1.0 2011-09-21 00:18:26 UTC 2015-10-09 22:31:08 UTC FDB022720 4-Aminohippuric acid 4-Aminohippuric acid is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. 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 Renal proximal tubules secrete various organic anions, including drugs and p-aminohippurate (PAH). Uptake of PAH from blood into tubule cells occurs by exchange with intracellular alpha-ketoglutarate and is mediated by the organic anion transporter 1. PAH exit into tubule lumen is species specific and may involve ATP-independent and -dependent transporters. (PMID 11443229) Enhanced secretion of p-aminohippuric acid occurs in Fanconi's syndrome (FS). FS is associated with numerous varieties of inherited and acquired conditions; FS is characterized by a generalized transport defect in the proximal tubules, leading to renal losses of glucose, phosphate, calcium, uric acid, amino acids, bicarbonates, and other organic compounds. (PMID 12552490) [HMDB] 4-Aminohippate 4-Aminohippic acid 4-Aminohippurate Aminohippate Aminohippic acid Aminohippurate Aminohippuric acid Chlorphentermine N-(4-Aminobenzoyl)glycine N-(p-Aminobenzoyl)aminoacetate N-(p-Aminobenzoyl)aminoacetic acid N-(p-Aminobenzoyl)glycine N-(para-aminobenzoyl)glycine Nefrotest P-Aminohippate P-Aminohippic acid p-Aminohippurate p-Aminohippuric acid PAH Paha Para-aminohippate Para-aminohippic acid para-Aminohippurate para-Aminohippuric acid Paraaminohippate Paraaminohippic acid paraaminohippuric acid C9H10N2O3 194.1873 194.069142196 2-[(4-aminophenyl)formamido]acetic acid aminohippurate 61-78-9 NC1=CC=C(C=C1)C(=O)NCC(O)=O InChI=1S/C9H10N2O3/c10-7-3-1-6(2-4-7)9(14)11-5-8(12)13/h1-4H,5,10H2,(H,11,14)(H,12,13) HSMNQINEKMPTIC-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 Amino acids Aminobenzamides Aniline and substituted anilines Benzoyl derivatives Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives N-acyl-alpha amino acids Organic oxides Organopnictogen compounds Primary amines Secondary carboxylic acid amides Alpha-amino acid or derivatives Amine Amino acid Amino acid or derivatives Aminobenzamide Aminobenzoic acid or derivatives Aniline or substituted anilines 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 Primary amine Secondary carboxylic acid amide N-acylglycine Solid logp 0.00 ALOGPS logs -1.79 ALOGPS solubility 3.13e+00 g/l ALOGPS logp -1 ChemAxon pka_strongest_acidic 2.7 ChemAxon pka_strongest_basic 4.24 ChemAxon iupac 2-[(4-aminophenyl)formamido]acetic acid ChemAxon average_mass 194.1873 ChemAxon mono_mass 194.069142196 ChemAxon smiles NC1=CC=C(C=C1)C(=O)NCC(O)=O ChemAxon formula C9H10N2O3 ChemAxon inchi InChI=1S/C9H10N2O3/c10-7-3-1-6(2-4-7)9(14)11-5-8(12)13/h1-4H,5,10H2,(H,11,14)(H,12,13) ChemAxon inchikey HSMNQINEKMPTIC-UHFFFAOYSA-N ChemAxon polar_surface_area 92.42 ChemAxon refractivity 50.82 ChemAxon polarizability 19.13 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::NmrTwoD 1707 Specdb::MsIr 1405 Specdb::MsIr 1406 Specdb::MsIr 1407 Specdb::CMs 783 Specdb::CMs 8831 Specdb::CMs 29918 Specdb::CMs 30662 Specdb::CMs 38156 Specdb::CMs 132862 Specdb::CMs 140596 Specdb::NmrOneD 1767 Specdb::NmrOneD 148420 Specdb::NmrOneD 148421 Specdb::NmrOneD 148422 Specdb::NmrOneD 148423 Specdb::NmrOneD 148424 Specdb::NmrOneD 148425 Specdb::NmrOneD 148426 Specdb::NmrOneD 148427 Specdb::NmrOneD 148428 Specdb::NmrOneD 148429 Specdb::NmrOneD 148430 Specdb::NmrOneD 148431 Specdb::NmrOneD 148432 Specdb::NmrOneD 148433 Specdb::NmrOneD 148434 Specdb::NmrOneD 148435 Specdb::NmrOneD 148436 Specdb::NmrOneD 148437 Specdb::NmrOneD 148438 Specdb::NmrOneD 148439 Specdb::MsMs 1750 Specdb::MsMs 1751 Specdb::MsMs 1752 Specdb::MsMs 262110 Specdb::MsMs 262111 Specdb::MsMs 262112 Specdb::MsMs 282042 Specdb::MsMs 282043 Specdb::MsMs 282044 Specdb::MsMs 2226543 Specdb::MsMs 2228204 Specdb::MsMs 2228942 Specdb::MsMs 2230477 Specdb::MsMs 2231285 Specdb::MsMs 2232937 Specdb::MsMs 2233592 Specdb::MsMs 2235325 Specdb::MsMs 2258640 Specdb::MsMs 2259942 Specdb::MsMs 3035795 Specdb::MsMs 3035796 Specdb::MsMs 3035797 Specdb::MsMs 3103685 Specdb::MsMs 3103686 Specdb::MsMs 3103687 HMDB01867 #<Reference:0x000055ce320fdc90> #<Reference:0x000055ce320fdad8> #<Reference:0x000055ce320fd920> #<Reference:0x000055ce320fd768> #<Reference:0x000055ce320fd5b0> #<Reference:0x000055ce320fd3f8> #<Reference:0x000055ce320fd240> #<Reference:0x000055ce320fd088> #<Reference:0x000055ce320fced0> #<Reference:0x000055ce320fcd18> #<Reference:0x000055ce320fcb60> Anatidae Type 1 specific Anatidae 8830 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 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 Glycine N-acyltransferase Q6IB77 GLYAT Glycine N-acyltransferase-like protein 1 Q969I3 GLYATL1 Glycine N-acyltransferase-like protein 2 Q8WU03 GLYATL2 Glycine N-acyltransferase-like protein 3 Q5SZD4 GLYATL3