ChemFOnt: Showing chemical card for Avenanthramide 2p (CFc000332882)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:12:26 UTC

Chemfont ID

CFc000332882

Molecule Identification

Common Name

Avenanthramide 2p

Definition

(z)-n-coumaroyl-5-hydroxyanthranilic acid is a member of the class of compounds known as avenanthramides. Avenanthramides are a group of phenolic alkaloids consisting of conjugate of three phenylpropanoids (ferulic, caffeic, or p-coumaric acid) and anthranilic acid (z)-n-coumaroyl-5-hydroxyanthranilic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). (z)-n-coumaroyl-5-hydroxyanthranilic acid can be found in cereals and cereal products and oat, which makes (z)-n-coumaroyl-5-hydroxyanthranilic acid a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-Hydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]benzoate	Kegg
5-Hydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]benzoic acid	Generator
(Z)-N-Coumaroyl-5-hydroxyanthranilate	Generator
5-Hydroxy-N-(4-hydroxycinnamoyl)anthranilic acid	HMDB
Avenalumin I	HMDB
Avenanthramide a	HMDB

Chemical Formula

C₁₆H₁₃NO₅

Average Molecular Weight

299.2781

Monoisotopic Molecular Weight

299.079372531

IUPAC Name

5-hydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]benzoic acid

Traditional Name

5-hydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]benzoic acid

CAS Registry Number

7664-41-7

SMILES

OC(=O)C1=CC(O)=CC=C1NC(=O)\C=C\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C16H13NO5/c18-11-4-1-10(2-5-11)3-8-15(20)17-14-7-6-12(19)9-13(14)16(21)22/h1-9,18-19H,(H,17,20)(H,21,22)/b8-3+

InChI Key

QGUMNWHANDITDB-FPYGCLRLSA-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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Avenanthramides

Alternative Parents

Substituents

Avenanthramide
N-cinnamoylanthranilic acid
Acylaminobenzoic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid amide
Hydroxybenzoic acid
Benzoic acid or derivatives
Anilide
Benzoic acid
N-arylamide
Styrene
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous amide
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

hydroxycinnamic acid (CHEBI:2939 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0000051)
Cell membrane (HMDB: HMDB0000051)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000051)

Source

Exogenous

Exogenous (HMDB: HMDB0000051)

Food

Food (HMDB: HMDB0000051)

Cereal and cereal product

Cereal

Oat (FooDB: FOOD00022)

Endogenous

Plant

Plant (HMDB: HMDB0000051)
Poaceae (HMDB: HMDB0000051)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0000051)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.045 g/L	ALOGPS
logP	2.96	ALOGPS
logP	3.27	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.86 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	82.56 m³·mol⁻¹	ChemAxon
Polarizability	30.33 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon