| Common Name |
Avenanthramide 1s
| Description |
Avenanthramide 1s is a polyphenol compound found in foods of plant origin (PMID: 20428313 ).Avenanthramide 1s belongs to the family of Aminobenzoic Acid Derivatives. These are organic compounds containing a benzoic acid moiety with an amine group attached to the benzene ring.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Structure for HMDB29285 (Avenanthramide 1s)
| Synonyms |
| Value |
Source |
N-[4-Hydroxy-3,5-dimethoxy-(e)-cinnamoyl]-anthranilic acidHMDB
| Chemical Formlia |
C18H17NO6
| Average Molecliar Weight |
343.3307
| Monoisotopic Molecliar Weight |
343.105587281
| IUPAC Name |
2-[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enamido]benzoic acid
| Traditional Name |
2-[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enamido]benzoic acid
| CAS Registry Number |
Not Available
| SMILES |
COC1=CC(C=CC(=O)NC2=CC=CC=C2C(O)=O)=CC(OC)=C1O
| InChI Identifier |
InChI=1S/C18H17NO6/c1-24-14-9-11(10-15(25-2)17(14)21)7-8-16(20)19-13-6-4-3-5-12(13)18(22)23/h3-10,21H,1-2H3,(H,19,20)(H,22,23)/b8-7+
| InChI Key |
RGFLTMLKBQWTSH-BQYQJAHWSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as avenanthramides. These are a group of phenolic alkaloids consisting of conjugate of three phenylpropanoids (ferliic, caffeic, or p-coumaric acid) and anthranilic acid.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Phenylpropanoids and polyketides
| Sub Class |
Cinnamic acids and derivatives
| Direct Parent |
Avenanthramides
| Alternative Parents |
N-cinnamoylanthranilic acids
Acylaminobenzoic acid and derivatives
Dimethoxybenzenes
Methoxyphenols
Anilides
Benzoic acids
Styrenes
Anisoles
Benzoyl derivatives
Phenoxy compounds
N-arylamides
Alkyl aryl ethers
Vinylogous amides
Secondary carboxylic acid amides
Carboxylic acids
Monocarboxylic acids and derivatives
Carbonyl compounds
Hydrocarbon derivatives
Organopnictogen compounds
Organic oxides
| Substituents |
Avenanthramide
N-cinnamoylanthranilic acid
Acylaminobenzoic acid or derivatives
Cinnamic acid amide
M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Benzoic acid
Anilide
Benzoic acid or derivatives
Phenoxy compound
Anisole
Benzoyl
Styrene
Methoxybenzene
Phenol ether
N-arylamide
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous amide
Secondary carboxylic acid amide
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Ether
Organooxygen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
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 |
Membrane
| 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 Solubility0.016 mg/mLALOGPS
logP2.76ALOGPS
logP3.26ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)3.55ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.09 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity93.5 m3·mol-1ChemAxon
Polarizability35.14 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 |
Membrane
| 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 |
536
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB000287
| KNApSAcK ID |
Not Available
| Chemspider ID |
9123115
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB29285
| Metagene Link |
HMDB29285
| METLIN ID |
Not Available
| PubChem Compound |
10947890
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: PIM447
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- 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. [PubMed:12537428 ]
- 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 ]
|
PMID: 11474424
