Record Information
Version3.6
Creation Date2008-08-13 11:32:19 UTC
Update Date2013-02-09 00:15:25 UTC
HMDB IDHMDB06842
Secondary Accession Numbers
  • HMDB00997
Metabolite Identification
Common Name5a-Cholesta-7,24-dien-3b-ol
Description5alpha-Cholesta-7,24-dien-3beta-ol is involved in the biosynthesis of steroids. 5alpha-Cholesta-7,24-dien-3beta-ol is reversibly converted to 5alpha-Cholest-7-en-3beta-ol by delta24-sterol reductase [EC:1.3.1.72]. 5alpha-Cholesta-7,24-dien-3beta-ol is also converted to zymosterol by cholestenol delta-isomerase [EC:5.3.3.5]. 5alpha-Cholesta-7,24-dien-3beta-ol is also converted to 7-Dehydrodesmosterol. 5a-Cholesta-7,24-dien-3b-ol is a substrate for 3-beta-hydroxysteroid-delta(8),delta(7)-isomerase.
Structure
Thumb
Synonyms
  1. 5 alpha-Cholesta-7,24-dien-3beta-ol
  2. 5alpha-Cholesta-7,24-dien-3beta-ol
Chemical FormulaC27H44O
Average Molecular Weight384.6377
Monoisotopic Molecular Weight384.33921603
IUPAC Name(2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
Traditional IUPAC Name(2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
CAS Registry Number651-54-7
SMILES
[H][C@@](C)(CCC=C(C)C)[C@@]1([H])CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)C3CC[C@]12C
InChI Identifier
InChI=1S/C27H44O/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/h7,10,19-21,23-25,28H,6,8-9,11-17H2,1-5H3/t19-,20+,21+,23-,24+,25?,26+,27-/m1/s1
InChI KeyPKEPPDGGTSZLBL-FZAJRYLSSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassPrenol Lipids
Sub ClassSesterterpenes
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Cholesterol and derivatives(KEGG)
Substituents
  • 3 Hydroxy Steroid
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Isoprene
  • Secondary Alcohol
  • Steroid
Direct ParentSesterterpenes
Ontology
StatusExpected and Not 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 (predicted from logP)
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point147 - 151 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility1.640E-04 g/LALOGPS
logP7.4ALOGPS
logP6.71ChemAxon
logS-6.4ALOGPS
pKa (strongest acidic)18.36ChemAxon
pKa (strongest basic)-1.3ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count1ChemAxon
polar surface area20.23ChemAxon
rotatable bond count4ChemAxon
refractivity121.47ChemAxon
polarizability49.73ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Steroid BiosynthesisSMP00023map00100
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 IDFDB024115
KNApSAcK IDNot Available
Chemspider ID389550
KEGG Compound IDC05439
BioCyc ID5-ALPHA-CHOLESTA-724-DIEN-3-BETA-OL
BiGG ID45811
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06842
Metagene LinkHMDB06842
METLIN ID5928
PubChem Compound440670
PDB IDNot Available
ChEBI ID16290
References
Synthesis ReferenceMoreau, Jacques P.; Aberhart, Donald J.; Caspi, Eliahu. Synthesis of 5a-cholesta-7,24-dien-3b-ol and cholesta-5,7,24-trien-3b-ol. Journal of Organic Chemistry (1974), 39(14), 2018-23.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
EBP
Uniprot ID:
Q15125
Reactions
Zymosterol intermediate 2 unknown 5a-Cholesta-7,24-dien-3b-oldetails
Gene Name:
DHCR24
Uniprot ID:
Q15392
Reactions
Lathosterol + NADP unknown 5a-Cholesta-7,24-dien-3b-ol + NADPH + Hydrogen Iondetails