Avenanthramide 2f (CHEM022982)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 20:46:01 UTC
Update Date2016-11-09 01:17:37 UTC
Accession NumberCHEM022982
Identification
Common NameAvenanthramide 2f
ClassSmall Molecule
DescriptionA monohydroxybenzoic acid resulting from the formal condensation of the carboxy group of ferulic acid with the amino group of 2-amino-5-hydroxybenzoic acid. It is an oat phytoalexin produced in response to pathogen attack and elicitation.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5-Hydroxy-2-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]amino}benzoic acidChEBI
Avenanthramide 1ChEBI
Avenanthramide 2FChEBI
Avenanthramide BFChEBI
N-[4'-Hydroxy-3'-methoxy-(e)-cinnamoyl]-5-hydroxyanthranilic acidChEBI
N-Feruloyl-5-hydroxyanthranilic acidChEBI
5-Hydroxy-2-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]amino}benzoateGenerator
N-[4'-Hydroxy-3'-methoxy-(e)-cinnamoyl]-5-hydroxyanthranilateGenerator
N-Feruloyl-5-hydroxyanthranilateGenerator
(Z)-N-Feruloyl-5-hydroxyanthranilateGenerator
Avenanthramide bHMDB
5-Hydroxy-2-{[(2E)-1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-ylidene]amino}benzoateGenerator
Chemical FormulaC17H15NO6
Average Molecular Mass329.304 g/mol
Monoisotopic Mass329.090 g/mol
CAS Registry Number108605-69-2
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
SMILESCOC1=C(O)C=CC(\C=C\C(=O)NC2=CC=C(O)C=C2C(O)=O)=C1
InChI IdentifierInChI=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
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
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0imi-0924000000-c3f6c91375c93d0a5c9cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-001i-1080590000-6045db6c80549a228c2dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0900000000-7cbaf29a9a688b59419bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0901000000-0163c92dd87682f74e49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0927000000-26acbd87ed1c4c7e9ca9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0911000000-78ce1bd1e9a10fec28aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zgi-2900000000-0c8824e0e7d9498b9b47Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0298000000-02ccc213e8295d0379f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00o0-0592000000-35fd0a16d32cdcf0bf2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-0910000000-fb965f111b5f23f3029fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0039000000-df10e0e447b7cc8a8f0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0159-0691000000-7f0a6fbb5ad61a39ab8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-0893000000-cd7163d8f0ff7a58fde9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01u0-0925000000-ab8d5673204674843b25Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-0961000000-e93728b9e83ed1cfbf37Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0910000000-dbd82e0cb572a5afa4a5Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0038575
FooDB IDFDB000285
Phenol Explorer ID534
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID8263492
ChEBI ID167489
PubChem Compound ID10087955
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10739096
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15272874
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17432911
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=30204484
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=31487918
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=33158678
7.
8. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.