You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2006-05-22 14:17:40 UTC
Update Date2013-07-24 17:53:43 UTC
HMDB IDHMDB02178
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 ).
Structure
Thumb
Synonyms
  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[8.7.0.0²,⁷.0¹¹,¹⁵]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
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])C[C@H](O)[C@]12C)[C@H](C)CCCC(C)C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12
InChI Identifier
InChI=1S/C48H80N7O20P3S/c1-25(29-10-11-30-36-31(20-34(58)48(29,30)6)47(5)14-12-28(56)18-27(47)19-32(36)57)8-7-9-26(2)45(63)79-17-16-50-35(59)13-15-51-43(62)40(61)46(3,4)22-72-78(69,70)75-77(67,68)71-21-33-39(74-76(64,65)66)38(60)44(73-33)55-24-54-37-41(49)52-23-53-42(37)55/h23-34,36,38-40,44,56-58,60-61H,7-22H2,1-6H3,(H,50,59)(H,51,62)(H,67,68)(H,69,70)(H2,49,52,53)(H2,64,65,66)/t25-,26?,27+,28-,29-,30+,31+,32-,33-,34+,36+,38-,39-,40+,44-,47+,48-/m1/s1
InChI KeyInChIKey=MNYDLIUNNOCPHG-TUTZYBGQSA-N
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
Substituents
  • 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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Lipid biosynthesis, Fatty acid transport
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.87 mg/mLALOGPS
logP1.21ALOGPS
logP-2.8ChemAxon
logS-3.1ALOGPS
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
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
METLIN ID6529
PubChem Compound15942872
PDB IDNot Available
ChEBI ID15493
References
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 ]

Enzymes

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:
SLC27A5
Uniprot ID:
Q9Y2P5
Molecular weight:
75384.375
Reactions
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:
RDH13
Uniprot ID:
Q8NBN7
Molecular weight:
35931.8
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:
ACAD8
Uniprot ID:
Q9UKU7
Molecular weight:
45069.39