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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-13 13:32:23 UTC
Update Date2022-03-07 02:49:33 UTC
HMDB IDHMDB0006847
Secondary Accession Numbers
  • HMDB06847
Metabolite Identification
Common NameEpisterol
DescriptionEpisterol 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. Thus, episterol is considered to be a sterol lipid molecule. Episterol is involved in the biosynthesis of steroids. Episterol is converted from 24-methylenelophenol. Episterol is converted into 5-dehydroepisterol by lathosterol oxidase (EC 1.14.21.6).
Structure
Data?1599761857
Synonyms
ValueSource
(3beta,5alpha)-Ergosta-7,24(28)-dien-3-olChEBI
Ergosta-7,24(28)-dien-3-olChEBI
(3b,5a)-Ergosta-7,24(28)-dien-3-olGenerator
(3Β,5α)-ergosta-7,24(28)-dien-3-olGenerator
Episterol, (3beta)-isomerMeSH
24-Methyl-5alpha-cholesta-7,24(28)-dien-3beta-olHMDB
24-Methyl-5α-cholesta-7,24(28)-dien-3β-olHMDB
24-Methylene-5alpha-cholest-7-en-3beta-olHMDB
24-Methylene-5α-cholest-7-en-3β-olHMDB
24-Methylenecholesta-7,24(28)-dien-3beta-olHMDB
24-Methylenecholesta-7,24(28)-dien-3β-olHMDB
5alpha-Ergosta-7,24(28)-dien-3beta-olHMDB
5α-Ergosta-7,24(28)-dien-3β-olHMDB
EpisterinHMDB
EpisterolHMDB
delta7,24(28)-ErgostadienolHMDB
Δ7,24(28)-ErgostadienolHMDB
Chemical FormulaC28H46O
Average Molecular Weight398.6642
Monoisotopic Molecular Weight398.354866094
IUPAC Name(1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
Traditional Name(1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-ol
CAS Registry Number474-68-0
SMILES
[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([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/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-JVAZTMFWSA-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
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability51.53 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-239.99130932474
DeepCCS[M+Na]+213.95830932474
AllCCS[M+H]+206.332859911
AllCCS[M+H-H2O]+204.232859911
AllCCS[M+NH4]+208.232859911
AllCCS[M+Na]+208.732859911
AllCCS[M-H]-205.332859911
AllCCS[M+Na-2H]-207.132859911
AllCCS[M+HCOO]-209.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Episterol[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=C)C(C)C2773.1Standard polar33892256
Episterol[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=C)C(C)C3242.2Standard non polar33892256
Episterol[H][C@@]1(CC[C@@]2([H])C3=CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=C)C(C)C3269.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Episterol,1TMS,isomer #1C=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C3345.7Semi standard non polar33892256
Episterol,1TBDMS,isomer #1C=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)C(C)C3579.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Episterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Episterol 10V, Positive-QTOFsplash10-001j-0019000000-4a337e3ab572869d59782016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Episterol 20V, Positive-QTOFsplash10-001j-6049000000-bccf170e8638d30f96582016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Episterol 40V, Positive-QTOFsplash10-001i-6194000000-1b24202010ace7360df42016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Episterol 10V, Negative-QTOFsplash10-0002-0009000000-f4a8a4bd75686a2c42642016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Episterol 20V, Negative-QTOFsplash10-0002-0009000000-3bad18e0101e63aec08d2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Episterol 40V, Negative-QTOFsplash10-001i-2019000000-89152080214a606e3f422016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Episterol 10V, Positive-QTOFsplash10-0002-0029000000-4b2163dd09b4a7542a362021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Episterol 20V, Positive-QTOFsplash10-0a59-9156000000-85e4ecbe743df768234d2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Episterol 40V, Positive-QTOFsplash10-0536-9500000000-11d7124be40b6765e3ab2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Episterol 10V, Negative-QTOFsplash10-0002-0009000000-0ca06bc1a59e9690d9392021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Episterol 20V, Negative-QTOFsplash10-0002-0009000000-1e3548d588af0130a1122021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Episterol 40V, Negative-QTOFsplash10-0002-0009000000-61513522be83c13652a02021-09-25Wishart LabView Spectrum
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 ID4446754
KEGG Compound IDC15777
BioCyc IDEPISTEROL
BiGG IDNot Available
Wikipedia LinkEpisterol
METLIN IDNot Available
PubChem Compound5283662
PDB IDNot Available
ChEBI ID23929
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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