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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:37 UTC
Update Date2021-09-14 15:00:08 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. In humans, 3-mercaptolactic acid is involved in the cysteine metabolism pathway. 3-Mercaptolactic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-mercaptolactic acid a potential biomarker for the consumption of these foods. 3-Mercaptolactic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on 3-Mercaptolactic acid.
Structure
Data?1582752230
Synonyms
ValueSource
3-MercaptolactateGenerator
b-MercaptolactateHMDB
b-Mercaptolactic acidHMDB
beta-MercaptolactateHMDB, MeSH
beta-Mercaptolactic acidHMDB
2-Hydroxy-3-mercaptopropionic acidMeSH, HMDB
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
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+123.2931661259
DarkChem[M-H]-116.98631661259
DeepCCS[M+H]+136.3230932474
DeepCCS[M-H]-133.55830932474
DeepCCS[M-2H]-170.030932474
DeepCCS[M+Na]+144.67130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Mercaptolactic acidOC(CS)C(O)=O2653.9Standard polar33892256
3-Mercaptolactic acidOC(CS)C(O)=O1194.2Standard non polar33892256
3-Mercaptolactic acidOC(CS)C(O)=O1219.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Mercaptolactic acid,1TMS,isomer #1C[Si](C)(C)OC(CS)C(=O)O1288.3Semi standard non polar33892256
3-Mercaptolactic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)C(O)CS1170.8Semi standard non polar33892256
3-Mercaptolactic acid,1TMS,isomer #3C[Si](C)(C)SCC(O)C(=O)O1330.4Semi standard non polar33892256
3-Mercaptolactic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(CS)O[Si](C)(C)C1305.4Semi standard non polar33892256
3-Mercaptolactic acid,2TMS,isomer #2C[Si](C)(C)OC(CS[Si](C)(C)C)C(=O)O1450.0Semi standard non polar33892256
3-Mercaptolactic acid,2TMS,isomer #3C[Si](C)(C)OC(=O)C(O)CS[Si](C)(C)C1378.5Semi standard non polar33892256
3-Mercaptolactic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(CS[Si](C)(C)C)O[Si](C)(C)C1493.1Semi standard non polar33892256
3-Mercaptolactic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(CS[Si](C)(C)C)O[Si](C)(C)C1445.2Standard non polar33892256
3-Mercaptolactic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(CS[Si](C)(C)C)O[Si](C)(C)C1456.2Standard polar33892256
3-Mercaptolactic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(CS)C(=O)O1537.4Semi standard non polar33892256
3-Mercaptolactic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(O)CS1423.1Semi standard non polar33892256
3-Mercaptolactic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)SCC(O)C(=O)O1565.2Semi standard non polar33892256
3-Mercaptolactic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(CS)O[Si](C)(C)C(C)(C)C1770.7Semi standard non polar33892256
3-Mercaptolactic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(CS[Si](C)(C)C(C)(C)C)C(=O)O1888.0Semi standard non polar33892256
3-Mercaptolactic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(O)CS[Si](C)(C)C(C)(C)C1839.8Semi standard non polar33892256
3-Mercaptolactic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(CS[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2127.8Semi standard non polar33892256
3-Mercaptolactic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(CS[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2106.8Standard non polar33892256
3-Mercaptolactic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(CS[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1914.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Mercaptolactic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-002g-9000000000-ec302f4694b6fbe742e42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Mercaptolactic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0101-6900000000-98313ee0ac74efcd81ec2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Mercaptolactic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptolactic acid 10V, Positive-QTOFsplash10-0ab9-2900000000-55f12b41f09e42cb47fe2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptolactic acid 20V, Positive-QTOFsplash10-05i0-9800000000-5b40640f82765202a9312017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptolactic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-8d35c46555f8bdd847ad2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptolactic acid 10V, Negative-QTOFsplash10-00di-5900000000-c6cd293513c4793101fa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptolactic acid 20V, Negative-QTOFsplash10-0fk9-6900000000-9ddf197cc5dea25f92f12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptolactic acid 40V, Negative-QTOFsplash10-05cu-9000000000-ebb35603167a0fe7949e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptolactic acid 10V, Negative-QTOFsplash10-00ei-9600000000-1bb94b127c625b0d2c7e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptolactic acid 20V, Negative-QTOFsplash10-001i-9000000000-942ac689538269d6ca7b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptolactic acid 40V, Negative-QTOFsplash10-001i-9000000000-942ac689538269d6ca7b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptolactic acid 10V, Positive-QTOFsplash10-0a4i-9800000000-84ad16e616d5892fcac42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptolactic acid 20V, Positive-QTOFsplash10-0a4i-9000000000-0d197946f5f3da97fbe62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Mercaptolactic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-2facde427c58aeabdf382021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents 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