2.0 2012-05-31 14:04:40 -0600 2015-09-13 12:56:13 -0600 ECMDB04088 M2MDB000604 Isocitric acid Isocitric 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 acid 1-Hydroxy-1,2,3-propanetricarboxylate 1-Hydroxy-1,2,3-propanetricarboxylic acid 1-Hydroxypropane-1,2,3-tricarboxylate 1-Hydroxypropane-1,2,3-tricarboxylic acid 1-Hydroxytricarballylate 1-Hydroxytricarballylic acid 3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylate 3-Carboxy-2,3-dideoxy-1-hydroxypropan-1,2,3-tricarboxylic acid 3-Carboxy-2,3-dideoxy-Pentarate 3-Carboxy-2,3-dideoxy-Pentaric acid D-<i>threo</i>-isocitric acid D-Isocitrate D-Isocitric acid D-Threo-isocitrate D-Threo-isocitric acid I-CIT Isocitrate Isocitric acid Threo-D(S)-iso-citrate Threo-D(S)-iso-citric acid Threo-D<SUB>s</SUB>-isocitrate Threo-Ds-isocitrate Threo-Ds-isocitric acid C6H8O7 192.1235 192.02700261 1-hydroxypropane-1,2,3-tricarboxylic acid isocitric acid 320-77-4 OC(C(CC(O)=O)C(O)=O)C(O)=O InChI=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-N Solid Cytosol logp -0.35 ALOGPS logs -0.56 ALOGPS solubility 5.25e+01 g/l ALOGPS melting_point 162-165 oC logp -1.4 ChemAxon pka_strongest_acidic 3.07 ChemAxon pka_strongest_basic -4 ChemAxon iupac 1-hydroxypropane-1,2,3-tricarboxylic acid ChemAxon average_mass 192.1235 ChemAxon mono_mass 192.02700261 ChemAxon smiles OC(C(CC(O)=O)C(O)=O)C(O)=O ChemAxon formula C6H8O7 ChemAxon inchi InChI=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) ChemAxon inchikey ODBLHEXUDAPZAU-UHFFFAOYSA-N ChemAxon polar_surface_area 132.13 ChemAxon refractivity 35.72 ChemAxon polarizability 15.55 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Glutathione metabolism The 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. PW000833 ec00480 Metabolic Citrate cycle (TCA cycle) ec00020 Reductive carboxylate cycle (CO2 fixation) ec00720 Glyoxylate and dicarboxylate metabolism ec00630 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 Secondary Metabolites: Glyoxylate cycle The 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. PW000967 Metabolic glycolate and glyoxylate degradation II Oxaloglycolate (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. PW002021 Metabolic mixed acid fermentation FERMENTATION-PWY respiration (anaerobic) ANARESP1-PWY glyoxylate cycle GLYOXYLATE-BYPASS TCA cycle I (prokaryotic) TCA Specdb::CMs 444 Specdb::CMs 445 Specdb::CMs 446 Specdb::CMs 447 Specdb::CMs 1485 Specdb::CMs 2897 Specdb::CMs 30196 Specdb::CMs 30299 Specdb::CMs 30863 Specdb::CMs 31062 Specdb::CMs 37349 Specdb::CMs 149653 Specdb::CMs 1053896 Specdb::CMs 1053898 Specdb::CMs 1053899 Specdb::CMs 1053901 Specdb::CMs 1053903 Specdb::CMs 1053905 Specdb::CMs 1053907 Specdb::CMs 1053908 Specdb::CMs 1053910 Specdb::CMs 1053912 Specdb::CMs 1053914 Specdb::CMs 1053916 Specdb::CMs 1053918 Specdb::NmrOneD 1169 Specdb::NmrOneD 142790 Specdb::NmrOneD 142791 Specdb::NmrOneD 142792 Specdb::NmrOneD 142793 Specdb::NmrOneD 142794 Specdb::NmrOneD 142795 Specdb::NmrOneD 142796 Specdb::NmrOneD 142797 Specdb::NmrOneD 142798 Specdb::NmrOneD 142799 Specdb::NmrOneD 142800 Specdb::NmrOneD 142801 Specdb::NmrOneD 142802 Specdb::NmrOneD 142803 Specdb::NmrOneD 142804 Specdb::NmrOneD 142805 Specdb::NmrOneD 142806 Specdb::NmrOneD 142807 Specdb::NmrOneD 142808 Specdb::NmrOneD 142809 Specdb::MsMs 310 Specdb::MsMs 311 Specdb::MsMs 312 Specdb::MsMs 3509 Specdb::MsMs 3510 Specdb::MsMs 3511 Specdb::MsMs 3512 Specdb::MsMs 3513 Specdb::MsMs 3514 Specdb::MsMs 3515 Specdb::MsMs 3516 Specdb::MsMs 3517 Specdb::MsMs 3518 Specdb::MsMs 3519 Specdb::MsMs 3520 Specdb::MsMs 3521 Specdb::MsMs 179079 Specdb::MsMs 179080 Specdb::MsMs 179081 Specdb::MsMs 181404 Specdb::MsMs 181405 Specdb::MsMs 181406 Specdb::MsMs 437925 Specdb::MsMs 437926 Specdb::MsMs 437927 Specdb::NmrTwoD 1198 HMDB00193 1198 1161 C00311 16087 THREO-DS-ISO-CITRATE Isocitric 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 Vijayendran, 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. 18402659 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 Zupke 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. 8579834 Hoffmann 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. 8412012 Guneral 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. 8087979 Stromme 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. 813176 Sutor 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. 213213 Ebeling 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. 595962 Sutor DJ, Percival JM, Doonan S: Urinary inhibitor of the formation of calcium oxalate. Br J Urol. 1979 Aug;51(4):253-5. 223711 Hennequin 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. 8389069 Kavanagh JP: Isocitric and citric acid in human prostatic and seminal fluid: implications for prostatic metabolism and secretion. Prostate. 1994;24(3):139-42. 8115279 Mikosha AS, Monissarenko VP, Bychkovskaia LA: [Properties of adrenocortical isocitrate dehydrogenase] Vopr Med Khim. 1981 Nov-Dec;27(6):736-9. 7336646 Sutor DJ, Percival JM: The estimation of D-isocitric acid in urine using isocitrate dehydrogenase. Clin Chim Acta. 1978 Jun;86(2):223-5. 657545 Finogenova, 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 continuous http://hmdb.ca/system/metabolites/msds/000/000/136/original/HMDB00193.pdf?1358461634 Isocitrate dehydrogenase [NADP] P08200 IDH_ECOLI icd http://ecmdb.ca/proteins/P08200.xml Isocitrate lyase P0A9G6 ACEA_ECOLI aceA http://ecmdb.ca/proteins/P0A9G6.xml Aconitate hydratase 1 P25516 ACON1_ECOLI acnA http://ecmdb.ca/proteins/P25516.xml Aconitate hydratase 2 P36683 ACON2_ECOLI acnB http://ecmdb.ca/proteins/P36683.xml Uncharacterized protein ybhJ P75764 YBHJ_ECOLI ybhJ http://ecmdb.ca/proteins/P75764.xml cis-Aconitic acid + Water <> Isocitric acid R01900 ACONITATEHYDR-RXN Isocitric acid + NADP <> alpha-Ketoglutarate + Carbon dioxide + NADPH R00267 Isocitric acid <> Glyoxylic acid + Succinic acid R00479 ISOCIT-CLEAV-RXN Isocitric acid + NADP <> alpha-Ketoglutarate + Carbon dioxide + NADPH + Hydrogen ion R00267 Citric acid <> Isocitric acid R01324 Isocitric acid + NADP <> Oxalosuccinic acid + NADPH + Hydrogen ion R01899 Isocitric acid <> cis-Aconitic acid + Water R01900 Isocitric acid + NADP > NADPH + Oxoglutaric acid + Carbon dioxide ISOCITDEH-RXN Isocitric acid + NADP > Oxalosuccinic acid + NADPH + Hydrogen ion R01899 RXN-9951 Isocitric acid > Succinic acid + Glyoxylic acid Citric acid > Isocitric acid Citric acid + cis-Aconitic acid + Water <> Isocitric acid R01324 Isocitric acid + NADP + Oxalosuccinic acid <> alpha-Ketoglutarate + Carbon dioxide + NADPH + Hydrogen ion R00267 Isocitric acid + NAD + Isocitric acid > Oxoglutaric acid + Carbon dioxide + NADH + Hydrogen ion PW_R002576 cis-Aconitic acid + Water <> Isocitric acid + Isocitric acid PW_R002584 Isocitric acid + Isocitric acid <> Succinic acid + Glyoxylic acid PW_R003710 cis-Aconitic acid + Water <> Isocitric acid Isocitric acid + NADP <> alpha-Ketoglutarate + Carbon dioxide + NADPH Isocitric acid <> Glyoxylic acid + Succinic acid Isocitric acid + NADP <> alpha-Ketoglutarate + Carbon dioxide + NADPH Isocitric acid <> Glyoxylic acid + Succinic acid