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Record Information
Creation Date2006-05-22 14:17:40 UTC
Update Date2013-07-24 17:53:43 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common Name3a,7a,12a-Trihydroxy-5b-cholestanoyl-CoA
Description3a,7a,12a-Trihydroxy-5b-cholestanoyl-CoA is an intermediate in the Bile acid biosynthesis pathway (KEGG). C27-bile acyl-CoAs are converted to their (S)-stereoisomers by the enzyme Alpha-methylacyl-CoA racemase (OMIM 604489 ).
  1. (25R)-3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholestan-26-oyl-CoA
  2. (25R)-3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholestan-26-oyl-Coenzyme A
  3. (25R)-3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholestanoyl-CoA
  4. (25R)-3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholestanoyl-Coenzyme A
  5. 25(S)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoA
  6. 25(S)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-Coenzyme A
  7. 25(S)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoyl-CoA
  8. 25(S)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoyl-Coenzyme A
  9. 25(S)-5beta-cholestane-3alpha,7alpha,12alpha-triol-26-oyl-CoA
  10. 25(S)-5beta-cholestane-3alpha,7alpha,12alpha-triol-26-oyl-Coenzyme A
  11. 25(S)-Trihydroxycoprostanoyl-CoA
  12. 25(S)-Trihydroxycoprostanoyl-Coenzyme A
  13. 3-alpha,7-alpha,12-alpha-Trihydroxy-5-beta- cholanoyl-CoA
  14. 3-alpha,7-alpha,12-alpha-Trihydroxy-5-beta- cholanoyl-Coenzyme A
  15. 3a,7a,12a-Trihydroxy-5b-cholestan-26-oyl-CoA
  16. 3a,7a,12a-Trihydroxy-5b-cholestan-26-oyl-Coenzyme A
  17. 3a,7a,12a-Trihydroxy-5b-cholestanoate
  18. 3a,7a,12a-Trihydroxy-5b-cholestanoic acid
  19. 3a,7a,12a-Trihydroxy-5b-cholestanoic acid coenzyme A ester
  20. 3a,7a,12a-Trihydroxy-5b-cholestanoyl CoA
  21. 3a,7a,12a-Trihydroxy-5b-cholestanoyl Coenzyme A
  22. 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoyl-CoA
  23. 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoyl-CoA(S)
  24. 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoyl-Coenzyme A
  25. 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestanoyl-Coenzyme A(S)
  26. S-(3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoyl)-coenzyme
  27. S-TrHCCoA
  28. S-TrHCCoenzyme A
Chemical FormulaC48H80N7O20P3S
Average Molecular Weight1200.17
Monoisotopic Molecular Weight1199.439168261
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-({2-[(2-{[(6R)-2-methyl-6-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Nametrihydroxycoprostanoyl-coa
CAS Registry Number57458-60-3
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 2,3,4-saturated fatty acyl coas. These are acyl-CoAs carrying a 2,3,4-saturated fatty acyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent2,3,4-saturated fatty acyl CoAs
Alternative Parents
  • Coenzyme a or derivatives
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • Trihydroxy bile acid, alcohol, or derivatives
  • Cholane-skeleton
  • Hydroxy bile acid, alcohol, or derivatives
  • Bile acid, alcohol, or derivatives
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • 12-hydroxysteroid
  • 3-hydroxysteroid
  • Steroid
  • N-glycosyl compound
  • Glycosyl compound
  • Beta amino acid or derivatives
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • N-acyl-amine
  • Monosaccharide
  • Fatty amide
  • Saccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Cyclic alcohol
  • Azole
  • Thiocarboxylic acid ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Polyol
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thioether
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
StatusExpected but not Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Lipid biosynthesis, Fatty acid transport
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
  • Peroxisome
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.87 mg/mLALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area424.32 Å2ChemAxon
Rotatable Bond Count26ChemAxon
Refractivity284.13 m3·mol-1ChemAxon
Polarizability118.88 Å3ChemAxon
Number of Rings7ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
  • Peroxisome
Biofluid LocationsNot Available
Tissue Location
  • Liver
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022888
KNApSAcK IDNot Available
Chemspider ID13085527
KEGG Compound IDC05448
BioCyc IDNot Available
BiGG ID44498
Wikipedia LinkA
NuGOwiki LinkHMDB02178
Metagene LinkHMDB02178
PubChem Compound15942872
PDB IDNot Available
ChEBI ID15493
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wanders RJ, Casteels M, Mannaerts GP, van Roermund CW, Schutgens RB, Kozich V, Zeman J, Hyanek J: Accumulation and impaired in vivo metabolism of di- and trihydroxycholestanoic acid in two patients. Clin Chim Acta. 1991 Oct 31;202(3):123-32. [1839974 ]
  2. Gan-Schreier H, Okun JG, Kohlmueller D, Langhans CD, Peters V, Ten Brink HJ, Verhoeven NM, Jakobs C, Voelkl A, Hoffmann GF: Measurement of bile acid CoA esters by high-performance liquid chromatography-electrospray ionisation tandem mass spectrometry (HPLC-ESI-MS/MS). J Mass Spectrom. 2005 Jul;40(7):882-9. [15892178 ]
  3. Pedersen JI, Veggan T, Bjorkhem I: Substrate stereospecificity in oxidation of (25S)-3 alpha, 7 alpha, 12 alpha-trihydroxy-5 beta-cholestanoyl-CoA by peroxisomal trihydroxy-5 beta-cholestanoyl-CoA oxidase. Biochem Biophys Res Commun. 1996 Jul 5;224(1):37-42. [8694830 ]


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:
Adenosine triphosphate + 3a,7a,12a-Trihydroxy-5b-cholestanoic acid + Coenzyme A → Adenosine monophosphate + Pyrophosphate + 3a,7a,12a-Trihydroxy-5b-cholestanoyl-CoAdetails
General function:
Involved in oxidoreductase activity
Specific function:
Does not exhibit retinol dehydrogenase (RDH) activity in vitro
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Has very high activity toward isobutyryl-CoA. Is an isobutyryl-CoA dehydrogenase that functions in valine catabolism. Plays a role in transcriptional coactivation within the ARC complex.
Gene Name:
Uniprot ID:
Molecular weight: