1.0 2016-09-30 22:33:48 UTC 2020-05-11 20:47:36 UTC BMDB0000625 BMDB00625 Gluconic acid Gluconic acid, also known as D-gluconate or dextronic acid, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Gluconic acid is a drug which is used for use as part of electrolyte supplementation in total parenteral nutrition [fda label]. Gluconic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Gluconic acid exists in all living species, ranging from bacteria to humans. In cattle, gluconic acid is involved in the metabolic pathway called the pentose phosphate pathway. (2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanoic acid D-Gluco-hexonic acid D-Gluconsaeure D-Glukonsaeure Dextronic acid Glycogenic acid Hexonic acid Maltonic acid D-Gluconate (2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanoate D-Gluco-hexonate Dextronate Glycogenate Hexonate Maltonate D-Gluconic acid Gluconate 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 GCO Glosanto Glyconate Glyconic acid Pentahydroxycaproate Pentahydroxycaproic acid Boron gluconate Gluconic acid, (113)indium-labeled Gluconic acid, calcium salt Gluconic acid, cesium(+3) salt Gluconic acid, lanthanum(+3) salt Gluconic acid, sodium salt Gluconic acid, strontium (2:1) salt Magnerot Manganese gluconate Sodium gluconate Zinc gluconate Gluconic acid, (159)dysprosium-labeled salt Gluconic acid, aluminum (3:1) salt Gluconic acid, ammonium salt Gluconic acid, magnesium (2:1) salt Gluconic acid, (14)C-labeled Gluconic acid, 1-(14)C-labeled Gluconic acid, 6-(14)C-labeled Gluconic acid, cobalt (2:1) salt Gluconic acid, copper salt Gluconic acid, manganese (2:1) salt Gluconic acid, potassium salt Gluconic acid, tin(+2) salt Gluconic acid, zinc salt Lithium gluconate Magnesium gluconate Gluconic acid, (99)technecium (5+) salt Gluconic acid, fe(+2) salt, dihydrate Gluconic acid, monolithium salt Gluconic acid, monopotassium salt Gluconic acid, monosodium salt 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 belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Sugar acids and derivatives Alpha hydroxy acids and derivatives Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Hydroxy fatty acids Medium-chain fatty acids Medium-chain hydroxy acids and derivatives Monocarboxylic acids and derivatives Monosaccharides Organic oxides Polyols Primary alcohols Secondary alcohols Alcohol Aliphatic acyclic compound Alpha-hydroxy acid Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Fatty acid Fatty acyl Gluconic_acid Hydrocarbon derivative Hydroxy acid Hydroxy fatty acid Medium-chain fatty acid Medium-chain hydroxy acid Monocarboxylic acid or derivatives Monosaccharide Organic oxide Polyol Primary alcohol Secondary alcohol Aliphatic acyclic compounds Uronic acids gluconic acid Solid melting_point 113 - 118 °C water_solubility 316 mg/mL at 25 °C MERCK INDEX (1996) logp -2.57 ALOGPS logs -0.09 ALOGPS 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 number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon 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 Specdb::MsIr 685 Specdb::MsIr 686 Specdb::MsIr 687 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 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Milk Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. 23438684 Milk Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. 25108860 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Prostate Tissue Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 FDB001980 DB13180 C00257 10240 10690 33198 GLUCONATE C00007303 Gluconic_acid 345 Anastassiadis, Savas; Morgunov, Igor G. Gluconic acid production. Recent Patents on Biotechnology (2007), 1(2), 167-180. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. 23438684 Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. 25108860