You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2008-08-13 13:30:12 UTC
Update Date2013-02-09 00:15:25 UTC
HMDB IDHMDB06846
Secondary Accession NumbersNone
Metabolite Identification
Common Name24-Methylenelophenol
Description24-Methylenelophenol is involved in the biosynthesis of steroids. 24-Methylenelophenol is converted from 4alpha-Methylfecosterol by cholestenol delta-isomerase [EC:5.3.3.5]. 24-Methylenelophenol is converted to 24-Ethylidene lophenol by 24-methylenesterol C-methyltransferase [EC:2.1.1.143]. 24-Methylenelophenol can also be converted to episterol.
Structure
Thumb
Synonyms
  1. (3beta,4alpha,5alpha)- 4-methyl-Ergosta-7,24(28)-dien-3-ol
  2. 24-Methylene lophenol
  3. 24-Methylene-Lophenol
  4. 24-Methylenelophenol
  5. 4-alpha-Methyl-5-alpha-ergosta-7,24-dien-3-beta-ol
  6. 4.alpha-Methylepisterol
  7. 4alpha.-Methyl-24-methylene-5alpha-cholest-7-en-3beta-ol
  8. 4alpha.-methyl-5alpha-Ergosta-7,24(28)-dien-3beta.-ol
  9. Gramisterin
  10. Gramisterol
Chemical FormulaC29H48O
Average Molecular Weight412.6908
Monoisotopic Molecular Weight412.370516158
IUPAC Name(1R,2S,5S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
Traditional IUPAC Name24-methylidenelophenol
CAS Registry Number1176-52-9
SMILES
[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])[C@H](C)[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/C29H48O/c1-18(2)19(3)8-9-20(4)23-12-13-25-22-10-11-24-21(5)27(30)15-17-29(24,7)26(22)14-16-28(23,25)6/h10,18,20-21,23-27,30H,3,8-9,11-17H2,1-2,4-7H3/t20-,21+,23-,24+,25+,26+,27+,28-,29+/m1/s1
InChI KeyRSMKYRDCCSNYFM-AAGDOFLISA-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 solubility1.920E-04 g/LALOGPS
logP6.99ALOGPS
logP7.42ChemAxon
logS-6.3ALOGPS
pKa (strongest acidic)18.96ChemAxon
pKa (strongest basic)-1.1ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count1ChemAxon
polar surface area20.23ChemAxon
rotatable bond count5ChemAxon
refractivity129.41ChemAxon
polarizability53.51ChemAxon
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 IDFDB011546
KNApSAcK IDC00007320
Chemspider ID4446733
KEGG Compound IDC11522
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06846
Metagene LinkHMDB06846
METLIN IDNot Available
PubChem Compound5283640
PDB IDNot Available
ChEBI ID29107
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in cholestenol delta-isomerase activity
Specific function:
Catalyzes the conversion of Delta(8)-sterols to their corresponding Delta(7)-isomers.
Gene Name:
EBP
Uniprot ID:
Q15125
Molecular weight:
26352.615
Reactions
4a-Methylfecosterol → 24-Methylenelophenoldetails