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Human Metabolome Database Version 3.5

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Showing metabocard for Avenasterol (HMDB02374)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:50 -0600
Update Date 2013-05-29 13:35:58 -0600
HMDB ID HMDB02374
Secondary Accession Numbers None
Metabolite Identification
Common Name Avenasterol
Description Avenasterol 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 Link_out, 16481154 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C29H48O
Average Molecular Weight 412.6908
Monoisotopic Molecular Weight 412.370516158
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 IUPAC Name isofucosterol
CAS Registry Number 481-14-1
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 Key OSELKOCHBMDKEJ-WGMIZEQOSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Stigmastanes and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Triterpenes
Substituents
  • 3 Hydroxy Steroid
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Isoprene
  • Secondary Alcohol
Direct Parent Stigmastanes and Derivatives
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 7.480E-05 g/L ALOGPS
LogP 7.60 ALOGPS
LogP 7.44 ChemAxon
LogS -6.74 ALOGPS
pKa (strongest acidic) 18.2 ChemAxon
pKa (strongest basic) -1.4 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 20.23 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 130.62 ChemAxon
Polarizability 53.63 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
1.45 +/- 0.48 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 106.4 +/- 1.94 uM Adult (>18 years old) Both Phytosterolemia
Associated Disorders and Diseases
Disease References
Sitosterolemia
  • 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 Link_out
    Associated OMIM IDs
    DrugBank ID Not Available
    DrugBank Metabolite ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB001315
    KNApSAcK ID C00003656 Link_out
    Chemspider ID 4444703 Link_out
    KEGG Compound ID C08821 Link_out
    BioCyc ID CPD-4126 Link_out
    BiGG ID Not Available
    Wikipedia Link Not Available
    NuGOwiki Link HMDB02374 Link_out
    Metagene Link HMDB02374 Link_out
    METLIN ID Not Available
    PubChem Compound 5281326 Link_out
    PDB ID Not Available
    ChEBI ID 1280721 Link_out
    References
    Synthesis Reference Not 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 Link_out
    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 Link_out
    Enzymes
    Name: 7-dehydrocholesterol reductase
    Reactions:
    5-Dehydroavenasterol unknown Avenasterol details
    Gene Name: DHCR7
    Uniprot ID: Q9UBM7 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Delta(24)-sterol reductase
    Reactions:
    Avenasterol + NADPH + Hydrogen Ion unknown Beta-Sitosterol + NADP details
    Gene Name: DHCR24
    Uniprot ID: Q15392 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA