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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-08-13 13:32:23 UTC
Update Date2020-02-26 21:26:49 UTC
HMDB IDHMDB0006847
Secondary Accession Numbers
  • HMDB06847
Metabolite Identification
Common NameEpisterol
DescriptionEpisterol is involved in the biosynthesis of steroids. Episterol is converted from 24-Methylenelophenol. Episterol is converted to 5-Dehydroepisterol by lathosterol oxidase [EC:1.14.21.6].
Structure
Data?1582752409
Synonyms
ValueSource
Episterol, (3beta)-isomerHMDB
Ergosta-7,24(28)-dien-3-olHMDB
Chemical FormulaC28H46O
Average Molecular Weight398.6642
Monoisotopic Molecular Weight398.354866094
IUPAC Name(2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-9-en-5-ol
Traditional Nameepisterol
CAS Registry Number474-68-0
SMILES
[H][C@@](C)(CCC(=C)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/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/h10,18,20-22,24-26,29H,3,7-9,11-17H2,1-2,4-6H3/t20-,21+,22+,24-,25+,26?,27+,28-/m1/s1
InChI KeyBTCAEOLDEYPGGE-LPWCLQGBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassErgostane steroids
Direct ParentErgosterols and derivatives
Alternative Parents
Substituents
  • Ergosterol-skeleton
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-7-steroid
  • Delta-7-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility0.00022 g/LALOGPS
logP7.16ALOGPS
logP7.05ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)18.36ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity124.94 m³·mol⁻¹ChemAxon
Polarizability51.4 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00si-1019000000-76f7fd5bec0007e262e5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4l-2004900000-65eeb2fa83daf62b0930Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0019000000-7ed3ee4bd58f9635cc5dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-5049000000-f2b54c130bc812b8787fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9087000000-3b6058a7b1c3f51be75bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-d4f039e0d311a5938fb9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-e3689294a0c5eb4abe9cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1019000000-54aa103cc2187580f2c2Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024116
KNApSAcK IDC00007272
Chemspider ID21865764
KEGG Compound IDC15777
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEpisterol
METLIN IDNot Available
PubChem Compound23724571
PDB IDNot Available
ChEBI ID50586
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in iron ion binding
Specific function:
Catalyzes a dehydrogenation to introduce C5-6 double bond into lathosterol.
Gene Name:
SC5DL
Uniprot ID:
O75845
Molecular weight:
35300.55
Reactions
Episterol → 5-Dehydroepisteroldetails
Episterol + NADP → 5,7,24(28)-Ergostatrienol + NADPH + Hydrogen Iondetails