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Record Information
Version3.6
Creation Date2006-05-22 14:17:37 UTC
Update Date2013-05-29 19:34:08 UTC
HMDB IDHMDB02127
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Mercaptolactic acid
Description3-Mercaptolactic acid is a thiol that has been confirmed to be found in urine (PMID 8852041 ).
Structure
Thumb
Synonyms
  1. 3-Mercaptolactate
  2. b-Mercaptolactate
  3. b-Mercaptolactic acid
  4. beta-Mercaptolactate
  5. beta-Mercaptolactic acid
Chemical FormulaC3H6O3S
Average Molecular Weight122.143
Monoisotopic Molecular Weight122.003764748
IUPAC Name2-hydroxy-3-sulfanylpropanoic acid
Traditional IUPAC Name3-mercaptolactic acid
CAS Registry Number2614-83-7
SMILES
OC(CS)C(O)=O
InChI Identifier
InChI=1S/C3H6O3S/c4-2(1-7)3(5)6/h2,4,7H,1H2,(H,5,6)
InChI KeyOLQOVQTWRIJPRE-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassOrganic Acids and Derivatives
ClassHydroxy Acids and Derivatives
Sub ClassAlpha Hydroxy Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Alkylthiol
  • Carboxylic Acid
  • Secondary Alcohol
  • Thiol (Sulfanyl Compound)
Direct ParentAlpha Hydroxy Acids and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility28.8 g/LALOGPS
logP-0.33ALOGPS
logP-0.42ChemAxon
logS-0.63ALOGPS
pKa (strongest acidic)3.73ChemAxon
pKa (strongest basic)-3.9ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count3ChemAxon
polar surface area57.53ChemAxon
rotatable bond count2ChemAxon
refractivity26.57ChemAxon
polarizability10.98ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Cysteine MetabolismSMP00013map00270
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022856
KNApSAcK IDNot Available
Chemspider ID141158
KEGG Compound IDC05823
BioCyc IDNot Available
BiGG ID46576
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02127
Metagene LinkHMDB02127
METLIN ID6499
PubChem Compound160645
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceCosta, Mara; Pensa, Bernardo; Iavarone, Carlo; Cavallini, Doriano. Preparation of 3-mercaptolactic acid and S-aminoethylmercaptolactic acid. Preparative Biochemistry (1982), 12(5), 417-27.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hannestad U, Sorbo B: Determination of 3-mercaptolactate, mercaptoacetate and N-acetylcysteine in urine by gas chromatography. Clin Chim Acta. 1979 Jul 16;95(2):189-200. Pubmed: 527218
  2. Wronski M: Separation of urinary thiols as tributyltinmercaptides and determination using capillary isotachophoresis. J Chromatogr B Biomed Appl. 1996 Feb 9;676(1):29-34. Pubmed: 8852041

Enzymes

General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Displays an lactate dehydrogenase activity. Significantly increases the transcriptional activity of JUN, when overexpressed.
Gene Name:
LDHAL6A
Uniprot ID:
Q6ZMR3
Molecular weight:
36507.015
Reactions
3-Mercaptolactic acid + NAD → 3-Mercaptopyruvic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Not Available
Gene Name:
LDHB
Uniprot ID:
P07195
Molecular weight:
36638.225
Reactions
3-Mercaptolactic acid + NAD → 3-Mercaptopyruvic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Possible role in sperm motility.
Gene Name:
LDHC
Uniprot ID:
P07864
Molecular weight:
36310.965
Reactions
3-Mercaptolactic acid + NAD → 3-Mercaptopyruvic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Not Available
Gene Name:
LDHA
Uniprot ID:
P00338
Molecular weight:
30204.975
Reactions
3-Mercaptolactic acid + NAD → 3-Mercaptopyruvic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Not Available
Gene Name:
LDHAL6B
Uniprot ID:
Q9BYZ2
Molecular weight:
41942.53
Reactions
3-Mercaptolactic acid + NAD → 3-Mercaptopyruvic acid + NADH + Hydrogen Iondetails