflux assay[2].

[Animal admin]

Mice[2] For atherosclerosis studies, 8-wk-old female LDLRKO mice are fed a Western diet (21% fat, 0.15% cholesterol; TD.88137) for 8 wk. One group of mice (baseline group) is euthanized at this time point for lesion measurement in the aortic root region and in the innominate artery. Atherosclerotic lesion in the whole aorta is not examined in the baseline group. The remaining mice are then divided into 2 groups and fed the following diets for another 15 wk before euthanasia: group 1, chow diet (5% fat, AIN-76A Rodent Diet); and group 2, chow diet + 1.25% (wt/wt) Hyodeoxycholic acid. For other studies, 8-wk-old female LDLRKO mice are fed a chow diet or chow diet + 1.25% Hyodeoxycholic acid for 3 wk before phenotype measurements. Food consumption and body weight are recorded weekly. Animals are measured for total body fat mass and lean mass by magnetic resonance imaging (MRI) using Bruker Minispec with software from Eco Medical Systems[2].

[References]

[1]. Sato H, et al. Novel potent and selective bile acid derivatives as TGR5 agonists: biological screening, structure-activity relationships, and molecular modeling studies. J Med Chem. 2008 Mar 27;51(6):1831-41.

[2]. Shih DM, et al. Hyodeoxycholic acid improves HDL function and inhibits atherosclerotic lesion formation in LDLR-knockout mice. FASEB J. 2013 Sep;27(9):3805-17.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
547.1±25.0 °C at 760 mmHg

[ Melting Point ]:
200-201 °C(lit.)

[ Molecular Formula ]:
C₂₄H₄₀O₄

[ Molecular Weight ]:
392.572

[ Flash Point ]:
298.8±19.7 °C

[ Exact Mass ]:
392.292664

[ PSA ]:
77.76000

[ LogP ]:
5.00

[ Vapour Pressure ]:
0.0±3.3 mmHg at 25°C

[ Index of Refraction ]:
1.543

[ Storage condition ]:
Refrigerator

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: FZ2050000

CHEMICAL NAME :: 5-beta-Cholan-24-oic acid, 3-alpha,6-alpha-dihydroxy-

CAS REGISTRY NUMBER :: 83-49-8

BEILSTEIN REFERENCE NO. :: 3218394

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C24-H40-O4

MOLECULAR WEIGHT :: 392.64

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Yeast - Saccharomyces cerevisiae

DOSE/DURATION :: 5600 umol/L

REFERENCE :: ARTODN Archives of Toxicology. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.32- 1974- Volume(issue)/page/year: 60,192,1987

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R36/37/38:Irritating to eyes, respiratory system and skin . R40:Limited evidence of a carcinogenic effect.

[ Safety Phrases ]:
S26-S36/37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
FZ2050000

Articles

Quantification of 15 bile acids in lake charr feces by ultra-high performance liquid chromatography-tandem mass spectrometry.

J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 1001 , 27-34, (2015)

Many fishes are hypothesized to use bile acids (BAs) as chemical cues, yet quantification of BAs in biological samples and the required methods remain limited. Here, we present an UHPLC-MS/MS method f...

Evaluation of cynomolgus monkeys for the identification of endogenous biomarkers for hepatic transporter inhibition and as a translatable model to predict pharmacokinetic interactions with statins in humans.

Drug Metab. Dispos. 43 , 851-63, (2015)

Inhibition of hepatic transporters such as organic anion transporting polypeptides (OATPs) 1B can cause drug-drug interactions (DDIs). Determining the impact of perpetrator drugs on the plasma exposur...

Bile diversion to the distal small intestine has comparable metabolic benefits to bariatric surgery.

Nat. Commun. 6 , 7715, (2015)

Roux-en-Y gastric bypass (RYGB) is highly effective in reversing obesity and associated diabetes. Recent observations in humans suggest a contributing role of increased circulating bile acids in media...

Related Compounds

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