2.02012-05-31 13:00:09 -06002015-09-13 12:56:08 -0600ECMDB00663M2MDB000168Glucaric acidGlucaric 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(<i>D</i>)-glucarate(D)-glucarate(D)-glucaric acid<i>D</i>-glucarateD-(+)-SaccharateD-(+)-Saccharic acidD-GlucarateD-Glucaric acidD-GlucosaccharateD-Glucosaccharic acidD-SaccharateD-Saccharic acidD-TetrahydroxyadipateD-Tetrahydroxyadipic acidDL-GlucarateDL-glucaric acidGKRGlucarateGlucaric acidGlucosaccharateGlucosaccharic acidL-GularateL-Gularic acidSaccharateSaccharate (6CI)Saccharic acidSaccharic acid (6CI)TetrahydroxyadipateTetrahydroxyadipic acidC6H10O8210.1388210.037567296(2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioic acidsaccharic acid87-73-0OC(C(O)C(O)C(O)=O)C(O)C(O)=OInChI=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-NCytosolExtra-organismPeriplasmlogp-1.77logs-0.52solubility6.31e+01 g/llogp-3.1pka_strongest_acidic2.83pka_strongest_basic-3.7iupac(2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioic acidaverage_mass210.1388mono_mass210.037567296smilesOC(C(O)C(O)C(O)=O)C(O)C(O)=OformulaC6H10O8inchiInChI=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)inchikeyDSLZVSRJTYRBFB-UHFFFAOYSA-Npolar_surface_area155.52refractivity38.14polarizability16.8rotatable_bond_count5acceptor_count8donor_count6physiological_charge-2formal_charge0Ascorbate and aldarate metabolismec00053Metabolic pathwayseco01100superpathway 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.PW000795Metabolic<i>D</i>-glucarate degradation IGLUCARDEG-PWYSpecdb::CMs592Specdb::CMs593Specdb::CMs594Specdb::CMs595Specdb::CMs1730Specdb::CMs6577Specdb::CMs30515Specdb::CMs31186Specdb::CMs31884Specdb::CMs37680Specdb::CMs136142Specdb::CMs143876Specdb::CMs146727Specdb::CMs146729Specdb::CMs146731Specdb::CMs279535Specdb::CMs1072024Specdb::CMs1072026Specdb::CMs1072028Specdb::CMs1072030Specdb::CMs1072031Specdb::CMs1072033Specdb::CMs1072035Specdb::CMs1072037Specdb::CMs1072039Specdb::NmrOneD1462Specdb::NmrOneD144770Specdb::NmrOneD144771Specdb::NmrOneD144772Specdb::NmrOneD144773Specdb::NmrOneD144774Specdb::NmrOneD144775Specdb::NmrOneD144776Specdb::NmrOneD144777Specdb::NmrOneD144778Specdb::NmrOneD144779Specdb::NmrOneD144780Specdb::NmrOneD144781Specdb::NmrOneD144782Specdb::NmrOneD144783Specdb::NmrOneD144784Specdb::NmrOneD144785Specdb::NmrOneD144786Specdb::NmrOneD144787Specdb::NmrOneD144788Specdb::NmrOneD144789Specdb::MsMs906Specdb::MsMs907Specdb::MsMs908Specdb::MsMs4342Specdb::MsMs4343Specdb::MsMs4344Specdb::MsMs4345Specdb::MsMs4346Specdb::MsMs248451Specdb::MsMs248452Specdb::MsMs248453Specdb::MsMs268392Specdb::MsMs268393Specdb::MsMs268394Specdb::MsMs438446Specdb::MsMs438447Specdb::MsMs438448Specdb::MsMs438449Specdb::MsMs438450Specdb::MsMs440113Specdb::MsMs451950Specdb::MsMs2244193Specdb::MsMs2245885Specdb::MsMs2246381Specdb::MsMs2247922Specdb::NmrTwoD1030Specdb::NmrTwoD1407HMDB00663587C0081817301D-GLUCARATEGlucaric acidKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510van 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 370:17-25.17765195Winder, 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 80:2939-2948.18331064Yannai, 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?1358462448Glucarate dehydrataseP0AES2GUDH_ECOLIgudDhttp://ecmdb.ca/proteins/P0AES2.xmlGlucarate dehydratase-related proteinQ46915GUDX_ECOLIgudXhttp://ecmdb.ca/proteins/Q46915.xmlProbable glucarate transporterQ46916GUDP_ECOLIgudPhttp://ecmdb.ca/proteins/Q46916.xmlProbable galactarate transporterP0AA80GARP_ECOLIgarPhttp://ecmdb.ca/proteins/P0AA80.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlGlucaric acid > 5-Dehydro-4-deoxy-D-glucarate + WaterGLUCARDEHYDRA-RXNL-idarate <> Glucaric acidRXN0-5285D-Glucarate + Glucaric acid <> 5-Dehydro-4-deoxy-D-glucarate + WaterR02752D-Glucaric acid + Glucaric acid > Water + 5-dehydro-4-deoxy-D-glucarate(2−)PW_R002724Glucaric acid > Water + 2-Dehydro-3-deoxy-D-glucaratePW_R005867