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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-08-13 11:22:33 UTC
Update Date2020-02-26 21:26:49 UTC
HMDB IDHMDB0006841
Secondary Accession Numbers
  • HMDB0006541
  • HMDB0059618
  • HMDB06541
  • HMDB06841
  • HMDB59618
Metabolite Identification
Common Name​5alpha-Cholest-8-en-3beta-ol
Description5alpha-Cholest-8-en-3beta-ol, also known as zymostenol, is a normal human metabolite and an intermediate of cholesterol synthesis. The concentrations of zymostenol are higher, both in the 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 decreased and cholesterol precursor sterols such as zymostenol increased (PMID: 15736111 , 16709621 , 16477216 , 12756385 ).
Structure
Data?1582752409
Synonyms
ValueSource
CholestenolChEBI
ZymostenolChEBI
(3beta,5alpha)CholestenolHMDB
3beta-Hydroxy-8(9)-cholesteneHMDB
3beta-Hydroxycholest-8(9)-eneHMDB
5-alpha-Cholest-8-en-3-beta-olHMDB
5alpha-Cholest-8(9)-en-3beta-olHMDB
5alpha-Cholest-8-en-3beta-olHMDB
Cholest-8(9)-en-3beta-olHMDB
Cholesta-8(9)-en-3beta-olHMDB
delta(8)-CholestenolHMDB
8(9)-CholestenolHMDB
Zymostenol, (3beta)-isomerHMDB
(3beta,5alpha)-Cholest-8-en-3-olHMDB
(3β,5α)-Cholest-8-en-3-olHMDB
3beta-Hydroxy-5alpha-cholest-8(9)-eneHMDB
3β-Hydroxy-5α-cholest-8(9)-eneHMDB
5a-Cholest-8-en-3b-olHMDB
5α-Cholest-8-en-3β-olHMDB
DihydrozymosterolHMDB
delta8-CholestenolHMDB
Δ8-CholestenolHMDB
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 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
CAS Registry Number566-97-2
SMILES
[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C[C@]1([H])CC3)[C@H](C)CCCC(C)C
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
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
  • 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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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 Solubility0.00022 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity120.35 m³·mol⁻¹ChemAxon
Polarizability50.46 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-076r-1019000000-da210f056bd723d532a1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-3105900000-25f7266fb84218fbea74Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0009000000-a776f0a6c0141e92ae73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05p9-3139000000-e84343d3954ffbe258f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-5249000000-5b6b7a2f03b59d093325Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-315c5133aa81b3939474Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-711bf432a79ce66b987fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ldi-1019000000-b4dfc241017aaa46ed22Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.000129 uMNewborn (0-30 days old)Not Specified
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024114
KNApSAcK IDC00033775
Chemspider ID91952
KEGG Compound IDC03845
BioCyc IDCPD-8621
BiGG ID42633
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101770
PDB IDNot Available
ChEBI ID16608
Food Biomarker OntologyNot Available
VMH IDNot Available
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. 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 ]
  2. 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 ]
  3. 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 ]
  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 → ​5alpha-Cholest-8-en-3beta-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 → ​5alpha-Cholest-8-en-3beta-ol + NADPdetails