Record Information
Version1.0
Creation date2010-04-08 22:04:30 UTC
Update date2019-11-26 02:54:37 UTC
Primary IDFDB000284
Secondary Accession Numbers
  • FDB017966
  • FDB018350
Chemical Information
FooDB NameAvenanthramide 2c
DescriptionAvenanthramide c 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 c is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Avenanthramide c can be found in cereals and cereal products, which makes avenanthramide c a potential biomarker for the consumption of this food product.
CAS Number7664-41-7
Structure
Thumb
Synonyms
SynonymSource
N-(3,4-Dihydroxycinnamoyl)-5-hydroxyanthranilic acidHMDB
AvenanthramideHMDB
Avenanthramide 2CHMDB
Avenanthramide-cHMDB
N-(3',4'-Dihydroxycinnamoyl)-5-hydroxyanthranilic acidHMDB
Avenanthramide-2CHMDB
2-{[(2E)-3-(3,4-dihydroxyphenyl)-1-hydroxyprop-2-en-1-ylidene]amino}-5-hydroxybenzoateGenerator
Avenanthramide C (Collins)db_source
N-[3',4'-Dihydroxy-(E)-cinnamoyl]-5-hydroxyanthranilic aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility0.086 g/LALOGPS
logP2.55ALOGPS
logP2.97ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.31ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.09 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity84.54 m³·mol⁻¹ChemAxon
Polarizability30.96 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H13NO6
IUPAC name2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]-5-hydroxybenzoic acid
InChI IdentifierInChI=1S/C16H13NO6/c18-10-3-4-12(11(8-10)16(22)23)17-15(21)6-2-9-1-5-13(19)14(20)7-9/h1-8,18-20H,(H,17,21)(H,22,23)/b6-2+
InChI KeyIDUUXROOZBOOPH-QHHAFSJGSA-N
Isomeric SMILESOC(=O)C1=CC(O)=CC=C1NC(=O)\C=C\C1=CC(O)=C(O)C=C1
Average Molecular Weight315.2775
Monoisotopic Molecular Weight315.074287153
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
  • Anilide
  • Benzoic acid or derivatives
  • Benzoic acid
  • Styrene
  • N-arylamide
  • Catechol
  • Benzoyl
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous amide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen 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 - Experimental
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 2c, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00kk-0961000000-44dbc62c555f06b47f7fSpectrum
Predicted GC-MSAvenanthramide 2c, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-1001090000-53a821e1e639ff675118Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0944000000-5e5598cbbeecb8348ac7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0920000000-1b9e5ede80b19281ed06Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-3900000000-46e41c6f4643f73a7a96Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03k9-0296000000-14b2323a1e6e5ff7cbadSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0h90-0691000000-8b8e4683c02f3c041f74Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1900000000-314538513f94732d5b12Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID533
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.