Record Information
Version2.0
Creation Date2014-08-29 06:17:54 UTC
Update Date2014-12-24 20:26:46 UTC
Accession NumberT3D4307
Identification
Common NameD-Lactic acid
ClassSmall Molecule
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). The concentrated form is used internally to prevent gastrointestinal fermentation.
Compound Type
  • Animal Toxin
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
Synonyms
Synonym
(-)-Lactate
(-)-Lactic acid
(R)-(-)-Lactate
(R)-(-)-Lactic 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
D-(-)-Lactate
D-(-)-Lactic acid
D-2-Hydroxypropanoate
D-2-Hydroxypropanoic acid
D-2-Hydroxypropionate
D-2-Hydroxypropionic acid
D-Lactate
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
Propel
Tisulac
Chemical FormulaC3H6O3
Average Molecular Mass90.078 g/mol
Monoisotopic Mass90.032 g/mol
CAS Registry Number10326-41-7
IUPAC Name(2S)-2-hydroxypropanoic acid
Traditional Name(α)-lactate
SMILES[H][C@](C)(O)C(O)=O
InChI IdentifierInChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m1/s1
InChI KeyInChIKey=JVTAAEKCZFNVCJ-UWTATZPHSA-N
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
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biofluid LocationsNot Available
Tissue Locations
  • Bladder
  • Brain
  • Fibroblasts
  • Gut
  • Intestine
  • Liver
  • Muscle
  • Neuron
  • Placenta
  • Platelet
  • Skeletal Muscle
  • Skin
  • Spleen
  • Stratum Corneum
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Pyruvaldehyde DegradationSMP00459 Not Available
Pyruvate MetabolismSMP00060 map00620
Biotinidase DeficiencySMP00174 Not Available
Leigh SyndromeSMP00196 Not Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point52.8°C
Boiling Point122°C at 1.50E+01 mm Hg
Solubility1E+006 mg/L
LogP-0.72
Predicted Properties
PropertyValueSource
logP-0.47ChemAxon
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
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00kb-0900000000-fb59ec16914501aa19ab2014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014j-0900000000-c4d9e12b4b0150eda54b2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0900000000-fb59ec16914501aa19ab2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-a3691f383d440fb00e1f2016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01b9-9620000000-f7faa7db9c1be3d9d9752017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-9000000000-1d5a5f55463acefb6fc72012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-000m-9000000000-c07133799d8f43d4c75a2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-000i-9000000000-ddb080250741e69ab1372012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-8f5d5eddb0b4b2a3b5412012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-3bcfc4cdc49230f156422012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9000000000-48b511409f4f60cec04e2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-365ea3c1bcfff2cab9382012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-9d0238aeeb837213e81d2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-8f5d5eddb0b4b2a3b5412017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-3bcfc4cdc49230f156422017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-48b511409f4f60cec04e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-365ea3c1bcfff2cab9382017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-9d0238aeeb837213e81d2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-014i-9000000000-046bb7f6cce9744388eb2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000f-9000000000-1c6ea519686b2066052f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-9000000000-013763552dec660fac8c2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-bc4403a40640361e5a522021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-9000000000-5f417f4a6d08f0ab00ed2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dm-9000000000-df7a94bb1a9cf6e78e1a2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-9000000000-dc2a1b965287b9dfee9c2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-c3686a681cc9bbf039e12016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-ddad20647c2ac56efd222016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-b728b45617afcc6b67da2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-b586cb8f053eb4465b4e2021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-400a5f1c0dfcc32ef2bb2021-09-25View Spectrum
MSMass Spectrum (Electron Ionization)splash10-002b-9000000000-50213d6b39ef9741c4662014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not Available2016-10-22View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Not Available2021-10-10View Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB03066
HMDB IDHMDB01311
PubChem Compound ID61503
ChEMBL IDCHEMBL358850
ChemSpider ID55423
KEGG IDC00256
UniProt IDNot Available
OMIM ID
ChEBI ID341
BioCyc IDD-LACTATE
CTD IDNot Available
Stitch IDNot Available
PDB IDLAC
ACToR IDNot Available
Wikipedia LinkDLA
References
Synthesis Reference

Hartmut Voelskow, Dieter Sukatsch, “Process for the production of D-lactic acid with the use of Lactobacillus bulgaricus DSM 2129.” U.S. Patent US4467034, issued May, 1979.

MSDSLink
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 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Oxidative rna demethylase activity
Specific Function:
Dioxygenase that repairs alkylated DNA and RNA by oxidative demethylation. Has highest activity towards single-stranded RNA containing 3-methyluracil, followed by single-stranded DNA containing 3-methylthymine. Has low demethylase activity towards single-stranded DNA containing 1-methyladenine or 3-methylcytosine (PubMed:18775698, PubMed:20376003). Specifically demethylates N(6)-methyladenosine (m6A) RNA, the most prevalent internal modification of messenger RNA (mRNA) in higher eukaryotes (PubMed:22002720, PubMed:26458103). Has no activity towards 1-methylguanine. Has no detectable activity towards double-stranded DNA. Requires molecular oxygen, alpha-ketoglutarate and iron. Contributes to the regulation of the global metabolic rate, energy expenditure and energy homeostasis. Contributes to the regulation of body size and body fat accumulation (PubMed:18775698, PubMed:20376003).
Gene Name:
FTO
Uniprot ID:
Q9C0B1
Molecular Weight:
58281.53 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC50>1000 uMNot AvailableBindingDB 50420196
References
  1. Aik W, Demetriades M, Hamdan MK, Bagg EA, Yeoh KK, Lejeune C, Zhang Z, McDonough MA, Schofield CJ: Structural basis for inhibition of the fat mass and obesity associated protein (FTO). J Med Chem. 2013 May 9;56(9):3680-8. doi: 10.1021/jm400193d. Epub 2013 Apr 23. [23547775 ]
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
May mediate the release of newly synthesized prostaglandins from cells, the transepithelial transport of prostaglandins, and the clearance of prostaglandins from the circulation. Transports PGD2, as well as PGE1, PGE2 and PGF2A.
Gene Name:
SLCO2A1
Uniprot ID:
Q92959
Molecular Weight:
70043.33 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory48 uMNot AvailableBindingDB 50420196
References
  1. Chan BS, Endo S, Kanai N, Schuster VL: Identification of lactate as a driving force for prostanoid transport by prostaglandin transporter PGT. Am J Physiol Renal Physiol. 2002 Jun;282(6):F1097-102. [11997326 ]
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da