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Record Information
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:41:55 UTC
NP-MRD IDNP0000980
Secondary Accession NumbersNone
Natural Product Identification
Common NameChenodeoxycholic acid
DescriptionChenodeoxycholic acid is a bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.G., Membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487 , 16037564 , 12576301 , 11907135 ). Usually conjugated with either glycine or taurine. It acts as a detergent to solubilize fats for intestinal absorption and is reabsorbed by the small intestine. It is used as cholagogue, a choleretic laxative, and to prevent or dissolve gallstones.
3alpha,7alpha-Dihydroxy-5beta-cholanic acidChEBI
7alpha-Hydroxylithocholic acidChEBI
Anthropodeoxycholic acidChEBI
Anthropodesoxycholic acidChEBI
Chenic acidChEBI
Gallodesoxycholic acidChEBI
3a,7a-Dihydroxy-5b-cholanic acidGenerator
3Α,7α-dihydroxy-5β-cholanic acidGenerator
7a-Hydroxylithocholic acidGenerator
7Α-hydroxylithocholic acidGenerator
(+)-Chenodeoxycholic acidHMDB
(3a,5b,7a)-3,7-Dihydroxy-cholan-24-Oic acidHMDB
3a,7a-Dihydroxy-5b,14a,17b-cholanic acidHMDB
3a,7a-Dihydroxy-5b-cholan-24-Oic acidHMDB
Acid, cheniqueHMDB
Acid, chenodeoxycholicHMDB
Chenodeoxycholate, sodiumHMDB
Solvay brand OF chenodeoxycholic acidHMDB
Antigen brand OF chenodeoxycholic acidHMDB
Falk brand OF chenodeoxycholic acidHMDB
Sodium chenodeoxycholateHMDB
Tramedico brand OF chenodeoxycholic acidHMDB
Zambon brand OF chenodeoxycholic acidHMDB
Acid, chenicHMDB
Acid, gallodesoxycholicHMDB
Chenique acidHMDB
Estedi brand OF chenodeoxycholic acidHMDB
Chemical FormulaC24H40O4
Average Mass392.5720 Da
Monoisotopic Mass392.29266 Da
IUPAC Name(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional Name(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
CAS Registry Number474-25-9
InChI Identifier
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
Cervus canadensisFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mus musculusLOTUS Database
Numida meleagrisFooDB
Ovis ariesFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Species Where Detected
Species NameSourceReference
Bos taurus domesticusKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
  • Dihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
Experimental Properties
Melting Point165 - 167 °CNot Available
Boiling Point547.15 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.09 mg/mLNot Available
LogP4.15Sangster, J. (1993). LOGKOW- a Databank of Evaluated Octanol-Water Partition Coefficients. Sangster Research Laboratories, Montreal.
Predicted Properties
Water Solubility0.02 g/LALOGPS
pKa (Strongest Acidic)4.6ChemAxon
pKa (Strongest Basic)-0.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.27 m³·mol⁻¹ChemAxon
Polarizability46.35 ųChemAxon
Number of Rings4ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
DrugBank IDDB06777
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022087
KNApSAcK IDC00050557
Chemspider ID9728
KEGG Compound IDC02528
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChenodiol
PubChem Compound10133
PDB IDNot Available
ChEBI ID16755
Good Scents IDrw1228061
General References
  1. Tadano T, Kanoh M, Matsumoto M, Sakamoto K, Kamano T: Studies of serum and feces bile acids determination by gas chromatography-mass spectrometry. Rinsho Byori. 2006 Feb;54(2):103-10. [PubMed:16548228 ]
  2. Smith JL, Lewindon PJ, Hoskins AC, Pereira TN, Setchell KD, O'Connell NC, Shepherd RW, Ramm GA: Endogenous ursodeoxycholic acid and cholic acid in liver disease due to cystic fibrosis. Hepatology. 2004 Jun;39(6):1673-82. [PubMed:15185309 ]
  3. Fiorucci S, Antonelli E, Morelli A: Nitric oxide and portal hypertension: a nitric oxide-releasing derivative of ursodeoxycholic acid that selectively releases nitric oxide in the liver. Dig Liver Dis. 2003 May;35 Suppl 2:S61-9. [PubMed:12846445 ]
  4. Meyers RL, Book LS, O'Gorman MA, Jackson WD, Black RE, Johnson DG, Matlak ME: High-dose steroids, ursodeoxycholic acid, and chronic intravenous antibiotics improve bile flow after Kasai procedure in infants with biliary atresia. J Pediatr Surg. 2003 Mar;38(3):406-11. [PubMed:12632357 ]
  5. Soderdahl G, Nowak G, Duraj F, Wang FH, Einarsson C, Ericzon BG: Ursodeoxycholic acid increased bile flow and affects bile composition in the early postoperative phase following liver transplantation. Transpl Int. 1998;11 Suppl 1:S231-8. [PubMed:9664985 ]
  6. Nobilis M, Pour M, Kunes J, Kopecky J, Kvetina J, Svoboda Z, Sladkova K, Vortel J: High-performance liquid chromatographic determination of ursodeoxycholic acid after solid phase extraction of blood serum and detection-oriented derivatization. J Pharm Biomed Anal. 2001 Mar;24(5-6):937-46. [PubMed:11248487 ]
  7. Dohmen K, Mizuta T, Nakamuta M, Shimohashi N, Ishibashi H, Yamamoto K: Fenofibrate for patients with asymptomatic primary biliary cirrhosis. World J Gastroenterol. 2004 Mar 15;10(6):894-8. [PubMed:15040040 ]
  8. Lupton JR, Steinbach G, Chang WC, O'Brien BC, Wiese S, Stoltzfus CL, Glober GA, Wargovich MJ, McPherson RS, Winn RJ: Calcium supplementation modifies the relative amounts of bile acids in bile and affects key aspects of human colon physiology. J Nutr. 1996 May;126(5):1421-8. [PubMed:8618139 ]
  9. Hillaire S, Ballet F, Franco D, Setchell KD, Poupon R: Effects of ursodeoxycholic acid and chenodeoxycholic acid on human hepatocytes in primary culture. Hepatology. 1995 Jul;22(1):82-7. [PubMed:7601437 ]
  10. Kitani K, Kanai S, Ivy GO, Carrillo MC: Pharmacological modifications of endogenous antioxidant enzymes with special reference to the effects of deprenyl: a possible antioxidant strategy. Mech Ageing Dev. 1999 Nov;111(2-3):211-21. [PubMed:10656538 ]
  11. Reyes H, Sjovall J: Bile acids and progesterone metabolites in intrahepatic cholestasis of pregnancy. Ann Med. 2000 Mar;32(2):94-106. [PubMed:10766400 ]
  12. Stark M, Jornvall H, Johansson J: Isolation and characterization of hydrophobic polypeptides in human bile. Eur J Biochem. 1999 Nov;266(1):209-14. [PubMed:10542066 ]
  13. Hofmann AF: The continuing importance of bile acids in liver and intestinal disease. Arch Intern Med. 1999 Dec 13-27;159(22):2647-58. [PubMed:10597755 ]
  14. Morton DH, Salen G, Batta AK, Shefer S, Tint GS, Belchis D, Shneider B, Puffenberger E, Bull L, Knisely AS: Abnormal hepatic sinusoidal bile acid transport in an Amish kindred is not linked to FIC1 and is improved by ursodiol. Gastroenterology. 2000 Jul;119(1):188-95. [PubMed:10889168 ]
  15. Virovic L, Supanc V, Duvnjak M: [Primary sclerosing cholangitis--diagnosis and therapy]. Acta Med Croatica. 2003;57(3):207-19. [PubMed:14582467 ]
  16. Gatzen M, Pausch J: [Treatment of cholestatic liver diseases]. Med Klin (Munich). 2002 Mar 15;97(3):152-9. [PubMed:11957790 ]
  17. Eriksson LS, Olsson R, Glauman H, Prytz H, Befrits R, Ryden BO, Einarsson K, Lindgren S, Wallerstedt S, Weden M: Ursodeoxycholic acid treatment in patients with primary biliary cirrhosis. A Swedish multicentre, double-blind, randomized controlled study. Scand J Gastroenterol. 1997 Feb;32(2):179-86. [PubMed:9051880 ]
  18. Lindblad A, Glaumann H, Strandvik B: A two-year prospective study of the effect of ursodeoxycholic acid on urinary bile acid excretion and liver morphology in cystic fibrosis-associated liver disease. Hepatology. 1998 Jan;27(1):166-74. [PubMed:9425933 ]
  19. Kowdley KV: Ursodeoxycholic acid therapy in hepatobiliary disease. Am J Med. 2000 Apr 15;108(6):481-6. [PubMed:10781781 ]
  20. Azer SA, Coverdale SA, Byth K, Farrell GC, Stacey NH: Sequential changes in serum levels of individual bile acids in patients with chronic cholestatic liver disease. J Gastroenterol Hepatol. 1996 Mar;11(3):208-15. [PubMed:8742915 ]
  21. St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. [PubMed:11316487 ]
  22. Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21. [PubMed:16037564 ]
  23. Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. [PubMed:12576301 ]
  24. Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. [PubMed:11907135 ]