1.02011-09-21 00:36:32 UTC2018-05-29 01:53:09 UTCFDB023896alpha-N-Phenylacetyl-L-glutaminePhenylacetylglutamine is a product formed by the conjugation of phenylacetate and glutamine. Technically it is the amino acid acetylation product of phenylacetate (or phenylbutyrate after beta-oxidation). Phenylacetylglutamine is a normal constituent of human urine, but other mammals including the dog, cat, rat, monkey, sheep and horse do not excrete this compound. Phenylacetyl CoA and glutamine react to form phenylacetyl glutamine and Coenzyme A. The enzyme (Glutamine N-acetyl transferase) that catalyzes this reaction has been purified from human liver mitochondria and shown to be a distinct polypeptide species from glycine-N-acyltransferase. Phenylacetylglutamine is a major nitrogenous metabolite that accumulates in uremia. (PMID: 2791363; PMID: 8972626). It has been shown that over 50% of urine phenylacetylglutamine may be derived from kidney conjugation of free plasma phenylacetic acid and/or from the kidney's preferential filtration of conjugated phenylacetic acid (PMID: 6420430)
In enzymology, a glutamine N-phenylacetyltransferase (EC 2.3.1.14) is an enzyme that catalyzes the chemical reaction
phenylacetyl-CoA + L-glutamine CoA + alpha-N-phenylacetyl-L-glutamine
Thus, the two substrates of this enzyme are phenylacetyl-CoA and L-glutamine, whereas its two products are CoA and alpha-N-phenylacetyl-L-glutamine. [HMDB]a-N-Phenylacetyl-L-glutaminealpha-N-Phenylacetyl-L-glutamineL-N(sup2)-(Phenylacetyl)glutamineN(2)-(Phenylacetyl)-L-glutaminePhenylacetyl-L-glutaminePhenylacetylglutamineα-N-phenylacetyl-L-glutamineC13H16N2O4264.2771264.11100701(2S)-4-carbamoyl-2-(2-phenylacetamido)butanoic acidphenylacetylglutamine28047-15-6NC(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(O)=OInChI=1S/C13H16N2O4/c14-11(16)7-6-10(13(18)19)15-12(17)8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H2,14,16)(H,15,17)(H,18,19)/t10-/m0/s1JFLIEFSWGNOPJJ-JTQLQIEISA-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 acidsOrganic compoundsOrganic acids and derivativesCarboxylic acids and derivativesAmino acids, peptides, and analoguesAromatic homomonocyclic compoundsBenzene and substituted derivativesCarbonyl compoundsCarboximidic acidsCarboxylic acidsHydrocarbon derivativesMonocarboxylic acids and derivativesOrganic oxidesOrganonitrogen compoundsOrganopnictogen compoundsPropargyl-type 1,3-dipolar organic compoundsAromatic homomonocyclic compoundBenzenoidCarbonyl groupCarboximidic acidCarboximidic acid derivativeCarboxylic acidHydrocarbon derivativeMonocarboxylic acid or derivativesMonocyclic benzene moietyN-acyl-alpha-amino acidOrganic 1,3-dipolar compoundOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPropargyl-type 1,3-dipolar organic compoundN(2)-phenylacetylglutamineSolidlogp-0.35logs-2.83solubility3.88e-01 g/llogp-0.086pka_strongest_acidic3.9pka_strongest_basic-1.5iupac(2S)-4-carbamoyl-2-(2-phenylacetamido)butanoic acidaverage_mass264.2771mono_mass264.11100701smilesNC(=O)CC[C@H](NC(=O)CC1=CC=CC=C1)C(O)=OformulaC13H16N2O4inchiInChI=1S/C13H16N2O4/c14-11(16)7-6-10(13(18)19)15-12(17)8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H2,14,16)(H,15,17)(H,18,19)/t10-/m0/s1inchikeyJFLIEFSWGNOPJJ-JTQLQIEISA-Npolar_surface_area109.49refractivity67.28polarizability26.55rotatable_bond_count7acceptor_count4donor_count3physiological_charge-1formal_charge0Phenylacetate MetabolismSMP00126map00360Specdb::CMs10064Specdb::CMs39005Specdb::CMs160456Specdb::NmrOneD68172Specdb::NmrOneD68173Specdb::NmrOneD68174Specdb::NmrOneD68175Specdb::NmrOneD68176Specdb::NmrOneD68177Specdb::NmrOneD68178Specdb::NmrOneD68179Specdb::NmrOneD68180Specdb::NmrOneD68181Specdb::NmrOneD68182Specdb::NmrOneD68183Specdb::NmrOneD68184Specdb::NmrOneD68185Specdb::NmrOneD68186Specdb::NmrOneD68187Specdb::NmrOneD68188Specdb::NmrOneD68189Specdb::NmrOneD68190Specdb::NmrOneD68191Specdb::MsMs94506Specdb::MsMs94507Specdb::MsMs94508Specdb::MsMs158538Specdb::MsMs158539Specdb::MsMs158540Specdb::MsMs439962Specdb::MsMs450249Specdb::MsMs450250Specdb::MsMs2236048Specdb::MsMs2237326Specdb::MsMs2238201Specdb::MsMs2239385Specdb::MsMs2240325Specdb::MsMs2241373Specdb::MsMs2242375Specdb::MsMs2243491Specdb::MsMs2246564Specdb::MsMs2247715Specdb::MsMs2253132Specdb::MsMs2253345Specdb::MsMs2255198Specdb::MsMs2255353Specdb::MsMs2257283Specdb::MsMs2257315HMDB06344#<Reference:0x0000555675ebd3b0>#<Reference:0x0000555675ebd1f8>#<Reference:0x0000555675ebd018>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823