1.0 2011-09-21 00:10:11 UTC 2015-10-09 22:33:39 UTC FDB022212 Hydroxyphenylacetylglycine Hydroxyphenylacetylglycine 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 Hydroxyphenylacetylglycine is an endogenous human metabolite. It can be originated from the metabolism of tyramine, itself is a monoamine compound derived from the amino acid tyrosine. Hydroxyphenylacetylglycine can also be derived from the metabolism of 3,4-dihydroxyphenylalanine (L-DOPA). In the metabolism of tyrosine, this compound is involved in the reaction Hydroxyphenylacetyl-CoA + Glycine <=> Hydroxyphenylacetylglycine + CoA, catalyzed by acyltransferase enzymes (EC 2.3.1.-). Hydroxyphenylacetylglycine has been identified in human biofluids. (PMID: 14201174, 912020, 716472, 7096501, 7438429, 7438430) [HMDB] [[(4-Hydroxyphenyl)acetyl]amino]acetate [[(4-Hydroxyphenyl)acetyl]amino]acetic acid 4-Hydroxyphenylacetylglycine N-[(4-hydroxyphenyl)acetyl]-Glycine N-[(p-hydroxyphenyl)acetyl]-Glycine p-Hydroxyphenylacetylglycine C10H11NO4 209.1986 209.068807845 2-[2-(4-hydroxyphenyl)acetamido]acetic acid p-hydroxyphenylacetylglycine 28116-23-6 OC(=O)CNC(=O)CC1=CC=C(O)C=C1 InChI=1S/C10H11NO4/c12-8-3-1-7(2-4-8)5-9(13)11-6-10(14)15/h1-4,12H,5-6H2,(H,11,13)(H,14,15) CPPDWYIPKSSNNM-UHFFFAOYSA-N belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-acyl-alpha amino acids Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds Phenylacetamides Secondary carboxylic acid amides 1-hydroxy-2-unsubstituted benzenoid Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxamide group Carboxylic acid Hydrocarbon derivative Monocarboxylic acid or derivatives Monocyclic benzene moiety N-acyl-alpha-amino acid Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenol Phenylacetamide Secondary carboxylic acid amide N-acylglycine monocarboxylic acid monocarboxylic acid amide Solid logp 0.46 ALOGPS logs -2.02 ALOGPS solubility 2.00e+00 g/l ALOGPS logp 0.2 ChemAxon pka_strongest_acidic 3.54 ChemAxon pka_strongest_basic -2.9 ChemAxon iupac 2-[2-(4-hydroxyphenyl)acetamido]acetic acid ChemAxon average_mass 209.1986 ChemAxon mono_mass 209.068807845 ChemAxon smiles OC(=O)CNC(=O)CC1=CC=C(O)C=C1 ChemAxon formula C10H11NO4 ChemAxon inchi InChI=1S/C10H11NO4/c12-8-3-1-7(2-4-8)5-9(13)11-6-10(14)15/h1-4,12H,5-6H2,(H,11,13)(H,14,15) ChemAxon inchikey CPPDWYIPKSSNNM-UHFFFAOYSA-N ChemAxon polar_surface_area 86.63 ChemAxon refractivity 52.15 ChemAxon polarizability 20.13 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::MsIr 808 Specdb::MsIr 809 Specdb::MsIr 810 Specdb::NmrOneD 1509 Specdb::NmrTwoD 1455 Specdb::CMs 26560 Specdb::CMs 37732 Specdb::CMs 165045 Specdb::CMs 1073034 Specdb::CMs 1073036 Specdb::CMs 1073038 Specdb::CMs 1073039 Specdb::CMs 1073041 Specdb::CMs 1073043 Specdb::CMs 1073045 Specdb::CMs 1073047 Specdb::CMs 1073048 Specdb::CMs 1073050 Specdb::CMs 1073052 Specdb::MsMs 1041 Specdb::MsMs 1042 Specdb::MsMs 1043 Specdb::MsMs 324892 Specdb::MsMs 324893 Specdb::MsMs 324894 Specdb::MsMs 373426 Specdb::MsMs 373427 Specdb::MsMs 373428 Specdb::MsMs 2674654 Specdb::MsMs 2674655 Specdb::MsMs 2674656 Specdb::MsMs 3034544 Specdb::MsMs 3034545 Specdb::MsMs 3034546 HMDB00735 #<Reference:0x0000561272d25070> #<Reference:0x0000561272d24e90> #<Reference:0x0000561272d24cb0> #<Reference:0x0000561272d24af8> #<Reference:0x0000561272d24940> #<Reference:0x0000561272d24788> 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 N-acetyltransferase ESCO1 Q5FWF5 ESCO1