| Common Name |
Avenanthramide 1c
| Description |
Avenanthramide 1c is a polyphenol compound found in foods of plant origin (PMID: 20428313 ).Avenanthramide 1c 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 HMDB29284 (Avenanthramide 1c)
| Synonyms |
| Value |
Source |
N-[3,4-Dihydroxy-(e)-cinnamoyl]-anthranilic acidHMDB
| Chemical Formlia |
C16H13NO5
| Average Molecliar Weight |
299.2781
| Monoisotopic Molecliar Weight |
299.079372531
| IUPAC Name |
2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]benzoic acid
| Traditional Name |
2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]benzoic acid
| CAS Registry Number |
Not Available
| SMILES |
OC(=O)C1=CC=CC=C1NC(=O)C=CC1=CC(O)=C(O)C=C1
| InChI Identifier |
InChI=1S/C16H13NO5/c18-13-7-5-10(9-14(13)19)6-8-15(20)17-12-4-2-1-3-11(12)16(21)22/h1-9,18-19H,(H,17,20)(H,21,22)/b8-6+
| InChI Key |
LLPIRWBXMYKFQM-SOFGYWHQSA-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
Anilides
Benzoic acids
Styrenes
N-arylamides
Catechols
Benzoyl derivatives
1-hydroxy-2-unsubstituted benzenoids
1-hydroxy-4-unsubstituted benzenoids
Vinylogous amides
Secondary carboxylic acid amides
Monocarboxylic acids and derivatives
Carboxylic acids
Carbonyl compounds
Hydrocarbon derivatives
Organic oxides
Organopnictogen compounds
| Substituents |
Avenanthramide
N-cinnamoylanthranilic acid
Acylaminobenzoic acid or derivatives
Cinnamic acid amide
Anilide
Benzoic acid or derivatives
Benzoic acid
Catechol
Styrene
N-arylamide
Benzoyl
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous amide
Carboxamide group
Secondary carboxylic acid amide
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
| 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 Solubility0.044 mg/mLALOGPS
logP3.01ALOGPS
logP3.27ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.55ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area106.86 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity82.56 m3·mol-1ChemAxon
Polarizability30.05 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 |
535
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB000286
| KNApSAcK ID |
Not Available
| Chemspider ID |
8036787
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB29284
| Metagene Link |
HMDB29284
| METLIN ID |
Not Available
| PubChem Compound |
9861088
| PDB ID |
Not Available
| ChEBI ID |
710546
Product: NAMI-A
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: 15661576
