Chenodeoxycholic acid (CHEM016254)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:24:40 UTC
Update Date2016-11-09 01:15:21 UTC
Accession NumberCHEM016254
Identification
Common NameChenodeoxycholic acid
ClassSmall Molecule
DescriptionChenodeoxycholic 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.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3alpha,7alpha-Dihydroxy-5beta-cholanic acidChEBI
7alpha-Hydroxylithocholic acidChEBI
Anthropodeoxycholic acidChEBI
Anthropodesoxycholic acidChEBI
CDCAChEBI
Chenic acidChEBI
ChenixChEBI
ChenodiolChEBI
Gallodesoxycholic acidChEBI
3a,7a-Dihydroxy-5b-cholanateGenerator
3a,7a-Dihydroxy-5b-cholanic acidGenerator
3alpha,7alpha-Dihydroxy-5beta-cholanateGenerator
3Α,7α-dihydroxy-5β-cholanateGenerator
3Α,7α-dihydroxy-5β-cholanic acidGenerator
7a-HydroxylithocholateGenerator
7a-Hydroxylithocholic acidGenerator
7alpha-HydroxylithocholateGenerator
7Α-hydroxylithocholateGenerator
7Α-hydroxylithocholic acidGenerator
AnthropodeoxycholateGenerator
AnthropodesoxycholateGenerator
ChenateGenerator
GallodesoxycholateGenerator
ChenodeoxycholateGenerator
(+)-ChenodeoxycholateHMDB
(+)-Chenodeoxycholic acidHMDB
(3a,5b,7a)-3,7-Dihydroxy-cholan-24-OateHMDB
(3a,5b,7a)-3,7-Dihydroxy-cholan-24-Oic acidHMDB
3a,7a-Dihydroxy-5b,14a,17b-cholanateHMDB
3a,7a-Dihydroxy-5b,14a,17b-cholanic acidHMDB
3a,7a-Dihydroxy-5b-cholan-24-OateHMDB
3a,7a-Dihydroxy-5b-cholan-24-Oic acidHMDB
7a-Hydroxy-desoxycholsaeureHMDB
ChenodesoxycholsaeureHMDB
Acid, cheniqueHMDB
ChenofalkHMDB
ChenophalkHMDB
Acid, chenodeoxycholicHMDB
Chenodeoxycholate, sodiumHMDB
QuenocolHMDB
Solvay brand OF chenodeoxycholic acidHMDB
Antigen brand OF chenodeoxycholic acidHMDB
Falk brand OF chenodeoxycholic acidHMDB
QuenobilanHMDB
Sodium chenodeoxycholateHMDB
Tramedico brand OF chenodeoxycholic acidHMDB
Zambon brand OF chenodeoxycholic acidHMDB
Acid, chenicHMDB
Acid, gallodesoxycholicHMDB
Chenique acidHMDB
Estedi brand OF chenodeoxycholic acidHMDB
HenoholHMDB
Chemical FormulaC24H40O4
Average Molecular Mass392.572 g/mol
Monoisotopic Mass392.293 g/mol
CAS Registry Number474-25-9
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
Traditional 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
SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(O)=O
InChI IdentifierInChI=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
InChI KeyRUDATBOHQWOJDD-BSWAIDMHSA-N
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
Substituents
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP3.01ALOGPS
logP3.71ChemAxon
logS-4.3ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0a6u-3920000000-ce93b24c6e2568b6087dSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a6u-3920000000-ce93b24c6e2568b6087dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01rt-0419000000-6a92f910581240163a99Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0006-1110390000-7a6c62344d1371b74081Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0a4i-0009000000-82ed6dc62b49ac0340e6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-01pa-2930000000-64edc819ad56b842cdbaSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-053r-6900000000-c97325e1ca9bcff75af1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0002-0009000000-ad2d2440db7f3f1c8a2eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-0009000000-2df562379077bf0f4b2aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-0009000000-ff13f6ad8405e3969b6cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-0009000000-1af3ba6ee17285da06a2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-5409557fb9a76a8a8e74Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-0009000000-c77d97d0dfe48497b263Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0006-0009000000-d38671ccaaa16ac6d1f1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0596-0529000000-1ed436cc96fa78f90b88Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-25ba2afe78d7d8070765Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-0019000000-c31d129de7de9df05167Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-0009000000-fc161813afdb6d319d8dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-0009000000-ee319e0cbd9987920debSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-858f2baceacfba406468Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0009000000-997e61e986e67265241cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0009000000-81134947694f847d1c65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02t9-1219000000-6a0ddebebacac090c27eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-efdaad69eee0ae934dd5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-1009000000-15b4edab9d05e4c3693aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9006000000-9291e69db3a3c47ecd97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-7631731446db77938069Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-0009000000-39e7e555dc6b36ada2afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1009000000-351c21e3dab693818b22Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB06777
HMDB IDHMDB0000518
FooDB IDFDB022087
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID207
PDB IDNot Available
Wikipedia LinkChenodiol
Chemspider ID9728
ChEBI ID16755
PubChem Compound ID10133
Kegg Compound IDC02528
YMDB IDNot Available
ECMDB IDM2MDB005111
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Sato, Yoshio; Ikekawa, Nobuo. Preparation of chenodeoxycholic acid. Journal of Organic Chemistry (1959), 24 1367-8.
2. Sato, Yoshio; Ikekawa, Nobuo. Preparation of chenodeoxycholic acid. Journal of Organic Chemistry (1959), 24 1367-8.
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.
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.
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.
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.
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.
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.
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.
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.
11. 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.
12. Reyes H, Sjovall J: Bile acids and progesterone metabolites in intrahepatic cholestasis of pregnancy. Ann Med. 2000 Mar;32(2):94-106.
13. Stark M, Jornvall H, Johansson J: Isolation and characterization of hydrophobic polypeptides in human bile. Eur J Biochem. 1999 Nov;266(1):209-14.
14. Hofmann AF: The continuing importance of bile acids in liver and intestinal disease. Arch Intern Med. 1999 Dec 13-27;159(22):2647-58.
15. 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.
16. Virovic L, Supanc V, Duvnjak M: [Primary sclerosing cholangitis--diagnosis and therapy]. Acta Med Croatica. 2003;57(3):207-19.
17. Gatzen M, Pausch J: [Treatment of cholestatic liver diseases]. Med Klin (Munich). 2002 Mar 15;97(3):152-9.
18. 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.
19. 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.
20. Kowdley KV: Ursodeoxycholic acid therapy in hepatobiliary disease. Am J Med. 2000 Apr 15;108(6):481-6.
21. 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.
22. 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.
23. 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.
24. 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.
25. 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.
26. 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.
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=11530998
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=16037564
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=24448653
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=24464484