2.02012-05-31 14:04:13 -06002015-09-13 12:56:13 -0600ECMDB04073M2MDB000596D-Glucuronic acidGlucuronic 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-Glucopyranuronatea-D-Glucopyranuronic acida-D-Glucuronatea-D-Glucuronic acida-delta-Glucopyranuronatea-delta-Glucopyranuronic acida-delta-Glucuronatea-delta-Glucuronic acida-δ-Glucopyranuronatea-δ-Glucopyranuronic acida-δ-Glucuronatea-δ-Glucuronic acidAlpha-D-GlucopyranuronateAlpha-D-Glucopyranuronic acidAlpha-D-GlucuronateAlpha-D-Glucuronic acidAlpha-delta-GlucopyranuronateAlpha-delta-Glucopyranuronic acidAlpha-delta-GlucuronateAlpha-delta-Glucuronic acidD-(+)-GlucuronateD-(+)-Glucuronic acidD-GlucopyranuronateD-glucopyranuronic acidD-GlucuronateD-Glucuronic acidDelta-(+)-GlucuronateDelta-(+)-Glucuronic acidDelta-GlucuronateDelta-Glucuronic acidGCUGlcAGlucosiduronateGlucosiduronic acidGlucuronateGlucuronic acidα-D-Glucopyranuronateα-D-Glucopyranuronic acidα-D-Glucuronateα-D-Glucuronic acidα-δ-Glucopyranuronateα-δ-Glucopyranuronic acidα-δ-Glucuronateα-δ-Glucuronic acidδ-(+)-Glucuronateδ-(+)-Glucuronic acidδ-Glucuronateδ-Glucuronic acidC6H10O7194.1394194.042652674(2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acidglucuronic acid6556-12-3O[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=OInChI=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/s1AEMOLEFTQBMNLQ-WAXACMCWSA-NSolidCytosolExtra-organismPeriplasmlogp-2.30logs0.18solubility2.95e+02 g/lmelting_point143-144 oClogp-2.6pka_strongest_acidic3.21pka_strongest_basic-3.7iupac(2S,3S,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acidaverage_mass194.1394mono_mass194.042652674smilesO[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=OformulaC6H10O7inchiInChI=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/s1inchikeyAEMOLEFTQBMNLQ-WAXACMCWSA-Npolar_surface_area127.45refractivity35.79polarizability16.32rotatable_bond_count1acceptor_count7donor_count5physiological_charge-1formal_charge0Starch and sucrose metabolismThe 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-phosphatePW000941ec00500MetabolicAscorbate and aldarate metabolismec00053Amino sugar and nucleotide sugar metabolismec00520Glycosaminoglycan degradationec00531Pentose and glucuronate interconversionsec00040Drug metabolism - other enzymesec00983Porphyrin and chlorophyll metabolismec00860Flavone and flavonol biosynthesisec00944Inositol phosphate metabolismec00562Metabolic pathwayseco01100β-D-glucuronide and D-glucuronate degradationGLUCUROCAT-PWYSpecdb::CMs24385Specdb::CMs37309Specdb::CMs172924Specdb::CMs1051028Specdb::CMs1051030Specdb::CMs1051032Specdb::CMs1051034Specdb::CMs1051036Specdb::CMs1051037Specdb::CMs1051039Specdb::CMs1051041Specdb::CMs1051043Specdb::CMs1051045Specdb::CMs1051047Specdb::CMs1051049Specdb::CMs1051050Specdb::CMs1051052Specdb::CMs1051054Specdb::CMs1051056Specdb::CMs1051058Specdb::CMs1051060Specdb::CMs1051062Specdb::CMs1051064Specdb::CMs1051066Specdb::CMs1051067Specdb::NmrOneD1098Specdb::NmrOneD1156Specdb::NmrOneD142390Specdb::NmrOneD142391Specdb::NmrOneD142392Specdb::NmrOneD142393Specdb::NmrOneD142394Specdb::NmrOneD142395Specdb::NmrOneD142396Specdb::NmrOneD142397Specdb::NmrOneD142398Specdb::NmrOneD142399Specdb::NmrOneD142400Specdb::NmrOneD142401Specdb::NmrOneD142402Specdb::NmrOneD142403Specdb::NmrOneD142404Specdb::NmrOneD142405Specdb::NmrOneD142406Specdb::NmrOneD142407Specdb::NmrOneD142408Specdb::NmrOneD142409Specdb::NmrOneD166527Specdb::MsMs192Specdb::MsMs193Specdb::MsMs319990Specdb::MsMs319991Specdb::MsMs319992Specdb::MsMs367270Specdb::MsMs367271Specdb::MsMs367272Specdb::MsMs2236268Specdb::MsMs2237099Specdb::MsMs2238362Specdb::MsMs2239234Specdb::MsMs2242475Specdb::MsMs2243401Specdb::MsMs2413042Specdb::MsMs2413043Specdb::MsMs2413044Specdb::MsMs2552132Specdb::MsMs2552133Specdb::MsMs2552134Specdb::NmrTwoD1156HMDB00127444791392615C00191GLUCURONATEGCUGCUKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510van 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 370:17-25.17765195Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). 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PCT Int. Appl. (2006), 21pp.http://hmdb.ca/system/metabolites/msds/000/000/088/original/HMDB00127.pdf?1358462123Beta-glucuronidaseP05804BGLR_ECOLIuidAhttp://ecmdb.ca/proteins/P05804.xml2-keto-3-deoxygluconate permeaseP0A712KDGT_ECOLIkdgThttp://ecmdb.ca/proteins/P0A712.xmlUronate isomeraseP0A8G3UXAC_ECOLIuxaChttp://ecmdb.ca/proteins/P0A8G3.xml2-keto-3-deoxygluconate permeaseP0A712KDGT_ECOLIkdgThttp://ecmdb.ca/proteins/P0A712.xmlHexuronate transporterP0AA78EXUT_ECOLIexuThttp://ecmdb.ca/proteins/P0AA78.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlD-Glucuronic acid <> D-FructuronateR01482GLUCUROISOM-RXNWater + beta-D-Glucuronoside + beta-D-Glucuronoside <> D-Glucuronic acid + Alcohol + AlcoholR01478Bilirubin diglucuronide + 2 Water + 3 Reduced acceptor <> D-Urobilinogen +2 D-Glucuronic acid +3 AcceptorR04979G13040 + Water <> G09660 + D-Glucuronic acidR07818Luteolin 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 acidR08127SN38 glucuronide + Water <> SN-38 + D-Glucuronic acidR08260Water + a β-D-glucuronoside > D-Glucuronic acid + an alcoholBETA-GLUCURONID-RXNA beta-D-glucuronoside + Water > D-Glucuronic acid + an alcoholD-Glucuronic acid > D-FructuronateBilirubin diglucuronide + Water > D-Glucuronic acid + Ribitol + RibitolPW_R003834