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Record Information
Version3.6
Creation Date2008-09-05 15:29:19 UTC
Update Date2013-05-13 21:57:57 UTC
HMDB IDHMDB06928
Secondary Accession Numbers
  • HMDB06844
  • HMDB11607
Metabolite Identification
Common NameDelta 8,14 -Sterol
DescriptionDelta 8,14 -Sterol is an intermediate in the biosynthesis of steroids (KEGG ID C11508), and is converted from O butusifoliol via the enzyme cytochrome P450, family 51, subfamily A (sterol 14-demethylase) [EC:1.14.13.70]. It is then converted to 4-alpha-methylfecosterol via the enzyme delta14-sterol reductase [EC:1.3.1.70].
Structure
Thumb
Synonyms
  1. 4-alpha-Methyl-5-alpha-ergosta-8,14,24(28)-trien-3-beta-ol
  2. 4a-Methyl-5a-ergosta-8,14,24(28)-trien-3b-ol
  3. 4a-Methylergosta-8,14,24(241)-trien-3b-ol
  4. 4alpha-Methyl-5alpha-ergosta-8,14,24(28)-trien-3beta-ol
  5. delta 8,14 -Sterol
Chemical FormulaC29H46O
Average Molecular Weight410.6749
Monoisotopic Molecular Weight410.354866094
IUPAC Name(2S,5S,6S,7S,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-5-ol
Traditional IUPAC Namedelta 8,14 -sterol
CAS Registry Number74635-33-9
SMILES
[H][C@@]1(CC=C2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC(=C)C(C)C
InChI Identifier
InChI=1S/C29H46O/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/h13,18,20-21,23-24,27,30H,3,8-12,14-17H2,1-2,4-7H3/t20-,21+,23-,24+,27+,28-,29+/m1/s1
InChI KeyHLAWVOWADPNAGN-BAHZUFOISA-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 solubility0.0016 g/LALOGPS
logP7ALOGPS
logP6.97ChemAxon
logS-5.4ALOGPS
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
refractivity130ChemAxon
polarizability53.07ChemAxon
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 IDFDB011216
KNApSAcK IDC00007523
Chemspider ID391501
KEGG Compound IDC11508
BioCyc IDCPD-9523
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06928
Metagene LinkHMDB06928
METLIN IDNot Available
PubChem Compound443237
PDB IDNot Available
ChEBI ID30109
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 monooxygenase activity
Specific function:
Catalyzes C14-demethylation of lanosterol; it transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
Gene Name:
CYP51A1
Uniprot ID:
Q16850
Molecular weight:
57277.81
Reactions
Obtusifoliol + Oxygen + NADPH → Delta 8,14 -Sterol + Formic acid + NADP + Waterdetails
Obtusifoliol + Oxygen + NADPH + Hydrogen Ion → Delta 8,14 -Sterol + Formic acid + NADP + Waterdetails