D-Lactic acid (PAMDB000334)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000334
Identification
Name: D-Lactic acid
Description:D-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
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 90.0779
Monoisotopic Molecular Weight: 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:(2R)-2-hydroxypropanoic acid
Traditional IUPAC Name: D-lactic acid
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: Solid
Charge:-1
Melting point: 52.8 C
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
Polarizability8.05 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
D-Lactic acid + NAD <> Hydrogen ion + NADH + Pyruvic acid
Water + S-Lactoylglutathione > Glutathione + Hydrogen ion + D-Lactic acid
D-Lactic acid + Ubiquinone-8 > Pyruvic acid + Ubiquinol-8
S-Lactoylglutathione + Water <> Glutathione + D-Lactic acid
an electron-transfer-related quinone + D-Lactic acid > an electron-transfer-related quinol + Pyruvic acid
D-Lactic acid + Hydrogen ion < Pyruvaldehyde + Water
N-Acetylmuramic acid 6-phosphate + Water <> N-Acetyl-D-Glucosamine 6-Phosphate + D-Lactic acid
D-Lactic acid + NAD > Pyruvic acid + NADH
D-Lactic acid > Pyruvaldehyde + Water
MurNAc-6-P + Water > D-Lactic acid + N-Acetylglucosamine 6-phosphate
Pathways:
  • Amino sugar and nucleotide sugar metabolism pae00520
  • Microbial metabolism in diverse environments pae01120
  • Pyruvate metabolism pae00620
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-9000000000-704f8ff33156c82a02d1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-000m-9000000000-023931446d9bb3330e7fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-000l-9000000000-0fb29afb128baea2240bView 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
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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

Protein Details
• D-lactate dehydrogenase_
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
Locus Tag:
PA0927
Molecular weight:
35.8 kDa
Reactions
(R)-lactate + NAD(+) = pyruvate + NADH.
Protein Details
• Molecular chaperone Hsp31 and glyoxalase 3
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
Locus Tag:
PA1135
Molecular weight:
31.9 kDa
Reactions
(R)-lactate = methylglyoxal + H(2)O.
(R)-lactate = methylglyoxal + H(2)O.

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