2.0 2012-05-31 10:22:01 -0600 2015-09-13 12:56:06 -0600 ECMDB00150 M2MDB000057 Gluconolactone Gluconolactone 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. &delta;-gluconolactone 1,5-D-Gluconolactone 1,5-delta-Gluconolactone 1,5-Gluconolactone 1,5-δ-Gluconolactone 3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-one 3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-one b-glucono-1,5-Lactone Beta-Glucono-1,5-Lactone D(+)-Gluconate g-lactone D(+)-Gluconate gamma-lactone D(+)-Gluconate γ-lactone D(+)-Gluconic acid g-lactone D(+)-Gluconic acid gamma-lactone D(+)-Gluconic acid γ-lactone D-(+)-Gluconate D-lactone D-(+)-Gluconate-delta lactone D-(+)-Gluconate-δ lactone D-(+)-Gluconic acid D-lactone D-(+)-Gluconic acid-delta lactone D-(+)-Gluconic acid-δ lactone D-Aldonolactone D-delta-Gluconolactone D-Gluconate 1,5-lactone D-Gluconate D-lactone D-Gluconate delta-lactone D-Gluconate lactone D-Gluconate δ-lactone D-Gluconate-1,5-lactone D-Gluconate-delta-lactone D-Gluconate-δ-lactone D-Gluconic acid 1,5-lactone D-Gluconic acid D-lactone D-Gluconic acid delta-lactone D-Gluconic acid lactone D-Gluconic acid δ-lactone D-Gluconic acid-1,5-lactone D-Gluconic acid-delta-lactone D-Gluconic acid-δ-lactone D-Gluconic delta-lactone D-Gluconic δ-lactone D-glucono-&delta;-lactone D-Glucono-1,5-lactone D-Glucono-D-lactone D-Glucono-delta-lactone D-glucono-δ-Lactone D-Gluconolactone D-δ-Gluconolactone Delta-(+)-Gluconate D-lactone Delta-(+)-Gluconate-delta lactone Delta-(+)-Gluconic acid D-lactone Delta-(+)-Gluconic acid-delta lactone Delta-Aldonolactone Delta-D-Gluconolactone Delta-delta-Gluconolactone Delta-Gluconate 1,5-lactone Delta-Gluconate D-lactone Delta-Gluconate delta-lactone Delta-Gluconate lactone Delta-Gluconate-1,5-lactone delta-Gluconate-delta-lactone Delta-Gluconic acid 1,5-lactone Delta-Gluconic acid D-lactone Delta-Gluconic acid delta-lactone Delta-Gluconic acid lactone Delta-Gluconic acid-1,5-lactone Delta-Gluconic acid-delta-lactone Delta-Gluconic delta-lactone Delta-Glucono-1,5-lactone Delta-Glucono-delta-lactone Delta-Gluconolactone Fujiglucon g-Gluconolactone Gamma-Gluconolactone Glucarolactone Gluconate lactone Gluconate, lactone Gluconic acid lactone Gluconic acid, lactone Gluconic delta-lactone Gluconic lactone Gluconic δ-lactone Glucono 1,5-lactone Glucono delta lactone Glucono delta-lactone glucono g-Lactone Glucono gamma-lactone glucono γ-Lactone glucono δ Lactone glucono δ-Lactone Glucono-&delta;-lactone Glucono-1,5-lactone Glucono-delta-lactone glucono-δ-Lactone Gluconolactone β-glucono-1,5-Lactone γ-Gluconolactone δ-(+)-Gluconate D-lactone δ-(+)-Gluconate-δ lactone δ-(+)-Gluconic acid D-lactone δ-(+)-Gluconic acid-δ lactone δ-Aldonolactone δ-D-Gluconolactone δ-Gluconate 1,5-lactone δ-Gluconate D-lactone δ-Gluconate lactone δ-Gluconate δ-lactone δ-Gluconate-1,5-lactone δ-Gluconate-δ-lactone δ-Gluconic acid 1,5-lactone δ-Gluconic acid D-lactone δ-Gluconic acid lactone δ-Gluconic acid δ-lactone δ-Gluconic acid-1,5-lactone δ-Gluconic acid-δ-lactone δ-Gluconic δ-lactone δ-glucono-1,5-Lactone δ-glucono-δ-Lactone δ-Gluconolactone δ-δ-Gluconolactone C6H10O6 178.14 178.047738052 (3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one gluconolactone 90-80-2 OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O InChI=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/s1 PHOQVHQSTUBQQK-SQOUGZDYSA-N Solid Cytoplasm Periplasm logp -2.16 ALOGPS logs 0.52 ALOGPS solubility 5.86e+02 g/l ALOGPS melting_point 151-155 oC logp -2.7 ChemAxon pka_strongest_acidic 11.62 ChemAxon pka_strongest_basic -3 ChemAxon iupac (3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one ChemAxon average_mass 178.14 ChemAxon mono_mass 178.047738052 ChemAxon smiles OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C6H10O6 ChemAxon inchi InChI=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/s1 ChemAxon inchikey PHOQVHQSTUBQQK-SQOUGZDYSA-N ChemAxon polar_surface_area 107.22 ChemAxon refractivity 34.78 ChemAxon polarizability 15.53 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Pentose phosphate pathway ec00030 Microbial metabolism in diverse environments ec01120 glucose and glucose-1-phosphate degradation GLUCOSE1PMETAB-PWY Specdb::CMs 373 Specdb::CMs 374 Specdb::CMs 375 Specdb::CMs 1604 Specdb::CMs 7058 Specdb::CMs 31025 Specdb::CMs 37322 Specdb::CMs 131136 Specdb::CMs 138870 Specdb::CMs 1051593 Specdb::CMs 1051595 Specdb::CMs 1051596 Specdb::CMs 1051598 Specdb::CMs 1051600 Specdb::CMs 1051602 Specdb::CMs 1051604 Specdb::CMs 1051606 Specdb::CMs 1051608 Specdb::CMs 1051610 Specdb::CMs 1051612 Specdb::CMs 1051614 Specdb::CMs 1051616 Specdb::CMs 1051617 Specdb::CMs 1051619 Specdb::CMs 1051621 Specdb::NmrOneD 1111 Specdb::NmrOneD 1172 Specdb::NmrOneD 5872 Specdb::NmrOneD 5873 Specdb::NmrOneD 5874 Specdb::NmrOneD 5875 Specdb::NmrOneD 5876 Specdb::NmrOneD 5877 Specdb::NmrOneD 5878 Specdb::NmrOneD 5879 Specdb::NmrOneD 5880 Specdb::NmrOneD 5881 Specdb::NmrOneD 5882 Specdb::NmrOneD 5883 Specdb::NmrOneD 5884 Specdb::NmrOneD 5885 Specdb::NmrOneD 5886 Specdb::NmrOneD 5887 Specdb::NmrOneD 5888 Specdb::NmrOneD 5889 Specdb::NmrOneD 5890 Specdb::NmrOneD 5891 Specdb::NmrOneD 166448 Specdb::MsMs 227 Specdb::MsMs 228 Specdb::MsMs 229 Specdb::MsMs 251499 Specdb::MsMs 251500 Specdb::MsMs 251501 Specdb::MsMs 271440 Specdb::MsMs 271441 Specdb::MsMs 271442 Specdb::MsMs 2252713 Specdb::MsMs 2253751 Specdb::MsMs 2254826 Specdb::MsMs 2255763 Specdb::MsMs 2256885 Specdb::MsMs 2257693 Specdb::MsMs 2258858 Specdb::MsMs 2259730 Specdb::MsMs 2744826 Specdb::MsMs 2744827 Specdb::MsMs 2744828 Specdb::MsMs 2937073 Specdb::MsMs 2937074 Specdb::MsMs 2937075 Specdb::NmrTwoD 971 Specdb::NmrTwoD 1170 HMDB00150 7027 6760 C00198 16217 GLC-D-LACTONE LGC Gluconolactone Keseler, I. 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Shipin Kexue (Beijing, China) (1985), 66 13-14. http://hmdb.ca/system/metabolites/msds/000/000/103/original/HMDB00150.pdf?1358461559 Quinoprotein glucose dehydrogenase P15877 DHG_ECOLI gcd http://ecmdb.ca/proteins/P15877.xml D-Glucose + Ubiquinone-1 <> Gluconolactone + Ubiquinol-8 R06620 b-D-Glucose + a ubiquinone > Gluconolactone + a ubiquinol GLUCDEHYDROG-RXN Gluconolactone + Water > Hydrogen ion + Gluconic acid GLUCONOLACT-RXN Gluconolactone + Hydrogen ion <> b-D-Glucose RXN0-6372 D-Glucose + Ubiquinone-10 > Gluconolactone + Ubiquinol-1 D-Glucose + Ubiquinone-1 <> Gluconolactone + Ubiquinol-8 D-Glucose + Ubiquinone-1 <> Gluconolactone + Ubiquinol-8 Gutnick 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 glucose Shake flask and filter culture 1040.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 4160000 0 Bennett, 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