ContaminantDB: Avenanthramide 2s

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

Record Information

Version

1.0

Creation Date

2016-05-25 20:46:06 UTC

Update Date

2016-11-09 01:17:37 UTC

Accession Number

CHEM022985

Identification

Common Name

Avenanthramide 2s

Class

Small Molecule

Description

Avenanthramide 2s is a polyphenol compound found in foods of plant origin (PMID: 20428313)

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-Hydroxy-2-{[(2E)-1-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-en-1-ylidene]amino}benzoate	HMDB

Chemical Formula

C₁₈H₁₇NO₇

Average Molecular Mass

359.330 g/mol

Monoisotopic Mass

359.101 g/mol

CAS Registry Number

Not Available

IUPAC Name

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

Traditional Name

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

SMILES

COC1=CC(\C=C\C(=O)NC2=CC=C(O)C=C2C(O)=O)=CC(OC)=C1O

InChI Identifier

InChI=1S/C18H17NO7/c1-25-14-7-10(8-15(26-2)17(14)22)3-6-16(21)19-13-5-4-11(20)9-12(13)18(23)24/h3-9,20,22H,1-2H3,(H,19,21)(H,23,24)/b6-3+

InChI Key

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

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	0.035 g/L	ALOGPS
logP	2.54	ALOGPS
logP	2.96	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.32 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	95.48 m³·mol⁻¹	ChemAxon
Polarizability	36.12 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	splash10-0k96-0917000000-8a8fe3466b148db2e1c1	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-03di-0060190000-8121e3fa449f7e3d1dd0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0w29-0809000000-58a85c2fc48a429d3f51	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0912000000-0a048db6efbe4739382d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zgi-2900000000-c634ab41e0a919127b44	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bt9-0129000000-de66cb2cecd76f73d4b3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bta-0598000000-d0eb276330504a5c280a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pb9-0910000000-51e16d367f68b4c71856	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0btc-0049000000-b4cc55661becf0f7f8a1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-08fu-0349000000-0519c687f62fc49a356a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zj0-0931000000-7c7889203fa9e3f43291	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dj-0059000000-7ef42b242e04c609832d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001j-0492000000-ec00d73b50bbf5294368	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ac0-0190000000-e9d0d0d8e4bd63b6e277	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

HMDB0029286

FooDB ID

FDB000288

Phenol Explorer ID

537

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

9199961

ChEBI ID

Not Available

PubChem Compound ID

11024779

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Bratt K, Sunnerheim K, Bryngelsson S, Fagerlund A, Engman L, Andersson RE, Dimberg LH: Avenanthramides in oats (Avena sativa L.) and structure-antioxidant activity relationships. J Agric Food Chem. 2003 Jan 29;51(3):594-600.

2. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8.

Avenanthramide 2s (CHEM022985)

Structure for CHEM022985: Avenanthramide 2s