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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:33 UTC
HMDB IDHMDB00908
Secondary Accession NumbersNone
Metabolite Identification
Common Name5alpha-Cholestanol
Description5alpha-Cholestanol is a cholesterol derivative found in human feces, gallstones, eggs, and other biological matter.
Structure
Thumb
Synonyms
ValueSource
(3b,5a)-Cholestan-3-olHMDB
3b-Hydroxy-5a-cholestaneHMDB
3b-HydroxycholestaneHMDB
5a-Cholestan-3b-olHMDB
5a-CholestanolHMDB
5a-DihydrocholesterolHMDB
Cholestan-3b-olHMDB
CholestanolHMDB
DihydrocholesterinHMDB
DihydrocholesterolHMDB
EpicholestanolHMDB
ZymostanolHMDB
Chemical FormulaC27H48O
Average Molecular Weight388.6694
Monoisotopic Molecular Weight388.370516158
IUPAC Name(1S,2S,5S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol
Traditional Namedihydrocholesterol
CAS Registry Number80-97-7
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
InChI Identifier
InChI=1S/C27H48O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h18-25,28H,6-17H2,1-5H3/t19-,20+,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChI KeyInChIKey=QYIXCDOBOSTCEI-QCYZZNICSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cholesterols and derivatives. These are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • Cholesterol
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
  • Microbial
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point140.0 - 142.0 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.51e-05 mg/mLALOGPS
logP7.02ALOGPS
logP7.52ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity119.77 m3·mol-1ChemAxon
Polarizability51.19 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0a7l-8910000000-cb54fe639b59ac574d48View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-1019000000-713d1937c93d1a00cc54View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000j-9002000000-f96eb85165088475ddbcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05o1-9200000000-8819828d6963c4e8290dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positivesplash10-0159-2971000000-c73c47a340a1d4a167e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-001c-9685000000-f1bd7d21900c66c26e86View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
Tissue Location
  • Brain
  • Eye Lens
  • Fibroblasts
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified9.26 +/- 5.40 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified9.0 +/- 2.5 uMAdult (>18 years old)BothCerebrotendinous xanthomatosis (CTX) details
BloodDetected and Quantified30.6 +/- 1.4 uMAdult (>18 years old)FemaleCirrhosis details
Associated Disorders and Diseases
Disease References
Cerebrotendinous xanthomatosis
  1. Halperin G, Elisaf M, Leitersdorf E, Harats D: A new method for determination of serum cholestanol by high-performance liquid chromatography with ultraviolet detection. J Chromatogr B Biomed Sci Appl. 2000 Jun 9;742(2):345-52. [10901139 ]
Cirrhosis
  1. Halperin G, Elisaf M, Leitersdorf E, Harats D: A new method for determination of serum cholestanol by high-performance liquid chromatography with ultraviolet detection. J Chromatogr B Biomed Sci Appl. 2000 Jun 9;742(2):345-52. [10901139 ]
Associated OMIM IDs
  • 213700 (Cerebrotendinous xanthomatosis)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012122
KNApSAcK IDNot Available
Chemspider ID6413
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00908
Metagene LinkHMDB00908
METLIN ID5864
PubChem Compound6665
PDB IDNot Available
ChEBI ID815842
References
Synthesis ReferenceBruce, W. F.; Ralls, J. O. Dihydrocholesterol (b-cholestanol). Organic Syntheses (1937), 17 45-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Gylling H, Vuoristo M, Farkkila M, Miettinen TA: The metabolism of cholestanol in primary biliary cirrhosis. J Hepatol. 1996 Apr;24(4):444-51. [8738731 ]
  2. Nikkila K, Hockerstedt K, Miettinen TA: Liver transplantation modifies serum cholestanol, cholesterol precursor and plant sterol levels. Clin Chim Acta. 1992 Jun 30;208(3):205-18. [1499139 ]
  3. Nakajima M, Yamato S, Wakabayashi H, Shimada K: High-performance liquid chromatographic determination of cholesterol and cholestanol in human serum by precolumn derivatization with 2-[2-(isocyanate)ethyl]-3-methyl-1,4-naphthoquinone combined with platinum catalyst reduction and electrochemical detection. Biol Pharm Bull. 1995 Dec;18(12):1762-4. [8787802 ]
  4. Salen G, Shefer S, Tint GS: Transformation of 4-cholesten-3-one and 7 alpha-hydroxy-4-cholesten-3-one into cholestanol and bile acids in cerebrotendinous xanthomatosis. Gastroenterology. 1984 Aug;87(2):276-83. [6735073 ]
  5. Koopman BJ, van der Molen JC, Wolthers BG, de Jager AE, Waterreus RJ, Gips CH: Capillary gas chromatographic determination of cholestanol/cholesterol ratio in biological fluids. Its potential usefulness for the follow-up of some liver diseases and its lack of specificity in diagnosing CTX (cerebrotendinous xanthomatosis). Clin Chim Acta. 1984 Mar 13;137(3):305-15. [6421514 ]
  6. Ballantyne CM, Vega GL, East C, Richards G, Grundy SM: Low-density lipoprotein metabolism in cerebrotendinous xanthomatosis. Metabolism. 1987 Mar;36(3):270-6. [3821507 ]
  7. Skrede S, Bjorkhem I, Buchmann MS, Hopen G, Fausa O: A novel pathway for biosynthesis of cholestanol with 7 alpha-hydroxylated C27-steroids as intermediates, and its importance for the accumulation of cholestanol in cerebrotendinous xanthomatosis. J Clin Invest. 1985 Feb;75(2):448-55. [3919058 ]
  8. Halperin G, Elisaf M, Leitersdorf E, Harats D: A new method for determination of serum cholestanol by high-performance liquid chromatography with ultraviolet detection. J Chromatogr B Biomed Sci Appl. 2000 Jun 9;742(2):345-52. [10901139 ]
  9. Canelas HM, Quintao EC, Scaff M, Vasconcelos KS, Brotto MW: Cerebrotendinous xanthomatosis: clinical and laboratory study of 2 cases. Acta Neurol Scand. 1983 May;67(5):305-11. [6410671 ]
  10. Verrips A, van Engelen BG, Wevers RA, van Geel BM, Cruysberg JR, van den Heuvel LP, Keyser A, Gabreels FJ: Presence of diarrhea and absence of tendon xanthomas in patients with cerebrotendinous xanthomatosis. Arch Neurol. 2000 Apr;57(4):520-4. [10768627 ]
  11. Heller R, Grau AJ, Schabitz WR, Schwaninger M: [Cerebrotendinous xanthomatosis, a treatable metabolic disorder] Nervenarzt. 2002 Dec;73(12):1160-6. [12486565 ]
  12. Serizawa S, Seyama Y, Otsuka H, Kasama T, Yamakawa T: Simplified determination of cholestanol in serum by gas-liquid chromatography: biochemical diagnosis of cerebrotendinous xanthomatosis. J Biochem (Tokyo). 1981 Jul;90(1):17-21. [7287675 ]
  13. Salen G, Berginer V, Shore V, Horak I, Horak E, Tint GS, Shefer S: Increased concentrations of cholestanol and apolipoprotein B in the cerebrospinal fluid of patients with cerebrotendinous xanthomatosis. Effect of chenodeoxycholic acid. N Engl J Med. 1987 May 14;316(20):1233-8. [3106810 ]
  14. Siman-Tov T, Meiner V, Gadoth N: Could steroids mask the diagnosis of cerebrotendinous xanthomatosis? J Neurol Sci. 2006 Apr 15;243(1-2):83-6. Epub 2006 Jan 30. [16445943 ]
  15. Baumgartner RW, Hauser V, Grob P, Waespe W: [Cerebrotendinous xanthomatosis] Schweiz Med Wochenschr. 1991 Jun 8;121(23):858-64. [1857943 ]
  16. Miettinen TA, Kesaniemi YA, Jarvinen H, Hastbacka J: Cholesterol precursor sterols, plant sterols, and cholestanol in human bile and gallstones. Gastroenterology. 1986 Apr;90(4):858-64. [3081398 ]