Showing metabocard for Avenasterol (BMDB0002374)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:54:46 UTC
Update Date2020-04-22 15:10:51 UTC
BMDB IDBMDB0002374
Secondary Accession Numbers
  • BMDB02374
Metabolite Identification
Common NameAvenasterol
DescriptionIsofucosterol, also known as δ(5)-avenasterol, belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Thus, isofucosterol is considered to be a sterol. Based on a literature review a significant number of articles have been published on Isofucosterol.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(24Z)-24-Ethylcholesta-5,24(28)-dien-3beta-olChEBI
(24Z)-EthylidenecholesterolChEBI
(3beta)-Stigmasta-5,24(28)-dien-3-olChEBI
(3beta,24Z)-Stigmasta-5,24(28)-dien-3-olChEBI
(Z)-24-Ethylcholesta-5,24(28)-dien-3beta-olChEBI
(Z)-24-EthylidenecholesterolChEBI
(Z)-Stigmasta-5,24(28)-dien-3beta-olChEBI
24Z-Ethylidene-cholest-5-en-3beta-olChEBI
28-IsofucosterolChEBI
Delta(5)-AvenasterolChEBI
delta5-AvenasterolChEBI
(24Z)-24-Ethylcholesta-5,24(28)-dien-3b-olGenerator
(24Z)-24-Ethylcholesta-5,24(28)-dien-3β-olGenerator
(3b)-Stigmasta-5,24(28)-dien-3-olGenerator
(3Β)-stigmasta-5,24(28)-dien-3-olGenerator
(3b,24Z)-Stigmasta-5,24(28)-dien-3-olGenerator
(3Β,24Z)-stigmasta-5,24(28)-dien-3-olGenerator
(Z)-24-Ethylcholesta-5,24(28)-dien-3b-olGenerator
(Z)-24-Ethylcholesta-5,24(28)-dien-3β-olGenerator
(Z)-Stigmasta-5,24(28)-dien-3b-olGenerator
(Z)-Stigmasta-5,24(28)-dien-3β-olGenerator
24Z-Ethylidene-cholest-5-en-3b-olGenerator
24Z-Ethylidene-cholest-5-en-3β-olGenerator
Δ(5)-avenasterolGenerator
Δ5-avenasterolGenerator
(24Z)-Stigmasta-5,24(28)-dien-3-olHMDB
(3.beta.,24Z)-stigmasta-5,24(28)-dien-3-olHMDB
29-IsofucosterolHMDB
FucosterolHMDB, MeSH
IsofucosterolHMDB
24Z-Ethylidenecholest-5-en-3b-olMeSH, HMDB
Fucosterol, 28-(14)C-labeled CPD, (e)-isomerMeSH, HMDB
Stigmasta-5,24-dien-3 beta-olMeSH, HMDB
24-Isoethylidenecholest-5-en-3 beta-ol,delta(5)-avenasterolMeSH, HMDB
Fucosterol, (3beta)-isomerMeSH, HMDB
(24E)-24-N-PropylidenecholesterolMeSH, HMDB
24(Z)-Ethylidenecholest-5-en-3beta-olHMDB
24(Z)-Ethylidenecholest-5-en-3β-olHMDB
24-Ethylcholesta-5,24(28)Z-dien-3beta-olHMDB
24-Ethylcholesta-5,24(28)Z-dien-3β-olHMDB
Stigmasta-5-cis,24(28)-dien-3beta-olHMDB
Stigmasta-5-cis,24(28)-dien-3β-olHMDB
Chemical FormulaC29H48O
Average Molecular Weight412.702
Monoisotopic Molecular Weight412.370516166
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R,5Z)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
Traditional Name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5Z)-5-isopropylhept-5-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
CAS Registry Number481-14-1
SMILES
C\C=C(\CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C
InChI Identifier
InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h7,10,19-20,23-27,30H,8-9,11-18H2,1-6H3/b21-7-/t20-,23+,24+,25-,26+,27+,28+,29-/m1/s1
InChI KeyOSELKOCHBMDKEJ-WGMIZEQOSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassStigmastanes and derivatives
Direct ParentStigmastanes and derivatives
Alternative Parents
Substituents
  • C24-propyl-sterol-skeleton
  • Stigmastane-skeleton
  • Triterpenoid
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • 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
logP7.6ALOGPS
logP7.44ChemAxon
logS-6.7ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity130.62 m³·mol⁻¹ChemAxon
Polarizability53.63 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-1109000000-109d24725226b225bf0bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-06di-2104900000-fd4678ce9164cc207101View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-1019500000-bcaac8318b52fbef2725View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-6259100000-c5a8fd880d63c55bcacfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-7094000000-d9a6cedb0a89fad97057View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-82a40a2a370fc124e6efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0005900000-96d823e5c0a704f96e3dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-2009000000-6ab638e744dcb194bcf2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-363450e12a0ea926276eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000900000-7b289abe7c3abd46f650View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1002900000-e69a5278bd381695c11fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-9e612794ea2c28ad6a2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i0c-5169000000-9c2cec3fb85ecb36abafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5d-9320000000-9cc3e8c4c8ef033f50cbView in MoNA
MSMass Spectrum (Electron Ionization)splash10-090r-6973000000-3f7408d99c0efb91ca34View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002374
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012493
KNApSAcK IDC00003656
Chemspider ID4444703
KEGG Compound IDC08821
BioCyc IDCPD-4127
BiGG IDNot Available
Wikipedia LinkIsofucosterol
METLIN IDNot Available
PubChem Compound5281326
PDB IDNot Available
ChEBI ID28604
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available