2.0 2012-05-31 14:22:58 -0600 2015-06-03 17:19:07 -0600 ECMDB20015 M2MDB000864 (R)-Malate Malic acid is a tart-tasting organic dicarboxylic acid that plays a role in many sour or tart foods. In its ionised form it is malate, an intermediate of the TCA cycle along with fumarate. It can also be formed from pyruvate as one of the anaplerotic reactions. (+)-D-malate (+)-D-malic acid (+-)-1-Hydroxy-1,2-ethanedicarboxylate (+-)-1-Hydroxy-1,2-ethanedicarboxylic acid (-)-1-Hydroxy-1,2-ethanedicarboxylate (-)-1-Hydroxy-1,2-ethanedicarboxylic acid (-)-hydroxysuccinate (-)-hydroxysuccinic acid (-)-L-malate (-)-L-malic acid (-)-malate (-)-malic acid (2R)-2-hydroxybutanedioate (2R)-2-hydroxybutanedioic acid (2S)-2-Hydroxybutanedioate (2S)-2-Hydroxybutanedioic acid (R)-(+)-2-Hydroxysuccinate (R)-(+)-2-Hydroxysuccinic acid (R)-hydroxybutanedioate (R)-hydroxybutanedioic acid (R)-malate (R)-Malic acid (S)-2-Hydroxybutanedioate (S)-2-Hydroxybutanedioic acid (S)-Hydroxybutanedioate (S)-Hydroxybutanedioic acid (S)-malate (S)-malic acid .+-.-malate .+-.-malic acid 2-Hydroxy-Butanedioate 2-Hydroxy-Butanedioic acid 2-HYDROXY-succinate 2-HYDROXY-SUCCINIC ACID 2-Hydroxybutanedioate 2-Hydroxybutanedioic acid 2-Hydroxydicarboxylate 2-Hydroxydicarboxylic acid 2-Hydroxyethane-1,2-dicarboxylate 2-Hydroxyethane-1,2-dicarboxylic acid 2-Hydroxysuccinate 2-Hydroxysuccinic acid A-Hydroxysuccinate A-Hydroxysuccinic acid Aepfelsaeure Alpha-Hydroxysuccinate Alpha-Hydroxysuccinic acid Apple acid Butanedioate, hydroxy-, (S)- (9CI) Butanedioate, hydroxy-, homopolymer Butanedioic acid, hydroxy-, (S)- (9CI) Butanedioic acid, hydroxy-, homopolymer D-(+)-Malate D-(+)-Malic acid D-Hydroxybutanedioate D-Hydroxybutanedioic acid D-Malate D-Malic acid Deoxytetrarate Deoxytetraric acid DL-hydroxybutanedioate DL-hydroxybutanedioic acid DL-Malate DL-malic acid DL-malic disodium salt DMR H2mal Hydroxy-(.+-.)-Butanedioate Hydroxy-(.+-.)-Butanedioic acid Hydroxy-(.+/-.)-Butanedioate Hydroxy-(.+/-.)-Butanedioic acid Hydroxy-(2S)-Butanedioate Hydroxy-(2S)-Butanedioic acid Hydroxy-(R)-Butanedioate Hydroxy-(R)-Butanedioic acid Hydroxy-(S)-Butanedioate Hydroxy-(S)-Butanedioic acid Hydroxy-Butanedioate Hydroxy-Butanedioic acid Hydroxy-Succinate Hydroxy-Succinic acid Hydroxybutandisaeure Hydroxybutanedioate Hydroxybutanedioate homopolymer Hydroxybutanedioic acid Hydroxybutanedioic acid homopolymer Hydroxysuccinate Hydroxysuccinic acid Hydroxysuccinnate (-) Hydroxysuccinnic acid (-) Kyselina hydroxybutandiova [czech] Kyselina jablecna Kyselina jablecna [czech] L(+)-Malate L(+)-Malic acid L-(-)-Malate L-(-)-Malic acid L-Mal L-Malate L-Malic acid MAL Malate Malate D-(+)-form Malate homopolymer Malate L-(-)-form Malate,(DL) Malic acid Malic acid D-(+)-form Malic acid homopolymer Malic acid L-(-)-form Malic acid,(DL) MLT Monohydroxybernsteinsaeure Musashi-no-ringosan Nchembio.145-comp29 OAA Poly (L-malate) Poly (L-malic acid) Poly(malate) Poly(malic acid) Pomalus acid R,S(+-)-Malate R,S(+-)-Malic acid R,S-Malate R,S-Malic acid R,Smalate R,Smalic acid R-Malate R-Malic acid S-(-)-Malate S-(-)-Malic acid S-2-Hydroxybutanedioate S-2-Hydroxybutanedioic acid TEO α-Hydroxysuccinate α-Hydroxysuccinic acid C4H6O5 134.0874 134.021523302 (2R)-2-hydroxybutanedioic acid .+-.-malic acid 636-61-3 O[C@H](CC(O)=O)C(O)=O InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m1/s1 BJEPYKJPYRNKOW-UWTATZPHSA-N Solid Cytosol Extra-organism Periplasm logp -0.87 ALOGPS logs 0.21 ALOGPS solubility 2.18e+02 g/l ALOGPS melting_point 131-133 oC logp -1.1 ChemAxon pka_strongest_acidic 3.2 ChemAxon pka_strongest_basic -3.9 ChemAxon iupac (2R)-2-hydroxybutanedioic acid ChemAxon average_mass 134.0874 ChemAxon mono_mass 134.021523302 ChemAxon smiles O[C@H](CC(O)=O)C(O)=O ChemAxon formula C4H6O5 ChemAxon inchi InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m1/s1 ChemAxon inchikey BJEPYKJPYRNKOW-UWTATZPHSA-N ChemAxon polar_surface_area 94.83 ChemAxon refractivity 24.88 ChemAxon polarizability 10.93 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Butanoate metabolism ec00650 Glyoxylate and dicarboxylate metabolism ec00630 D-malate degradation PWY0-1465 Specdb::CMs 23910 Specdb::CMs 30181 Specdb::CMs 30859 Specdb::CMs 42516 Specdb::CMs 100826 Specdb::CMs 100827 Specdb::CMs 148797 Specdb::NmrOneD 164429 Specdb::NmrOneD 164430 Specdb::NmrOneD 164431 Specdb::NmrOneD 164432 Specdb::NmrOneD 164433 Specdb::NmrOneD 164434 Specdb::NmrOneD 164435 Specdb::NmrOneD 164436 Specdb::NmrOneD 164437 Specdb::NmrOneD 164438 Specdb::NmrOneD 164439 Specdb::NmrOneD 164440 Specdb::NmrOneD 164441 Specdb::NmrOneD 164442 Specdb::NmrOneD 164443 Specdb::NmrOneD 164444 Specdb::NmrOneD 164445 Specdb::NmrOneD 164446 Specdb::NmrOneD 164447 Specdb::NmrOneD 164448 Specdb::MsMs 28544 Specdb::MsMs 28545 Specdb::MsMs 28546 Specdb::MsMs 35102 Specdb::MsMs 35103 Specdb::MsMs 35104 Specdb::MsMs 439057 Specdb::MsMs 2236633 Specdb::MsMs 2238789 Specdb::MsMs 2238815 Specdb::MsMs 2346419 Specdb::MsMs 2346420 Specdb::MsMs 2346421 Specdb::MsMs 2593054 Specdb::MsMs 2593055 Specdb::MsMs 2593056 92824 510 C00497 30796 CPD-660 MLT 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 D-malate dehydrogenase [decarboxylating] P76251 DMLA_ECOLI dmlA http://ecmdb.ca/proteins/P76251.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 Aerobic C4-dicarboxylate transport protein P0A830 DCTA_ECOLI dctA http://ecmdb.ca/proteins/P0A830.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 (R)-Malate + NAD <> Carbon dioxide + NADH + Pyruvic acid R00215 1.1.1.83-RXN (R)-Malate + NAD <> Pyruvic acid + Carbon dioxide + NADH + Hydrogen ion R00215 1.1.1.83-RXN NAD + (R)-Malate > NADH + Carbon dioxide + Pyruvic acid 1.1.1.83-RXN