1.02011-09-21 00:27:21 UTC2015-07-21 06:57:37 UTCFDB023278D-Glucuronic acid 1-phosphateD-Glucuronic acid 1-phosphate is an end product of the UDP-glucuronic acid pathway. Formation of free glucuronic acid from UDP-glucuronic acid can be considered as the first step in the synthesis of vitamin C, a pathway that occurs in most vertebrates, although not in guinea pigs and primates, including humans. Free glucuronic acid can also be converted to pentose phosphate intermediates via the 'pentose pathway'. The latter is interrupted in subjects with pentosuria, who have a deficiency in l-xylulose reductase (EC 1.1.1.10, an enzyme that belongs to the short-chain dehydrogenase/reductase family) and excrete abnormal amounts of l-xylulose. Some xenobiotics stimulate the formation of vitamin C in animals and enhance the excretion of l-xylulose in humans with pentosuria and have shown that aminopyrine, metyrapone and other xenobiotics cause an almost instantaneous increase in the conversion of UDP-glucuronic acid to glucuronic acid. It is usually stated that glucuronic acid formation from UDP-glucuronic acid is the result of two successive reactions comprising the hydrolysis of UDP-glucuronic acid to glucuronic acid 1-phosphate and UMP by nucleotide pyrophosphatase (E-NPP3, EC 3.6.1.9), followed by dephosphorylation of glucuronic acid 1-phosphate. Glucuronidation is responsible for conjugating potentially toxic lipophilic compounds with glucuronic acid, thereby producing molecules with greater aqueous solubility that is excreted more readily into urine and bile. The rate at which any compound may be glucuronidated depends on the concentration and activity of the UDP-glucuronosyltransferases as well as the concentration of the cofactor UDP-glucuronic acid. UDP-glucuronic acid is formed after oxidation of UDP-glucose by UDP-glucose dehydrogenase (UGDH, EC 1.1.1.22) with NAD as the electron acceptor. UDP-glucuronic acid may then be either used as the glucuronic acid donor for xenobiotic conjugation reactions by UDPglucuronosyltransferases (GlcAT-P, EC 2.4.1.17), or degraded to D-glucuronic acid 1-phosphate after the phosphodiester bond is cleaved by E-NPP3. E-NPP3 is the same enzyme that further reduces D-Glucuronic acid 1-phosphate to free D-glucuronic acid. Decreases in UDP-glucuronic acid concentration may be due to reduced availability of UDP-glucose or decreased UGDH activity or to increased activities of GlcAT-P or E-NPP3. Exposure to volatile anesthetics reduces hepatic UDP-glucuronic acid concentrations, and alters the rate of conjugation of compounds such as acetaminophen, bilirubin, diethylstilbestrol, iopanoic acid and valproic acid in a non-sex-dependent fashion in experimental mice. The depletion of UDP-glucuronic acid by anesthetics is caused by altered activity of microsomal E-NPP3. (PMID: 2167093, 16689937, 1276) [HMDB]1-O-a-D-Glucuronate1-O-alpha-delta-Glucuronate1-O-ONO-D-Glucopyranuronic acid1-O-ONO-delta-Glucopyranuronic acid1-O-Phosphono-D-glucopyranuronic acid1-O-Phosphono-delta-glucopyranuronic acid1-phospho-a-D-glucuronate1-phospho-alpha-delta-glucuronatea-D-Glucopyranuronic acid 1-atea-D-Glucopyranuronic acid 1-phosphatea-D-Glucuronic acid 1-atea-D-Glucuronic acid 1-phosphatealpha-D-Glucuronate 1-atealpha-D-glucuronate 1-phosphatealpha-D-Glucuronic acid 1-atealpha-D-glucuronic acid 1-phosphatealpha-delta-Glucopyranuronic acid 1-atealpha-delta-Glucopyranuronic acid 1-phosphatealpha-delta-Glucuronate 1-atealpha-delta-glucuronate 1-phosphatealpha-delta-Glucuronic acid 1-atealpha-delta-Glucuronic acid 1-phosphateD-Glucuronate 1-ateD-Glucuronate 1-phosphateD-Glucuronate-1-ateD-glucuronate-1-PD-glucuronate-1-phosphateD-Glucuronic acid 1-ateD-glucuronic acid 1-phosphatedelta-Glucuronate 1-atedelta-Glucuronate 1-phosphatedelta-Glucuronate-1-atedelta-glucuronate-1-Pdelta-glucuronate-1-phosphatedelta-Glucuronic acid 1-atedelta-glucuronic acid 1-phosphateGlucuronate-1-ateglucuronate-1-Pglucuronate-1-phosphateGlucuronic acid 1-ateGlucuronic acid 1-phosphateC6H11O10P274.1193274.008983084(2S,3S,4S,5R)-3,4,5-trihydroxy-6-(phosphonooxy)oxane-2-carboxylic acidglucuronic acid 1-phosphate13168-11-1O[C@@H]1[C@@H](O)C(OP(O)(O)=O)O[C@@H]([C@H]1O)C(O)=OInChI=1S/C6H11O10P/c7-1-2(8)4(5(10)11)15-6(3(1)9)16-17(12,13)14/h1-4,6-9H,(H,10,11)(H2,12,13,14)/t1-,2-,3+,4-,6?/m0/s1AIQDYKMWENWVQJ-AQKNRBDQSA-N belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.Glucuronic acid derivativesOrganic compoundsOrganic oxygen compoundsOrganooxygen compoundsCarbohydrates and carbohydrate conjugatesAliphatic heteromonocyclic compoundsBeta hydroxy acids and derivativesCarbonyl compoundsCarboxylic acidsHexosesHydrocarbon derivativesMonoalkyl phosphatesMonocarboxylic acids and derivativesMonosaccharide phosphatesOrganic oxidesOxacyclic compoundsOxanesPolyolsPyransSecondary alcoholsAlcoholAliphatic heteromonocyclic compoundAlkyl phosphateBeta-hydroxy acidCarbonyl groupCarboxylic acidCarboxylic acid derivativeGlucuronic acid or derivativesHexose monosaccharideHydrocarbon derivativeHydroxy acidMonoalkyl phosphateMonocarboxylic acid or derivativesMonosaccharideMonosaccharide phosphateOrganic oxideOrganic phosphoric acid derivativeOrganoheterocyclic compoundOxacycleOxanePhosphoric acid esterPolyolPyranSecondary alcoholuronic acid phosphateSolidlogp-1.69logs-0.91solubility3.38e+01 g/llogp-2.7pka_strongest_acidic1.15pka_strongest_basic-3.7iupac(2S,3S,4S,5R)-3,4,5-trihydroxy-6-(phosphonooxy)oxane-2-carboxylic acidaverage_mass274.1193mono_mass274.008983084smilesO[C@@H]1[C@@H](O)C(OP(O)(O)=O)O[C@@H]([C@H]1O)C(O)=OformulaC6H11O10PinchiInChI=1S/C6H11O10P/c7-1-2(8)4(5(10)11)15-6(3(1)9)16-17(12,13)14/h1-4,6-9H,(H,10,11)(H2,12,13,14)/t1-,2-,3+,4-,6?/m0/s1inchikeyAIQDYKMWENWVQJ-AQKNRBDQSA-Npolar_surface_area173.98refractivity46.66polarizability20.54rotatable_bond_count3acceptor_count9donor_count6physiological_charge-3formal_charge0Specdb::CMs20725Specdb::CMs38682Specdb::MsMs312157Specdb::MsMs312158Specdb::MsMs312159Specdb::MsMs357337Specdb::MsMs357338Specdb::MsMs357339HMDB0397635145#<Reference:0x0000555674ba5750>#<Reference:0x0000555674ba5520>#<Reference:0x0000555674ba5318>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 scrofa9823UDP-glucuronosyltransferase 1-1P22309UGT1A1UDP-glucuronosyltransferase 1-4P22310UGT1A4UDP-glucuronosyltransferase 1-6P19224UGT1A6UDP-glucuronosyltransferase 1-9O60656UGT1A9UDP-glucuronosyltransferase 2B4P06133UGT2B4UDP-glucuronosyltransferase 2B7P16662UGT2B7