Hmdb loader
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
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-10-13 04:31:45 UTC
HMDB IDHMDB0000908
Secondary Accession Numbers
  • HMDB00908
Metabolite Identification
Common Name5alpha-Cholestanol
Description5alpha-Cholestanol, also known as cholestanol or dihydrocholesterol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 5alpha-cholestanol is considered to be a sterol lipid molecule. 5alpha-Cholestanol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 5alpha-Cholestanol is a potentially toxic compound.
Structure
Data?1582752164
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 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[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-ol
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
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 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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point140.0 - 142.0 °CNot Available
Boiling Point455.53 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.00034 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP10.065 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.5e-05 g/LALOGPS
logP10(7.02) g/LALOGPS
logP10(7.52) g/LChemAxon
logS10(-7.4) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+197.52431661259
DarkChem[M-H]-194.54831661259
AllCCS[M+H]+204.86632859911
AllCCS[M-H]-201.75332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5alpha-Cholestanol[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)C2298.6Standard polar33892256
5alpha-Cholestanol[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)C3127.2Standard non polar33892256
5alpha-Cholestanol[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)C3232.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5alpha-Cholestanol,1TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3096.0Semi standard non polar33892256
5alpha-Cholestanol,1TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3327.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 5alpha-Cholestanol GC-MS (1 TMS)splash10-0a7l-8910000000-cb54fe639b59ac574d482014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5alpha-Cholestanol EI-B (Non-derivatized)splash10-0159-2971000000-c73c47a340a1d4a167e12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5alpha-Cholestanol EI-B (Non-derivatized)splash10-001c-9685000000-f1bd7d21900c66c26e862017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5alpha-Cholestanol GC-MS (Non-derivatized)splash10-0a7l-8910000000-cb54fe639b59ac574d482017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5alpha-Cholestanol GC-EI-TOF (Non-derivatized)splash10-0a4m-3920000000-deaba49a3e34c5a9a9982017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Cholestanol GC-MS (Non-derivatized) - 70eV, Positivesplash10-05i0-0109000000-761dcf3fe040f44fa80e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Cholestanol GC-MS (1 TMS) - 70eV, Positivesplash10-0002-3104900000-654dcbe9dd07b5a589f22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Cholestanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Cholestanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5alpha-Cholestanol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 5alpha-Cholestanol Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000i-1019000000-713d1937c93d1a00cc542012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5alpha-Cholestanol Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-000j-9002000000-f96eb85165088475ddbc2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5alpha-Cholestanol Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-05o1-9200000000-8819828d6963c4e8290d2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5alpha-Cholestanol EI-B (SHIMADZU LKB-9000B) , Positive-QTOFsplash10-0159-2971000000-c73c47a340a1d4a167e12012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5alpha-Cholestanol EI-B (JEOL JMS-01-SG-2) , Positive-QTOFsplash10-001c-9685000000-f1bd7d21900c66c26e862012-08-31HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanol 10V, Positive-QTOFsplash10-0079-0009000000-57023400d5e478a8c7462017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanol 20V, Positive-QTOFsplash10-00dr-3039000000-9ce6c0a362b9f376d3f02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanol 40V, Positive-QTOFsplash10-0ab9-4159000000-32959ebb75235db63ac32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanol 10V, Negative-QTOFsplash10-000i-0009000000-134a888410f8beddca3b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanol 20V, Negative-QTOFsplash10-000i-0009000000-c42f43f5e21141f5a9092017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanol 40V, Negative-QTOFsplash10-0ab9-1009000000-8096d56c7bfdd221f9c22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanol 10V, Positive-QTOFsplash10-000i-0009000000-44afea742dee80d0734e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanol 20V, Positive-QTOFsplash10-0a4i-9032000000-166905331dad000292e62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanol 40V, Positive-QTOFsplash10-0a4j-9820000000-f066461902c4fe39e2d42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanol 10V, Negative-QTOFsplash10-000i-0009000000-34ef429285e58bb4b3142021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanol 20V, Negative-QTOFsplash10-000i-0009000000-780ac33d63315f6581592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5alpha-Cholestanol 40V, Negative-QTOFsplash10-000i-0009000000-2b8e0e9916832dc478762021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Brain
  • Eye Lens
  • Fibroblasts
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified9.26 +/- 5.40 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified2.573-12.864 uMNot SpecifiedNot SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
BloodDetected and Quantified60.720-122.726 uMAdult (>18 years old)Male
27-hydroxylase deficiency
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
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. [PubMed:10901139 ]
  2. 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. [PubMed:16445943 ]
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. [PubMed:10901139 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012122
KNApSAcK IDC00053136
Chemspider ID6413
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5864
PubChem Compound6665
PDB IDNot Available
ChEBI ID86570
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000281
Good Scents IDrw1133261
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:10768627 ]
  11. Heller R, Grau AJ, Schabitz WR, Schwaninger M: [Cerebrotendinous xanthomatosis, a treatable metabolic disorder]. Nervenarzt. 2002 Dec;73(12):1160-6. [PubMed: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. 1981 Jul;90(1):17-21. [PubMed: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. [PubMed: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. [PubMed:16445943 ]
  15. Baumgartner RW, Hauser V, Grob P, Waespe W: [Cerebrotendinous xanthomatosis]. Schweiz Med Wochenschr. 1991 Jun 8;121(23):858-64. [PubMed: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. [PubMed:3081398 ]