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delta7-Avenasterol (FDB012733)

Record Information
Version1.0
Creation date2010-04-08 22:10:20 UTC
Update date2019-11-26 03:07:29 UTC
Primary IDFDB012733
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namedelta7-Avenasterol
DescriptionConstituent of oats and pumpkin seeds delta7-Avenasterol is an intermediate in the biosynthesis of steroids (KEGG ID C15782). It is the 4th to last step in the synthesis of Stigmasterol and is converted from 24-Ethylidenelophenol. It is then converted to 5-dehydroavenasterol via the enzyme lathosterol oxidase [EC:1.14.21.6]. delta7-Avenasterol is found in many foods, some of which are robusta coffee, sunflower, oat, and common walnut.
CAS Number23290-26-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility9.2e-05 g/LALOGPS
logP7.62ALOGPS
logP7.44ChemAxon
logS-6.6ALOGPS
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
Refractivity130.62 m³·mol⁻¹ChemAxon
Polarizability52.62 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC29H48O
IUPAC name(2S,5S,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-9-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/h7,11,19-20,22-23,25-27,30H,8-10,12-18H2,1-6H3/b21-7-/t20-,22?,23+,25?,26?,27?,28+,29-/m1/s1
InChI KeyMCWVPSBQQXUCTB-RFOHPFAESA-N
Isomeric SMILESC\C=C(/C(C)C)CC[C@@H](C)C1CCC2C3=CCC4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C
Average Molecular Weight412.6908
Monoisotopic Molecular Weight412.370516158
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
  • Triterpenoid
  • Stigmastane-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
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 84.40%; H 11.72%; O 3.88%DFC
Melting PointMp 148-151°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]22D +12.7 (c, 1.28 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-1029500000-45ff0eb2df08c7df752e2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-5259100000-c06db0458e7d10b538642016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-8193000000-c336481807521e5eb61c2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0002900000-deb0e640600cab8805772016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0005900000-81cff700d3ed911177bd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-2009000000-6ab638e744dcb194bcf22016-08-03View Spectrum
NMRNot Available
ChemSpider ID24850097
ChEMBL IDNot Available
KEGG Compound IDC15782
Pubchem Compound ID12795736
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06851
CRC / DFC (Dictionary of Food Compounds) IDHGC33-I:HKG89-Z
EAFUS IDNot Available
Dr. Duke IDDELTA-7-AVENASTEROL
BIGG IDNot Available
KNApSAcK IDC00007322
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 / Bioactivities
DescriptorIDDefinitionReference
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.