L-Lactic acid (PAMDB000079)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000079
Identification
Name: L-Lactic acid
Description:Lactic acid plays a role in several biochemical processes. Pseudomonas aeruginosa produces lactic acid from pyruvate in a process of normal metabolism. The lactic acid produced by Pseudomonas aeruginosa 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)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (+)-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
Chemical Formula: C3H6O3
Average Molecular Weight: 90.0779
Monoisotopic Molecular Weight: 90.031694058
InChI Key: JVTAAEKCZFNVCJ-REOHCLBHSA-N
InChI:InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m0/s1
CAS number: 79-33-4
IUPAC Name:(2S)-2-hydroxypropanoic acid
Traditional IUPAC Name: (α)-lactate
SMILES:C[C@H](O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Hydroxy acids and derivatives
Sub ClassAlpha hydroxy acids and derivatives
Direct Parent Alpha hydroxy acids and derivatives
Alternative Parents
Substituents
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Liquid
Charge:-1
Melting point: 16.8 °C (BP = 119 oC)
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility562.0 mg/mLALOGPS
logP-0.79ALOGPS
logP-0.47ChemAxon
logS0.79ALOGPS
pKa (Strongest Acidic)3.78ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity18.84 m3·mol-1ChemAxon
Polarizability8.06 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
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
L-Lactic acid + 2 Ferricytochrome c + Ferricytochrome c <> Pyruvic acid +2 Ferrocytochrome c +2 Hydrogen ion + Ferrocytochrome c
Lactaldehyde + NAD + Water <> L-Lactic acid + NADH + Hydrogen ion
an oxidized electron acceptor + L-Lactic acid > a reduced electron acceptor + Pyruvic acid
Pyruvic acid + Hydrogen ion > L-Lactic acid
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
L-Lactic acid + oxidized electron acceptor + L-Lactic acid > Reduced acceptor + Pyruvic acid
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00kb-0900000000-fb59ec16914501aa19abView in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-9000000000-1d5a5f55463acefb6fc7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-000m-9000000000-c07133799d8f43d4c75aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-000i-9000000000-ddb080250741e69ab137View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-8f5d5eddb0b4b2a3b541View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-3bcfc4cdc49230f15642View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9000000000-48b511409f4f60cec04eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-365ea3c1bcfff2cab938View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-9d0238aeeb837213e81dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-002b-9000000000-50213d6b39ef9741c466View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Bairaktari E, Katopodis K, Siamopoulos KC, Tsolas O: Paraquat-induced renal injury studied by 1H nuclear magnetic resonance spectroscopy of urine. Clin Chem. 1998 Jun;44(6 Pt 1):1256-61. Pubmed: 9625050
  • Commodari F, Arnold DL, Sanctuary BC, Shoubridge EA: 1H NMR characterization of normal human cerebrospinal fluid and the detection of methylmalonic acid in a vitamin B12 deficient patient. NMR Biomed. 1991 Aug;4(4):192-200. Pubmed: 1931558
  • 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. Pubmed: 8412012
  • Isotalo T, Talja M, Hellstrom P, Perttila I, Valimaa T, Tormala P, Tammela TL: A double-blind, randomized, placebo-controlled pilot study to investigate the effects of finasteride combined with a biodegradable self-reinforced poly L-lactic acid spiral stent in patients with urinary retention caused by bladder outlet obstruction from benign prostatic hyperplasia. BJU Int. 2001 Jul;88(1):30-4. Pubmed: 11446841
  • 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. Pubmed: 22080510
  • Kaya M, Moriwaki Y, Ka T, Inokuchi T, Yamamoto A, Takahashi S, Tsutsumi Z, Tsuzita J, Oku Y, Yamamoto T: Plasma concentrations and urinary excretion of purine bases (uric acid, hypoxanthine, and xanthine) and oxypurinol after rigorous exercise. Metabolism. 2006 Jan;55(1):103-7. Pubmed: 16324927
  • 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. Pubmed: 21097882
  • Khan SA, Cox IJ, Hamilton G, Thomas HC, Taylor-Robinson SD: In vivo and in vitro nuclear magnetic resonance spectroscopy as a tool for investigating hepatobiliary disease: a review of H and P MRS applications. Liver Int. 2005 Apr;25(2):273-81. Pubmed: 15780050
  • Menard, S., Candalh, C., Bambou, J. C., Terpend, K., Cerf-Bensussan, N., Heyman, M. (2004). "Lactic acid bacteria secrete metabolites retaining anti-inflammatory properties after intestinal transport." Gut 53:821-828. Pubmed: 15138208
  • Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. Pubmed: 15882454
  • Nicholson JK, Buckingham MJ, Sadler PJ: High resolution 1H n.m.r. studies of vertebrate blood and plasma. Biochem J. 1983 Jun 1;211(3):605-15. Pubmed: 6411064
  • Nielsen J, Ytrebo LM, Borud O: Lactate and pyruvate concentrations in capillary blood from newborns. Acta Paediatr. 1994 Sep;83(9):920-2. Pubmed: 7819686
  • Redjems-Bennani N, Jeandel C, Lefebvre E, Blain H, Vidailhet M, Gueant JL: Abnormal substrate levels that depend upon mitochondrial function in cerebrospinal fluid from Alzheimer patients. Gerontology. 1998;44(5):300-4. Pubmed: 9693263
  • Shirai Y, Kamimura K, Seki T, Morohashi M: L-lactic acid as a mosquito (Diptera: Culicidae) repellent on human and mouse skin. J Med Entomol. 2001 Jan;38(1):51-4. Pubmed: 11268691
  • Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. Pubmed: 12097436
  • Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25. Pubmed: 15627241
  • Valenza F, Aletti G, Fossali T, Chevallard G, Sacconi F, Irace M, Gattinoni L: Lactate as a marker of energy failure in critically ill patients: hypothesis. Crit Care. 2005;9(6):588-93. Epub 2005 Sep 28. Pubmed: 16356243
  • 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. Pubmed: 17765195
  • Walenta S, Schroeder T, Mueller-Klieser W: Lactate in solid malignant tumors: potential basis of a metabolic classification in clinical oncology. Curr Med Chem. 2004 Aug;11(16):2195-204. Pubmed: 15279558
  • Wevers RA, Engelke U, Wendel U, de Jong JG, Gabreels FJ, Heerschap A: Standardized method for high-resolution 1H-NMR of cerebrospinal fluid. Clin Chem. 1995 May;41(5):744-51. Pubmed: 7729054
  • 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. Pubmed: 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. Pubmed: 8579834
Synthesis Reference: Lao, Hanzhang; Sun, Jianrong; Wang, Jian; Qian, Zhiliang. Process for preparation of high-purity L-lactic acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 9pp.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID16651
HMDB IDHMDB00190
Pubchem Compound ID107689
Kegg IDC00186
ChemSpider ID96860
WikipediaLactate
BioCyc IDL-LACTATE
EcoCyc IDL-LACTATE
Ligand Expo2OP

Enzymes

Protein Details
• L-lactate dehydrogenase [cytochrome]
General function:
Involved in catalytic activity
Specific function:
(S)-lactate + 2 ferricytochrome c = pyruvate + 2 ferrocytochrome c + 2 H(+)
Gene Name:
lldD
Locus Tag:
PA4771
Molecular weight:
41.1 kDa
Reactions
(S)-lactate + 2 ferricytochrome c = pyruvate + 2 ferrocytochrome c + 2 H(+).

Transporters

Protein Details
• L-lactate permease
General function:
Involved in lactate transmembrane transporter activity
Specific function:
Transports L-lactate across the membrane. Can also transport D-lactate and glycolate. Seems to be driven by a proton motive force
Gene Name:
lldP
Locus Tag:
PA4770
Molecular weight:
58.7 kDa