(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid

• ChemBase ID: 4476
• Molecular Formular: C24H40O4
• Molecular Mass: 392.572
• Monoisotopic Mass: 392.29265976
• SMILES: C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]1[C@H]2[C@@H](C[C@H]2[C@@]1(CC[C@H](C2)O)C)O)C
• Canonical SMILES: O[C@@H]1CC[C@]2([C@@H](C1)C[C@H]([C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=O)O)C)C)O)C
• InChI: InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1
• InChIKey: RUDATBOHQWOJDD-BSWAIDMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid; (4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0?,?.0??,??]heptadecan-14-yl]pentanoic acid; (4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoic acid
• IUPAC Traditional name: chendol; chenodeoxycholic acid
• Brand Name: Chenodal; Chenodiol; Chenix
• Synonyms: (3α,5β,7α)-3,7-Dihydroxycholan-24-oic Acid; (+)-Chenodeoxycholic Acid; 17β-(1-Methyl-3-carboxypropyl)etiocholane-3α,7α-diol; Chenodeoxycholic Acid; CDC; Chendol; Chenocol; Fluibil; Chenodiol; Chenodesoxycholic acid; Chenocholic acid; Chenodeoxycholic acid; 5 β-Cholanic acid-3,7-diol; 3α,7α-Dihydroxy-5β-cholanic acid; 3α,7α-Dihydroxy-5β-cholanic acid; 5β-Cholanic acid-3α,7α-diol; Chenodeoxycholic acid

Database IDs

• CAS Number: 474-25-9
• EC Number: 207-481-8
• MDL Number: MFCD00064142
• Beilstein Number: 3219887
• PubChem SID: 99443291; 160967908; 24893153
• PubChem CID: 10133
• CHEBI ID: 16755
• ATC CODE: A05AA01
• CHEMBL: 240597
• Chemspider ID: 9728
• DrugBank ID: DB06777
• KEGG ID: C02528
• Unique Ingredient Identifier: 0GEI24LG0J
• Wikipedia Title: Chenodeoxycholic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.595946
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.7592297
• LogD (pH = 7.4): 0.98345095
• Log P: 3.7133055
• Molar Refractivity: 109.2738 cm^3
• Polarizability: 43.768806 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.01
• LOG S: -4.3
• Solubility (Water): 1.97e-02 g/l

PROPERTIES

Physical Property

• Solubility: Acetone; Methanol
• Apperance: Off-White Solid
• Melting Point: 115-117°C; 160-165°C; 165-167 °C; 165-167 °C(lit.)
• Optical Rotation: [α]20/D +12±1°, c = 2% in ethanol
• Critical Micelle Concentration: 3

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS: FZ1980000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... CYP1A2(1544)

Product Information

• Purity: ≥97%; ≥98.0% (T)
• Salt Data: Free Base
• Description: anionic
• Impurities: ≤0.5% cholic acid (TLC)
• Empirical Formula (Hill Notation): C24H40O4

DETAILS

MP Biomedicals - 02105647

Induces dissolution of cholesterol and gallstones.

DrugBank - DB06777

• Drug Groups: approved
• Description: Chenodeoxycholic acid (or Chenodiol) is an epimer of ursodeoxycholic acid (DB01586). Chenodeoxycholic acid is a bile acid naturally found in the body. It works by dissolving the cholesterol that makes gallstones and inhibiting production of cholesterol in the liver and absorption in the intestines, which helps to decrease the formation of gallstones. It can also reduce the amount of other bile acids that can be harmful to liver cells when levels are elevated.
• Indication: Chenodiol is indicated for patients with radiolucent stones in well-opacifying gallbladders, in whom selective surgery would be undertaken except for the presence of increased surgical risk due to systemic disease or age. Chenodiol will not dissolve calcified (radiopaque) or radiolucent bile pigment stones.
• Pharmacology: It acts by reducing levels of cholesterol in the bile, helping gallstones that are made predominantly of cholesterol to dissolve. Chenodeoxycholic acid is ineffective with stones of a high calcium or bile acid content.
• Toxicity: Hepatotoxic.
• Biotransformation: Chenodiol is well absorbed from the small intestine and taken up by the liver where it is converted to its taurine and glycine conjugates and secreted in bile. At steady-state, an amount of chenodiol near the daily dose escapes to the colon and is converted by bacterial action to lithocholic acid. About 80% of the lithocholate is excreted in the feces; the remainder is absorbed and converted in the liver to its poorly absorbed sulfolithocholyl conjugates. During chenodiol therapy there is only a minor increase in biliary lithocholate, while fecal bile acids are increased three- to fourfold.
• Absorption: Chenodiol is well absorbed from the small intestine.
• Elimination: About 80% of its bacterial metabolite lithocholate is excreted in the feces.
• External Links: Wikipedia; Drugs.com

Selleck Chemicals - S1843

Research Area: Metabolic Disease
Biological Activity:
Chenodeoxycholic acid is a naturally occurring human bile acid. Chenodeoxycholic acid is indicated for dissolution of cholesterol gallstones in selected patients with uncomplicated radiolucent gallstone disease and functioning gallbladder. Although the exact mechanism of chenodiol’s anticholelithic action is not completely understood, chenodiol given orally in pharmacological doses contributes to desaturation of the bile by increasing the ratio of bile acids to cholesterol. The reduced cholesterol saturation allows for the gradual solubilization of cholesterol from gallstones, resulting in their eventual dissolution. [1]

Toronto Research Chemicals - C291900

A major bile acid in many vertebrates, occurring as the N-glycine and/or N-taurine conjugate. With other bile acids, forms mixed micelles with lecithin in bile which solubilize cholesterol and thus facilitates its excretion. Fcilitates fat absorption in t

Sigma Aldrich - C9377

Biochem/physiol Actions
Bile Acid
Packaging
100 mg in glass bottle
5, 25 g in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C9377.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C9377.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 22510

Application
Discovered as glycine and taurine conjugate in bile

REFERENCES

• Danzinger, R.G., et al., N. Engl. J. Med. , 286 : 1-8 (1972).
• Danzinger, et al.: N. Engl. J. Med., 286, 1 (1972)
• Iser, J.H., et al.: Drugs, 21, 90 (1972)
• Tint, G.S., et al.: Gastroenterology, 91, 1007 (1972)