5alpha-Cholestanol (CHEM003275)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-08-29 06:20:05 UTC
Update Date2026-04-06 12:55:16 UTC
Accession NumberCHEM003275
Identification
Common Name5alpha-Cholestanol
ClassSmall Molecule
Description5alpha-Cholestanol is a cholesterol derivative found in human feces, gallstones, eggs, and other biological matter.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Animal Toxin
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3beta,5alpha)-Cholestan-3-olChEBI
CholestanolChEBI
DihydrocholesterolChEBI
ZymostanolChEBI
(3b,5a)-Cholestan-3-olGenerator
(3Β,5α)-cholestan-3-olGenerator
5a-CholestanolGenerator
5Α-cholestanolGenerator
5 alpha Cholestan 3 beta olHMDB
5 beta Cholestan 3 beta olHMDB
5 beta-Cholestan-3 beta-olHMDB
beta CholestanolHMDB
beta-Ol, 5 beta-cholestan-3HMDB
5 alpha Cholestan 3 alpha olHMDB
5 alpha-Cholestan-3 beta-olHMDB
Cholestan 3 olHMDB
Cholestanol, (3alpha, 5beta)-isomerHMDB
CoprosterolHMDB
beta-CholestanolHMDB
5 beta-Cholestan-3 alpha-olHMDB
CoprostanolHMDB
5 alpha-Cholestan-3 alpha-olHMDB
Cholestan-3-olHMDB
beta-Cholestan-3 beta-ol, 5HMDB
3b-Hydroxy-5a-cholestaneHMDB
3b-HydroxycholestaneHMDB
5a-Cholestan-3b-olHMDB
5a-DihydrocholesterolHMDB
Cholestan-3b-olHMDB
DihydrocholesterinHMDB
EpicholestanolHMDB
5alpha-CholestanolChEBI
Chemical FormulaC27H48O
Average Molecular Mass388.669 g/mol
Monoisotopic Mass388.371 g/mol
CAS Registry Number80-97-7
IUPAC NameNot Available
Traditional Name(1S,2S,5S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol
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 IdentifierInChI=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 KeyQYIXCDOBOSTCEI-QCYZZNICSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives 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
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Brain
  • Eye Lens
  • Fibroblasts
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Cerebrotendinous Xanthomatosis (CTX)SMP00315 Not Available
Zellweger SyndromeSMP00316 Not Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point140.0 - 142.0°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.5e-05 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity119.77 m³·mol⁻¹ChemAxon
Polarizability51.27 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0a7l-8910000000-cb54fe639b59ac574d48Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0159-2971000000-c73c47a340a1d4a167e1Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001c-9685000000-f1bd7d21900c66c26e86Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a7l-8910000000-cb54fe639b59ac574d48Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4m-3920000000-deaba49a3e34c5a9a998Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05i0-0109000000-761dcf3fe040f44fa80eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-3104900000-654dcbe9dd07b5a589f2Spectrum
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 (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-1019000000-713d1937c93d1a00cc54Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000j-9002000000-f96eb85165088475ddbcSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05o1-9200000000-8819828d6963c4e8290dSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positivesplash10-0159-2971000000-c73c47a340a1d4a167e1Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-001c-9685000000-f1bd7d21900c66c26e86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0009000000-57023400d5e478a8c746Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-3039000000-9ce6c0a362b9f376d3f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-4159000000-32959ebb75235db63ac3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-134a888410f8beddca3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-c42f43f5e21141f5a909Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-1009000000-8096d56c7bfdd221f9c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-44afea742dee80d0734eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9032000000-166905331dad000292e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-9820000000-f066461902c4fe39e2d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-34ef429285e58bb4b314Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-780ac33d63315f658159Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0009000000-2b8e0e9916832dc47876Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000908
FooDB IDFDB012122
Phenol Explorer IDNot Available
KNApSAcK IDC00053136
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5864
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID6413
ChEBI ID86570
PubChem Compound ID6665
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceBruce, W. F.; Ralls, J. O. Dihydrocholesterol (b-cholestanol). Organic Syntheses (1937), 17 45-7.
MSDSLink
General References
1. Bruce, W. F.; Ralls, J. O. Dihydrocholesterol (b-cholestanol). Organic Syntheses (1937), 17 45-7.
2. 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.
3. 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.
4. 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.
5. Ballantyne CM, Vega GL, East C, Richards G, Grundy SM: Low-density lipoprotein metabolism in cerebrotendinous xanthomatosis. Metabolism. 1987 Mar;36(3):270-6.
6. 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.
7. 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.
8. 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.
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.
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.
11. Heller R, Grau AJ, Schabitz WR, Schwaninger M: [Cerebrotendinous xanthomatosis, a treatable metabolic disorder]. Nervenarzt. 2002 Dec;73(12):1160-6.
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. 1981 Jul;90(1):17-21.
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.
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.
15. Baumgartner RW, Hauser V, Grob P, Waespe W: [Cerebrotendinous xanthomatosis]. Schweiz Med Wochenschr. 1991 Jun 8;121(23):858-64.
16. Gylling H, Vuoristo M, Farkkila M, Miettinen TA: The metabolism of cholestanol in primary biliary cirrhosis. J Hepatol. 1996 Apr;24(4):444-51.
17. 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.