2.0 2012-05-31 10:23:21 -0600 2015-09-13 12:56:06 -0600 ECMDB00190 M2MDB000079 L-Lactic acid Lactic acid plays a role in several biochemical processes. E. coli produces lactic acid from pyruvate in a process of normal metabolism. The lactic acid produced by E. coli and other probiotics (mostly lactic acid bacteria) can lower the pH in mammalian host intestines and therefore, it inhibits the growth of proteolytic bacteria and have a beneficial effect on intestinal inflammation. (PMID 15138208) (+)-Lactate (+)-Lactic acid (a)-Lactate (a)-Lactic acid (alpha)-Lactate (alpha)-Lactic acid (S)-(+)-2-Hydroxypropanoate (S)-(+)-2-Hydroxypropanoic acid (S)-2-hydroxy-Propanoate (S)-2-hydroxy-Propanoic acid (S)-2-Hydroxypropanoate (S)-2-Hydroxypropanoic acid (S)-2-Hydroxypropionate (S)-2-Hydroxypropionic acid (S)-Lactate (S)-Lactic acid (α)-Lactate (α)-Lactic acid 1-Hydroxyethane 1-carboxylate 1-Hydroxyethane 1-carboxylic acid 1-Hydroxyethanecarboxylate 1-Hydroxyethanecarboxylic acid 2-Hydroxypropanoate 2-Hydroxypropanoic acid 2-Hydroxypropionate 2-Hydroxypropionic acid A-Hydroxypropanoate A-Hydroxypropanoic acid A-Hydroxypropionate A-Hydroxypropionic acid Alpha-Hydroxypropanoate Alpha-Hydroxypropanoic acid Alpha-Hydroxypropionate Alpha-Hydroxypropionic acid L(+)-Lactate L(+)-Lactic acid L-(+)- Lactate L-(+)- Lactic acid L-2-Hydroxypropanoate L-2-Hydroxypropanoic acid L-Lactate L-Lactic acid Lactate Lactic acid Milk acid Sarcolactate Sarcolactic acid α-Hydroxypropanoate α-Hydroxypropanoic acid α-Hydroxypropionate α-Hydroxypropionic acid C3H6O3 90.0779 90.031694058 (2R)-2-hydroxypropanoic acid D-lactic acid 79-33-4 C[C@H](O)C(O)=O InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m0/s1 JVTAAEKCZFNVCJ-REOHCLBHSA-N Liquid Cytosol Extra-organism Periplasm logp -0.79 ALOGPS logs 0.79 ALOGPS solubility 5.62e+02 g/l ALOGPS melting_point 16.8 oC (BP = 119 oC) logp -0.47 ChemAxon pka_strongest_acidic 3.78 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (2R)-2-hydroxypropanoic acid ChemAxon average_mass 90.0779 ChemAxon mono_mass 90.031694058 ChemAxon smiles C[C@H](O)C(O)=O ChemAxon formula C3H6O3 ChemAxon inchi InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m0/s1 ChemAxon inchikey JVTAAEKCZFNVCJ-REOHCLBHSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 18.84 ChemAxon polarizability 8.05 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Glycolysis / Gluconeogenesis ec00010 Pyruvate metabolism ec00620 Propanoate metabolism Starting from L-threonine, this compound is deaminated through a threonine deaminase resulting in a hydrogen ion, a water molecule and a (2z)-2-aminobut-2-enoate. The latter compound then isomerizes to a 2-iminobutanoate, This compound then reacts spontaneously with hydrogen ion and a water molecule resulting in a ammonium and a 2-Ketobutyric acid. The latter compound interacts with CoA through a pyruvate formate-lyase / 2-ketobutyrate formate-lyase resulting in a formic acid and a propionyl-CoA. Propionyl-CoA can then be processed either into a 2-methylcitric acid or into a propanoyl phosphate. Propionyl-CoA interacts with oxalacetic acid and a water molecule through a 2-methylcitrate synthase resulting in a hydrogen ion, a CoA and a 2-Methylcitric acid.The latter compound is dehydrated through a 2-methylcitrate dehydratase resulting in a water molecule and cis-2-methylaconitate. The latter compound is then dehydrated by a bifunctional aconitate hydratase 2 and 2-methylisocitrate dehydratase resulting in a water molecule and methylisocitric acid. The latter compound is then processed by 2-methylisocitrate lyase resulting in a release of succinic acid and pyruvic acid. Succinic acid can then interact with a propionyl-CoA through a propionyl-CoA:succinate CoA transferase resulting in a propionic acid and a succinyl CoA. Succinyl-CoA is then isomerized through a methylmalonyl-CoA mutase resulting in a methylmalonyl-CoA. This compound is then decarboxylated through a methylmalonyl-CoA decarboxylase resulting in a release of Carbon dioxide and Propionyl-CoA. ropionyl-CoA interacts with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate. Propionyl-CoA can react with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate. The latter compound is then dephosphorylated through a ADP driven acetate kinase/propionate kinase protein complex resulting in an ATP and Propionic acid. Propionic acid can be processed by a reaction with CoA through a ATP-driven propionyl-CoA synthetase resulting in a pyrophosphate, an AMP and a propionyl-CoA. PW000940 ec00640 Metabolic Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 fucose and rhamnose degradation In E. coli, L-fucose and L-rhamnose are metabolized through parallel pathways. The pathways converge after their corresponding aldolase reactions yielding the same products: lactaldehye. Via reactions catalyzed by proteins encoded in linked operons comprising a regulon, the methylpentose, alpha-L-rhamnopyranose and/or beta-L-rhamnopyranose, is taken into the cell through a proton symporter and metabolized, enabling E. coli to grow on it as a total source of carbon and energy. For alpha-L-rhamnopyranose, it is isomerized by a l-rhamnose mutarotase resulting in a beta-L-rhamnopyranose which is then isomerized into a keto-L-rhamnulose by a l-rhamnose isomerase. The keto-L-rhamnulose spontaneously changes into a L-rhamnulofuranose which is phosphorylated by a rhamnulokinase resulting in a L-rhamnulose 1-phosphate. This compound reacts with a rhamnulose-1-phosphate aldolase resulting in a dihydroxyacetone phosphate and a lactaldehyde. For beta-L-rhamnopyranose, it is isomerized by a L-fucose mutarotase resulting in a alpha-L-fucopyranose. This compound is then isomerized by an L-fucose isomerase resulting in a L-fuculose which in turn gets phosphorylated into an L-fuculose 1-phosphate through an L-fuculokinase. The compound L-fuculose 1-phosphate reacts with an L-fuculose phosphate aldolase through a dihydroxyacetone phosphate and a lactaldehyde. Two pathways can be used for degradation of L-lactaldehyde. Aerobically, it is converted via lactate to pyruvate, also an intermediate of glycolysis. Anaerobically, lactaldehyde reductase is induced which converts lactaldehyde into propane-1,2-diol. Under aerobic conditions, L-lactaldehyde is oxidized in two steps to pyruvate, thereby channeling all the carbons from fucose or rhamnose into central metabolic pathways. Under anaerobic conditions, L-lactaldehyde is reduced to L-1,2-propanediol, which is secreted into the environment. PW000826 Metabolic L-lactaldehyde degradation (aerobic) L-lactaldehyde is one of two products resulting from degradation of the two methylpentoses L-fucose and rhamnose, which are metabolized by an analogous series of reactions. Aerobically, lactaldehyde is oxidized in two steps to pyruvate, which enters central metabolism. PW002073 Metabolic methylglyoxal degradation IV In this pathway, which has been characterized in Escherichia coli K-12, methylglyoxal is reduced to lactaldehyde by the enzyme methylglyoxal reductase. (S)-lactaldehyde is then reduced to (S)-lactate which is finally converted to pyruvate and joins the pool of central metobolites. Methylglyoxal reductases have been characterized in bacteria and fungi. Some of the enzymes are NADP-linked, while others are NAD-linked. Two variants of this pathway have been entered in MetaCyc to reflect the different biochemistry of the last enzyme, L-lactate dehydrogenase. The Escherichia coli K-12 enzyme encoded by gene lldD uses an unidentified electron acceptor, while the Saccharomyces cerevisiae enzyme uses an an oxidized c-type cytochrome. (EcoCyc) PW002078 Metabolic L-lactaldehyde degradation (aerobic) PWY0-1317 Specdb::CMs 2962 Specdb::CMs 38017 Specdb::CMs 102652 Specdb::CMs 102653 Specdb::CMs 102654 Specdb::CMs 160511 Specdb::EiMs 1989 Specdb::NmrOneD 1680 Specdb::NmrOneD 4830 Specdb::NmrOneD 4831 Specdb::NmrOneD 147310 Specdb::NmrOneD 147311 Specdb::NmrOneD 147312 Specdb::NmrOneD 147313 Specdb::NmrOneD 147314 Specdb::NmrOneD 147315 Specdb::NmrOneD 147316 Specdb::NmrOneD 147317 Specdb::NmrOneD 147318 Specdb::NmrOneD 147319 Specdb::NmrOneD 147320 Specdb::NmrOneD 147321 Specdb::NmrOneD 147322 Specdb::NmrOneD 147323 Specdb::NmrOneD 147324 Specdb::NmrOneD 147325 Specdb::NmrOneD 147326 Specdb::NmrOneD 147327 Specdb::NmrOneD 147328 Specdb::NmrOneD 147329 Specdb::MsMs 1513 Specdb::MsMs 1514 Specdb::MsMs 1515 Specdb::MsMs 179190 Specdb::MsMs 179191 Specdb::MsMs 179192 Specdb::MsMs 181515 Specdb::MsMs 181516 Specdb::MsMs 181517 Specdb::MsMs 438632 Specdb::MsMs 2248919 Specdb::MsMs 2249456 Specdb::MsMs 2250911 Specdb::MsMs 3048284 Specdb::MsMs 3048285 Specdb::MsMs 3048286 Specdb::MsMs 3096055 Specdb::MsMs 3096056 Specdb::MsMs 3096057 Specdb::NmrTwoD 1063 Specdb::NmrTwoD 1621 HMDB00190 107689 96860 C00186 16651 L-LACTATE 2OP Lactate Keseler, I. 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Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 9pp. http://hmdb.ca/system/metabolites/msds/000/000/133/original/HMDB00190.pdf?1358462381 D-lactate dehydrogenase P06149 DLD_ECOLI dld http://ecmdb.ca/proteins/P06149.xml Hydroxyacylglutathione hydrolase P0AC84 GLO2_ECOLI gloB http://ecmdb.ca/proteins/P0AC84.xml Lactaldehyde dehydrogenase P25553 ALDA_ECOLI aldA http://ecmdb.ca/proteins/P25553.xml L-lactate dehydrogenase [cytochrome] P33232 LLDD_ECOLI lldD http://ecmdb.ca/proteins/P33232.xml Uncharacterized protein ykgE P77252 YKGE_ECOLI ykgE http://ecmdb.ca/proteins/P77252.xml Uncharacterized protein ykgG P77433 YKGG_ECOLI ykgG http://ecmdb.ca/proteins/P77433.xml Uncharacterized electron transport protein ykgF P77536 YKGF_ECOLI ykgF http://ecmdb.ca/proteins/P77536.xml L-lactate permease P33231 LLDP_ECOLI lldP http://ecmdb.ca/proteins/P33231.xml Glycolate permease glcA Q46839 GLCA_ECOLI glcA http://ecmdb.ca/proteins/Q46839.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 L-Lactic acid + Ubiquinone-8 > Pyruvic acid + Ubiquinol-8 L-Lactic acid + Menaquinone 8 > Menaquinol 8 + Pyruvic acid Water + Lactaldehyde + NAD + (S)-Lactaldehyde <>2 Hydrogen ion + L-Lactic acid + NADH R01446 LACTALDDEHYDROG-RXN L-Lactic acid + 2 Ferricytochrome c + Ferricytochrome c <> Pyruvic acid +2 Ferrocytochrome c +2 Hydrogen ion + Ferrocytochrome c R00196 Lactaldehyde + NAD + Water <> L-Lactic acid + NADH + Hydrogen ion R01446 an oxidized electron acceptor + L-Lactic acid > a reduced electron acceptor + Pyruvic acid L-LACTDEHYDROGFMN-RXN Water + NAD + Lactaldehyde > Hydrogen ion + NADH + L-Lactic acid R01446 LACTALDDEHYDROG-RXN Pyruvic acid + Hydrogen ion > L-Lactic acid RXN0-5269 Lactaldehyde + NAD + Water > L-Lactic acid + NADH L-Lactic acid + 2 Ferricytochrome c > Pyruvic acid +2 Ferrocytochrome c +2 Hydrogen ion NAD + Water + (S)-lactaldehyde + Lactaldehyde > NADH +2 Hydrogen ion + L-Lactic acid + L-Lactic acid PW_R002976 L-Lactic acid + oxidized electron acceptor + L-Lactic acid > Reduced acceptor + Pyruvic acid PW_R002978 L-Lactic acid + oxidized electron acceptor > Pyruvic acid + reduced electron acceptor PW_R006056 L-Lactic acid + Ubiquinone-6 > Pyruvic acid + Ubiquinol-6 PW_R006151 S-Lactoylglutathione + Water > Glutathione + Hydrogen ion + L-Lactic acid PW_R006150 L-Lactic acid + 2 Ferricytochrome c <> Pyruvic acid +2 Ferrocytochrome c +2 Hydrogen ion L-Lactic acid + 2 Ferricytochrome c <> Pyruvic acid +2 Ferrocytochrome c +2 Hydrogen ion