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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 02:40:30 UTC
HMDB IDHMDB0001311
Secondary Accession Numbers
  • HMDB0000171
  • HMDB00171
  • HMDB01311
Metabolite Identification
Common NameD-Lactic acid
DescriptionLactic acid is an organic acid. It is a chiral molecule, consisting of two optical isomers, L-lactic acid and D-lactic acid, with the L-isomer being the most common in living organisms. Lactic acid plays a role in several biochemical processes and is produced in the muscles during intense activity. D-Lactic acid is the end product of the enzyme glyoxalase II (or hydroxyacyl-glutathione hydrolase) (EC 3.1.2.6), which converts the intermediate substrate S-lactoyl-glutathione to reduced glutathione and D-lactate (OMIM: 138790 ).
Structure
Thumb
Synonyms
ValueSource
(-)-Lactic acidChEBI
(R)-(-)-Lactic acidChEBI
D-2-Hydroxypropanoic acidChEBI
D-2-Hydroxypropionic acidChEBI
D-MilchsaeureChEBI
LACTIC ACIDChEBI
(-)-LactateGenerator
D-LactateGenerator
(R)-(-)-LactateGenerator
D-2-HydroxypropanoateGenerator
D-2-HydroxypropionateGenerator
LACTateGenerator
(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
2 Hydroxypropanoic acidMeSH
2 Hydroxypropionic acidMeSH
2-Hydroxypropanoic acidMeSH
Ammonium lactateMeSH
L Lactic acidMeSH
2-Hydroxypropionic acidMeSH
Sarcolactic acidMeSH
D Lactic acidMeSH
Lactate, ammoniumMeSH
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 KeyJVTAAEKCZFNVCJ-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
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

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 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
Polarizability8.05 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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-9000000000-704f8ff33156c82a02d1View 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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-000i-9000000000-d7cd347946e49a57860eView 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 NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C 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
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Locations
  • Bladder
  • Brain
  • Fibroblasts
  • Gut
  • Intestine
  • Liver
  • Muscle
  • Neuron
  • Placenta
  • Platelet
  • Skeletal Muscle
  • Skin
  • Spleen
  • Stratum Corneum
  • Testes
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
BloodDetected and Quantified600 uMChildren (1-13 years old)MaleD-Lactic Acidosis details
BloodDetected and Quantified3100-20200 uMAdult (>18 years old)BothD-Lactic Acidosis and Short Bowel Syndrome details
BloodDetected and Quantified4000-10000 uMChildren (1-13 years old)MaleD-Lactic Acidosis and Short Bowel Syndrome details
BloodDetected and Quantified6700 uMAdolescent (13-18 years old)MaleD-Lactic Acidosis and Short Bowel Syndrome details
Cerebrospinal Fluid (CSF)Detected and Quantified600 uMChildren (1-13 years old)MaleD-Lactic Acidosis details
Cerebrospinal Fluid (CSF)Detected and Quantified>2300 uMChildren (1-13 years old)Not SpecifiedMetabolic Disorder details
UrineDetected and Quantified466.667-1933.333 umol/mmol creatinineChildren (1-13 years old)MaleD-Lactic Acidosis details
UrineDetected and Quantified6783.6 umol/mmol creatinineChildren (1-13 years old)MaleD-Lactic Acidosis and Short Bowel Syndrome details
UrineDetected and Quantified2190-20000 umol/mmol creatinineAdult (>18 years old)BothD-Lactic Acidosis and Short Bowel Syndrome 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. [PubMed: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. [PubMed:25004141 ]
D-Lactic Acidosis
  1. Duran M, Van Biervliet JP, Kamerling JP, Wadman SK: D-lactic aciduria, an inborn error of metabolism? Clin Chim Acta. 1977 Feb 1;74(3):297-300. [PubMed:832430 ]
D-Lactic Acidosis and Short Bowel Syndrome
  1. Uribarri J, Oh MS, Carroll HJ: D-lactic acidosis. A review of clinical presentation, biochemical features, and pathophysiologic mechanisms. Medicine (Baltimore). 1998 Mar;77(2):73-82. [PubMed:9556700 ]
Associated OMIM IDs
DrugBank IDDB03066
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003293
KNApSAcK IDC00019549
Chemspider ID55423
KEGG Compound IDC00256
BioCyc IDD-LACTATE
BiGG ID34414
Wikipedia LinkLactic_acid
METLIN ID6150
PubChem Compound61503
PDB IDLAC
ChEBI ID42111
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. [PubMed: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. [PubMed: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. [PubMed:6113819 ]
  4. Pedersen M: Ciliary activity and pollution. Lung. 1990;168 Suppl:368-76. [PubMed:2117139 ]
  5. McLellan AC, Phillips SA, Thornalley PJ: Fluorimetric assay of D-lactate. Anal Biochem. 1992 Oct;206(1):12-6. [PubMed:1456422 ]
  6. Schmid-Schonbein GW: Microlymphatics and lymph flow. Physiol Rev. 1990 Oct;70(4):987-1028. [PubMed: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. [PubMed:9476251 ]
  8. Brandt RB, Siegel SA: Methylglyoxal production in human blood. Ciba Found Symp. 1978;(67):211-23. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:9786900 ]