1.0 2010-04-08 22:05:07 UTC 2025-11-18 22:33:05 UTC FDB001819 Hippuric acid Hippuric acid (Gr. hippos, horse, ouron, urine) is a carboxylic acid found in the urine of horses and other herbivores. Hippuric acid crystallizes in rhombic prisms which are readily soluble in hot water, melt at 187 °C and decompose at about 240 °C. High concentrations of hippuric acid can also indicate a toluene intoxication. When many aromatic compounds such as benzoic acid and toluene are taken internally, they are converted to hippuric acid by reaction with the amino acid, glycine.; Hippuric acid is an acyl glycine formed by the conjugation of benzoic aicd with glycine. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine < -- > CoA + N-acylglycine. Hippuric acid is a normal component of urine and is typically increased with increased consumption of phenolic compounds (tea, wine, fruit juices). These phenols are converted to benzoic acid which is then converted to hippuric acid and excreted in the urine. Hippuric acid is the most frequently used biomarker in the biological monitoring of occupational exposure to toluene. This product of solvent biotransformation may be also found in the urine of individuals who have not been exposed to the solvent. A smaller fraction of the absorbed toluene is oxidized to aromatic compounds including ortho-cresol, which is not found significantly in the urine of nonexposed individuals. The concentration of hippuric acid in the urine of individuals exposed to a low toluene concentration does not differ from that of individuals not exposed to the solvent. This has led to the conclusion that hippuric acid should not be utilized in the biological monitoring of occupational exposure to low levels of toluene in the air.; Protein-bound organic acids such as hippuric acid are markedly accumulated in uremic plasma and produce defective protein binding of drugs. (PMID: 9120876, 8734460). (benzoylamino)-acetate (benzoylamino)-acetic acid (benzoylamino)acetic acid 2-benzamido-acetic acid 2-Benzamidoacetate 2-Benzamidoacetic acid 532-93-4 (mono-ammonium salt) 532-94-5 (mono-hydrochloride salt) 583-10-8 (mono-potassium salt) Acetic acid, (benzoylamino)- Acetic acid,benzamide hippuric acid Acido ippurico Benzamidoacetate Benzamidoacetic acid Benzaminoacetic acid Benzenecarboxamide, n-carboxymethyl- Benzoylaminoacetic acid Benzoylglycin Benzoylglycine Benzoylglycocoll Glycine, n-benzoyl- Hippurate Hippuricum acidum N-(phenylcarbonyl)glycine N-benzoyl-glycin N-benzoylglycine Phenylcarbonylaminoacetate Phenylcarbonylaminoacetic acid C9H9NO3 179.1727 179.058243159 2-(phenylformamido)acetic acid hippuric acid 495-69-2 OC(=O)CNC(=O)C1=CC=CC=C1 InChI=1S/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12) QIAFMBKCNZACKA-UHFFFAOYSA-N belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine. Hippuric acids Organic compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Aromatic homomonocyclic compounds Benzoyl derivatives Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives N-acyl-alpha amino acids Organic oxides Organonitrogen compounds Organopnictogen compounds Secondary carboxylic acid amides Alpha-amino acid or derivatives Aromatic homomonocyclic compound Benzoyl Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Hippuric acid Hydrocarbon derivative Monocarboxylic acid or derivatives N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Secondary carboxylic acid amide N-acylglycine logp 0.23 ALOGPS logs -2.18 ALOGPS solubility 1.18e+00 g/l ALOGPS melting_point 187-191 oC logp 0.53 ChemAxon pka_strongest_acidic 3.59 ChemAxon pka_strongest_basic -1.3 ChemAxon iupac 2-(phenylformamido)acetic acid ChemAxon average_mass 179.1727 ChemAxon mono_mass 179.058243159 ChemAxon smiles OC(=O)CNC(=O)C1=CC=CC=C1 ChemAxon formula C9H9NO3 ChemAxon inchi InChI=1S/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12) ChemAxon inchikey QIAFMBKCNZACKA-UHFFFAOYSA-N ChemAxon polar_surface_area 66.4 ChemAxon refractivity 46.12 ChemAxon polarizability 17.57 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Metabolism and Physiological Effects of Hippuric Acid SMP0123209 Metabolism and Physiological Effects of 4-Hydroxyhippuric Acid SMP0125537 Specdb::EiMs 1197 Specdb::NmrTwoD 1440 Specdb::MsIr 775 Specdb::MsIr 776 Specdb::MsIr 777 Specdb::NmrOneD 1258 Specdb::NmrOneD 1494 Specdb::NmrOneD 2398 Specdb::NmrOneD 3089 Specdb::NmrOneD 166438 Specdb::CMs 620 Specdb::CMs 621 Specdb::CMs 1522 Specdb::CMs 1523 Specdb::CMs 5897 Specdb::CMs 27217 Specdb::CMs 27218 Specdb::CMs 27538 Specdb::CMs 30567 Specdb::CMs 30568 Specdb::CMs 31204 Specdb::CMs 31205 Specdb::CMs 31985 Specdb::CMs 31986 Specdb::CMs 37714 Specdb::CMs 152992 Specdb::CMs 1072708 Specdb::CMs 1072709 Specdb::CMs 1072711 Specdb::MsMs 996 Specdb::MsMs 997 Specdb::MsMs 998 Specdb::MsMs 4493 Specdb::MsMs 4494 Specdb::MsMs 4495 Specdb::MsMs 4496 Specdb::MsMs 4497 Specdb::MsMs 4498 Specdb::MsMs 4499 Specdb::MsMs 8873 Specdb::MsMs 8874 Specdb::MsMs 8875 Specdb::MsMs 15545 Specdb::MsMs 15546 Specdb::MsMs 15547 Specdb::MsMs 437875 Specdb::MsMs 437876 Specdb::MsMs 437877 Specdb::MsMs 437878 Specdb::MsMs 437879 Specdb::MsMs 438635 Specdb::MsMs 439487 Specdb::MsMs 440148 Specdb::MsMs 451977 HMDB00714 18089 American cranberry Type 1 specific Vaccinium macrocarpon 13750 Anatidae Type 1 specific Anatidae 8830 Avocado Type 1 specific Persea americana 3435 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Milk (Cow) Type 2 specific 111.374286 227.93 65.0 uM Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Anti bacterial 145 A substance that kills or slows the growth of bacteria. Pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.