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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:29:25 UTC
Update Date2019-07-23 06:03:43 UTC
HMDB IDHMDB0029284
Secondary Accession Numbers
  • HMDB29284
Metabolite Identification
Common NameAvenanthramide 1c
DescriptionAvenanthramide 1c is a polyphenol compound found in foods of plant origin (PMID: 20428313 )
Structure
Data?1563861823
Synonyms
ValueSource
N-[3,4-Dihydroxy-(e)-cinnamoyl]-anthranilic acidHMDB
Chemical FormulaC16H13NO5
Average Molecular Weight299.2781
Monoisotopic Molecular Weight299.079372531
IUPAC Name2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]benzoic acid
Traditional Name2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]benzoic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1=CC=CC=C1NC(=O)\C=C\C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C16H13NO5/c18-13-7-5-10(9-14(13)19)6-8-15(20)17-12-4-2-1-3-11(12)16(21)22/h1-9,18-19H,(H,17,20)(H,21,22)/b8-6+
InChI KeyLLPIRWBXMYKFQM-SOFGYWHQSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Anilide
  • Benzoic acid or derivatives
  • Benzoic acid
  • Catechol
  • Styrene
  • N-arylamide
  • Benzoyl
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous amide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • 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 DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.044 g/LALOGPS
logP3.01ALOGPS
logP3.27ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.55ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area106.86 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity82.56 m³·mol⁻¹ChemAxon
Polarizability30.05 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ei-0970000000-0f85089d01f3c6f013baJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0pi3-3011930000-9f3c51403a36032bb96cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0944000000-572f97b2d1cb962f6090JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1910000000-99d60d003d66b05a9174JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-8900000000-9a6c0c6b575ceac4051eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0190000000-85572801e7260d0ffc48JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-1490000000-186ab994a2d992f6eec2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-8900000000-a4a60e0c0ca8e12f7d50JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID535
FoodDB IDFDB000286
KNApSAcK IDNot Available
Chemspider ID8036787
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9861088
PDB IDNot Available
ChEBI ID710546
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  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:12537428 ]
  2. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]