Record Information
Version2.0
Creation Date2012-05-31 13:49:42 -0600
Update Date2015-09-13 12:56:10 -0600
Secondary Accession Numbers
  • ECMDB01311
Identification
Name:D-Lactic acid
DescriptionD-Lactic acid is the end product of the enzyme Glyoxalase ([EC:3.1.2.6] hydroxyacyl-glutathione hydrolase) which converts the intermediate substrate S-lactoyl-glutathione to reduced glutathione and D-lactate. (OMIM 138790)
Structure
Thumb
Synonyms:
  • (-)-Lactate
  • (-)-Lactic acid
  • (R)-2-hydroxypropanate
  • (R)-(-)-Lactate
  • (R)-(-)-Lactic acid
  • (R)-2-hydroxypropanate
  • (R)-2-hydroxypropanic acid
  • (R)-2-Hydroxypropanoate
  • (R)-2-Hydroxypropanoic acid
  • (R)-2-Hydroxypropionate
  • (R)-2-Hydroxypropionic acid
  • (R)-a-Hydroxypropionate
  • (R)-a-Hydroxypropionic acid
  • (R)-alpha-Hydroxypropionate
  • (R)-alpha-Hydroxypropionic acid
  • (R)-Lactate
  • (R)-Lactic acid
  • (R)-α-Hydroxypropionate
  • (R)-α-Hydroxypropionic acid
  • D-(-)-Lactate
  • D-(-)-Lactic acid
  • D-2-Hydroxypropanoate
  • D-2-Hydroxypropanoic acid
  • D-2-Hydroxypropionate
  • D-2-Hydroxypropionic acid
  • D-Lactate
  • D-Lactic acid
  • Delta-(-)-Lactate
  • Delta-(-)-Lactic acid
  • Delta-2-Hydroxypropanoate
  • Delta-2-Hydroxypropanoic acid
  • Delta-2-Hydroxypropionate
  • Delta-2-Hydroxypropionic acid
  • Delta-Lactate
  • Delta-Lactic acid
  • DLA
  • L-(+)-Lactate
  • L-(+)-Lactic acid
  • L-Lactate
  • L-Lactic acid
  • Propel
  • Tisulac
  • δ-(-)-Lactate
  • δ-(-)-Lactic acid
  • δ-2-Hydroxypropanoate
  • δ-2-Hydroxypropanoic acid
  • δ-2-Hydroxypropionate
  • δ-2-Hydroxypropionic acid
  • δ-Lactate
  • δ-Lactic acid
Chemical Formula:C3H6O3
Weight:Average: 90.0779
Monoisotopic: 90.031694058
InChI Key:JVTAAEKCZFNVCJ-UWTATZPHSA-N
InChI:InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m1/s1
CAS number:10326-41-7
IUPAC Name:(2S)-2-hydroxypropanoic acid
Traditional IUPAC Name:(α)-lactate
SMILES:C[C@@H](O)C(O)=O
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassAlpha hydroxy acids and derivatives
Direct ParentAlpha hydroxy acids and derivatives
Alternative Parents
Substituents
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:52.8 C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility562 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity18.84 m³·mol⁻¹ChemAxon
Polarizability8.06 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
1,6-anhydro-<i>N</i>-acetylmuramic acid recyclingPW002064 ThumbThumb?image type=greyscaleThumb?image type=simple
Amino sugar and nucleotide sugar metabolism IPW000886 ThumbThumb?image type=greyscaleThumb?image type=simple
Amino sugar and nucleotide sugar metabolism IIPW000887 ThumbThumb?image type=greyscaleThumb?image type=simple
Amino sugar and nucleotide sugar metabolism IIIPW000895 ThumbThumb?image type=greyscaleThumb?image type=simple
methylglyoxal degradation IIPW002084 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Amino sugar and nucleotide sugar metabolism ec00520
  • Microbial metabolism in diverse environments ec01120
  • Pyruvate metabolism ec00620
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00kb-0900000000-fb59ec16914501aa19abView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014j-0900000000-c4d9e12b4b0150eda54bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0900000000-fb59ec16914501aa19abView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-a3691f383d440fb00e1fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01b9-9620000000-f7faa7db9c1be3d9d975View in MoNA
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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-8f5d5eddb0b4b2a3b541View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-3bcfc4cdc49230f15642View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-48b511409f4f60cec04eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-365ea3c1bcfff2cab938View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-9d0238aeeb837213e81dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-9000000000-5f417f4a6d08f0ab00edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dm-9000000000-df7a94bb1a9cf6e78e1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-9000000000-dc2a1b965287b9dfee9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-c3686a681cc9bbf039e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-ddad20647c2ac56efd22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-b728b45617afcc6b67daView in MoNA
MSMass Spectrum (Electron Ionization)splash10-002b-9000000000-50213d6b39ef9741c466View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Brandt RB, Siegel SA: Methylglyoxal production in human blood. Ciba Found Symp. 1978;(67):211-23. Pubmed: 259500
  • Ellis LC, Groesbeck MD, Farr CH, Tesi RJ: Contractility of seminiferous tubules as related to sperm transport in the male. Arch Androl. 1981 Jun;6(4):283-94. Pubmed: 6113819
  • Hasegawa H, Fukushima T, Lee JA, Tsukamoto K, Moriya K, Ono Y, Imai K: Determination of serum D-lactic and L-lactic acids in normal subjects and diabetic patients by column-switching HPLC with pre-column fluorescence derivatization. Anal Bioanal Chem. 2003 Nov;377(5):886-91. Epub 2003 Jul 19. Pubmed: 12879188
  • Hoijer MA, Melief MJ, van Helden-Meeuwsen CG, Eulderink F, Hazenberg MP: Detection of muramic acid in a carbohydrate fraction of human spleen. Infect Immun. 1995 May;63(5):1652-7. Pubmed: 7729869
  • 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
  • Kaneko T, Bando Y, Kurihara H, Satomi K, Nonoyama K, Matsuura N: Fecal microflora in a patient with short-bowel syndrome and identification of dominant lactobacilli. J Clin Microbiol. 1997 Dec;35(12):3181-5. Pubmed: 9399516
  • 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
  • McLellan AC, Phillips SA, Thornalley PJ: Fluorimetric assay of D-lactate. Anal Biochem. 1992 Oct;206(1):12-6. Pubmed: 1456422
  • Pedersen M: Ciliary activity and pollution. Lung. 1990;168 Suppl:368-76. Pubmed: 2117139
  • Schmid-Schonbein GW: Microlymphatics and lymph flow. Physiol Rev. 1990 Oct;70(4):987-1028. Pubmed: 2217560
  • Smith SM, Eng RH, Buccini F: Use of D-lactic acid measurements in the diagnosis of bacterial infections. J Infect Dis. 1986 Oct;154(4):658-64. Pubmed: 3528318
  • Solito R, Alessandrini C, Fruschelli M, Pucci AM, Gerli R: An immunological correlation between the anchoring filaments of initial lymph vessels and the neighboring elastic fibers: a unified morphofunctional concept. Lymphology. 1997 Dec;30(4):194-202. Pubmed: 9476251
  • Tanyel FC, Ulusu NN, Tezcan EF, Buyukpamukcu N: Total calcium content of sacs associated with inguinal hernia, hydrocele or undescended testis reflects differences dictated by programmed cell death. Urol Int. 2003;70(3):211-5. Pubmed: 12660459
  • 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
  • Zhang YJ, O'Neal WK, Randell SH, Blackburn K, Moyer MB, Boucher RC, Ostrowski LE: Identification of dynein heavy chain 7 as an inner arm component of human cilia that is synthesized but not assembled in a case of primary ciliary dyskinesia. J Biol Chem. 2002 May 17;277(20):17906-15. Epub 2002 Mar 4. Pubmed: 11877439
Synthesis Reference:Hsieh, Chun Lung; Houng, Jer Yiing. Preparation of D-lactic acid from D,L-lactic acid ester using wheat germ or pancreatic lipase. U.S. (1997), 5 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID341
HMDB IDHMDB01311
Pubchem Compound ID61503
Kegg IDC00256
ChemSpider ID55423
WikipediaDLA
BioCyc IDD-LACTATE
EcoCyc IDD-LACTATE
Ligand ExpoLAC

Enzymes

General function:
Involved in flavin adenine dinucleotide binding
Specific function:
First component of the membrane-bound D-lactate oxidase, which is believed to play an important role in the energization of the active transport of a variety of sugars and amino acids
Gene Name:
dld
Uniprot ID:
P06149
Molecular weight:
64612
Reactions
(R)-lactate + NAD(+) = pyruvate + NADH.
General function:
Involved in hydrolase activity
Specific function:
Thiolesterase that catalyzes the hydrolysis of S-D- lactoyl-glutathione to form glutathione and D-lactic acid
Gene Name:
gloB
Uniprot ID:
P0AC84
Molecular weight:
28434
Reactions
S-(2-hydroxyacyl)glutathione + H(2)O = glutathione + a 2-hydroxy carboxylate.
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Fermentative lactate dehydrogenase
Gene Name:
ldhA
Uniprot ID:
P52643
Molecular weight:
36535
Reactions
(R)-lactate + NAD(+) = pyruvate + NADH.
General function:
Involved in carbon-oxygen lyase activity
Specific function:
Specifically catalyzes the cleavage of the D-lactyl ether substituent of MurNAc 6-phosphate, producing GlcNAc 6- phosphate and D-lactate. Is required for growth on MurNAc as the sole source of carbon and energy. Together with AnmK, is also required for the utilization of anhydro-N-acetylmuramic acid (anhMurNAc) either imported from the medium or derived from its own cell wall murein, and thus plays a role in cell wall recycling
Gene Name:
murQ
Uniprot ID:
P76535
Molecular weight:
31220
Reactions
N-acetylmuramate 6-phosphate + H(2)O = N-acetyl-D-glucosamine 6-phosphate + D-lactate.
General function:
Not Available
Specific function:
Functions as a holding molecular chaperone (holdase) which stabilizes unfolding intermediates and rapidly releases them in an active form once stress has abated. Plays an important role in protecting cells from severe heat shock and starvation, as well as in acid resistance of stationary-phase cells. It uses temperature-induced exposure of structured hydrophobic domains to capture and stabilizes early unfolding and denatured protein intermediates under severe thermal stress. Catalyzes the conversion of methylglyoxal (MG) to D-lactate in a single glutathione (GSH)-independent step. It can also use phenylglyoxal as substrate. Glyoxalase activity protects cells against dicarbonyl stress. Displays an aminopeptidase activity that is specific against peptide substrates with alanine or basic amino acids (lysine, arginine) at N-terminus. Functions as a holding molecular chaperone (holdase) which stabilizes unfolding intermediates and rapidly releases them in an active form once stress has abated. Plays an important role in protecting cells from severe heat shock and starvation, as well as in acid resistance of stationary-phase cells. It uses temperature-induced exposure of structured hydrophobic domains to capture and stabilizes early unfolding and denatured protein intermediates under severe thermal stress. Catalyzes the conversion of methylglyoxal (MG) to D-lactate in a single glutathione (GSH)-independent step. It can also use phenylglyoxal as substrate. Glyoxalase activity protects cells against dicarbonyl stress. Displays an aminopeptidase activity that is specific against peptide substrates with alanine or basic amino acids (lysine, arginine) at N-terminus.
Gene Name:
hchA
Uniprot ID:
P31658
Molecular weight:
Not Available
Reactions
(R)-lactate = methylglyoxal + H(2)O.
(R)-lactate = methylglyoxal + H(2)O.

Transporters

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
Uniprot ID:
P33231
Molecular weight:
59168
General function:
Involved in lactate transmembrane transporter activity
Specific function:
Transports glycolate across the membrane. Can also transport L-lactate and D-lactate. Seems to be driven by a proton motive force
Gene Name:
glcA
Uniprot ID:
Q46839
Molecular weight:
58920
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368