| Common Name |
Avenanthramide A2
| Description |
Avenanthramide A2 is a polyphenol compound found in foods of plant origin (PMID: 20428313 ).Avenanthramide A2 belongs to the family of Anilides. These are organic compounds derived fromA oxoacidsA RkE(=O)l(OH)mA (lA a 0) by replacing anA OHA group by theA NHPh group or derivative formed by ring substitution[1]. (Reference: [1] IUPAC. Compendium of Chemical Terminology, 2nd ed. (the “Gold Book”). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. doi:10.1351/goldbook. (PAC, 1995, 67, 1307 (Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995)) on page 1348).).
| Structure |
MOLSDFPDBSMILESInChI
Structure for HMDB29297 (Avenanthramide A2)
| Synonyms |
| Value |
Source |
N-[4'-Hydroxy-3'-methoxy-(e)-cinnamoyl]-5-hydroxy-4-methoxyanthranilic acidHMDB
| Chemical Formlia |
C18H19NO7
| Average Molecliar Weight |
361.346
| Monoisotopic Molecliar Weight |
361.116151967
| IUPAC Name |
(2E)-N-[2-(dihydroxymethyl)-4-hydroxy-5-methoxyphenyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
| Traditional Name |
(2E)-N-[2-(dihydroxymethyl)-4-hydroxy-5-methoxyphenyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
| CAS Registry Number |
Not Available
| SMILES |
COC1=C(O)C=CC(C=CC(=O)NC2=CC(OC)=C(O)C=C2C(O)O)=C1
| InChI Identifier |
InChI=1S/C18H19NO7/c1-25-15-7-10(3-5-13(15)20)4-6-17(22)19-12-9-16(26-2)14(21)8-11(12)18(23)24/h3-9,18,20-21,23-24H,1-2H3,(H,19,22)/b6-4+
| InChI Key |
PESXZYVWZYEQPY-GQCTYLIASA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as hydroxycinnamic acids and derivatives. These are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Phenylpropanoids and polyketides
| Sub Class |
Cinnamic acids and derivatives
| Direct Parent |
Hydroxycinnamic acids and derivatives
| Alternative Parents |
Cinnamic acid amides
Methoxyphenols
Methoxyanilines
Anilides
Styrenes
Phenoxy compounds
N-arylamides
Methoxybenzenes
Anisoles
1-hydroxy-2-unsubstituted benzenoids
Alkyl aryl ethers
Secondary carboxylic acid amides
Aromatic alcohols
Carbonyl compounds
Hydrocarbon derivatives
Organic oxides
Organopnictogen compounds
| Substituents |
Cinnamic acid amide
Hydroxycinnamic acid or derivatives
Methoxyphenol
Anilide
Methoxyaniline
Anisole
Phenoxy compound
Phenol ether
Styrene
N-arylamide
Methoxybenzene
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Ether
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Aromatic alcohol
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Hydrocarbon derivative
Aromatic homomonocyclic compound
| Molecliar Framework |
Aromatic homomonocyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
Not Available
| Application |
Nutrient
| Cellliar locations |
Cytoplasm
Extracellliar
| Physical Properties |
| State |
Not Available
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.13 mg/mLALOGPS
logP1.25ALOGPS
logP1.52ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area128.48 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity96.07 m3·mol-1ChemAxon
Polarizability36.76 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
Extracellliar
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
558
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB000303
| KNApSAcK ID |
Not Available
| Chemspider ID |
Not Available
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB29297
| Metagene Link |
HMDB29297
| METLIN ID |
Not Available
| PubChem Compound |
Not Available
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Corticotropin-releasing factor (ovine)
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- 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. [PubMed:20428313 ]
- (). Dimberg LH, Theander O, Lingnert H: Avenanthramides – A group of phenolic antioxidants in oats. Cereal Chemistry. 1993 Nov-Dec;70(6):637-641 [Structure] [Isolation]. .
|
PMID: 24389031
