1.0 2011-09-21 00:27:21 UTC 2015-07-21 06:57:37 UTC FDB023278 D-Glucuronic acid 1-phosphate D-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-Glucuronate 1-O-alpha-delta-Glucuronate 1-O-ONO-D-Glucopyranuronic acid 1-O-ONO-delta-Glucopyranuronic acid 1-O-Phosphono-D-glucopyranuronic acid 1-O-Phosphono-delta-glucopyranuronic acid 1-phospho-a-D-glucuronate 1-phospho-alpha-delta-glucuronate a-D-Glucopyranuronic acid 1-ate a-D-Glucopyranuronic acid 1-phosphate a-D-Glucuronic acid 1-ate a-D-Glucuronic acid 1-phosphate alpha-D-Glucuronate 1-ate alpha-D-glucuronate 1-phosphate alpha-D-Glucuronic acid 1-ate alpha-D-glucuronic acid 1-phosphate alpha-delta-Glucopyranuronic acid 1-ate alpha-delta-Glucopyranuronic acid 1-phosphate alpha-delta-Glucuronate 1-ate alpha-delta-glucuronate 1-phosphate alpha-delta-Glucuronic acid 1-ate alpha-delta-Glucuronic acid 1-phosphate D-Glucuronate 1-ate D-Glucuronate 1-phosphate D-Glucuronate-1-ate D-glucuronate-1-P D-glucuronate-1-phosphate D-Glucuronic acid 1-ate D-glucuronic acid 1-phosphate delta-Glucuronate 1-ate delta-Glucuronate 1-phosphate delta-Glucuronate-1-ate delta-glucuronate-1-P delta-glucuronate-1-phosphate delta-Glucuronic acid 1-ate delta-glucuronic acid 1-phosphate Glucuronate-1-ate glucuronate-1-P glucuronate-1-phosphate Glucuronic acid 1-ate Glucuronic acid 1-phosphate C6H11O10P 274.1193 274.008983084 (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(phosphonooxy)oxane-2-carboxylic acid glucuronic acid 1-phosphate 13168-11-1 O[C@@H]1[C@@H](O)C(OP(O)(O)=O)O[C@@H]([C@H]1O)C(O)=O InChI=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/s1 AIQDYKMWENWVQJ-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 derivatives Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Hexoses Hydrocarbon derivatives Monoalkyl phosphates Monocarboxylic acids and derivatives Monosaccharide phosphates Organic oxides Oxacyclic compounds Oxanes Polyols Pyrans Secondary alcohols Alcohol Aliphatic heteromonocyclic compound Alkyl phosphate Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Glucuronic acid or derivatives Hexose monosaccharide Hydrocarbon derivative Hydroxy acid Monoalkyl phosphate Monocarboxylic acid or derivatives Monosaccharide Monosaccharide phosphate Organic oxide Organic phosphoric acid derivative Organoheterocyclic compound Oxacycle Oxane Phosphoric acid ester Polyol Pyran Secondary alcohol uronic acid phosphate Solid logp -1.69 ALOGPS logs -0.91 ALOGPS solubility 3.38e+01 g/l ALOGPS logp -2.7 ChemAxon pka_strongest_acidic 1.15 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(phosphonooxy)oxane-2-carboxylic acid ChemAxon average_mass 274.1193 ChemAxon mono_mass 274.008983084 ChemAxon smiles O[C@@H]1[C@@H](O)C(OP(O)(O)=O)O[C@@H]([C@H]1O)C(O)=O ChemAxon formula C6H11O10P ChemAxon inchi InChI=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/s1 ChemAxon inchikey AIQDYKMWENWVQJ-AQKNRBDQSA-N ChemAxon polar_surface_area 173.98 ChemAxon refractivity 46.66 ChemAxon polarizability 20.54 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 9 ChemAxon donor_count 6 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 20725 Specdb::CMs 38682 Specdb::MsMs 312157 Specdb::MsMs 312158 Specdb::MsMs 312159 Specdb::MsMs 357337 Specdb::MsMs 357338 Specdb::MsMs 357339 HMDB03976 35145 #<Reference:0x000055ce2ec20db0> #<Reference:0x000055ce2ec20860> #<Reference:0x000055ce2ec205e0> 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 UDP-glucuronosyltransferase 1-1 P22309 UGT1A1 UDP-glucuronosyltransferase 1-4 P22310 UGT1A4 UDP-glucuronosyltransferase 1-6 P19224 UGT1A6 UDP-glucuronosyltransferase 1-9 O60656 UGT1A9 UDP-glucuronosyltransferase 2B4 P06133 UGT2B4 UDP-glucuronosyltransferase 2B7 P16662 UGT2B7