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Record Information
Version1.0
Creation Date2016-07-13 19:43:56 UTC
Update Date2016-07-20 21:03:33 UTC
LmdbLMDB00172
Secondary Accession NumbersNone
Metabolite 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.
Structure
Thumb
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 Weight392.572
Monoisotopic Molecular Weight392.292659768
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
CAS Registry Number474-25-9
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 Identifier
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
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
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
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
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine
    • Natalja P. Nørsko...
details
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
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [11316487 ]
  2. 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. [16037564 ]
  3. 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. [12576301 ]
  4. 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. [11907135 ]