Avenanthramide 1s (CHEM022984)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 20:46:04 UTC
Update Date2016-11-09 01:17:37 UTC
Accession NumberCHEM022984
Identification
Common NameAvenanthramide 1s
ClassSmall Molecule
DescriptionAvenanthramide 1s is a polyphenol compound found in foods of plant origin (PMID: 20428313)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
N-[4-Hydroxy-3,5-dimethoxy-(e)-cinnamoyl]-anthranilic acidHMDB
2-{[(2E)-1-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-ylidene]amino}benzoateHMDB
Chemical FormulaC18H17NO6
Average Molecular Mass343.331 g/mol
Monoisotopic Mass343.106 g/mol
CAS Registry NumberNot Available
IUPAC Name2-[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enamido]benzoic acid
Traditional Name2-[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enamido]benzoic acid
SMILESCOC1=CC(\C=C\C(=O)NC2=CC=CC=C2C(O)=O)=CC(OC)=C1O
InChI IdentifierInChI=1S/C18H17NO6/c1-24-14-9-11(10-15(25-2)17(14)21)7-8-16(20)19-13-6-4-3-5-12(13)18(22)23/h3-10,21H,1-2H3,(H,19,20)(H,22,23)/b8-7+
InChI KeyRGFLTMLKBQWTSH-BQYQJAHWSA-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
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxyphenol
  • Benzoic acid
  • Anilide
  • Benzoic acid or derivatives
  • Phenoxy compound
  • Anisole
  • Benzoyl
  • Styrene
  • Methoxybenzene
  • Phenol ether
  • N-arylamide
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous amide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Organooxygen compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organonitrogen 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 Solubility0.016 g/LALOGPS
logP2.76ALOGPS
logP3.26ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)3.55ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.09 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity93.5 m³·mol⁻¹ChemAxon
Polarizability35.14 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, Positivesplash10-004r-1955000000-564736af845bb0a51278Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9243700000-43632e64182dba9bc3d2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-0927000000-e5d58a2a6d94e0c81805Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1921000000-47b213268a64bc7c0277Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7c-5900000000-f3f4ed879aaefc57398dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0197000000-7d69fc260eea4ff9e9ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000w-1291000000-055f9d8ef39d27d8a689Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-6920000000-02b0a938a9a5166c0f60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0694000000-66d11b75dd9029d84131Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0950000000-f0d118cd615062d02818Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-1940000000-349643528b7f0a3e36c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0049000000-94f6ad9f0e27a9d34656Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0091000000-639f7b338d7e724c452dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-2192000000-a4ac72f382e99750095dSpectrum
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 IDHMDB0029285
FooDB IDFDB000287
Phenol Explorer ID536
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID9123115
ChEBI IDNot Available
PubChem Compound ID10947890
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.
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.