2.0 2012-05-31 14:04:13 -0600 2015-09-13 12:56:13 -0600 ECMDB04073 M2MDB000596 D-Glucuronic acid Glucuronic acid is a carboxylic acid that has the structure of a glucose molecule that has had its sixth carbon atom (of six total) oxidized. The salts of glucuronic acid are known as glucuronates. Glucuronic acid is highly soluble in water. a-D-Glucopyranuronate a-D-Glucopyranuronic acid a-D-Glucuronate a-D-Glucuronic acid a-delta-Glucopyranuronate a-delta-Glucopyranuronic acid a-delta-Glucuronate a-delta-Glucuronic acid a-δ-Glucopyranuronate a-δ-Glucopyranuronic acid a-δ-Glucuronate a-δ-Glucuronic acid Alpha-D-Glucopyranuronate Alpha-D-Glucopyranuronic acid Alpha-D-Glucuronate Alpha-D-Glucuronic acid Alpha-delta-Glucopyranuronate Alpha-delta-Glucopyranuronic acid Alpha-delta-Glucuronate Alpha-delta-Glucuronic acid D-(+)-Glucuronate D-(+)-Glucuronic acid D-Glucopyranuronate D-glucopyranuronic acid D-Glucuronate D-Glucuronic acid Delta-(+)-Glucuronate Delta-(+)-Glucuronic acid Delta-Glucuronate Delta-Glucuronic acid GCU GlcA Glucosiduronate Glucosiduronic acid Glucuronate Glucuronic acid α-D-Glucopyranuronate α-D-Glucopyranuronic acid α-D-Glucuronate α-D-Glucuronic acid α-δ-Glucopyranuronate α-δ-Glucopyranuronic acid α-δ-Glucuronate α-δ-Glucuronic acid δ-(+)-Glucuronate δ-(+)-Glucuronic acid δ-Glucuronate δ-Glucuronic acid C6H10O7 194.1394 194.042652674 (2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid glucuronic acid 6556-12-3 O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6-/m0/s1 AEMOLEFTQBMNLQ-WAXACMCWSA-N Solid Cytosol Extra-organism Periplasm logp -2.30 ALOGPS logs 0.18 ALOGPS solubility 2.95e+02 g/l ALOGPS melting_point 143-144 oC logp -2.6 ChemAxon pka_strongest_acidic 3.21 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid ChemAxon average_mass 194.1394 ChemAxon mono_mass 194.042652674 ChemAxon smiles O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O ChemAxon formula C6H10O7 ChemAxon inchi InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/t1-,2-,3+,4-,6-/m0/s1 ChemAxon inchikey AEMOLEFTQBMNLQ-WAXACMCWSA-N ChemAxon polar_surface_area 127.45 ChemAxon refractivity 35.79 ChemAxon polarizability 16.32 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Starch and sucrose metabolism The metabolism of starch and sucrose begins with D-fructose interacting with a D-glucose in a reversible reaction through a maltodextrin glucosidase resulting in a water molecule and a sucrose. D-fructose is phosphorylated through an ATP driven fructokinase resulting in the release of an ADP, a hydrogen ion and a Beta-D-fructofuranose 6-phosphate. This compound can also be introduced into the cytoplasm through either a mannose PTS permease or a hexose-6-phosphate:phosphate antiporter. The Beta-D-fructofuranose 6-phosphate is isomerized through a phosphoglucose isomerase resulting in a Beta-D-glucose 6-phosphate. This compound can also be incorporated by glucose PTS permease or a hexose-6-phosphate:phosphate antiporter. The beta-D-glucose 6 phosphate can also be produced by a D-glucose being phosphorylated by an ATP-driven glucokinase resulting in a ADP, a hydrogen ion and a Beta-D-glucose 6 phosphate. The beta-D-glucose can produce alpha-D-glucose-1-phosphate by two methods: 1.-Beta-D-glucose is isomerized into an alpha-D-Glucose 6-phosphate and then interacts in a reversible reaction through a phosphoglucomutase-1 resulting in a alpha-D-glucose-1-phosphate. 2.-Beta-D-glucose interacts with a putative beta-phosphoglucomutase resulting in a Beta-D-glucose 1-phosphate. Beta-D-glucose 1-phosphate can be incorporated into the cytoplasm through a glucose PTS permease. This compound is then isomerized into a Alpha-D-glucose-1-phosphate The beta-D-glucose can cycle back into a D-fructose by first interacting with D-fructose in a reversible reaction through a Polypeptide: predicted glucosyltransferase resulting in the release of a phosphate and a sucrose. The sucrose then interacts in a reversible reaction with a water molecule through a maltodextrin glucosidase resulting in a D-glucose and a D-fructose. Alpha-D-glucose-1-phosphate can produce glycogen in by two different sets of reactions: 1.-Alpha-D-glucose-1-phosphate interacts with a hydrogen ion and an ATP through a glucose-1-phosphate adenylyltransferase resulting in a pyrophosphate and an ADP-glucose. The ADP-glucose then interacts with an amylose through a glycogen synthase resulting in the release of an ADP and an Amylose. The amylose then interacts with 1,4-α-glucan branching enzyme resulting in glycogen 2.- Alpha-D-glucose-1-phosphate interacts with amylose through a maltodextrin phosphorylase resulting in a phosphate and a glycogen. Alpha-D-glucose-1-phosphate can also interacts with UDP-galactose through a galactose-1-phosphate uridylyltransferase resulting in a galactose 1-phosphate and a Uridine diphosphate glucose. The UDP-glucose then interacts with an alpha-D-glucose 6-phosphate through a trehalose-6-phosphate synthase resulting in a uridine 5'-diphosphate, a hydrogen ion and a Trehalose 6- phosphate. The latter compound can also be incorporated into the cytoplasm through a trehalose PTS permease. Trehalose interacts with a water molecule through a trehalose-6-phosphate phosphatase resulting in the release of a phosphate and an alpha,alpha-trehalose.The alpha,alpha-trehalose can also be obtained from glycogen being metabolized through a glycogen debranching enzyme resulting in a the alpha, alpha-trehalose. This compound ca then be hydrated through a cytoplasmic trehalase resulting in the release of an alpha-D-glucose and a beta-d-glucose. Glycogen is then metabolized by reacting with a phosphate through a glycogen phosphorylase resulting in a alpha-D-glucose-1-phosphate and a dextrin. The dextrin is then hydrated through a glycogen phosphorylase-limit dextrin α-1,6-glucohydrolase resulting in the release of a debranched limit dextrin and a maltotetraose. This compound can also be incorporated into the cytoplasm through a maltose ABC transporter. The maltotetraose interacts with a phosphate through a maltodextrin phosphorylase releasing a alpha-D-glucose-1-phosphate and a maltotriose. The maltotriose can also be incorporated through a maltose ABC transporter. The maltotriose can then interact with water through a maltodextrin glucosidase resulting in a D-glucose and a D-maltose. D-maltose can also be incorporated through a maltose ABC transporter The D-maltose can then interact with a maltotriose through a amylomaltase resulting in a maltotetraose and a D-glucose. The D-glucose is then phosphorylated through an ATP driven glucokinase resulting in a hydrogen ion, an ADP and a Beta-D-glucose 6-phosphate PW000941 ec00500 Metabolic Ascorbate and aldarate metabolism ec00053 Amino sugar and nucleotide sugar metabolism ec00520 Glycosaminoglycan degradation ec00531 Pentose and glucuronate interconversions ec00040 Drug metabolism - other enzymes ec00983 Porphyrin and chlorophyll metabolism ec00860 Flavone and flavonol biosynthesis ec00944 Inositol phosphate metabolism ec00562 Metabolic pathways eco01100 &beta;-D-glucuronide and D-glucuronate degradation GLUCUROCAT-PWY Specdb::CMs 24385 Specdb::CMs 37309 Specdb::CMs 172924 Specdb::CMs 1051028 Specdb::CMs 1051030 Specdb::CMs 1051032 Specdb::CMs 1051034 Specdb::CMs 1051036 Specdb::CMs 1051037 Specdb::CMs 1051039 Specdb::CMs 1051041 Specdb::CMs 1051043 Specdb::CMs 1051045 Specdb::CMs 1051047 Specdb::CMs 1051049 Specdb::CMs 1051050 Specdb::CMs 1051052 Specdb::CMs 1051054 Specdb::CMs 1051056 Specdb::CMs 1051058 Specdb::CMs 1051060 Specdb::CMs 1051062 Specdb::CMs 1051064 Specdb::CMs 1051066 Specdb::CMs 1051067 Specdb::NmrOneD 1098 Specdb::NmrOneD 1156 Specdb::NmrOneD 142390 Specdb::NmrOneD 142391 Specdb::NmrOneD 142392 Specdb::NmrOneD 142393 Specdb::NmrOneD 142394 Specdb::NmrOneD 142395 Specdb::NmrOneD 142396 Specdb::NmrOneD 142397 Specdb::NmrOneD 142398 Specdb::NmrOneD 142399 Specdb::NmrOneD 142400 Specdb::NmrOneD 142401 Specdb::NmrOneD 142402 Specdb::NmrOneD 142403 Specdb::NmrOneD 142404 Specdb::NmrOneD 142405 Specdb::NmrOneD 142406 Specdb::NmrOneD 142407 Specdb::NmrOneD 142408 Specdb::NmrOneD 142409 Specdb::NmrOneD 166527 Specdb::MsMs 192 Specdb::MsMs 193 Specdb::MsMs 319990 Specdb::MsMs 319991 Specdb::MsMs 319992 Specdb::MsMs 367270 Specdb::MsMs 367271 Specdb::MsMs 367272 Specdb::MsMs 2236268 Specdb::MsMs 2237099 Specdb::MsMs 2238362 Specdb::MsMs 2239234 Specdb::MsMs 2242475 Specdb::MsMs 2243401 Specdb::MsMs 2413042 Specdb::MsMs 2413043 Specdb::MsMs 2413044 Specdb::MsMs 2552132 Specdb::MsMs 2552133 Specdb::MsMs 2552134 Specdb::NmrTwoD 1156 HMDB00127 444791 392615 C00191 GLUCURONATE GCU GCU Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. 2026685 Nishida T, Gatmaitan Z, Roy-Chowdhry J, Arias IM: Two distinct mechanisms for bilirubin glucuronide transport by rat bile canalicular membrane vesicles. Demonstration of defective ATP-dependent transport in rats (TR-) with inherited conjugated hyperbilirubinemia. J Clin Invest. 1992 Nov;90(5):2130-5. 1430236 Jowett TP, Slater JD: A radioimmunoassay for the measurement of tetrahydroaldosterone 3-glucosiduronic acid in human plasma. Clin Chim Acta. 1981 Jan 22;109(2):133-44. 7193539 Schmitt G, Aderjan R, Keller T, Wu M: Ethyl glucuronide: an unusual ethanol metabolite in humans. Synthesis, analytical data, and determination in serum and urine. J Anal Toxicol. 1995 Mar-Apr;19(2):91-4. 7769794 Karasawa E: [Supplementary findings on urinary glucuronic acid excretion in pediatrics. I. Total glucuronic acid in 24-hour urine of normal infants determined by the modified Fishman's method with NaBH4] Nippon Shonika Gakkai Zasshi. 1968 Aug 1;72(8):1122-7. 5755643 Carpenter PC, Mattox VR: Isolation, determination of structure and synthesis of the acid-labile conjugate of aldosterone. Biochem J. 1976 Jul 1;157(1):1-14. 962850 Raju U, Sklarew RJ, Post J, Levitz M: Steroid metabolism in human breast cancer cell lines. Steroids. 1978 Dec;32(5):669-80. 734701 Stearns RA, Miller RR, Doss GA, Chakravarty PK, Rosegay A, Gatto GJ, Chiu SH: The metabolism of DuP 753, a nonpeptide angiotensin II receptor antagonist, by rat, monkey, and human liver slices. Drug Metab Dispos. 1992 Mar-Apr;20(2):281-7. 1352222 Little JM, St Pyrek J, Lester R: Hepatic metabolism of 3 alpha-hydroxy-5 beta-etianic acid (3 alpha-hydroxy-5 beta-androstan-17 beta-carboxylic acid) in the adult rat. J Clin Invest. 1983 Jan;71(1):73-80. 6848561 Pfeiffer E, Graf E, Gerstner S, Metzler M: Stimulation of estradiol glucuronidation: a protective mechanism against estradiol-mediated carcinogenesis? Mol Nutr Food Res. 2006 Apr;50(4-5):385-9. 16598814 McDonagh AF, Palma LA, Lauff JJ, Wu TW: Origin of mammalian biliprotein and rearrangement of bilirubin glucuronides in vivo in the rat. J Clin Invest. 1984 Sep;74(3):763-70. 6470139 Murano PS, Robichaud VY, Webb RE: Urinary excretion of sulfate and glucuronate conjugates in a free living population of adult males. Bull Environ Contam Toxicol. 1989 Jul;43(1):13-6. 2758129 Hamayasu, Kenichi; Tadokoro, Hiroki; Kishino, Eriko; Ito, Tetsuya; Fujita, Koki; Hara, Kozo. Preparation of glucuronic acid and/or glucuronolactone from sucrose. PCT Int. Appl. (2006), 21pp. http://hmdb.ca/system/metabolites/msds/000/000/088/original/HMDB00127.pdf?1358462123 Beta-glucuronidase P05804 BGLR_ECOLI uidA http://ecmdb.ca/proteins/P05804.xml 2-keto-3-deoxygluconate permease P0A712 KDGT_ECOLI kdgT http://ecmdb.ca/proteins/P0A712.xml Uronate isomerase P0A8G3 UXAC_ECOLI uxaC http://ecmdb.ca/proteins/P0A8G3.xml 2-keto-3-deoxygluconate permease P0A712 KDGT_ECOLI kdgT http://ecmdb.ca/proteins/P0A712.xml Hexuronate transporter P0AA78 EXUT_ECOLI exuT http://ecmdb.ca/proteins/P0AA78.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml D-Glucuronic acid <> D-Fructuronate R01482 GLUCUROISOM-RXN Water + beta-D-Glucuronoside + beta-D-Glucuronoside <> D-Glucuronic acid + Alcohol + Alcohol R01478 Bilirubin diglucuronide + 2 Water + 3 Reduced acceptor <> D-Urobilinogen +2 D-Glucuronic acid +3 Acceptor R04979 G13040 + Water <> G09660 + D-Glucuronic acid R07818 Luteolin 7-O-[beta-D-glucuronosyl-(1->2)-beta-D-glucuronide]-4'-O-beta-D-glucuronide + Water <> Luteolin 7-O-[beta-D-glucuronosyl-(1->2)-beta-D-glucuronide] + D-Glucuronic acid R08127 SN38 glucuronide + Water <> SN-38 + D-Glucuronic acid R08260 Water + a &beta;-D-glucuronoside > D-Glucuronic acid + an alcohol BETA-GLUCURONID-RXN A beta-D-glucuronoside + Water > D-Glucuronic acid + an alcohol D-Glucuronic acid > D-Fructuronate Bilirubin diglucuronide + Water > D-Glucuronic acid + Ribitol + Ribitol PW_R003834