2.0 2012-05-31 13:02:24 -0600 2015-09-13 12:56:09 -0600 ECMDB00956 M2MDB000206 Tartaric acid Tartaric acid is a white crystalline organic acid. Salts of tartaric acid are known as tartrates. It is a dihydroxy derivative of dicarboxylic acid. Naturally-occurring tartaric acid is chiral, meaning that it has molecules that are non-superimposable on their mirror-images. It is a useful raw material in organic chemistry for the synthesis of other chiral molecules. The naturally occurring form of the acid is L-(+)-tartaric acid or dextrotartaric acid. The mirror-image (enantiomeric) form, levotartaric acid or D-(-)-tartaric acid, and the achiral form, mesotartaric acid, can be made artificially. (Wikipedia) In E. coli K-12, tartaric acid is involved in glyoxylate and dicarboxylate metabolism. (KEGG) (+)-(2R,3R)-Tartarate (+)-(2R,3R)-Tartaric acid (+)-tartarate (+)-tartaric acid (+)-tartrate (+)-tartric acid (1R,2R)-1,2-Dihydroxyethane-1,2-dicarboxylate (1R,2R)-1,2-Dihydroxyethane-1,2-dicarboxylic acid (2R,3R)-2,3-dihydroxybutanedioate (2R,3R)-2,3-dihydroxybutanedioic acid (2R,3R)-2,3-dihydroxysuccinate (2R,3R)-2,3-dihydroxysuccinic acid (2R,3R)-2,3-tartarate (2R,3R)-2,3-tartaric acid (2R,3R)-Tartarate (2R,3R)-Tartaric acid (2R,3R)-tartrate (2R,3R)-tartric acid (R,R)-(+)-tartarate (R,R)-(+)-tartaric acid (R,R)-tartarate (R,R)-tartaric acid (R,R)-tartrate (R,R)-tartric acid 1,2-Dihydroxyethane-1,2-dicarboxylate 1,2-Dihydroxyethane-1,2-dicarboxylic acid 2,3-Dihydroxy-succinate 2,3-Dihydroxy-succinic acid 2,3-Dihydroxybutanedioate 2,3-Dihydroxybutanedioic acid 2,3-Dihydroxysuccinate 2,3-Dihydroxysuccinic acid D-a,b-Dihydroxysuccinate D-a,b-Dihydroxysuccinic acid D-Tartarate D-Tartaric acid Dextrotartarate Dextrotartaric acid L(+)-Tartarate L(+)-Tartaric acid L-(+)-Tartarate L-(+)-Tartaric acid L-Tartarate L-Tartaric acid L-Threarate L-Threaric acid Natural tartarate Natural tartaric acid Rechtsweinsaeure TAR Tartarate Tartaric acid Tartrate Tartric acid Threarate Threaric acid TLA Weinsaeure C4H6O6 150.0868 150.016437924 (2R,3R)-2,3-dihydroxybutanedioic acid L(+)-tartaric acid 87-69-4 O[C@H]([C@@H](O)C(O)=O)C(O)=O InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2-/m1/s1 FEWJPZIEWOKRBE-JCYAYHJZSA-N Solid Cytosol Extra-organism Periplasm logp -1.27 ALOGPS logs 0.03 ALOGPS solubility 1.61e+02 g/l ALOGPS melting_point 169 oC logp -1.8 ChemAxon pka_strongest_acidic 2.72 ChemAxon pka_strongest_basic -4.3 ChemAxon iupac (2R,3R)-2,3-dihydroxybutanedioic acid ChemAxon average_mass 150.0868 ChemAxon mono_mass 150.016437924 ChemAxon smiles O[C@H]([C@@H](O)C(O)=O)C(O)=O ChemAxon formula C4H6O6 ChemAxon inchi InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2-/m1/s1 ChemAxon inchikey FEWJPZIEWOKRBE-JCYAYHJZSA-N ChemAxon polar_surface_area 115.06 ChemAxon refractivity 26.21 ChemAxon polarizability 11.33 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Butanoate metabolism ec00650 Glyoxylate and dicarboxylate metabolism ec00630 inner membrane transport list of inner membrane transport complexes, transporting compounds from the periplasmic space to the cytosol This pathway should be updated regularly with the new inner membrae transports added PW000786 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 Specdb::CMs 684 Specdb::CMs 1308 Specdb::CMs 6360 Specdb::CMs 30027 Specdb::CMs 30587 Specdb::CMs 31268 Specdb::CMs 149840 Specdb::CMs 1082476 Specdb::CMs 1082477 Specdb::CMs 1082478 Specdb::CMs 1082479 Specdb::CMs 1082480 Specdb::CMs 1082481 Specdb::CMs 1082482 Specdb::CMs 1082483 Specdb::CMs 1082484 Specdb::CMs 1082485 Specdb::CMs 1082486 Specdb::CMs 1082487 Specdb::CMs 1082488 Specdb::CMs 1082489 Specdb::CMs 1082490 Specdb::CMs 1082491 Specdb::CMs 1082492 Specdb::CMs 1082493 Specdb::EiMs 2005 Specdb::NmrOneD 1621 Specdb::NmrOneD 8042 Specdb::NmrOneD 8043 Specdb::NmrOneD 8044 Specdb::NmrOneD 8045 Specdb::NmrOneD 8046 Specdb::NmrOneD 8047 Specdb::NmrOneD 8048 Specdb::NmrOneD 8049 Specdb::NmrOneD 8050 Specdb::NmrOneD 8051 Specdb::NmrOneD 8052 Specdb::NmrOneD 8053 Specdb::NmrOneD 8054 Specdb::NmrOneD 8055 Specdb::NmrOneD 8056 Specdb::NmrOneD 8057 Specdb::NmrOneD 8058 Specdb::NmrOneD 8059 Specdb::NmrOneD 8060 Specdb::NmrOneD 8061 Specdb::MsMs 1354 Specdb::MsMs 1355 Specdb::MsMs 1356 Specdb::MsMs 4963 Specdb::MsMs 4964 Specdb::MsMs 4965 Specdb::MsMs 4966 Specdb::MsMs 4967 Specdb::MsMs 247110 Specdb::MsMs 247111 Specdb::MsMs 247112 Specdb::MsMs 267054 Specdb::MsMs 267055 Specdb::MsMs 267056 Specdb::MsMs 438513 Specdb::MsMs 438514 Specdb::MsMs 438515 Specdb::MsMs 438516 Specdb::MsMs 438517 Specdb::MsMs 2256903 Specdb::MsMs 2257705 Specdb::MsMs 2258850 Specdb::MsMs 2259705 Specdb::MsMs 2736833 Specdb::MsMs 2736834 Specdb::NmrTwoD 1050 Specdb::NmrTwoD 1562 HMDB00956 444305 392277 C00898 15671 TARTRATE TLA Tartaric 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 Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. 19212411 Petrarulo M, Marangella M, Bianco O, Linari F: Ion-chromatographic determination of L-tartrate in urine samples. Clin Chem. 1991 Jan;37(1):90-3. 1988215 Lord RS, Burdette CK, Bralley JA: Significance of urinary tartaric acid. Clin Chem. 2005 Mar;51(3):672-3. 15738524 Milas, N. A.; Terry, Ethel M. Oxidation of fumaric and of maleic acids to tartaric acid. Journal of the American Chemical Society (1925), 47 1412-8. http://hmdb.ca/system/metabolites/msds/000/000/860/original/HMDB00956.pdf?1358461643 L(+)-tartrate dehydratase subunit alpha P05847 TTDA_ECOLI ttdA http://ecmdb.ca/proteins/P05847.xml L(+)-tartrate dehydratase subunit beta P0AC35 TTDB_ECOLI ttdB http://ecmdb.ca/proteins/P0AC35.xml D-malate dehydrogenase [decarboxylating] P76251 DMLA_ECOLI dmlA http://ecmdb.ca/proteins/P76251.xml L-tartrate/succinate antiporter P39414 TTDT_ECOLI ttdT http://ecmdb.ca/proteins/P39414.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 Tartaric acid <> Water + Oxalacetic acid R00339 LTARTDEHYDRA-RXN Tartaric acid <> Glyceric acid + Carbon dioxide R01751 Tartaric acid + NAD <> 2-Hydroxy-3-oxosuccinate + NADH + Hydrogen ion R06180 Tartaric acid > Oxalacetic acid + Water