Showing Compound Card for Avenasterol (CDB005338)

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Record Information
Version1.0
Created at2020-04-17 19:33:11 UTC
Updated at2020-12-07 19:11:58 UTC
CannabisDB IDCDB005338
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameAvenasterol
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. Avenasterol is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight412.7
Monoisotopic Molecular Weight412.3705
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point118–120 °CWikipedia
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-090r-6973000000-3f7408d99c0efb91ca342015-03-01View Spectrum
Predicted GC-MSAvenasterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000t-1109000000-109d24725226b225bf0bSpectrum
Predicted GC-MSAvenasterol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06di-2104900000-fd4678ce9164cc207101Spectrum
Predicted GC-MSAvenasterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-1019500000-bcaac8318b52fbef27252016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-6259100000-c5a8fd880d63c55bcacf2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-7094000000-d9a6cedb0a89fad970572016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-82a40a2a370fc124e6ef2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0005900000-96d823e5c0a704f96e3d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-2009000000-6ab638e744dcb194bcf22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-363450e12a0ea926276e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000900000-7b289abe7c3abd46f6502021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1002900000-e69a5278bd381695c11f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-9e612794ea2c28ad6a2c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i0c-5169000000-9c2cec3fb85ecb36abaf2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5d-9320000000-9cc3e8c4c8ef033f50cb2021-09-24View Spectrum
NMR
TypeDescriptionView
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
7-dehydrocholesterol reductaseDHCR711q13.4Q9UBM7 details
Delta(24)-sterol reductaseDHCR241p32.3Q15392 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0002374
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
General ReferencesNot Available

Enzymes

Enzyme Details
1. 7-dehydrocholesterol reductase
General function:
Involved in 7-dehydrocholesterol reductase activity
Specific function:
Production of cholesterol by reduction of C7-C8 double bond of 7-dehydrocholesterol (7-DHC).
Gene Name:
DHCR7
Uniprot ID:
Q9UBM7
Molecular weight:
54488.98
Enzyme Details
2. Delta(24)-sterol reductase
General function:
Energy production and conversion
Specific function:
Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
Gene Name:
DHCR24
Uniprot ID:
Q15392
Molecular weight:
60100.805