Record Information
Creation date2010-04-08 22:04:30 UTC
Update date2019-11-26 02:54:37 UTC
Primary IDFDB000283
Secondary Accession Numbers
  • FDB017967
  • FDB018348
Chemical Information
FooDB NameAvenanthramide 2p
Description(z)-n-coumaroyl-5-hydroxyanthranilic acid 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 (z)-n-coumaroyl-5-hydroxyanthranilic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). (z)-n-coumaroyl-5-hydroxyanthranilic acid can be found in cereals and cereal products and oat, which makes (z)-n-coumaroyl-5-hydroxyanthranilic acid a potential biomarker for the consumption of these food products.
CAS Number7664-41-7
5-Hydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]benzoic acidGenerator
5-Hydroxy-N-(4-hydroxycinnamoyl)anthranilic acidHMDB
Avenalumin IHMDB
Avenanthramide aHMDB
Avenanthramide A (Collins)db_source
Avenanthramide A4 (Dimberg)db_source
N-[4'-Hydroxy-(E)cinnamoyl]-5-hydroxyanthranilic aciddb_source
Predicted PropertiesNot Available
Chemical FormulaC16H13NO5
IUPAC name
InChI IdentifierInChI=1S/C16H13NO5/c18-11-4-1-10(2-5-11)3-8-15(20)17-14-7-6-12(19)9-13(14)16(21)22/h1-9,18-19H,(H,17,20)(H,21,22)/b8-3+
Isomeric SMILESOC(=O)C1=CC(O)=CC=C1NC(=O)\C=C\C1=CC=C(O)C=C1
Average Molecular Weight299.2781
Monoisotopic Molecular Weight299.079372531
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
  • Avenanthramide
  • N-cinnamoylanthranilic acid
  • Acylaminobenzoic acid or derivatives
  • Coumaric acid or derivatives
  • Cinnamic acid amide
  • Hydroxybenzoic acid
  • Benzoic acid or derivatives
  • Anilide
  • Benzoic acid
  • N-arylamide
  • Styrene
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous amide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors

Route of exposure:

Biological location:



Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
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
EI-MS/GC-MSNot Available
MS/MSNot Available
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 ID532
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
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
MSDSNot Available
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.