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Avenanthramide 2f (FDB000285)

Record Information
Version1.0
Creation date2010-04-08 22:04:30 UTC
Update date2019-11-26 02:54:37 UTC
Primary IDFDB000285
Secondary Accession Numbers
  • FDB017965
  • FDB018349
Chemical Information
FooDB NameAvenanthramide 2f
DescriptionAvenanthramide b is a member of the class of compounds known as avenanthramides. Avenanthramides are a group of phenolic alkaloids consisting of conjugate of three phenylpropanoids (ferulic, caffeic, or p-coumaric acid) and anthranilic acid. Avenanthramide b is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Avenanthramide b can be found in cereals and cereal products, which makes avenanthramide b a potential biomarker for the consumption of this food product.
CAS Number7664-41-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.024 g/LALOGPS
logP2.89ALOGPS
logP3.11ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)3.31ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.09 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity89.02 m³·mol⁻¹ChemAxon
Polarizability33.12 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H15NO6
IUPAC name5-hydroxy-2-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]benzoic acid
InChI IdentifierInChI=1S/C17H15NO6/c1-24-15-8-10(2-6-14(15)20)3-7-16(21)18-13-5-4-11(19)9-12(13)17(22)23/h2-9,19-20H,1H3,(H,18,21)(H,22,23)/b7-3+
InChI KeyJXFZHMCSCYADIX-XVNBXDOJSA-N
Isomeric SMILESCOC1=C(O)C=CC(\C=C\C(=O)NC2=CC=C(O)C=C2C(O)=O)=C1
Average Molecular Weight329.3041
Monoisotopic Molecular Weight329.089937217
Classification
Description Belongs to the class of organic compounds known as avenanthramides. These are a group of phenolic alkaloids consisting of conjugate of three phenylpropanoids (ferulic, caffeic, or p-coumaric acid) and anthranilic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentAvenanthramides
Alternative Parents
Substituents
  • Avenanthramide
  • N-cinnamoylanthranilic acid
  • Acylaminobenzoic acid or derivatives
  • Cinnamic acid amide
  • Hydroxybenzoic acid
  • Methoxyphenol
  • Anilide
  • Benzoic acid
  • Benzoic acid or derivatives
  • Phenoxy compound
  • Methoxybenzene
  • N-arylamide
  • Styrene
  • Phenol ether
  • Benzoyl
  • Anisole
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous amide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Ether
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAvenanthramide 2f, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0imi-0924000000-c3f6c91375c93d0a5c9cSpectrum
Predicted GC-MSAvenanthramide 2f, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-1080590000-6045db6c80549a228c2dSpectrum
Predicted GC-MSAvenanthramide 2f, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0900000000-7cbaf29a9a688b59419b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0901000000-0163c92dd87682f74e492017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0927000000-26acbd87ed1c4c7e9ca92016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0911000000-78ce1bd1e9a10fec28aa2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zgi-2900000000-0c8824e0e7d9498b9b472016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0298000000-02ccc213e8295d0379f22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00o0-0592000000-35fd0a16d32cdcf0bf2f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-0910000000-fb965f111b5f23f3029f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0039000000-df10e0e447b7cc8a8f0c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0159-0691000000-7f0a6fbb5ad61a39ab8e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-0893000000-cd7163d8f0ff7a58fde92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01u0-0925000000-ab8d5673204674843b252021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-0961000000-e93728b9e83ed1cfbf372021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0910000000-dbd82e0cb572a5afa4a52021-09-23View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI ID165178
Phenol-Explorer ID534
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
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 Reference
  1. Bratt K, Sunnerheim K, Bryngelsson S, Fagerlund A, Engman L, Andersson RE, Dimberg LH: Avenanthramides in oats (Avena sativa L.) and structure-antioxidant activity relationships. J Agric Food Chem. 2003 Jan 29;51(3):594-600. Pubmed [Structure]
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.