ChemFOnt: Showing chemical card for Avenanthramide 2f (CFc000332884)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:12:27 UTC

Chemfont ID

CFc000332884

Molecule Identification

Common Name

Avenanthramide 2f

Definition

Avenanthramide b 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. Avenanthramide b is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Avenanthramide b can be found in cereals and cereal products, which makes avenanthramide b a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-Hydroxy-2-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]amino}benzoic acid	ChEBI
Avenanthramide 1	ChEBI
Avenanthramide 2F	ChEBI
Avenanthramide BF	ChEBI
N-[4'-Hydroxy-3'-methoxy-(e)-cinnamoyl]-5-hydroxyanthranilic acid	ChEBI
N-Feruloyl-5-hydroxyanthranilic acid	ChEBI
5-Hydroxy-2-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]amino}benzoate	Generator
N-[4'-Hydroxy-3'-methoxy-(e)-cinnamoyl]-5-hydroxyanthranilate	Generator
N-Feruloyl-5-hydroxyanthranilate	Generator
(Z)-N-Feruloyl-5-hydroxyanthranilate	Generator
Avenanthramide b	HMDB
5-Hydroxy-2-{[(2E)-1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-ylidene]amino}benzoate	Generator

Chemical Formula

C₁₇H₁₅NO₆

Average Molecular Weight

329.3041

Monoisotopic Molecular Weight

329.089937217

IUPAC Name

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

Traditional Name

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

CAS Registry Number

7664-41-7

SMILES

COC1=C(O)C=CC(\C=C\C(=O)NC2=CC=C(O)C=C2C(O)=O)=C1

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+

InChI Key

JXFZHMCSCYADIX-XVNBXDOJSA-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
Cinnamic acid amide
Hydroxybenzoic acid
Methoxyphenol
Anilide
Benzoic acid
Benzoic acid or derivatives
Phenoxy compound
Methoxybenzene
N-arylamide
Styrene
Phenol ether
Benzoyl
Anisole
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous amide
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Ether
Organonitrogen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

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	0.024 g/L	ALOGPS
logP	2.89	ALOGPS
logP	3.11	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.09 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	89.02 m³·mol⁻¹	ChemAxon
Polarizability	33.12 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

External Links

HMDB ID

HMDB0038575

DrugBank ID

Not Available

Phenol Explorer Compound ID

534

FooDB ID

FDB000285

KNApSAcK ID

Not Available

Chemspider ID

8263492

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10087955

PDB ID

Not Available

ChEBI ID

167489

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Avenanthramide 2f (CFc000332884)

MOL for CFc000332884 (Avenanthramide 2f)

3D MOL for CFc000332884 (Avenanthramide 2f)

3D SDF for CFc000332884 (Avenanthramide 2f)

3D-SDF for CFc000332884 (Avenanthramide 2f)

PDB for CFc000332884 (Avenanthramide 2f)

3D PDB for CFc000332884 (Avenanthramide 2f)

SMILES for CFc000332884 (Avenanthramide 2f)

INCHI for CFc000332884 (Avenanthramide 2f)

Structure for CFc000332884 (Avenanthramide 2f)

3D Structure for CFc000332884 (Avenanthramide 2f)