1.0 2010-04-08 22:04:30 UTC 2025-11-18 22:16:48 UTC FDB000285 Avenanthramide 2f Avenanthramide b 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 b is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Avenanthramide b can be found in cereals and cereal products, which makes avenanthramide b a potential biomarker for the consumption of this food product. Avenanthramide A1 Avenanthramide B (Collins) N-[4'-Hydroxy-3'-methoxy-(E)-cinnamoyl]-5-hydroxyanthranilic acid C17H15NO6 329.3041 329.089937217 5-hydroxy-2-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]benzoic acid 5-hydroxy-2-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]benzoic acid 7664-41-7 COC1=C(O)C=CC(\C=C\C(=O)NC2=CC=C(O)C=C2C(O)=O)=C1 InChI=1S/C17H15NO6/c1-24-15-8-10(2-6-14(15)20)3-7-16(21)18-13-5-4-11(19)9-12(13)17(22)23/h2-9,19-20H,1H3,(H,18,21)(H,22,23)/b7-3+ JXFZHMCSCYADIX-XVNBXDOJSA-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 Acylaminobenzoic acid and derivatives Alkyl aryl ethers Anilides Anisoles Benzoic acids Benzoyl derivatives Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Hydroxybenzoic acid derivatives Methoxybenzenes Methoxyphenols Monocarboxylic acids and derivatives N-arylamides N-cinnamoylanthranilic acids Organic oxides Organopnictogen compounds Phenoxy compounds Secondary carboxylic acid amides Styrenes Vinylogous amides 1-hydroxy-2-unsubstituted benzenoid Acylaminobenzoic acid or derivatives Alkyl aryl ether Anilide Anisole Aromatic homomonocyclic compound Avenanthramide Benzenoid Benzoic acid Benzoic acid or derivatives Benzoyl Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Cinnamic acid amide Ether Hydrocarbon derivative Hydroxybenzoic acid Methoxybenzene Methoxyphenol 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 Phenol ether Phenoxy compound Secondary carboxylic acid amide Styrene Vinylogous amide logp 2.89 ALOGPS logs -4.14 ALOGPS solubility 2.40e-02 g/l ALOGPS logp 3.11 ChemAxon pka_strongest_acidic 3.31 ChemAxon pka_strongest_basic -2 ChemAxon iupac 5-hydroxy-2-[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamido]benzoic acid ChemAxon average_mass 329.3041 ChemAxon mono_mass 329.089937217 ChemAxon smiles COC1=C(O)C=CC(\C=C\C(=O)NC2=CC=C(O)C=C2C(O)=O)=C1 ChemAxon formula C17H15NO6 ChemAxon inchi InChI=1S/C17H15NO6/c1-24-15-8-10(2-6-14(15)20)3-7-16(21)18-13-5-4-11(19)9-12(13)17(22)23/h2-9,19-20H,1H3,(H,18,21)(H,22,23)/b7-3+ ChemAxon inchikey JXFZHMCSCYADIX-XVNBXDOJSA-N ChemAxon polar_surface_area 116.09 ChemAxon refractivity 89.02 ChemAxon polarizability 33.12 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 23272 Specdb::CMs 45918 Specdb::CMs 173504 Specdb::MsMs 55731 Specdb::MsMs 55732 Specdb::MsMs 55733 Specdb::MsMs 110943 Specdb::MsMs 110944 Specdb::MsMs 110945 Specdb::MsMs 451849 Specdb::MsMs 451850 Specdb::MsMs 2304594 Specdb::MsMs 2304595 Specdb::MsMs 2304596 Specdb::MsMs 2657125 Specdb::MsMs 2657126 Specdb::MsMs 2657127 HMDB0038575 165178 Oat Type 1 specific Avena sativa 4498 3.891667 8.125 0.899999976 mg/100 g