Identification

PhytoHub ID
PHUB000569
Name
Avenanthramide 2c
Systematic Name
Not Available
Synonyms
  • Avenanthramide C
  • N-[3',4'-Dihydroxy-(E)-cinnamoyl]-5-hydroxyanthranilic acid
CAS Number
Not Available
Average Mass
315.281
Monoisotopic Mass
315.074287143
Chemical Formula
C16H13NO6
IUPAC Name
2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]-5-hydroxybenzoic acid
InChI Key
IDUUXROOZBOOPH-QHHAFSJGSA-N
InChI Identifier
InChI=1S/C16H13NO6/c18-10-3-4-12(11(8-10)16(22)23)17-15(21)6-2-9-1-5-13(19)14(20)7-9/h1-8,18-20H,(H,17,21)(H,22,23)/b6-2+
SMILES
OC(=O)C1=CC(O)=CC=C1NC(=O)\C=C\C1=CC(O)=C(O)C=C1
Structure

Calculated Properties

Solubility (ALOGPS)
8.57e-02 g/l
LogS (ALOGPS)
-3.57
LogP (ALOGPS)
2.55
Hydrogen Acceptors
6
Hydrogen Donors
5
Rotatable Bond Count
4
Polar Surface Area
127.09000000000002
Refractivity
84.53609999999999
Polarizability
30.962789503911615
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-2.032265536964912
pKa (strongest acidic)
3.307118911932904
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 2cN-containing compoundsAlkaloidsMiscellaneous alkaloidsShow Food Phytochemical
Avenanthramide ON-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", "1-hydroxy-4-unsubstituted benzenoids", "Acylaminobenzoic acid and derivatives", "Anilides", "Benzoic acids", "Benzoyl derivatives", "Carbonyl compounds", "Carboxylic acids", "Catechols", "Hydrocarbon derivatives", "Hydroxybenzoic acid derivatives", "Monocarboxylic acids and derivatives", "N-arylamides", "N-cinnamoylanthranilic acids", "Organic oxides", "Organopnictogen compounds", "Secondary carboxylic acid amides", "Styrenes", "Vinylogous amides"]
External Descriptor Annotations
Not Available
Substituent Names
["1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "Acylaminobenzoic acid or derivatives", "Anilide", "Aromatic homomonocyclic compound", "Avenanthramide", "Benzenoid", "Benzoic acid", "Benzoic acid or derivatives", "Benzoyl", "Carbonyl group", "Carboxamide group", "Carboxylic acid", "Carboxylic acid derivative", "Catechol", "Cinnamic acid amide", "Hydrocarbon derivative", "Hydroxybenzoic acid", "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", "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 2c Avenanthramide 2chumanplasmaunchanged1h-3h<20 nmol/LNot AvailableC16H13NO6315.074287143 Publications
Avenanthramide 2c dihydroavenanthramide 2cNot AvailableNot Availablegut microbiota metaboliteNot AvailableNot AvailableNot AvailableC17H17NO6331.105587271 Publications
Avenanthramide O Avenanthramide 2chumanplasmaunknown1h-3h20-50 nmol/LNot AvailableC16H13NO6315.074287143 Publications

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
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