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Showing Compound D5-Avenasterol (FDB012493)

Record Information
Version1.0
Creation date2010-04-08 22:10:12 UTC
Update date2020-09-17 15:42:00 UTC
Primary IDFDB012493
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameD5-Avenasterol
DescriptionAvenasterol, also known as 29-isofucosterol, 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, avenasterol is considered to be a sterol lipid molecule. Avenasterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
CAS Number18472-36-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(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
24-Ethylidenecholesterolmanual
D5-Avenasterinmanual
D5-Avenasteroldb_source
D5-Avenosterolmanual
Stigmasta-5,24(28)-dien-3b-olmanual
Predicted Properties
PropertyValueSource
Water Solubility7.5e-05 g/LALOGPS
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC29H48O
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
InChI IdentifierInChI=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
Isomeric SMILESC\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
Average Molecular Weight412.702
Monoisotopic Molecular Weight412.370516166
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 84.40%; H 11.72%; O 3.88%DFC
Melting PointMp 137°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]26D -37.6 (CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-090r-6973000000-3f7408d99c0efb91ca34Spectrum
Predicted GC-MSD5-Avenasterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000t-1109000000-109d24725226b225bf0bSpectrum
Predicted GC-MSD5-Avenasterol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06di-2104900000-fd4678ce9164cc207101Spectrum
Predicted GC-MSD5-Avenasterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-1019500000-bcaac8318b52fbef2725Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-6259100000-c5a8fd880d63c55bcacfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-7094000000-d9a6cedb0a89fad97057Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-82a40a2a370fc124e6efSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0005900000-96d823e5c0a704f96e3dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-2009000000-6ab638e744dcb194bcf2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-363450e12a0ea926276eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000900000-7b289abe7c3abd46f650Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1002900000-e69a5278bd381695c11fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-9e612794ea2c28ad6a2cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i0c-5169000000-9c2cec3fb85ecb36abafSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5d-9320000000-9cc3e8c4c8ef033f50cbSpectrum
NMR
TypeDescriptionView
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHHL06-C:HHL07-D
EAFUS IDNot Available
Dr. Duke ID5-AVENASTEROL|DELTA-5-STIGMASTEROL
BIGG IDNot Available
KNApSAcK IDC00003645
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).