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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:37 UTC
Update Date2020-02-26 21:23:50 UTC
HMDB IDHMDB0002127
Secondary Accession Numbers
  • HMDB02127
Metabolite Identification
Common Name3-Mercaptolactic acid
Description3-Mercaptolactic acid, also known as 3-mercaptolactate, belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. 3-Mercaptolactic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-mercaptolactic acid can be converted into 3-mercaptopyruvic acid through the action of the enzyme L-lactate dehydrogenase. In humans, 3-mercaptolactic acid is involved in cystinosis, ocular nonnephropathic. 3-Mercaptolactic acid is a thiol that has been confirmed to be found in urine (PMID 8852041 ).
Structure
Data?1582752230
Synonyms
ValueSource
3-MercaptolactateGenerator
b-MercaptolactateHMDB
b-Mercaptolactic acidHMDB
beta-MercaptolactateHMDB
beta-Mercaptolactic acidHMDB
2-Hydroxy-3-mercaptopropionic acidHMDB
Chemical FormulaC3H6O3S
Average Molecular Weight122.143
Monoisotopic Molecular Weight122.003764748
IUPAC Name2-hydroxy-3-sulfanylpropanoic acid
Traditional Nameβ-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
Description belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Monosaccharide
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alkylthiol
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

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 Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.57 m³·mol⁻¹ChemAxon
Polarizability10.98 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002g-9000000000-ec302f4694b6fbe742e4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0101-6900000000-98313ee0ac74efcd81ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-2900000000-55f12b41f09e42cb47feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05i0-9800000000-5b40640f82765202a931Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-8d35c46555f8bdd847adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-5900000000-c6cd293513c4793101faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-6900000000-9ddf197cc5dea25f92f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05cu-9000000000-ebb35603167a0fe7949eSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.910-4.430 umol/mmol creatinineNot SpecifiedBothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified58.7 umol/mmol creatinineAdult (>18 years old)FemaleBeta-mercaptolactate-cysteine Disulfiduria details
Associated Disorders and Diseases
Disease References
Beta-mercaptolactate-cysteine Disulfiduria
  1. Hannestad U, Martensson J, Sjodahl R, Sorbo B: 3-mercaptolactate cysteine disulfiduria: biochemical studies on affected and unaffected members of a family. Biochem Med. 1981 Aug;26(1):106-14. [PubMed:6945862 ]
Associated OMIM IDs
  • 249650 (Beta-mercaptolactate-cysteine Disulfiduria)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022856
KNApSAcK IDNot Available
Chemspider ID141158
KEGG Compound IDC05823
BioCyc IDNot Available
BiGG ID46576
Wikipedia LinkNot Available
METLIN ID6499
PubChem Compound160645
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDMERCPLAC
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