Identification

PhytoHub ID
PHUB000570
Name
Avenanthramide 2f
Systematic Name
Not Available
Synonyms
  • Avenanthramide A1
  • Avenanthramide B
  • N-[4'-Hydroxy-3'-methoxy-(E)-cinnamoyl]-5-hydroxyanthranilic acid
CAS Number
Not Available
Average Mass
329.308
Monoisotopic Mass
329.089937207
Chemical Formula
C17H15NO6
IUPAC Name
5-hydroxy-2-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]benzoic acid
InChI Key
JXFZHMCSCYADIX-XVNBXDOJSA-N
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+
SMILES
COC1=C(O)C=CC(\C=C\C(=O)NC2=CC=C(O)C=C2C(O)=O)=C1
Structure

Calculated Properties

Solubility (ALOGPS)
2.40e-02 g/l
LogS (ALOGPS)
-4.14
LogP (ALOGPS)
2.89
Hydrogen Acceptors
6
Hydrogen Donors
4
Rotatable Bond Count
5
Polar Surface Area
116.09000000000002
Refractivity
89.01839999999999
Polarizability
33.118066162714555
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-2.031672753251153
pKa (strongest acidic)
3.3071193313077383
Number of Rings
2
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Food Phytochemical

Family
N-containing compounds
Class
Alkaloids
Sub-class
Miscellaneous alkaloids

Taxonomy as Metabolite

Metabolite Family
N-containing compound metabolites
Metabolite Class
Alkaloid metabolites
Metabolite Sub-class
Aventhramides

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
Avenanthramide 2fN-containing compoundsAlkaloidsMiscellaneous alkaloidsShow Food Phytochemical

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Cinnamic acids and derivatives
Super-class
Phenylpropanoids and polyketides
Sub-class
Hydroxycinnamic acids and derivatives
Direct Parent Name
Avenanthramides
Alternative Parent Names
["1-hydroxy-2-unsubstituted benzenoids", "Acylaminobenzoic acid and derivatives", "Alkyl aryl ethers", "Anilides", "Anisoles", "Benzoic acids", "Benzoyl derivatives", "Carbonyl compounds", "Carboxylic acids", "Hydrocarbon derivatives", "Hydroxybenzoic acid derivatives", "Methoxybenzenes", "Methoxyphenols", "Monocarboxylic acids and derivatives", "N-arylamides", "N-cinnamoylanthranilic acids", "Organic oxides", "Organopnictogen compounds", "Phenoxy compounds", "Secondary carboxylic acid amides", "Styrenes", "Vinylogous amides"]
External Descriptor Annotations
Not Available
Substituent Names
["1-hydroxy-2-unsubstituted benzenoid", "Acylaminobenzoic acid or derivatives", "Alkyl aryl ether", "Anilide", "Anisole", "Aromatic homomonocyclic compound", "Avenanthramide", "Benzenoid", "Benzoic acid", "Benzoic acid or derivatives", "Benzoyl", "Carbonyl group", "Carboxamide group", "Carboxylic acid", "Carboxylic acid derivative", "Cinnamic acid amide", "Ether", "Hydrocarbon derivative", "Hydroxybenzoic acid", "Methoxybenzene", "Methoxyphenol", "Monocarboxylic acid or derivatives", "Monocyclic benzene moiety", "N-arylamide", "N-cinnamoylanthranilic acid", "Organic nitrogen compound", "Organic oxide", "Organic oxygen compound", "Organonitrogen compound", "Organooxygen compound", "Organopnictogen compound", "Phenol", "Phenol ether", "Phenoxy compound", "Secondary carboxylic acid amide", "Styrene", "Vinylogous amide"]

Spectra from Online Resources

No spectra information available

Food Sources

No food source information available

Food Sources of its Food Phytochemical(s)

No food source information available of its precursor(s)

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Avenanthramide 2f Avenanthramide 2fhumanplasmaunchanged<1h20-50 nmol/LNot AvailableC17H15NO6329.089937207 Publications
Avenanthramide 2f dihydroavenanthramide 2fhumanurinegut microbiota metaboliteNot AvailableNot Available<1% Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
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