1.0 2010-04-08 22:04:30 UTC 2025-11-18 22:16:48 UTC FDB000284 Avenanthramide 2c Avenanthramide c is a member of the class of compounds known as avenanthramides. Avenanthramides are a group of phenolic alkaloids consisting of conjugate of three phenylpropanoids (ferulic, caffeic, or p-coumaric acid) and anthranilic acid. Avenanthramide c is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Avenanthramide c can be found in cereals and cereal products, which makes avenanthramide c a potential biomarker for the consumption of this food product. Avenanthramide C (Collins) N-[3',4'-Dihydroxy-(E)-cinnamoyl]-5-hydroxyanthranilic acid C16H13NO6 315.2775 315.074287153 2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]-5-hydroxybenzoic acid 2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]-5-hydroxybenzoic acid 7664-41-7 OC(=O)C1=CC(O)=CC=C1NC(=O)\C=C\C1=CC(O)=C(O)C=C1 InChI=1S/C16H13NO6/c18-10-3-4-12(11(8-10)16(22)23)17-15(21)6-2-9-1-5-13(19)14(20)7-9/h1-8,18-20H,(H,17,21)(H,22,23)/b6-2+ IDUUXROOZBOOPH-QHHAFSJGSA-N 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. Avenanthramides Organic compounds Phenylpropanoids and polyketides Cinnamic acids and derivatives Hydroxycinnamic acids and derivatives Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Acylaminobenzoic acid and derivatives Anilides Benzoic acids Benzoyl derivatives Carbonyl compounds Carboxylic acids Catechols Hydrocarbon derivatives Hydroxybenzoic acid derivatives Monocarboxylic acids and derivatives N-arylamides N-cinnamoylanthranilic acids Organic oxides Organopnictogen compounds Secondary carboxylic acid amides Styrenes Vinylogous amides 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Acylaminobenzoic acid or derivatives Anilide Aromatic homomonocyclic compound Avenanthramide Benzenoid Benzoic acid Benzoic acid or derivatives Benzoyl Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Catechol Cinnamic acid amide Hydrocarbon derivative Hydroxybenzoic acid Monocarboxylic acid or derivatives Monocyclic benzene moiety N-arylamide N-cinnamoylanthranilic acid Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenol Secondary carboxylic acid amide Styrene Vinylogous amide logp 2.55 ALOGPS logs -3.57 ALOGPS solubility 8.57e-02 g/l ALOGPS logp 2.97 ChemAxon pka_strongest_acidic 3.31 ChemAxon pka_strongest_basic -2 ChemAxon iupac 2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]-5-hydroxybenzoic acid ChemAxon average_mass 315.2775 ChemAxon mono_mass 315.074287153 ChemAxon smiles OC(=O)C1=CC(O)=CC=C1NC(=O)\C=C\C1=CC(O)=C(O)C=C1 ChemAxon formula C16H13NO6 ChemAxon inchi InChI=1S/C16H13NO6/c18-10-3-4-12(11(8-10)16(22)23)17-15(21)6-2-9-1-5-13(19)14(20)7-9/h1-8,18-20H,(H,17,21)(H,22,23)/b6-2+ ChemAxon inchikey IDUUXROOZBOOPH-QHHAFSJGSA-N ChemAxon polar_surface_area 127.09 ChemAxon refractivity 84.54 ChemAxon polarizability 30.96 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 23376 Specdb::CMs 45919 Specdb::CMs 170830 Specdb::MsMs 59034 Specdb::MsMs 59035 Specdb::MsMs 59036 Specdb::MsMs 115077 Specdb::MsMs 115078 Specdb::MsMs 115079 Specdb::MsMs 2721225 Specdb::MsMs 2721226 Specdb::MsMs 2721227 Specdb::MsMs 2960562 Specdb::MsMs 2960563 Specdb::MsMs 2960564 HMDB0038576 Oat Type 1 specific Avena sativa 4498 2.375 3.850000064 0.899999976 mg/100 g