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Record Information
Version3.6
Creation Date2008-08-13 11:22:33 UTC
Update Date2013-05-29 19:45:17 UTC
HMDB IDHMDB06841
Secondary Accession Numbers
  • HMDB06541
  • HMDB59618
Metabolite Identification
Common Name5a-Cholest-8-en-3b-ol
Description5a-Cholest-8-en-3b-ol is a normal human metabolite and an intermediate of cholesterol synthesis. The concentrations of zymostenol are higher, both in serum and bile of patients with cerebrotendinous xanthomatosis, compared to controls or in patients with cerebrotendinous xanthomatosis treated with chenodeoxycholic acid. Kidney transplant recipients had lower serum zymostenol when compared to controls. During consumption of plant stanol ester spread by hypercholesterolemic children, plant sterols in the plasma decrease and cholesterol precursor sterols such as zymostenol increase. (PMID: 15736111 , 16709621 , 16477216 , 12756385 ).
Structure
Thumb
Synonyms
  1. (3beta,5alpha)Cholestenol
  2. 3beta-hydroxy-8(9)-cholestene
  3. 3beta-hydroxycholest-8(9)-ene
  4. 5-alpha-Cholest-8-en-3-beta-ol
  5. 5alpha-Cholest-8(9)-en-3beta-ol
  6. 5alpha-cholest-8-en-3beta-ol
  7. Cholest-8(9)-en-3beta-ol
  8. Cholesta-8(9)-en-3beta-ol
  9. delta(8)-Cholestenol
Chemical FormulaC27H46O
Average Molecular Weight386.6535
Monoisotopic Molecular Weight386.354866094
IUPAC Name(2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol
Traditional Name5α-cholest-8-en-3β-ol
CAS Registry Number566-97-2
SMILES
[H][C@@](C)(CCCC(C)C)[C@@]1([H])CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C[C@]1([H])CC3
InChI Identifier
InChI=1S/C27H46O/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/h18-21,23-24,28H,6-17H2,1-5H3/t19-,20+,21+,23-,24+,26+,27-/m1/s1
InChI KeyQETLKNDKQOXZRP-XTGBIJOFSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassCholesterols and Derivatives
Other Descriptors
  • 3beta-sterol(ChEBI)
  • Aliphatic Homopolycyclic Compounds
  • Cholesterol and derivatives(Lipidmaps)
Substituents
  • 3 Hydroxy Steroid
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Secondary Alcohol
  • Sesterterpene
Direct ParentCholesterols and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
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
  • Endoplasmic reticulum
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 Solubility0.000222ALOGPS
logP6.59ALOGPS
logP7.07ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)18.36ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity120.35 m3·mol-1ChemAxon
Polarizability50.66 Å3ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Steroid BiosynthesisSMP00023map00100
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 IDFDB024114
KNApSAcK IDNot Available
Chemspider ID91952
KEGG Compound IDC03845
BioCyc IDCPD-8621
BiGG ID42633
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06841
Metagene LinkHMDB06841
METLIN IDNot Available
PubChem Compound101770
PDB IDNot Available
ChEBI ID16608
References
Synthesis ReferenceReindel, F.; Weickmann, A. Zymosterol. Ann. (1929), 475 86-100. CAN 24:5322 AN 1930:5322
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Siirtola A, Ketomaki A, Miettinen TA, Gylling H, Lehtimaki T, Holmberg C, Salo MK, Antikainen M: Cholesterol absorption and synthesis in pediatric kidney, liver, and heart transplant recipients. Transplantation. 2006 Feb 15;81(3):327-34. Pubmed: 16477216
  2. Clarenbach JJ, Lindenthal B, Dotti MT, Federico A, Kelleher JK, von Bergmann K: Isotopomer spectral analysis of intermediates of cholesterol synthesis in patients with cerebrotendinous xanthomatosis. Metabolism. 2005 Mar;54(3):335-44. Pubmed: 15736111
  3. Oostendorp M, Engelke UF, Willemsen MA, Wevers RA: Diagnosing inborn errors of lipid metabolism with proton nuclear magnetic resonance spectroscopy. Clin Chem. 2006 Jul;52(7):1395-405. Epub 2006 May 18. Pubmed: 16709621
  4. Ketomaki AM, Gylling H, Antikainen M, Siimes MA, Miettinen TA: Red cell and plasma plant sterols are related during consumption of plant stanol and sterol ester spreads in children with hypercholesterolemia. J Pediatr. 2003 May;142(5):524-31. Pubmed: 12756385

Enzymes

General function:
Involved in cholestenol delta-isomerase activity
Specific function:
Catalyzes the conversion of Delta(8)-sterols to their corresponding Delta(7)-isomers.
Gene Name:
EBP
Uniprot ID:
Q15125
Molecular weight:
26352.615
Reactions
Lathosterol → 5a-Cholest-8-en-3b-oldetails
General function:
Energy production and conversion
Specific function:
Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
Gene Name:
DHCR24
Uniprot ID:
Q15392
Molecular weight:
60100.805
Reactions
Zymosterol intermediate 2 + NADPH + Hydrogen Ion → 5a-Cholest-8-en-3b-ol + NADPdetails