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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-10-12 18:32:35 UTC
HMDB IDHMDB01311
Secondary Accession Numbers
  • HMDB00171
Metabolite Identification
Common NameD-Lactic acid
DescriptionD-Lactic acid is the end product of the enzyme Glyoxalase II ([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
ValueSource
D-LactateKegg
D-2-Hydroxypropanoic acidKegg
D-2-Hydroxypropionic acidKegg
D-2-HydroxypropanoateGenerator
D-2-HydroxypropionateGenerator
(-)-LactateHMDB
(-)-Lactic acidHMDB
(R)-(-)-LactateHMDB
(R)-(-)-Lactic acidHMDB
(R)-2-HydroxypropanoateHMDB
(R)-2-Hydroxypropanoic acidHMDB
(R)-2-HydroxypropionateHMDB
(R)-2-Hydroxypropionic acidHMDB
(R)-a-HydroxypropionateHMDB
(R)-a-Hydroxypropionic acidHMDB
(R)-alpha-HydroxypropionateHMDB
(R)-alpha-Hydroxypropionic acidHMDB
(R)-LactateHMDB
(R)-Lactic acidHMDB
D-(-)-LactateHMDB
D-(-)-Lactic acidHMDB
delta-(-)-LactateHMDB
delta-(-)-Lactic acidHMDB
delta-2-HydroxypropanoateHMDB
delta-2-Hydroxypropanoic acidHMDB
delta-2-HydroxypropionateHMDB
delta-2-Hydroxypropionic acidHMDB
delta-LactateHMDB
delta-Lactic acidHMDB
DLAHMDB
L-(+)-LactateHMDB
L-Lactic acidHMDB
PropelHMDB
TisulacHMDB
Chemical FormulaC3H6O3
Average Molecular Weight90.0779
Monoisotopic Molecular Weight90.031694058
IUPAC Name(2R)-2-hydroxypropanoic acid
Traditional NameD-lactic acid
CAS Registry Number10326-41-7
SMILES
C[C@@H](O)C(O)=O
InChI Identifier
InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m1/s1
InChI KeyInChIKey=JVTAAEKCZFNVCJ-UWTATZPHSA-N
Chemical 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.
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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Extracellular
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point52.8 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-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
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Bladder
  • Brain
  • Fibroblasts
  • Gut
  • Intestine
  • Liver
  • Muscle
  • Neuron
  • Placenta
  • Platelet
  • Skeletal Muscle
  • Skin
  • Spleen
  • Stratum Corneum
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Leigh SyndromeSMP00196Not Available
Primary hyperoxaluria II, PH2SMP00558Not Available
Pyruvaldehyde DegradationSMP00459Not Available
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)SMP00334Not Available
Pyruvate Dehydrogenase Complex DeficiencySMP00212Not Available
Pyruvate kinase deficiencySMP00559Not Available
Pyruvate MetabolismSMP00060map00620
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified11.0 +/- 1.2 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified7.26 +/- 0.481 uMAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified8 +/- 4.6 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified508+/-293 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified20.0 +/- 1.3 uMAdult (>18 years old)BothDiabetes details
BloodDetected and Quantified13.1 +/- 1.42 uMAdult (>18 years old)Both
Schizophrenia
details
Cerebrospinal Fluid (CSF)Detected and Quantified>2300 uMChildren (1-13 years old)Not SpecifiedMetabolic Disorder details
Associated Disorders and Diseases
Disease References
Diabetes mellitus type 2
  1. McLellan AC, Phillips SA, Thornalley PJ: Fluorimetric assay of D-lactate. Anal Biochem. 1992 Oct;206(1):12-6. [1456422 ]
Schizophrenia
  1. Fukushima T, Iizuka H, Yokota A, Suzuki T, Ohno C, Kono Y, Nishikiori M, Seki A, Ichiba H, Watanabe Y, Hongo S, Utsunomiya M, Nakatani M, Sadamoto K, Yoshio T: Quantitative analyses of schizophrenia-associated metabolites in serum: serum D-lactate levels are negatively correlated with gamma-glutamylcysteine in medicated schizophrenia patients. PLoS One. 2014 Jul 8;9(7):e101652. doi: 10.1371/journal.pone.0101652. eCollection 2014. [25004141 ]
Associated OMIM IDs
DrugBank IDDB03066
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003293
KNApSAcK IDC00019549
Chemspider ID55423
KEGG Compound IDC00256
BioCyc IDD-LACTATE
BiGG ID34414
Wikipedia LinkDLA
NuGOwiki LinkHMDB01311
Metagene LinkHMDB01311
METLIN ID6150
PubChem Compound61503
PDB IDLAC
ChEBI ID341
References
Synthesis ReferenceHsieh, 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)
General References
  1. 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. [12879188 ]
  2. 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. [3528318 ]
  3. 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. [6113819 ]
  4. Pedersen M: Ciliary activity and pollution. Lung. 1990;168 Suppl:368-76. [2117139 ]
  5. McLellan AC, Phillips SA, Thornalley PJ: Fluorimetric assay of D-lactate. Anal Biochem. 1992 Oct;206(1):12-6. [1456422 ]
  6. Schmid-Schonbein GW: Microlymphatics and lymph flow. Physiol Rev. 1990 Oct;70(4):987-1028. [2217560 ]
  7. 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. [9476251 ]
  8. Brandt RB, Siegel SA: Methylglyoxal production in human blood. Ciba Found Symp. 1978;(67):211-23. [259500 ]
  9. 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. [11877439 ]
  10. 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. [12660459 ]
  11. 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. [9399516 ]
  12. 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. [7729869 ]

Enzymes

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:
HAGH
Uniprot ID:
Q16775
Molecular weight:
28859.855
Reactions
S-Lactoylglutathione + Water → Glutathione + D-Lactic aciddetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
LDHD
Uniprot ID:
Q86WU2
Molecular weight:
54870.18
Reactions
D-Lactic acid + ferricytochrome c → Pyruvic acid + ferrocytochrome c + Hydrogen Iondetails
D-Lactic acid + Ferricytochrome c → Pyruvic acid + Ferrocytochrome c + Hydrogen Iondetails
General function:
Involved in hydrolase activity
Specific function:
Hydrolase acting on ester bonds (Potential).
Gene Name:
HAGHL
Uniprot ID:
Q6PII5
Molecular weight:
Not Available
Reactions
S-Lactoylglutathione + Water → Glutathione + D-Lactic aciddetails

Transporters

General function:
Involved in transmembrane transport
Specific function:
Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate
Gene Name:
SLC16A3
Uniprot ID:
O15427
Molecular weight:
49468.9
References
  1. Manning Fox JE, Meredith D, Halestrap AP: Characterisation of human monocarboxylate transporter 4 substantiates its role in lactic acid efflux from skeletal muscle. J Physiol. 2000 Dec 1;529 Pt 2:285-93. [11101640 ]
General function:
Involved in transmembrane transport
Specific function:
Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate
Gene Name:
SLC16A1
Uniprot ID:
P53985
Molecular weight:
53957.7
References
  1. Lin RY, Vera JC, Chaganti RS, Golde DW: Human monocarboxylate transporter 2 (MCT2) is a high affinity pyruvate transporter. J Biol Chem. 1998 Oct 30;273(44):28959-65. [9786900 ]
  2. Tamai I, Sai Y, Ono A, Kido Y, Yabuuchi H, Takanaga H, Satoh E, Ogihara T, Amano O, Izeki S, Tsuji A: Immunohistochemical and functional characterization of pH-dependent intestinal absorption of weak organic acids by the monocarboxylic acid transporter MCT1. J Pharm Pharmacol. 1999 Oct;51(10):1113-21. [10579682 ]
  3. Takanaga H, Tamai I, Inaba S, Sai Y, Higashida H, Yamamoto H, Tsuji A: cDNA cloning and functional characterization of rat intestinal monocarboxylate transporter. Biochem Biophys Res Commun. 1995 Dec 5;217(1):370-7. [8526936 ]
General function:
Involved in transmembrane transport
Specific function:
Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate. MCT2 is a high affinity pyruvate transporter
Gene Name:
SLC16A7
Uniprot ID:
O60669
Molecular weight:
52185.7
References
  1. Lin RY, Vera JC, Chaganti RS, Golde DW: Human monocarboxylate transporter 2 (MCT2) is a high affinity pyruvate transporter. J Biol Chem. 1998 Oct 30;273(44):28959-65. [9786900 ]