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Record Information
Version3.6
Creation Date2008-08-13 13:49:58 UTC
Update Date2013-02-09 00:15:26 UTC
HMDB IDHMDB06852
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Dehydroavenasterol
Description5-Dehydroavenasterol is an intermediate in the biosynthesis of steroids (KEGG ID C15783). It is the third to last step in the synthesis of Stigmasterol and is converted from delta 7-Avenasterol via the enzyme lathosterol oxidase [EC:1.14.21.6]. It is then converted to Isofucosterol via the enzyme 7-dehydrocholesterol reductase [EC:1.3.1.21].
Structure
Thumb
SynonymsNot Available
Chemical FormulaC29H46O
Average Molecular Weight410.6749
Monoisotopic Molecular Weight410.354866094
IUPAC Name(2R,5S,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}]heptadeca-7,9-dien-5-ol
Traditional IUPAC Name(2R,5S,15R)-14-[(2R,5Z)-5-isopropylhept-5-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol
CAS Registry NumberNot Available
SMILES
C\C=C(/C(C)C)CC[C@@H](C)C1CCC2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C
InChI Identifier
InChI=1S/C29H46O/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/h7,10-11,19-20,23,25-27,30H,8-9,12-18H2,1-6H3/b21-7-/t20-,23+,25?,26?,27?,28+,29-/m1/s1
InChI KeyXPRWWANUPMYKMF-UUHDPGOWSA-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
  • Isoprene
  • Secondary Alcohol
Direct ParentStigmastanes and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • 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 solubility2.620E-04 g/LALOGPS
logP8.24ALOGPS
logP7.03ChemAxon
logS-6.2ALOGPS
pKa (strongest acidic)18.27ChemAxon
pKa (strongest basic)-1.4ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count1ChemAxon
polar surface area20.23ChemAxon
rotatable bond count5ChemAxon
refractivity131.47ChemAxon
polarizability51.98ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
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 IDFDB024118
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC15783
BioCyc IDCPD-4126
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06852
Metagene LinkHMDB06852
METLIN IDNot Available
PubChem Compound23724575
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in iron ion binding
Specific function:
Catalyzes a dehydrogenation to introduce C5-6 double bond into lathosterol.
Gene Name:
SC5DL
Uniprot ID:
O75845
Molecular weight:
35300.55
Reactions
Delta7-Avenasterol → 5-Dehydroavenasteroldetails
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