ChemFOnt: Showing chemical card for Avenanthramide 2c (CFc000332883)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:12:27 UTC

Chemfont ID

CFc000332883

Molecule Identification

Common Name

Avenanthramide 2c

Definition

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

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-(3,4-Dihydroxycinnamoyl)-5-hydroxyanthranilic acid	HMDB
Avenanthramide	MeSH, HMDB
Avenanthramide 2C	MeSH, HMDB
Avenanthramide-c	MeSH, HMDB
N-(3',4'-Dihydroxycinnamoyl)-5-hydroxyanthranilic acid	MeSH, HMDB
Avenanthramide-2C	MeSH, HMDB
2-{[(2E)-3-(3,4-dihydroxyphenyl)-1-hydroxyprop-2-en-1-ylidene]amino}-5-hydroxybenzoate	Generator

Chemical Formula

C₁₆H₁₃NO₆

Average Molecular Weight

315.2775

Monoisotopic Molecular Weight

315.074287153

IUPAC Name

2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]-5-hydroxybenzoic acid

Traditional Name

2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]-5-hydroxybenzoic acid

CAS Registry Number

7664-41-7

SMILES

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

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+

InChI Key

IDUUXROOZBOOPH-QHHAFSJGSA-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
Anilide
Benzoic acid or derivatives
Benzoic acid
Styrene
N-arylamide
Catechol
Benzoyl
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous amide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen 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	0.086 g/L	ALOGPS
logP	2.55	ALOGPS
logP	2.97	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.09 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	84.54 m³·mol⁻¹	ChemAxon
Polarizability	30.96 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

HMDB0038576

DrugBank ID

Not Available

Phenol Explorer Compound ID

533

FooDB ID

FDB000284

KNApSAcK ID

Not Available

Chemspider ID

9897916

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11723200

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Avenanthramide 2c (CFc000332883)

MOL for CFc000332883 (Avenanthramide 2c)

3D MOL for CFc000332883 (Avenanthramide 2c)

3D SDF for CFc000332883 (Avenanthramide 2c)

3D-SDF for CFc000332883 (Avenanthramide 2c)

PDB for CFc000332883 (Avenanthramide 2c)

3D PDB for CFc000332883 (Avenanthramide 2c)

SMILES for CFc000332883 (Avenanthramide 2c)

INCHI for CFc000332883 (Avenanthramide 2c)

Structure for CFc000332883 (Avenanthramide 2c)

3D Structure for CFc000332883 (Avenanthramide 2c)