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Record Information
Version3.6
Creation Date2008-08-13 13:36:27 UTC
Update Date2013-02-09 00:15:26 UTC
HMDB IDHMDB06848
Secondary Accession NumbersNone
Metabolite Identification
Common Name5-Dehydroepisterol
Description5-Dehydroepisterol is an intermediate in the biosynthesis of steroids (KEGG ID C15780), and is converted from Episterol via the enzyme lathosterol oxidase [EC:1.14.21.6]. It is then converted to 24-Methylenecholesterol via the enzyme 7-dehydrocholesterol reductase [EC:1.3.1.21].
Structure
Thumb
Synonyms
  1. Campesta-7,24(28)-dien-3beta-ol
  2. Ergosta-5,7,24(28)-trien-3beta-ol
Chemical FormulaC28H44O
Average Molecular Weight396.6484
Monoisotopic Molecular Weight396.33921603
IUPAC Name(1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol
Traditional IUPAC Name5-dehydroepisterol
CAS Registry Number23582-83-4
SMILES
[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=C)C(C)C
InChI Identifier
InChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9-10,18,20,22,24-26,29H,3,7-8,11-17H2,1-2,4-6H3/t20-,22+,24-,25+,26+,27+,28-/m1/s1
InChI KeyZEPNVCGPJXYABB-LOIOQLKMSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassErgosterols and Derivatives
Other Descriptors
  • 3beta-sterol(ChEBI)
  • Aliphatic Homopolycyclic Compounds
  • Ergosterols and C24-methyl derivatives(KEGG)
  • Ergosterols and C24-methyl derivatives(Lipidmaps)
  • Triterpenes
Substituents
  • 3 Hydroxy Steroid
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Isoprene
  • Secondary Alcohol
Direct ParentErgosterols 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 Solubility6.030E-04 g/LALOGPS
logP7.64ALOGPS
logP6.65ChemAxon
logS-5.8ALOGPS
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
Refractivity125.79ChemAxon
Polarizability50.73ChemAxon
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 IDFDB024117
KNApSAcK IDNot Available
Chemspider ID9069833
KEGG Compound IDC15780
BioCyc IDCPD-700
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06848
Metagene LinkHMDB06848
METLIN IDNot Available
PubChem Compound10894570
PDB IDNot Available
ChEBI ID52972
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
Episterol → 5-Dehydroepisteroldetails
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-Dehydroepisterol → 24-Methylenecholesteroldetails