1.0 2010-04-08 22:04:30 UTC 2025-11-18 22:16:48 UTC FDB000283 Avenanthramide 2p (z)-n-coumaroyl-5-hydroxyanthranilic acid 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 (z)-n-coumaroyl-5-hydroxyanthranilic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). (z)-n-coumaroyl-5-hydroxyanthranilic acid can be found in cereals and cereal products and oat, which makes (z)-n-coumaroyl-5-hydroxyanthranilic acid a potential biomarker for the consumption of these food products. Avenanthramide A (Collins) Avenanthramide A4 (Dimberg) N-[4'-Hydroxy-(E)cinnamoyl]-5-hydroxyanthranilic acid C16H13NO5 299.2781 299.079372531 5-hydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]benzoic acid 5-hydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]benzoic acid 7664-41-7 OC(=O)C1=CC(O)=CC=C1NC(=O)\C=C\C1=CC=C(O)C=C1 InChI=1S/C16H13NO5/c18-11-4-1-10(2-5-11)3-8-15(20)17-14-7-6-12(19)9-13(14)16(21)22/h1-9,18-19H,(H,17,20)(H,21,22)/b8-3+ QGUMNWHANDITDB-FPYGCLRLSA-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 Anilides Benzoic acids Benzoyl derivatives Carbonyl compounds Carboxylic acids Coumaric acids and derivatives 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 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 Cinnamic acid amide Coumaric acid or derivatives 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 hydroxycinnamic acid logp 2.96 ALOGPS logs -3.82 ALOGPS solubility 4.50e-02 g/l ALOGPS logp 3.27 ChemAxon pka_strongest_acidic 3.31 ChemAxon pka_strongest_basic -2 ChemAxon iupac 5-hydroxy-2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]benzoic acid ChemAxon average_mass 299.2781 ChemAxon mono_mass 299.079372531 ChemAxon smiles OC(=O)C1=CC(O)=CC=C1NC(=O)\C=C\C1=CC=C(O)C=C1 ChemAxon formula C16H13NO5 ChemAxon inchi InChI=1S/C16H13NO5/c18-11-4-1-10(2-5-11)3-8-15(20)17-14-7-6-12(19)9-13(14)16(21)22/h1-9,18-19H,(H,17,20)(H,21,22)/b8-3+ ChemAxon inchikey QGUMNWHANDITDB-FPYGCLRLSA-N ChemAxon polar_surface_area 106.86 ChemAxon refractivity 82.56 ChemAxon polarizability 30.33 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 5616 Specdb::CMs 45920 Specdb::CMs 164965 Specdb::MsMs 81507 Specdb::MsMs 81508 Specdb::MsMs 81509 Specdb::MsMs 142629 Specdb::MsMs 142630 Specdb::MsMs 142631 Specdb::MsMs 374157 Specdb::MsMs 451848 Specdb::MsMs 452091 Specdb::MsMs 2471637 Specdb::MsMs 2471638 Specdb::MsMs 2471639 Specdb::MsMs 2494253 Specdb::MsMs 2494254 Specdb::MsMs 2494255 HMDB0038577 Oat Type 1 specific Avena sativa 4498 1.78 2.699999854 0.860000014 mg/100 g