2.02012-05-31 14:04:40 -06002015-09-13 12:56:13 -0600ECMDB04088M2MDB000604Isocitric acidIsocitric acid is a protonated form of isocitrate, which is a substrate of the citric acid cycle. Isocitrate is formed from citrate with the help of the enzyme aconitase, and is acted upon by isocitrate dehydrogenase. Salts and esters of isocitric acid are known as isocitrates. (Wikipedia)(1<i>R</i>, 2<i>S</i>)-1-hydroxypropane-1,2,3-tricarboxylate(1R, 2S)-1-hydroxypropane-1,2,3-tricarboxylate(1R, 2S)-1-hydroxypropane-1,2,3-tricarboxylic acid1-Hydroxy-1,2,3-propanetricarboxylate1-Hydroxy-1,2,3-propanetricarboxylic acid1-Hydroxypropane-1,2,3-tricarboxylate1-Hydroxypropane-1,2,3-tricarboxylic acid1-Hydroxytricarballylate1-Hydroxytricarballylic acid3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylate3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acid3-Carboxy-2,3-dideoxy-Pentarate3-Carboxy-2,3-dideoxy-Pentaric acidD-<i>threo</i>-isocitric acidD-IsocitrateD-Isocitric acidD-Threo-isocitrateD-Threo-isocitric acidI-CITIsocitrateIsocitric acidThreo-D(S)-iso-citrateThreo-D(S)-iso-citric acidThreo-D<SUB>s</SUB>-isocitrateThreo-Ds-isocitrateThreo-Ds-isocitric acidC6H8O7192.1235192.027002611-hydroxypropane-1,2,3-tricarboxylic acidisocitric acid320-77-4OC(C(CC(O)=O)C(O)=O)C(O)=OInChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13)ODBLHEXUDAPZAU-UHFFFAOYSA-NSolidCytosollogp-0.35logs-0.56solubility5.25e+01 g/lmelting_point162-165 oClogp-1.4pka_strongest_acidic3.07pka_strongest_basic-4iupac1-hydroxypropane-1,2,3-tricarboxylic acidaverage_mass192.1235mono_mass192.02700261smilesOC(C(CC(O)=O)C(O)=O)C(O)=OformulaC6H8O7inchiInChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13)inchikeyODBLHEXUDAPZAU-UHFFFAOYSA-Npolar_surface_area132.13refractivity35.72polarizability15.55rotatable_bond_count5acceptor_count7donor_count4physiological_charge-3formal_charge0Glutathione metabolismThe biosynthesis of glutathione starts with the introduction of L-glutamic acid through either a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a
glutamate / aspartate ABC transporter. Once in the cytoplasm, L-glutamice acid reacts with L-cysteine through an ATP glutamate-cysteine ligase resulting in gamma-glutamylcysteine. This compound reacts which Glycine through an ATP driven glutathione synthetase thus catabolizing Glutathione.
This compound is metabolized through a spontaneous reaction with an oxidized glutaredoxin resulting in a reduced glutaredoxin and an oxidized glutathione. This compound is reduced by a NADPH glutathione reductase resulting in a glutathione.
PW000833ec00480MetabolicCitrate cycle (TCA cycle)ec00020Reductive carboxylate cycle (CO2 fixation)ec00720Glyoxylate and dicarboxylate metabolismec00630Microbial metabolism in diverse environmentsec01120Metabolic pathwayseco01100Secondary Metabolites: Glyoxylate cycleThe glyoxylate cycle starts with the interaction of Acetyl-Coa with a water molecule and Oxalacetic acid interact through a Citrate synthase resulting in a release of a coenzyme a and citric acid. The citric acid gets dehydrated through a citrate hydro-lyase resulting in the release of a water molecule and cis-Aconitic acid. The cis-Aconitic acid is then hydrated in an reversible reaction through an aconitate hydratase resulting in an Isocitric acid. The isocitric acid then interacts in a reversible reaction through isocitrate lyase resulting in the release of a succinic acid and a glyoxylic acid. The glyoxylic acid then reacts in a reversible reaction with an acetyl-coa, and a water molecule in a reversible reaction, resulting in a release of a coenzyme A, a hydrogen ion and an L-malic acid. The L-malic acid interacts in a reversible reaction through a NAD driven malate dehydrogenase resulting in the release of NADH, a hydrogen ion and an Oxalacetic acid.PW000967Metabolicglycolate and glyoxylate degradation IIOxaloglycolate (2-Hydroxy-3-oxosuccinate) interacts with a tartrate dehydrogenase resulting in a L-tartrate. L-tartrate then interacts with tartrate dehydrogenase resulting in a Oxaloacetate. Oxaloacetate and acetyl-coa interact to result in a citrate which is processed by a aconitate hydratase resulting in a cis-Aconitate and further more into a isocitrate which will eventually be procressed into a glyoxylic acid. Glyoxylic acid can either be metabolized into L-malic acid by a reaction with acetyl-CoA and Water through a malate synthase G which also releases hydrogen ion and Coenzyme A. L-malic acid is then incorporated into the TCA cycle. Glyoxylic acid can also be metabolized by glyoxylate carboligase, releasing a carbon dioxide and tartronate semialdehyde. The latter compound is then reduced by an NADH driven tartronate semialdehyde reductase 2 resulting in glyceric acid. Glyceric acid is phosphorylated by a glycerate kinase 2 resulting in a 3-phosphoglyceric acid. This compound is then integrated into various other pathways: cysteine biosynthesis, serine biosynthesis and glycolysis and pyruvate dehydrogenase.PW002021Metabolicmixed acid fermentationFERMENTATION-PWYrespiration (anaerobic)ANARESP1-PWYglyoxylate cycleGLYOXYLATE-BYPASSTCA cycle I (prokaryotic)TCASpecdb::CMs444Specdb::CMs445Specdb::CMs446Specdb::CMs447Specdb::CMs1485Specdb::CMs2897Specdb::CMs30196Specdb::CMs30299Specdb::CMs30863Specdb::CMs31062Specdb::CMs37349Specdb::CMs149653Specdb::CMs1053896Specdb::CMs1053898Specdb::CMs1053899Specdb::CMs1053901Specdb::CMs1053903Specdb::CMs1053905Specdb::CMs1053907Specdb::CMs1053908Specdb::CMs1053910Specdb::CMs1053912Specdb::CMs1053914Specdb::CMs1053916Specdb::CMs1053918Specdb::NmrOneD1169Specdb::NmrOneD142790Specdb::NmrOneD142791Specdb::NmrOneD142792Specdb::NmrOneD142793Specdb::NmrOneD142794Specdb::NmrOneD142795Specdb::NmrOneD142796Specdb::NmrOneD142797Specdb::NmrOneD142798Specdb::NmrOneD142799Specdb::NmrOneD142800Specdb::NmrOneD142801Specdb::NmrOneD142802Specdb::NmrOneD142803Specdb::NmrOneD142804Specdb::NmrOneD142805Specdb::NmrOneD142806Specdb::NmrOneD142807Specdb::NmrOneD142808Specdb::NmrOneD142809Specdb::MsMs3513Specdb::MsMs3514Specdb::MsMs3515Specdb::MsMs3516Specdb::MsMs3517Specdb::MsMs3518Specdb::MsMs3519Specdb::MsMs3520Specdb::MsMs3521Specdb::MsMs437925Specdb::MsMs437926Specdb::MsMs437927Specdb::MsMs437928Specdb::MsMs437929Specdb::MsMs438892Specdb::MsMs438893Specdb::MsMs440051Specdb::MsMs2244892Specdb::MsMs2245241Specdb::MsMs2247279Specdb::MsMs2248997Specdb::MsMs2249406Specdb::MsMs2250975Specdb::MsMs2251419Specdb::MsMs310Specdb::NmrTwoD1198HMDB0019311981161C0031116087THREO-DS-ISO-CITRATEIsocitric 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-D114.22080510Vijayendran, 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:R72.18402659van 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 80:2939-2948.18331064Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36.8579834Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69.8412012Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6.8087979Stromme JH, Borud O, Moe PJ: Fatal lactic acidosis in a newborn attributable to a congenital defect of pyruvate dehydrogenase. Pediatr Res. 1976 Jan;10(1):62-6.813176Sutor DJ, Percival JM, Doonan S: Isolation and identification of some urinary inhibitors of calcium phosphate formation. Clin Chim Acta. 1978 Oct 16;89(2):273-8.213213Ebeling K, Ruckhaberle KE, Bilek K: [Studies on the recording of cytostatic effects on organ cultures of squamous cell carcinoma of the uterine cervix] Zentralbl Gynakol. 1977;99(20):1249-59.595962Sutor DJ, Percival JM, Doonan S: Urinary inhibitor of the formation of calcium oxalate. Br J Urol. 1979 Aug;51(4):253-5.223711Hennequin C, Lalanne V, Daudon M, Lacour B, Drueke T: A new approach to studying inhibitors of calcium oxalate crystal growth. Urol Res. 1993 Mar;21(2):101-8.8389069Kavanagh JP: Isocitric and citric acid in human prostatic and seminal fluid: implications for prostatic metabolism and secretion. Prostate. 1994;24(3):139-42.8115279Mikosha AS, Monissarenko VP, Bychkovskaia LA: [Properties of adrenocortical isocitrate dehydrogenase] Vopr Med Khim. 1981 Nov-Dec;27(6):736-9.7336646Sutor DJ, Percival JM: The estimation of D-isocitric acid in urine using isocitrate dehydrogenase. Clin Chim Acta. 1978 Jun;86(2):223-5.657545Finogenova, T. V.; Kamzolova, S. V.; Dedyukhina, E. G.; Shishkanova, N. V.; Il'chenko, A. P.; Morgunov, I. G.; Chernyavskaya, O. G.; Sokolov, A. P. Biosynthesis of citric and isocitric acids from ethanol by mutant Yarrowia lipolytica N 1 under continuoushttp://hmdb.ca/system/metabolites/msds/000/000/136/original/HMDB00193.pdf?1358461634Isocitrate dehydrogenase [NADP]P08200IDH_ECOLIicdhttp://ecmdb.ca/proteins/P08200.xmlIsocitrate lyaseP0A9G6ACEA_ECOLIaceAhttp://ecmdb.ca/proteins/P0A9G6.xmlAconitate hydratase 1P25516ACON1_ECOLIacnAhttp://ecmdb.ca/proteins/P25516.xmlAconitate hydratase 2P36683ACON2_ECOLIacnBhttp://ecmdb.ca/proteins/P36683.xmlUncharacterized protein ybhJP75764YBHJ_ECOLIybhJhttp://ecmdb.ca/proteins/P75764.xmlcis-Aconitic acid + Water <> Isocitric acidR01900ACONITATEHYDR-RXNIsocitric acid + NADP <> alpha-Ketoglutarate + Carbon dioxide + NADPHR00267Isocitric acid <> Glyoxylic acid + Succinic acidR00479ISOCIT-CLEAV-RXNIsocitric acid + NADP <> alpha-Ketoglutarate + Carbon dioxide + NADPH + Hydrogen ionR00267Citric acid <> Isocitric acidR01324Isocitric acid + NADP <> Oxalosuccinic acid + NADPH + Hydrogen ionR01899Isocitric acid <> cis-Aconitic acid + WaterR01900Isocitric acid + NADP > NADPH + Oxoglutaric acid + Carbon dioxideISOCITDEH-RXNIsocitric acid + NADP > Oxalosuccinic acid + NADPH + Hydrogen ionR01899RXN-9951Isocitric acid > Succinic acid + Glyoxylic acidCitric acid > Isocitric acidCitric acid + cis-Aconitic acid + Water <> Isocitric acidR01324 Isocitric acid + NADP + Oxalosuccinic acid <> alpha-Ketoglutarate + Carbon dioxide + NADPH + Hydrogen ionR00267 Isocitric acid + NAD + Isocitric acid > Oxoglutaric acid + Carbon dioxide + NADH + Hydrogen ionPW_R002576cis-Aconitic acid + Water <> Isocitric acid + Isocitric acidPW_R002584Isocitric acid + Isocitric acid <> Succinic acid + Glyoxylic acidPW_R003710cis-Aconitic acid + Water <> Isocitric acidIsocitric acid + NADP <> alpha-Ketoglutarate + Carbon dioxide + NADPHIsocitric acid <> Glyoxylic acid + Succinic acidIsocitric acid + NADP <> alpha-Ketoglutarate + Carbon dioxide + NADPHIsocitric acid <> Glyoxylic acid + Succinic acid