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Record Information
Version3.6
Creation Date2008-08-13 13:21:54 UTC
Update Date2013-02-09 00:15:25 UTC
HMDB IDHMDB06845
Secondary Accession Numbers
  • HMDB06925
Metabolite Identification
Common Name4a-Methylfecosterol
Description4alpha-Methylfecosterol is involved in the biosynthesis of steroids. 4alpha-Methylfecosterol is converted from delta8,14 -Sterol by delta14-sterol reductase [EC:1.3.1.70]. 4alpha-Methylfecosterol is converted to 24-Methylene lophenol by cholestenol delta-isomerase [EC:5.3.3.5].
Structure
Thumb
Synonyms
  1. 4alpha-Methylfecosterol
Chemical FormulaC29H48O
Average Molecular Weight412.6908
Monoisotopic Molecular Weight412.370516158
IUPAC Name(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-1(10)-en-5-ol
Traditional IUPAC Name4a-methylfecosterol
CAS Registry NumberNot Available
SMILES
[H][C@@](C)(CCC(=C)C(C)C)[C@@]1([H])CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3
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/h18,20-21,23-25,27,30H,3,8-17H2,1-2,4-7H3/t20-,21+,23-,24+,25+,27+,28-,29+/m1/s1
InChI KeyQLDNWJOJCDIMKK-XLFBYWHPSA-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
  • 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 solubility6.900E-04 g/LALOGPS
logP6.64ALOGPS
logP7.37ChemAxon
logS-5.8ALOGPS
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
refractivity129.15ChemAxon
polarizability53.59ChemAxon
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 IDFDB012688
KNApSAcK IDC00007524
Chemspider ID167937
KEGG Compound IDC15776
BioCyc IDCPD-4081
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06845
Metagene LinkHMDB06845
METLIN IDNot Available
PubChem Compound193524
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 delta14-sterol reductase activity
Specific function:
Involved in the conversion of lanosterol to cholesterol.
Gene Name:
TM7SF2
Uniprot ID:
O76062
Molecular weight:
46405.345
Reactions
Delta 8,14 -Sterol + NADPH + Hydrogen Ion → 4a-Methylfecosterol + NADPdetails
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