3-Mercaptolactate-cysteine disulfide (CHEM003363)

Record Information
Version1.0
Creation Date2014-08-29 06:50:59 UTC
Update Date2026-04-06 12:17:21 UTC
Accession NumberCHEM003363
Identification
Common Name3-Mercaptolactate-cysteine disulfide
ClassSmall Molecule
Description
3-mercaptolactate-cysteine disulfide is a compound analog of cysteine excreted in the urine of patients affected by Mercaptolactate-cysteine disulfiduria (MCDU, OMIM 249650), the product of disorder of sulfur amino acid metabolism and a reduced activity of the enzyme mercaptopyruvate sulfurtransferase (MST, EC 2.8.1.2). Reduction of protein in the diet, addition of pyridoxine or of neomycin did not affect the urinary excretion of beta-mercaptolactate-cysteine disulfide of a mentally defective patient who was excreting this mixed disulfide. Addition of cysteine to the diet did increase the excretion of this disulfide (1, 2, 3, 4).
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
Contaminant Type
  • Amine
  • Animal Toxin
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3-Mercaptolactate-cysteine disulphideGenerator
3-Mercaptolactic acid-cysteine disulfideGenerator
3-Mercaptolactic acid-cysteine disulphideGenerator
S-(2-Hydroxy-2-carboxyethylthio)cysteineMeSH
beta-Mercaptolactate cysteine disulfideMeSH
3-((2-Carboxy-2-hydroxyethyl)dithio)-L-alanineHMDB
HcetcHMDB
3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}-2-hydroxypropanoateGenerator, HMDB
3-{[(2R)-2-amino-2-carboxyethyl]disulphanyl}-2-hydroxypropanoateGenerator, HMDB
3-{[(2R)-2-amino-2-carboxyethyl]disulphanyl}-2-hydroxypropanoic acidGenerator, HMDB
3-Mercaptolactate-cysteine disulfideMeSH
Chemical FormulaC6H11NO5S2
Average Molecular Mass241.285 g/mol
Monoisotopic Mass241.008 g/mol
CAS Registry Number18841-42-4
IUPAC Name3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}-2-hydroxypropanoic acid
Traditional Namehcetc
SMILESN[C@@H](CSSCC(O)C(O)=O)C(O)=O
InChI IdentifierInChI=1S/C6H11NO5S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4,8H,1-2,7H2,(H,9,10)(H,11,12)/t3-,4?/m0/s1
InChI KeyMAFDYIDMXCXBRB-WUCPZUCCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-cysteine-S-conjugates
Alternative Parents
Substituents
  • L-cysteine-s-conjugate
  • Alpha-amino acid
  • L-alpha-amino acid
  • Alpha-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Monosaccharide
  • Amino acid
  • Dialkyldisulfide
  • Organic disulfide
  • Secondary alcohol
  • Carboxylic acid
  • Sulfenyl compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Carbonyl group
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organosulfur compound
  • Primary amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Beta-mercaptolactate-cysteine disulfiduriaSMP00499 Not Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility28.3 g/LALOGPS
logP-3.1ALOGPS
logP-3.6ChemAxon
logS-0.93ALOGPS
pKa (Strongest Acidic)1.68ChemAxon
pKa (Strongest Basic)9.04ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area120.85 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity53.21 m³·mol⁻¹ChemAxon
Polarizability22.11 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
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
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0006512
FooDB IDFDB023951
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID2742951
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID167948
ChEBI ID140723
PubChem Compound ID193536
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceKobayashi, Kanji; Ikegami, Takuma; Ubuka, Toshihiko. New metabolites of cystine. II. Chemical and biochemical properties of S-(2-oxo-2-carboxyethylthio)cysteine. Physiological Chemistry and Physics (1973), 5(2), 167-71.
MSDSNot Available
General References
1. Kobayashi, Kanji; Ikegami, Takuma; Ubuka, Toshihiko. New metabolites of cystine. II. Chemical and biochemical properties of S-(2-oxo-2-carboxyethylthio)cysteine. Physiological Chemistry and Physics (1973), 5(2), 167-71.
2. Crawhall JC: A review of the clinical presentation and laboratory findings in two uncommon hereditary disorders of sulfur amino acid metabolism, beta-mercaptolactate cysteine disulfideuria and sulfite oxidase deficiency. Clin Biochem. 1985 Jun;18(3):139-42.
3. 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.
4. 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.
5. Crawhall JC, Parker R, Sneddon W, Young EP, Ampola MG, Efron ML, Bixby EM: Beta mercaptolactate-cysteine disulfide: analog of cystine in the urine of a mentally retarded patient. Science. 1968 Apr 26;160(3826):419-20.
6. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19.