2.0 2012-05-31 10:27:58 -0600 2015-09-13 12:56:08 -0600 ECMDB00625 M2MDB000160 Gluconic acid Gluconic acid occurs naturally in fruit, honey and wine and is used as a food additive, an acidity regulator. It is also used in cleaning products where it helps cleaning up mineral deposits. It is a strong chelating agent, especially in alkaline solution. It chelates the anions of calcium, iron, aluminium, copper, and other heavy metals. Glucono delta lactone is a cyclic ester of D-gluconic acid. 2,3,4,5,6-Pentahydroxy-hexanoate 2,3,4,5,6-Pentahydroxy-hexanoic acid 2,3,4,5,6-Pentahydroxyhexanoate 2,3,4,5,6-Pentahydroxyhexanoic acid Aldonate Aldonic acid D-Gluco-hexonate D-Gluco-hexonic acid D-Gluconate D-Gluconic acid D-Gluconsaeure D-Glukonsaeure Dextronate Dextronic acid GCO Glosanto Gluconate Gluconic acid Glycogenate Glycogenic acid Glyconate Glyconic acid Hexonate Hexonic acid Maltonate Maltonic acid Pentahydroxycaproate Pentahydroxycaproic acid C6H12O7 196.1553 196.058302738 (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid gluconate 526-95-4 OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3-,4+,5-/m1/s1 RGHNJXZEOKUKBD-SQOUGZDYSA-N Solid Cytosol Extra-organism Periplasm logp -2.57 ALOGPS logs -0.09 ALOGPS solubility 1.59e+02 g/l ALOGPS melting_point 113-118 oC logp -3.4 ChemAxon pka_strongest_acidic 3.39 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid ChemAxon average_mass 196.1553 ChemAxon mono_mass 196.058302738 ChemAxon smiles OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O ChemAxon formula C6H12O7 ChemAxon inchi InChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3-,4+,5-/m1/s1 ChemAxon inchikey RGHNJXZEOKUKBD-SQOUGZDYSA-N ChemAxon polar_surface_area 138.45 ChemAxon refractivity 38.27 ChemAxon polarizability 17.15 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 7 ChemAxon donor_count 6 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Pentose phosphate pathway ec00030 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 ketogluconate metabolism PW002003 Metabolic glucose and glucose-1-phosphate degradation GLUCOSE1PMETAB-PWY ketogluconate metabolism KETOGLUCONMET-PWY D-gluconate degradation GLUCONSUPER-PWY L-idonate degradation IDNCAT-PWY Specdb::CMs 579 Specdb::CMs 580 Specdb::CMs 581 Specdb::CMs 1720 Specdb::CMs 3107 Specdb::CMs 30549 Specdb::CMs 31175 Specdb::CMs 32022 Specdb::CMs 32345 Specdb::CMs 37658 Specdb::CMs 135231 Specdb::CMs 142965 Specdb::CMs 146715 Specdb::CMs 279531 Specdb::CMs 1070454 Specdb::CMs 1070456 Specdb::CMs 1070457 Specdb::CMs 1070459 Specdb::CMs 1070461 Specdb::CMs 1070463 Specdb::CMs 1070464 Specdb::CMs 1070466 Specdb::CMs 1070468 Specdb::CMs 1070470 Specdb::CMs 1070471 Specdb::NmrOneD 1442 Specdb::NmrOneD 4873 Specdb::NmrOneD 4874 Specdb::NmrOneD 20482 Specdb::NmrOneD 20483 Specdb::NmrOneD 20484 Specdb::NmrOneD 20485 Specdb::NmrOneD 20486 Specdb::NmrOneD 20487 Specdb::NmrOneD 20488 Specdb::NmrOneD 20489 Specdb::NmrOneD 20490 Specdb::NmrOneD 20491 Specdb::NmrOneD 20492 Specdb::NmrOneD 20493 Specdb::NmrOneD 20494 Specdb::NmrOneD 20495 Specdb::NmrOneD 20496 Specdb::NmrOneD 20497 Specdb::NmrOneD 20498 Specdb::NmrOneD 20499 Specdb::NmrOneD 20500 Specdb::NmrOneD 20501 Specdb::MsMs 849 Specdb::MsMs 850 Specdb::MsMs 851 Specdb::MsMs 4235 Specdb::MsMs 4236 Specdb::MsMs 4237 Specdb::MsMs 4238 Specdb::MsMs 4239 Specdb::MsMs 179097 Specdb::MsMs 179098 Specdb::MsMs 179099 Specdb::MsMs 181422 Specdb::MsMs 181423 Specdb::MsMs 181424 Specdb::MsMs 437711 Specdb::MsMs 437712 Specdb::MsMs 437713 Specdb::MsMs 437714 Specdb::MsMs 437715 Specdb::MsMs 2226753 Specdb::MsMs 2226945 Specdb::MsMs 2227786 Specdb::MsMs 2227953 Specdb::MsMs 2229194 Specdb::MsMs 2230283 Specdb::NmrTwoD 1025 Specdb::NmrTwoD 1387 HMDB00625 10690 10240 C00257 33198 GLUCONATE GCO Gluconic acid 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 Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. 18402659 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 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 Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. 19212411 Harkness 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. 3128683 Anastassiadis, Savas; Morgunov, Igor G. Gluconic acid production. Recent Patents on Biotechnology (2007), 1(2), 167-180. http://hmdb.ca/system/metabolites/msds/000/000/544/original/HMDB00625.pdf?1358462617 Gluconate 5-dehydrogenase P0A9P9 IDNO_ECOLI idnO http://ecmdb.ca/proteins/P0A9P9.xml Quinoprotein glucose dehydrogenase P15877 DHG_ECOLI gcd http://ecmdb.ca/proteins/P15877.xml Glyoxylate/hydroxypyruvate reductase B P37666 GHRB_ECOLI ghrB http://ecmdb.ca/proteins/P37666.xml 2,3-diketo-L-gulonate reductase P37672 DLGD_ECOLI dlgD http://ecmdb.ca/proteins/P37672.xml Thermosensitive gluconokinase P39208 IDNK_ECOLI idnK http://ecmdb.ca/proteins/P39208.xml Thermoresistant gluconokinase P46859 GNTK_ECOLI gntK http://ecmdb.ca/proteins/P46859.xml Soluble aldose sugar dehydrogenase yliI P75804 YLII_ECOLI yliI http://ecmdb.ca/proteins/P75804.xml Gnt-II system L-idonate transporter P39344 IDNT_ECOLI idnT http://ecmdb.ca/proteins/P39344.xml High-affinity gluconate transporter P0AC94 GNTP_ECOLI gntP http://ecmdb.ca/proteins/P0AC94.xml Low-affinity gluconate transporter P0AC96 GNTU_ECOLI gntU http://ecmdb.ca/proteins/P0AC96.xml High-affinity gluconate transporter P39835 GNTT_ECOLI gntT http://ecmdb.ca/proteins/P39835.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 Ubiquinone-8 + D-Glucose + Water > Ubiquinol-8 + Gluconic acid + Hydrogen ion Adenosine triphosphate + Gluconic acid <> 6-Phosphogluconic acid + ADP + Hydrogen ion R01737 GLUCONOKIN-RXN 2 -Dehydro-L-gulonate + Hydrogen ion + NADH > Gluconic acid + NAD 2 -Dehydro-L-gulonate + Hydrogen ion + NADPH > Gluconic acid + NADP 5-Keto-D-gluconate + Hydrogen ion + NADPH <> Gluconic acid + NADP Adenosine triphosphate + Gluconic acid <> ADP + 6-Phosphogluconic acid R01737 GLUCONOKIN-RXN Gluconic acid + NADP <> 2-Keto-D-gluconic acid + NADPH + Hydrogen ion + 2-Dehydro-D-gluconate R01739 NADP + Gluconic acid <> Hydrogen ion + 2-Dehydro-D-gluconate + NADPH 1.1.1.215-RXN NAD(P)⁺ + Gluconic acid <> NAD(P)H + 5-Keto-D-gluconate + Hydrogen ion GLUCONATE-5-DEHYDROGENASE-RXN Adenosine triphosphate + Gluconic acid > Hydrogen ion + ADP + 6-Phosphogluconic acid GLUCONOKIN-RXN Gluconolactone + Water > Hydrogen ion + Gluconic acid GLUCONOLACT-RXN 6-Phosphogluconic acid + Water > Gluconic acid + Phosphate RXN0-5185 Gluconic acid + NADP > 2-Dehydro-D-gluconate + NADPH 1.1.1.215-RXN Adenosine triphosphate + Gluconic acid > ADP + 6-Phosphogluconic acid Gluconic acid + NAD(P)(+) > 5-Keto-D-gluconate + NAD(P)H Gluconic acid + NAD + NADP <> 5-Keto-D-gluconate + NADH + NADPH + Hydrogen ion R01738 R01740 2-Keto-L-gluconate + NADPH + Hydrogen ion + 2-Dehydro-D-gluconate + NADPH > Gluconic acid + NADP PW_R005689 5-Keto-D-gluconate + Hydrogen ion + NADPH + 5-Keto-D-gluconate + NADPH > NADP + Gluconic acid PW_R005687 Gluconic acid + Adenosine triphosphate > ADP + Hydrogen ion + gluconate 6-phosphate PW_R005694 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 41.6 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 166400 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