1.0 2011-09-21 00:37:21 UTC 2024-11-29 22:26:18 UTC FDB023950 2,3-Diketo-L-gulonate 2,3-Diketo-L-gulonate is an intermediate in Ascorbate and aldarate metabolism. 2,3-Diketo-L-gulonate is produced from Dehydroascorbate and then converted to L-Xylonate via the enzyme Lyases (EC 4.1.1.-). [HMDB] Diketogulonic acid (DKG) is a metabolite of the degradation of vitamin C, the nonenzymatic hydrolysis-product of dehydroascorbate. Dehydroascorbate can be reduced back to ascorbate or hydrolyzed to DKG; the latter reaction is irreversible and DKG is devoid of antiscorbutic activity. The degradation pathway of vitamin C continues to produce l-erythrulose and oxalate as final products. DKG appears in human urine and represents approximately 20% of the vitamin C by-products (oxalate being approximately 44% and dehydroascorbate 20%). A major catabolic event in man is the cleavage of the molecule (presumably a spontaneous cleavage of DKG) between C2 and C3, with little if any decarboxylation. The oxalate formed in this way may contribute to the formation of kidney stones in susceptible individuals. However, the association between ascorbate supplementation and increased risk of kidney stone formation remains a matter of controversy. (PMID: 16698813, 17222174) [HMDB] (4R,5S)-4,5,6-Trihydroxy-2,3-dioxohexanoate (4R,5S)-4,5,6-Trihydroxy-2,3-dioxohexanoic acid 2,3-Diketo-L gulonic acid 2,3-Diketo-L-gulonic acid 2,3-Diketogulonic acid 2,3-Dioxo-D-gulonate Diketogulonate Diketogulonic acid L-threo-2,3-Hexodiulosonic acid L-threo-Hexo-2,3-diulosonic acid C6H8O7 192.1235 192.02700261 (5S)-4,5,6-trihydroxy-2,3-dioxohexanoic acid (5S)-4,5,6-trihydroxy-2,3-dioxohexanoic acid 3445-22-5 OC[C@H](O)C(O)C(=O)C(=O)C(O)=O InChI=1S/C6H8O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-3,7-9H,1H2,(H,12,13)/t2-,3?/m0/s1 GJQWCDSAOUMKSE-SCQFTWEKSA-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. Sugar acids and derivatives Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic acyclic compounds Acyloins Alpha-diketones Alpha-hydroxy ketones Alpha-keto acids and derivatives Beta-hydroxy ketones Beta-keto acids and derivatives Carboxylic acids Hexoses Hydrocarbon derivatives Medium-chain keto acids and derivatives Monocarboxylic acids and derivatives Organic oxides Polyols Primary alcohols Secondary alcohols Acyloin Alcohol Aliphatic acyclic compound Alpha-diketone Alpha-hydroxy ketone Alpha-keto acid Beta-hydroxy ketone Beta-keto acid Carbonyl group Carboxylic acid Carboxylic acid derivative Hexose monosaccharide Hydrocarbon derivative Keto acid Ketone Medium-chain keto acid Monocarboxylic acid or derivatives Monosaccharide Organic oxide Polyol Primary alcohol Secondary alcohol Sugar acid Solid logp -1.77 ALOGPS logs -0.51 ALOGPS solubility 5.99e+01 g/l ALOGPS logp -1.6 ChemAxon pka_strongest_acidic 2.38 ChemAxon pka_strongest_basic -3 ChemAxon iupac (5S)-4,5,6-trihydroxy-2,3-dioxohexanoic acid ChemAxon average_mass 192.1235 ChemAxon mono_mass 192.02700261 ChemAxon smiles OC[C@H](O)C(O)C(=O)C(=O)C(O)=O ChemAxon formula C6H8O7 ChemAxon inchi InChI=1S/C6H8O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-3,7-9H,1H2,(H,12,13)/t2-,3?/m0/s1 ChemAxon inchikey GJQWCDSAOUMKSE-SCQFTWEKSA-N ChemAxon polar_surface_area 132.13 ChemAxon refractivity 37.04 ChemAxon polarizability 15.77 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Metabolism and Physiological Effects of Oxalic acid SMP0124875 Specdb::CMs 9927 Specdb::CMs 39031 Specdb::CMs 161176 Specdb::MsMs 287950 Specdb::MsMs 287951 Specdb::MsMs 287952 Specdb::MsMs 326920 Specdb::MsMs 326921 Specdb::MsMs 326922 Specdb::MsMs 2691722 Specdb::MsMs 2691723 Specdb::MsMs 2691724 Specdb::MsMs 2989793 Specdb::MsMs 2989794 Specdb::MsMs 2989795 Specdb::NmrOneD 150260 Specdb::NmrOneD 150261 Specdb::NmrOneD 150262 Specdb::NmrOneD 150263 Specdb::NmrOneD 150264 Specdb::NmrOneD 150265 Specdb::NmrOneD 150266 Specdb::NmrOneD 150267 Specdb::NmrOneD 150268 Specdb::NmrOneD 150269 Specdb::NmrOneD 150270 Specdb::NmrOneD 150271 Specdb::NmrOneD 150272 Specdb::NmrOneD 150273 Specdb::NmrOneD 150274 Specdb::NmrOneD 150275 Specdb::NmrOneD 150276 Specdb::NmrOneD 150277 Specdb::NmrOneD 150278 Specdb::NmrOneD 150279 HMDB06511 15622 Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823