You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:54:04 UTC
Update Date2019-07-23 06:27:01 UTC
HMDB IDHMDB0038577
Secondary Accession Numbers
  • HMDB38577
Metabolite Identification
Common Name(Z)-N-Coumaroyl-5-hydroxyanthranilic acid
Description(Z)-N-Coumaroyl-5-hydroxyanthranilic acid is found in cereals and cereal products. (Z)-N-Coumaroyl-5-hydroxyanthranilic acid is isolated from oats (Avena sativa).
Structure
Data?1563863221
Synonyms
ValueSource
5-Hydroxy-N-(4-hydroxycinnamoyl)anthranilic acidHMDB
Avenalumin IHMDB
Avenanthramide aHMDB
Chemical FormulaC16H13NO5
Average Molecular Weight299.2781
Monoisotopic Molecular Weight299.079372531
IUPAC Name5-hydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]benzoic acid
Traditional Name5-hydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]benzoic acid
CAS Registry Number108605-70-5
SMILES
OC(=O)C1=CC(O)=CC=C1NC(=O)\C=C\C1=CC=C(O)C=C1
InChI Identifier
InChI=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+
InChI KeyQGUMNWHANDITDB-FPYGCLRLSA-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
  • 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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point277 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.045 g/LALOGPS
logP2.96ALOGPS
logP3.27ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.31ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area106.86 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity82.56 m³·mol⁻¹ChemAxon
Polarizability30.33 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, Positivesplash10-0ue9-0980000000-5ff674d142cf4aef9af4JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-4040970000-1cc5a65d02b8330e143cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qToF , Positivesplash10-0002-0900000000-6f538a3ee4a8f4537cc2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0900000000-6f538a3ee4a8f4537cc2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-1900000000-9558a527d5becfe510a0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0944000000-e4bf26fe5a3717ab4f60JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0920000000-4fdb81cd65ed4d4fc5f4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-100r-4900000000-b64973d21c9e8333fdc3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0190000000-5c1d411b255629965b77JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-0690000000-dd4c217c818be429dd84JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1900000000-89daf2d6294feb8ca7e6JSpectraViewer | 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 ID532
FoodDB IDFDB018348
KNApSAcK IDC00001527
Chemspider ID4444597
KEGG Compound IDC08472
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281157
PDB IDNot Available
ChEBI ID2939
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.. .