2.0 2012-05-31 13:00:09 -0600 2015-09-13 12:56:08 -0600 ECMDB00663 M2MDB000168 Glucaric acid Glucaric acid is a sugar acid derived from D-glucose in which both the aldehydic carbon atom and the carbon atom bearing the primary hydroxyl group are oxidized to carboxylic acid groups. (2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioate (2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioic acid (D)-glucarate (D)-glucarate (D)-glucaric acid D-glucarate D-(+)-Saccharate D-(+)-Saccharic acid D-Glucarate D-Glucaric acid D-Glucosaccharate D-Glucosaccharic acid D-Saccharate D-Saccharic acid D-Tetrahydroxyadipate D-Tetrahydroxyadipic acid DL-Glucarate DL-glucaric acid GKR Glucarate Glucaric acid Glucosaccharate Glucosaccharic acid L-Gularate L-Gularic acid Saccharate Saccharate (6CI) Saccharic acid Saccharic acid (6CI) Tetrahydroxyadipate Tetrahydroxyadipic acid C6H10O8 210.1388 210.037567296 (2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioic acid saccharic acid 87-73-0 OC(C(O)C(O)C(O)=O)C(O)C(O)=O InChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14) DSLZVSRJTYRBFB-UHFFFAOYSA-N Cytosol Extra-organism Periplasm logp -1.77 ALOGPS logs -0.52 ALOGPS solubility 6.31e+01 g/l ALOGPS logp -3.1 ChemAxon pka_strongest_acidic 2.83 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioic acid ChemAxon average_mass 210.1388 ChemAxon mono_mass 210.037567296 ChemAxon smiles OC(C(O)C(O)C(O)=O)C(O)C(O)=O ChemAxon formula C6H10O8 ChemAxon inchi InChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14) ChemAxon inchikey DSLZVSRJTYRBFB-UHFFFAOYSA-N ChemAxon polar_surface_area 155.52 ChemAxon refractivity 38.14 ChemAxon polarizability 16.8 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 8 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Ascorbate and aldarate metabolism ec00053 Metabolic pathways eco01100 superpathway of D-glucarate and D-galactarate degradation Galactarate is a naturally occurring dicarboxylic acid analog of D-galactose. E. coli can use both diacid sugars galactarate and D-glucarate as the sole source of carbon for growth. The initial step in the degradation of galactarate is its dehydration to 5-dehydro-4-deoxy-D-glucarate(2--) by galactarate dehydratase. Glucaric acid can also be dehydrated by a glucarate dehydratase resulting in water and 5-dehydro-4-deoxy-D-glucarate(2--). The 5-dehydro-4-deoxy-D-glucarate(2--) is then metabolized by a alpha-dehydro-beta-deoxy-D-glucarate aldolase resulting in pyruvic acid and a tartonate semialdehyde. Pyruvic acid interacts with coenzyme A through a NAD driven Pyruvate dehydrogenase complex resulting in a carbon dioxide, an NADH and an acetyl-CoA. The tartronate semialdehyde interacts with a hydrogen ion through a NADPH driven tartronate semialdehyde reductase resulting in a NADP and a glyceric acid. The glyceric acid is phosphorylated by an ATP-driven glycerate kinase 2 resulting in an ADP, a hydrogen ion and a 2-phosphoglyceric acid. The latter compound is dehydrated by an enolase resulting in the release of water and a phosphoenolpyruvic acid. The phosphoenolpyruvic acid interacts with a hydrogen ion through an ADP driven pyruvate kinase resulting in an ATP and a pyruvic acid. The pyruvic acid then interacts with water and an ATP through a phosphoenolpyruvate synthetase resulting in the release of a hydrogen ion, a phosphate, an AMP and a Phosphoenolpyruvic acid. PW000795 Metabolic D-glucarate degradation I GLUCARDEG-PWY Specdb::CMs 592 Specdb::CMs 593 Specdb::CMs 594 Specdb::CMs 595 Specdb::CMs 1730 Specdb::CMs 6577 Specdb::CMs 30515 Specdb::CMs 31186 Specdb::CMs 31884 Specdb::CMs 37680 Specdb::CMs 136142 Specdb::CMs 143876 Specdb::CMs 146727 Specdb::CMs 146729 Specdb::CMs 146731 Specdb::CMs 279535 Specdb::CMs 1072024 Specdb::CMs 1072026 Specdb::CMs 1072028 Specdb::CMs 1072030 Specdb::CMs 1072031 Specdb::CMs 1072033 Specdb::CMs 1072035 Specdb::CMs 1072037 Specdb::CMs 1072039 Specdb::NmrOneD 1462 Specdb::NmrOneD 144770 Specdb::NmrOneD 144771 Specdb::NmrOneD 144772 Specdb::NmrOneD 144773 Specdb::NmrOneD 144774 Specdb::NmrOneD 144775 Specdb::NmrOneD 144776 Specdb::NmrOneD 144777 Specdb::NmrOneD 144778 Specdb::NmrOneD 144779 Specdb::NmrOneD 144780 Specdb::NmrOneD 144781 Specdb::NmrOneD 144782 Specdb::NmrOneD 144783 Specdb::NmrOneD 144784 Specdb::NmrOneD 144785 Specdb::NmrOneD 144786 Specdb::NmrOneD 144787 Specdb::NmrOneD 144788 Specdb::NmrOneD 144789 Specdb::MsMs 906 Specdb::MsMs 907 Specdb::MsMs 908 Specdb::MsMs 4342 Specdb::MsMs 4343 Specdb::MsMs 4344 Specdb::MsMs 4345 Specdb::MsMs 4346 Specdb::MsMs 248451 Specdb::MsMs 248452 Specdb::MsMs 248453 Specdb::MsMs 268392 Specdb::MsMs 268393 Specdb::MsMs 268394 Specdb::MsMs 438446 Specdb::MsMs 438447 Specdb::MsMs 438448 Specdb::MsMs 438449 Specdb::MsMs 438450 Specdb::MsMs 440113 Specdb::MsMs 451950 Specdb::MsMs 2244193 Specdb::MsMs 2245885 Specdb::MsMs 2246381 Specdb::MsMs 2247922 Specdb::NmrTwoD 1030 Specdb::NmrTwoD 1407 HMDB00663 587 C00818 17301 D-GLUCARATE Glucaric 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 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 Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC. http://hmdb.ca/system/metabolites/msds/000/000/582/original/HMDB00663.pdf?1358462448 Glucarate dehydratase P0AES2 GUDH_ECOLI gudD http://ecmdb.ca/proteins/P0AES2.xml Glucarate dehydratase-related protein Q46915 GUDX_ECOLI gudX http://ecmdb.ca/proteins/Q46915.xml Probable glucarate transporter Q46916 GUDP_ECOLI gudP http://ecmdb.ca/proteins/Q46916.xml Probable galactarate transporter P0AA80 GARP_ECOLI garP http://ecmdb.ca/proteins/P0AA80.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 Glucaric acid > 5-Dehydro-4-deoxy-D-glucarate + Water GLUCARDEHYDRA-RXN L-idarate <> Glucaric acid RXN0-5285 D-Glucarate + Glucaric acid <> 5-Dehydro-4-deoxy-D-glucarate + Water R02752 D-Glucaric acid + Glucaric acid > Water + 5-dehydro-4-deoxy-D-glucarate(2−) PW_R002724 Glucaric acid > Water + 2-Dehydro-3-deoxy-D-glucarate PW_R005867