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Record Information
Version3.6
Creation Date2008-08-13 13:39:23 UTC
Update Date2013-02-09 00:15:26 UTC
HMDB IDHMDB06849
Secondary Accession NumbersNone
Metabolite Identification
Common Name24-Methylenecholesterol
Description24-Methylenecholesterol is involved in the biosynthesis of steroids. 24-Methylenecholesterol is converted from 5-Dehydroepisterol by 7-dehydrocholesterol reductase [EC:1.3.1.21]. 24-Methylenecholesterol is converted to Campesterol by delta24-sterol reductase [EC:1.3.1.72].
Structure
Thumb
Synonyms
  1. (3b)-Ergosta-5,24(28)-dien-3-ol
  2. 24-Methylencholesterol
  3. 24-Methylene-Cholesterol
  4. Chalinasterol
  5. Ergosta-5, 24(28)-dien-3b-ol
  6. Ergosta-5,24(28)-dien-3-ol
  7. Ergosta-5,24(28)-dien-3b-ol
  8. Ostreasterol
Chemical FormulaC28H46O
Average Molecular Weight398.6642
Monoisotopic Molecular Weight398.354866094
IUPAC Name(1S,2R,5S,11S,14R,15R)-2,15-dimethyl-14-[(2S)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
Traditional IUPAC Name(1S,2R,5S,11S,14R,15R)-2,15-dimethyl-14-[(2S)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
CAS Registry Number474-63-5
SMILES
[H][C@@]1(CC[C@@]2([H])C3CC=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/C28H46O/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/h9,18,20,22-26,29H,3,7-8,10-17H2,1-2,4-6H3/t20-,22-,23?,24+,25-,26-,27-,28+/m0/s1
InChI KeyINDVLXYUCBVVKW-CPEKGPMFSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassErgosterols and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Triterpenes
  • a steroid(Cyc)
Substituents
  • 3 Hydroxy Steroid
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • 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 solubility1.900E-04 g/LALOGPS
logP6.61ALOGPS
logP7.05ChemAxon
logS-6.3ALOGPS
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
refractivity124.94ChemAxon
polarizability51.06ChemAxon
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 IDFDB001361
KNApSAcK IDC00007271
Chemspider IDNot Available
KEGG Compound IDC15781
BioCyc IDCPD-706
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06849
Metagene LinkHMDB06849
METLIN IDNot Available
PubChem Compound53477901
PDB IDNot Available
ChEBI ID19812
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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-Dehydroepisterol → 24-Methylenecholesteroldetails
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
24-Methylenecholesterol + NADPH + Hydrogen Ion → Campesterol + NADPdetails