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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:53:57 UTC
Update Date2019-07-23 06:27:01 UTC
HMDB IDHMDB0038575
Secondary Accession Numbers
  • HMDB38575
Metabolite Identification
Common Name(Z)-N-Feruloyl-5-hydroxyanthranilic acid
Description(Z)-N-Feruloyl-5-hydroxyanthranilic acid is found in cereals and cereal products. (Z)-N-Feruloyl-5-hydroxyanthranilic acid is isolated from oats (Avena sativa).
Structure
Data?1563863221
Synonyms
ValueSource
Avenanthramide 1HMDB
Avenanthramide bHMDB
N-Feruloyl-5-hydroxyanthranilic acidHMDB
Chemical FormulaC17H15NO6
Average Molecular Weight329.3041
Monoisotopic Molecular Weight329.089937217
IUPAC Name5-hydroxy-2-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]benzoic acid
Traditional Name5-hydroxy-2-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]benzoic acid
CAS Registry Number108605-69-2
SMILES
COC1=C(O)C=CC(\C=C\C(=O)NC2=CC=C(O)C=C2C(O)=O)=C1
InChI Identifier
InChI=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
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
  • 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point246 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot 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
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, Positivesplash10-0imi-0924000000-c3f6c91375c93d0a5c9cJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-001i-1080590000-6045db6c80549a228c2dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0900000000-7cbaf29a9a688b59419bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0901000000-0163c92dd87682f74e49JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0927000000-26acbd87ed1c4c7e9ca9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0911000000-78ce1bd1e9a10fec28aaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zgi-2900000000-0c8824e0e7d9498b9b47JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0298000000-02ccc213e8295d0379f2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00o0-0592000000-35fd0a16d32cdcf0bf2fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-0910000000-fb965f111b5f23f3029fJSpectraViewer | 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 ID534
FoodDB IDFDB017965
KNApSAcK IDNot Available
Chemspider ID8263492
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10087955
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .