2.02012-05-31 10:22:01 -06002015-09-13 12:56:06 -0600ECMDB00150M2MDB000057GluconolactoneGluconolactone is a lactone or oxidized derivative of glucose. Gluconolactone is a polyhydroxy acid (PHA) that is capable of chelating metals and may also function by scavenging free radicals. When dissolved in water, it is partially hydrolysed to gluconic acid, with the balance between the lactone form and the acid form established as a chemical equilibrium. The rate of hydrolysis of gluconolactone is increased by heat and high pH. It is an intermediate in glucose and glucose-1-phosphate degradation.δ-gluconolactone1,5-D-Gluconolactone1,5-delta-Gluconolactone1,5-Gluconolactone1,5-δ-Gluconolactone3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-one3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-oneb-glucono-1,5-LactoneBeta-Glucono-1,5-LactoneD(+)-Gluconate g-lactoneD(+)-Gluconate gamma-lactoneD(+)-Gluconate γ-lactoneD(+)-Gluconic acid g-lactoneD(+)-Gluconic acid gamma-lactoneD(+)-Gluconic acid γ-lactoneD-(+)-Gluconate D-lactoneD-(+)-Gluconate-delta lactoneD-(+)-Gluconate-δ lactoneD-(+)-Gluconic acid D-lactoneD-(+)-Gluconic acid-delta lactoneD-(+)-Gluconic acid-δ lactoneD-AldonolactoneD-delta-GluconolactoneD-Gluconate 1,5-lactoneD-Gluconate D-lactoneD-Gluconate delta-lactoneD-Gluconate lactoneD-Gluconate δ-lactoneD-Gluconate-1,5-lactoneD-Gluconate-delta-lactoneD-Gluconate-δ-lactoneD-Gluconic acid 1,5-lactoneD-Gluconic acid D-lactoneD-Gluconic acid delta-lactoneD-Gluconic acid lactoneD-Gluconic acid δ-lactoneD-Gluconic acid-1,5-lactoneD-Gluconic acid-delta-lactoneD-Gluconic acid-δ-lactoneD-Gluconic delta-lactoneD-Gluconic δ-lactoneD-glucono-δ-lactoneD-Glucono-1,5-lactoneD-Glucono-D-lactoneD-Glucono-delta-lactoneD-glucono-δ-LactoneD-GluconolactoneD-δ-GluconolactoneDelta-(+)-Gluconate D-lactoneDelta-(+)-Gluconate-delta lactoneDelta-(+)-Gluconic acid D-lactoneDelta-(+)-Gluconic acid-delta lactoneDelta-AldonolactoneDelta-D-GluconolactoneDelta-delta-GluconolactoneDelta-Gluconate 1,5-lactoneDelta-Gluconate D-lactoneDelta-Gluconate delta-lactoneDelta-Gluconate lactoneDelta-Gluconate-1,5-lactonedelta-Gluconate-delta-lactoneDelta-Gluconic acid 1,5-lactoneDelta-Gluconic acid D-lactoneDelta-Gluconic acid delta-lactoneDelta-Gluconic acid lactoneDelta-Gluconic acid-1,5-lactoneDelta-Gluconic acid-delta-lactoneDelta-Gluconic delta-lactoneDelta-Glucono-1,5-lactoneDelta-Glucono-delta-lactoneDelta-GluconolactoneFujiglucong-GluconolactoneGamma-GluconolactoneGlucarolactoneGluconate lactoneGluconate, lactoneGluconic acid lactoneGluconic acid, lactoneGluconic delta-lactoneGluconic lactoneGluconic δ-lactoneGlucono 1,5-lactoneGlucono delta lactoneGlucono delta-lactoneglucono g-LactoneGlucono gamma-lactoneglucono γ-Lactoneglucono δ Lactoneglucono δ-LactoneGlucono-δ-lactoneGlucono-1,5-lactoneGlucono-delta-lactoneglucono-δ-LactoneGluconolactoneβ-glucono-1,5-Lactoneγ-Gluconolactoneδ-(+)-Gluconate D-lactoneδ-(+)-Gluconate-δ lactoneδ-(+)-Gluconic acid D-lactoneδ-(+)-Gluconic acid-δ lactoneδ-Aldonolactoneδ-D-Gluconolactoneδ-Gluconate 1,5-lactoneδ-Gluconate D-lactoneδ-Gluconate lactoneδ-Gluconate δ-lactoneδ-Gluconate-1,5-lactoneδ-Gluconate-δ-lactoneδ-Gluconic acid 1,5-lactoneδ-Gluconic acid D-lactoneδ-Gluconic acid lactoneδ-Gluconic acid δ-lactoneδ-Gluconic acid-1,5-lactoneδ-Gluconic acid-δ-lactoneδ-Gluconic δ-lactoneδ-glucono-1,5-Lactoneδ-glucono-δ-Lactoneδ-Gluconolactoneδ-δ-GluconolactoneC6H10O6178.14178.047738052(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-onegluconolactone90-80-2OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1OInChI=1S/C6H10O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-5,7-10H,1H2/t2-,3-,4+,5-/m1/s1PHOQVHQSTUBQQK-SQOUGZDYSA-NSolidCytoplasmPeriplasmlogp-2.16logs0.52solubility5.86e+02 g/lmelting_point151-155 oClogp-2.7pka_strongest_acidic11.62pka_strongest_basic-3iupac(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-oneaverage_mass178.14mono_mass178.047738052smilesOC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1OformulaC6H10O6inchiInChI=1S/C6H10O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-5,7-10H,1H2/t2-,3-,4+,5-/m1/s1inchikeyPHOQVHQSTUBQQK-SQOUGZDYSA-Npolar_surface_area107.22refractivity34.78polarizability15.53rotatable_bond_count1acceptor_count5donor_count4physiological_charge0formal_charge0Pentose phosphate pathwayec00030Microbial metabolism in diverse environmentsec01120glucose and glucose-1-phosphate degradationGLUCOSE1PMETAB-PWYSpecdb::CMs373Specdb::CMs374Specdb::CMs375Specdb::CMs1604Specdb::CMs7058Specdb::CMs31025Specdb::CMs37322Specdb::CMs131136Specdb::CMs138870Specdb::CMs1051593Specdb::CMs1051595Specdb::CMs1051596Specdb::CMs1051598Specdb::CMs1051600Specdb::CMs1051602Specdb::CMs1051604Specdb::CMs1051606Specdb::CMs1051608Specdb::CMs1051610Specdb::CMs1051612Specdb::CMs1051614Specdb::CMs1051616Specdb::CMs1051617Specdb::CMs1051619Specdb::CMs1051621Specdb::NmrOneD1111Specdb::NmrOneD1172Specdb::NmrOneD5872Specdb::NmrOneD5873Specdb::NmrOneD5874Specdb::NmrOneD5875Specdb::NmrOneD5876Specdb::NmrOneD5877Specdb::NmrOneD5878Specdb::NmrOneD5879Specdb::NmrOneD5880Specdb::NmrOneD5881Specdb::NmrOneD5882Specdb::NmrOneD5883Specdb::NmrOneD5884Specdb::NmrOneD5885Specdb::NmrOneD5886Specdb::NmrOneD5887Specdb::NmrOneD5888Specdb::NmrOneD5889Specdb::NmrOneD5890Specdb::NmrOneD5891Specdb::NmrOneD166448Specdb::MsMs227Specdb::MsMs228Specdb::MsMs229Specdb::MsMs251499Specdb::MsMs251500Specdb::MsMs251501Specdb::MsMs271440Specdb::MsMs271441Specdb::MsMs271442Specdb::MsMs2252713Specdb::MsMs2253751Specdb::MsMs2254826Specdb::MsMs2255763Specdb::MsMs2256885Specdb::MsMs2257693Specdb::MsMs2258858Specdb::MsMs2259730Specdb::MsMs2744826Specdb::MsMs2744827Specdb::MsMs2744828Specdb::MsMs2937073Specdb::MsMs2937074Specdb::MsMs2937075Specdb::NmrTwoD971Specdb::NmrTwoD1170HMDB0015070276760C0019816217GLC-D-LACTONELGCGluconolactoneKeseler, 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-D114.22080510Winder, 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 80:2939-2948.18331064Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599.19561621Rakotomanga S, Baillet A, Pellerin F, Baylocq-Ferrier D: Simultaneous determination of gluconolactone, galactonolactone and galactitol in urine by reversed-phase liquid chromatography: application to galactosemia. J Chromatogr. 1991 Oct 4;570(2):277-84.1797843Harkness RA, Purkiss P, Duffy S, Chalmers RA, Jones M: The effects of fetal energy depletion on amniotic fluid concentrations of amino acids, organic acids and related metabolites. J Inherit Metab Dis. 1988;11(1):103-13.3128683Hunt MJ, Barnetson RS: A comparative study of gluconolactone versus benzoyl peroxide in the treatment of acne. Australas J Dermatol. 1992;33(3):131-4.1303072Steinberg KK, Needham LL: A comparison of two methods for quantifying D-glucaric acid. J Anal Toxicol. 1986 Jul-Aug;10(4):139-41.3747452Friedrich T, Strohdeicher M, Hofhaus G, Preis D, Sahm H, Weiss H: The same domain motif for ubiquinone reduction in mitochondrial or chloroplast NADH dehydrogenase and bacterial glucose dehydrogenase. FEBS Lett. 1990 Jun 4;265(1-2):37-40.2142103Puri RN, Zhou FX, Colman RF, Colman RW: Plasmin-induced platelet aggregation is accompanied by cleavage of aggregin and indirectly mediated by calpain. Am J Physiol. 1990 Dec;259(6 Pt 1):C862-8.2148055van Weely S, Brandsma M, Strijland A, Tager JM, Aerts JM: Demonstration of the existence of a second, non-lysosomal glucocerebrosidase that is not deficient in Gaucher disease. Biochim Biophys Acta. 1993 Mar 24;1181(1):55-62.8457606MacNeil ML, Steinberg KK, Yeager PR, Smith SJ: A semiautomated procedure for urinary D-glucaric acid using a centrifugal analyzer. J Anal Toxicol. 1986 Jan-Feb;10(1):15-7.3951202Chu, Lijia. Technology for industrial production of d-gluconolactone. Shipin Kexue (Beijing, China) (1985), 66 13-14. http://hmdb.ca/system/metabolites/msds/000/000/103/original/HMDB00150.pdf?1358461559Quinoprotein glucose dehydrogenaseP15877DHG_ECOLIgcdhttp://ecmdb.ca/proteins/P15877.xmlD-Glucose + Ubiquinone-1 <> Gluconolactone + Ubiquinol-8R06620b-D-Glucose + a ubiquinone > Gluconolactone + a ubiquinolGLUCDEHYDROG-RXNGluconolactone + Water > Hydrogen ion + Gluconic acidGLUCONOLACT-RXNGluconolactone + Hydrogen ion <> b-D-GlucoseRXN0-6372D-Glucose + Ubiquinone-10 > Gluconolactone + Ubiquinol-1D-Glucose + Ubiquinone-1 <> Gluconolactone + Ubiquinol-8D-Glucose + Ubiquinone-1 <> Gluconolactone + Ubiquinol-8Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseShake flask and filter culture1040.0uM0.037 oCK12 NCM3722Mid-Log Phase41600000Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599.19561621