ContaminantDB: Avenanthramide 2p

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 20:45:59 UTC

Update Date

2016-11-09 01:17:37 UTC

Accession Number

CHEM022980

Identification

Common Name

Avenanthramide 2p

Class

Small Molecule

Description

(Z)-N-Coumaroyl-5-hydroxyanthranilic acid is found in cereals and cereal products. (Z)-N-Coumaroyl-5-hydroxyanthranilic acid is isolated from oats (Avena sativa).

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical 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 Mass

299.278 g/mol

Monoisotopic Mass

299.079 g/mol

CAS Registry Number

108605-70-5

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

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ue9-0980000000-5ff674d142cf4aef9af4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0udi-4040970000-1cc5a65d02b8330e143c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qToF , Positive	splash10-0002-0900000000-6f538a3ee4a8f4537cc2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0002-0900000000-6f538a3ee4a8f4537cc2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0002-1900000000-9558a527d5becfe510a0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0944000000-e4bf26fe5a3717ab4f60	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0920000000-4fdb81cd65ed4d4fc5f4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-100r-4900000000-b64973d21c9e8333fdc3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f6t-0190000000-5c1d411b255629965b77	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udj-0690000000-dd4c217c818be429dd84	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-1900000000-89daf2d6294feb8ca7e6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0932000000-41d35e197bc1bd76d45f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ot-0910000000-3899a82200af21e97ff1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066r-1920000000-57726dd7b1b33db7fd4c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0290000000-438c4dcba155df866234	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0930000000-27770e34f1baac319675	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-2900000000-f25c88dc5bddd9a01af1	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

FooDB ID

Phenol Explorer ID

KNApSAcK ID

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Avenanthramide 2p (CHEM022980)

Structure for CHEM022980: Avenanthramide 2p