Avenanthramide A2 (CHEM022998)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 20:46:31 UTC
Update Date2016-11-09 01:17:37 UTC
Accession NumberCHEM022998
Identification
Common NameAvenanthramide A2
ClassSmall Molecule
DescriptionAvenanthramide A2 is a polyphenol compound found in foods of plant origin (PMID: 20428313)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
N-[4'-Hydroxy-3'-methoxy-(e)-cinnamoyl]-5-hydroxy-4-methoxyanthranilic acidHMDB
(2E)-N-[2-(Dihydroxymethyl)-4-hydroxy-5-methoxyphenyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enimidateHMDB
Chemical FormulaC18H19NO7
Average Molecular Mass361.346 g/mol
Monoisotopic Mass361.116 g/mol
CAS Registry NumberNot Available
IUPAC Name(2E)-N-[2-(dihydroxymethyl)-4-hydroxy-5-methoxyphenyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
Traditional Name(2E)-N-[2-(dihydroxymethyl)-4-hydroxy-5-methoxyphenyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
SMILESCOC1=C(O)C=CC(\C=C\C(=O)NC2=CC(OC)=C(O)C=C2C(O)O)=C1
InChI IdentifierInChI=1S/C18H19NO7/c1-25-15-7-10(3-5-13(15)20)4-6-17(22)19-12-9-16(26-2)14(21)8-11(12)18(23)24/h3-9,18,20-21,23-24H,1-2H3,(H,19,22)/b6-4+
InChI KeyPESXZYVWZYEQPY-GQCTYLIASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. Hydroxycinnamic acids and derivatives are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids and derivatives
Alternative Parents
Substituents
  • Cinnamic acid amide
  • Hydroxycinnamic acid or derivatives
  • Methoxyphenol
  • Anilide
  • Methoxyaniline
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Styrene
  • N-arylamide
  • Methoxybenzene
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Ether
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Aromatic alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • 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 Solubility0.13 g/LALOGPS
logP1.25ALOGPS
logP1.52ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area128.48 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity96.07 m³·mol⁻¹ChemAxon
Polarizability36.76 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, Positivesplash10-00kp-0908000000-6672b52c11cb13e46f20Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-01qi-1021149000-8fc98f67cab61ff4ebd6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ec-0709000000-2906ffab4aac65dcf04cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-0902000000-d6f17d7423b77b67f403Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0900000000-7f456bd0dc1988cad152Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0119000000-1c1b1ff826ca53381875Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-0789000000-f5d7ec72976d57ae7beaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lf-1910000000-54ee91275f21b88b2236Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009000000-74f230bf0aaddad5334cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0209000000-8672bdfd75621e6b5340Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0571-2941000000-9cb3126ba89bf252aac2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0019000000-daf659ff8bf5b55ef598Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052b-0389000000-a02f8e45ce50699bf8e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5j-0694000000-9ab30e37091fe6533664Spectrum
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 IDHMDB0029297
FooDB IDFDB000303
Phenol Explorer ID558
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30776766
ChEBI IDNot Available
PubChem Compound ID131750842
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.
2. Dimberg LH, Theander O, Lingnert H: Avenanthramides - A group of phenolic antioxidants in oats. Cereal Chemistry. 1993 Nov-Dec;70(6):637-641 [Structure] [Isolation]