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Record Information
Version3.6
Creation Date2006-05-22 14:17:50 UTC
Update Date2013-05-29 19:35:58 UTC
HMDB IDHMDB02374
Secondary Accession NumbersNone
Metabolite Identification
Common NameAvenasterol
DescriptionAvenasterol is a phytosterol. Phytosterols, or plant sterols, are compounds that occur naturally and bear close structural resemblance to cholesterol, but have different side-chain configurations. Phytosterols are relevant in pharmaceuticals (production of therapeutic steroids), nutrition (anti-cholesterol additives in functional foods, anti-cancer properties), and cosmetics (creams, lipstick). Phytosterols can be obtained from vegetable oils or from industrial wastes, which gives an added value to the latter. Considerable efforts have been recently dedicated to the development of efficient processes for phytosterol isolation from natural sources. The present work aims to summarize information on the applications of phytosterols and to review recent approaches, mainly from the industry, for the large-scale recovery of phytosterols. (PMID: 17123816 , 16481154 ).
Structure
Thumb
Synonyms
  1. (24Z)-Ethylidenecholesterol
  2. (24Z)-Stigmasta-5,24(28)-dien-3-ol
  3. (3.beta.,24Z)-Stigmasta-5,24(28)-dien-3-ol
  4. (3b,24Z)-Stigmasta-5,24(28)-dien-3-ol
  5. (Z)-24-Ethylidenecholesterol
  6. (Z)-Stigmasta-5,24(28)-dien-3b-ol
  7. 29-Isofucosterol
  8. Delta5-Avenasterol
  9. Fucosterol
  10. Isofucosterol
Chemical FormulaC29H48O
Average Molecular Weight412.6908
Monoisotopic Molecular Weight412.370516158
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R,5Z)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
Traditional Nameisofucosterol
CAS Registry Number481-14-1
SMILES
C\C=C(\CC[C@@H](C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)C
InChI Identifier
InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h7,10,19-20,23-27,30H,8-9,11-18H2,1-6H3/b21-7-/t20-,23+,24+,25-,26+,27+,28+,29-/m1/s1
InChI KeyOSELKOCHBMDKEJ-WGMIZEQOSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassStigmastanes and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Triterpenes
Substituents
  • 3 Hydroxy Steroid
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Isoprene
  • Secondary Alcohol
Direct ParentStigmastanes and Derivatives
Ontology
StatusDetected and 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
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 Solubility7.480E-05 g/LALOGPS
logP7.6ALOGPS
logP7.44ChemAxon
logS-6.7ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity130.62ChemAxon
Polarizability53.63ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.45 +/- 0.48 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified106.4 +/- 1.94 uMAdult (>18 years old)BothPhytosterolemia details
Associated Disorders and Diseases
Disease References
Sitosterolemia
  1. Lutjohann D, Bjorkhem I, Beil UF, von Bergmann K: Sterol absorption and sterol balance in phytosterolemia evaluated by deuterium-labeled sterols: effect of sitostanol treatment. J Lipid Res. 1995 Aug;36(8):1763-73. Pubmed: 7595097
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001315
KNApSAcK IDC00003656
Chemspider ID4444703
KEGG Compound IDC08821
BioCyc IDCPD-4126
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02374
Metagene LinkHMDB02374
METLIN IDNot Available
PubChem Compound5281326
PDB IDNot Available
ChEBI ID1280721
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Fernandes P, Cabral JM: Phytosterols: applications and recovery methods. Bioresour Technol. 2007 Sep;98(12):2335-50. Epub 2006 Nov 22. Pubmed: 17123816
  2. Perona JS, Cabello-Moruno R, Ruiz-Gutierrez V: The role of virgin olive oil components in the modulation of endothelial function. J Nutr Biochem. 2006 Jul;17(7):429-45. Epub 2005 Dec 12. Pubmed: 16481154

Enzymes

General function:
Involved in 7-dehydrocholesterol reductase activity
Specific function:
Production of cholesterol by reduction of C7-C8 double bond of 7-dehydrocholesterol (7-DHC).
Gene Name:
DHCR7
Uniprot ID:
Q9UBM7
Molecular weight:
54488.98
Reactions
5-Dehydroavenasterol → Avenasteroldetails
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
Avenasterol + NADPH + Hydrogen Ion → Beta-Sitosterol + NADPdetails