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Record Information
StatusExpected but not Quantified
Creation Date2007-05-22 21:57:36 UTC
Update Date2020-02-26 21:26:19 UTC
Secondary Accession Numbers
  • HMDB0002325
  • HMDB02325
  • HMDB06292
Metabolite Identification
Common NameChenodeoxycholoyl-CoA
DescriptionChenodeoxycholoyl-CoA is bile acid Coenzyme A ester. In humans, bile acids conjugated with glycine and taurine are the major solutes in bile, and unconjugated bile acids are almost nondetectable in normal bile. Conjugated bile acids are less toxic and are more efficient promoters of intestinal absorption of dietary lipid than unconjugated bile acids. The synthesis of bile acid and amino acid conjugates in human liver is the result of two independent enzymatic reactions with a bile acid coenzyme A thioester intermediate formation of bile acid-CoA esters, considered the rate-limiting step in bile acid amidation and catalyzed by an ATP-dependent microsomal enzyme, bile acid-CoA synthetase (EC In the second reaction, the thioester bond is cleaved, and an amide bond is formed between the bile acid and the amino acids glycine or taurine. The bile acid-CoA:amino acid N-acyltransferase (EC catalyzes this reaction in the cytosol prior to secretion into bile. In human liver the formation of bile acid-CoA thioesters is localized both to the microsomal fraction catalysed by an ATP-dependent synthetase and to the peroxisomal fraction catalysed by the thiolase in the last step of the beta-oxidative cleavage of the 5beta-cholestanoyl side chain. The highest specific amidation activity of both chenodeoxycholoyl-CoA is always found in the most peroxisome-rich subcellular fractions. (PMID: 2722825 , 10817395 , 11673457 , 10884298 ).
5'-{3-[(3R)-4-{[3-({2-[(3alpha,7alpha-dihydroxy-5beta-cholan-24-oyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-3-hydroxy-2,2-dimethyl-4-oxobutyl] dihydrogen diphosphate}3'-phosphoadenosineHMDB
Chenodeoxycholoyl coenzyme AHMDB
Chemical FormulaC45H74N7O19P3S
Average Molecular Weight1142.091
Monoisotopic Molecular Weight1141.397303447
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[3-({2-[(2-{[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
Traditional Name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-[({[3-({2-[(2-{[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxyphosphonic acid
CAS Registry Number60731-52-4
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
Sub ClassGlycerophosphoethanolamines
Direct ParentPhosphatidylethanolamines
Alternative Parents
  • Diacylglycero-3-phosphoethanolamine
  • Phosphoethanolamine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Primary amine
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors

Route of exposure:


Biological location:


Naturally occurring process:


Biological role:

Industrial application:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.41HANSCH,C ET AL. (1995)
Predicted Properties
Water Solubility1.01 g/LALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area404.09 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity268.84 m³·mol⁻¹ChemAxon
Polarizability113.69 ųChemAxon
Number of Rings7ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1900111000-49f063c429232551ee17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900215000-8d2226be8c0c4bc5d849Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900001000-7a0a8e03b96562805e53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00al-2902140300-27178d920f5623fe9229Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3901120100-6b56cd2f9088ae3e0e8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900100000-5f68bcc57183d55aa9fcSpectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023880
KNApSAcK IDNot Available
Chemspider ID10140198
KEGG Compound IDC05337
BioCyc IDNot Available
BiGG ID45602
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11953854
PDB IDNot Available
ChEBI ID28701
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
Synthesis ReferenceKillenberg, Paul G.; Dukes, Diane F. Coenzyme A derivatives of bile acids - chemical synthesis, purification, and utilization in enzymic preparation of taurine conjugates. Journal of Lipid Research (1976), 17(5), 451-5.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kase BF, Bjorkhem I: Peroxisomal bile acid-CoA:amino-acid N-acyltransferase in rat liver. J Biol Chem. 1989 Jun 5;264(16):9220-3. [PubMed:2722825 ]
  2. Solaas K, Sletta RJ, Soreide O, Kase BF: Presence of choloyl- and chenodeoxycholoyl-coenzyme A thioesterase activity in human liver. Scand J Clin Lab Invest. 2000 Apr;60(2):91-102. [PubMed:10817395 ]
  3. Hunt MC, Solaas K, Kase BF, Alexson SE: Characterization of an acyl-coA thioesterase that functions as a major regulator of peroxisomal lipid metabolism. J Biol Chem. 2002 Jan 11;277(2):1128-38. Epub 2001 Oct 22. [PubMed:11673457 ]
  4. Solaas K, Ulvestad A, Soreide O, Kase BF: Subcellular organization of bile acid amidation in human liver: a key issue in regulating the biosynthesis of bile salts. J Lipid Res. 2000 Jul;41(7):1154-62. [PubMed:10884298 ]


General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Abolishes BNIP3-mediated apoptosis and mitochondrial damage.
Gene Name:
Uniprot ID:
Molecular weight:
Propionyl-CoA + Chenodeoxycholoyl-CoA → Coenzyme A + 3a,7a-Dihydroxy-5b-cholestanoyl-CoAdetails
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight:
Propionyl-CoA + Chenodeoxycholoyl-CoA → Coenzyme A + 3a,7a-Dihydroxy-5b-cholestanoyl-CoAdetails
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight:
Propionyl-CoA + Chenodeoxycholoyl-CoA → Coenzyme A + 3a,7a-Dihydroxy-5b-cholestanoyl-CoAdetails
General function:
Involved in oxidoreductase activity
Specific function:
Mediates in vitro the transfer of all common phospholipids, cholesterol and gangliosides between membranes. May play a role in regulating steroidogenesis.
Gene Name:
Uniprot ID:
Molecular weight:
Propionyl-CoA + Chenodeoxycholoyl-CoA → Coenzyme A + 3a,7a-Dihydroxy-5b-24-oxocholestanoyl-CoAdetails
General function:
Involved in thiolester hydrolase activity
Specific function:
Involved in bile acid metabolism. In liver hepatocytes catalyzes the second step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi. The major components of bile are cholic acid and chenodeoxycholic acid. In a first step the bile acids are converted to an acyl-CoA thioester, either in peroxisomes (primary bile acids deriving from the cholesterol pathway), or cytoplasmic at the endoplasmic reticulum (secondary bile acids). May catalyze the conjugation of primary or secondary bile acids, or both. The conjugation increases the detergent properties of bile acids in the intestine, which facilitates lipid and fat-soluble vitamin absorption. In turn, bile acids are deconjugated by bacteria in the intestine and are recycled back to the liver for reconjugation (secondary bile acids). May also act as an acyl-CoA thioesterase that regulates intracellular levels of free fatty acids. In vitro, catalyzes the hydrolysis of long- and very long-chain saturated acyl-CoAs to the free fatty acid and coenzyme A (CoASH), and conjugates glycine to these acyl-CoAs.
Gene Name:
Uniprot ID:
Molecular weight:
Chenodeoxycholoyl-CoA + Glycine → Chenodeoxycholic acid glycine conjugate + Coenzyme Adetails
Chenodeoxycholoyl-CoA + Taurine → Taurochenodesoxycholic acid + Coenzyme Adetails
General function:
Involved in acyl-CoA thioesterase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May mediate Nef-induced down-regulation of CD4. Major thioesterase in peroxisomes. Competes with BAAT (Bile acid CoA: amino acid N-acyltransferase) for bile acid-CoA substrate (such as chenodeoxycholoyl-CoA). Shows a preference for medium-length fatty acyl-CoAs (By similarity). May be involved in the metabolic regulation of peroxisome proliferation.
Gene Name:
Uniprot ID:
Molecular weight:
Chenodeoxycholic acid + Coenzyme A → Chenodeoxycholoyl-CoA + Waterdetails
General function:
Involved in catalytic activity
Specific function:
Acyl-CoA synthetase involved in bile acid metabolism. Proposed to catalyze the first step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi by activating them to their CoA thioesters. Seems to activate secondary bile acids entering the liver from the enterohepatic circulation. In vitro, also activates 3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholestanate (THCA), the C27 precursor of cholic acid deriving from the de novo synthesis from cholesterol.
Gene Name:
Uniprot ID:
Molecular weight:
Chenodeoxycholoyl-CoA + Adenosine monophosphate + Pyrophosphate → Chenodeoxycholic acid + Coenzyme A + Adenosine triphosphatedetails