S-Sulfocysteine (CHEM003394)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (28)XML
Record Information
Version1.0
Creation Date2014-08-29 06:51:15 UTC
Update Date2026-05-14 18:07:53 UTC
Accession NumberCHEM003394
Identification
Common NameS-Sulfocysteine
ClassSmall Molecule
DescriptionS-Sulfocysteine is an endogenous organic compound with the formula C3H6NO5S2 and an average molecular weight of 200.21 g/mol. It exists as a solid at room temperature. S-Sulfocysteine belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. Biologically, it functions as both a human metabolite and a plant metabolite. It has been detected in brain tissue and interacts with two protein targets: glutamine synthetase (GLUL) and the glutamate--cysteine ligase catalytic subunit (GCLC). Additionally, S-Sulfocysteine is recorded as being found in or released from television systems within electrical and electronic equipment.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • T3DB toxins
Contaminant Type
  • Amine
  • Animal Toxin
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R)-2-Ammonio-3-(sulfonatosulfanyl)propanoateChEBI
(R)-2-Amino-3-(sulfothio)propanoateChEBI
Cytosine S-sulfateChEBI
S-SulfO-L-cysteinateChEBI
S-SulfO-L-cysteinate anionChEBI
S-SulfO-L-cysteineChEBI
S-SulfO-L-cysteine(1-)ChEBI
(2R)-2-Ammonio-3-(sulfonatosulfanyl)propanoic acidGenerator
(2R)-2-Ammonio-3-(sulphonatosulphanyl)propanoateGenerator
(2R)-2-Ammonio-3-(sulphonatosulphanyl)propanoic acidGenerator
(R)-2-Amino-3-(sulfothio)propanoic acidGenerator
(R)-2-Amino-3-(sulphothio)propanoateGenerator
(R)-2-Amino-3-(sulphothio)propanoic acidGenerator
Cytosine S-sulfuric acidGenerator
Cytosine S-sulphateGenerator
Cytosine S-sulphuric acidGenerator
S-SulfO-L-cysteinic acidGenerator
S-SulphO-L-cysteinateGenerator
S-SulphO-L-cysteinic acidGenerator
S-SulfO-L-cysteinic acid anionGenerator
S-SulphO-L-cysteinate anionGenerator
S-SulphO-L-cysteinic acid anionGenerator
S-SulphO-L-cysteineGenerator
S-SulphO-L-cysteine(1-)Generator
S-SulphocysteineGenerator
Chemical FormulaC3H6NO5S2
Average Molecular Mass200.214 g/mol
Monoisotopic Mass199.969 g/mol
CAS Registry Number1637-71-4
IUPAC Name(2R)-2-amino-3-(sulfosulfanyl)propanoic acid
Traditional NameS-sulfo-L-cysteinate
SMILES[H][C@](N)(CSS(O)(=O)=O)C([O-])=O
InChI IdentifierInChI=1S/C3H7NO5S2/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)/p-1/t2-/m0/s1
InChI KeyNOKPBJYHPHHWAN-REOHCLBHSA-M
Chemical Taxonomy
Description belongs to the class of organic compounds known as s-sulfo-l-cysteines. These are s-conjugated L-cysteine where the S-substituent is specified as a sulfo group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentS-sulfo-L-cysteines
Alternative Parents
Substituents
  • S-sulfo-l-cysteine
  • Alpha-amino acid
  • L-alpha-amino acid
  • S-alkyl thiosulfate
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Sulfenyl compound
  • Organic oxygen compound
  • Amine
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytosol
  • Extracellular
  • Membrane
  • Mitochondrion
  • Plasma Membrane
  • Synaptic Vesicle
Biofluid LocationsNot Available
Tissue Locations
  • Brain
Pathways
NameSMPDB LinkKEGG Link
Sulfur metabolismNot Availablemap00920
ApoptosisNot Availablemap04210
Glutathione biosynthesisNot AvailableNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility32.4 g/LALOGPS
logP-2ALOGPS
logP-2.3ChemAxon
logS-0.83ALOGPS
pKa (Strongest Acidic)-1.9ChemAxon
pKa (Strongest Basic)8.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area120.52 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity49.48 m³·mol⁻¹ChemAxon
Polarizability16.04 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1290000000-a605fed1bb7274e85c43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-639e8d434476b29e7cd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9200000000-a5114d144db3232e05ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-2900000000-37ede646876591d2cf08Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ds-9700000000-9e4da406118a2ae63d68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-9200000000-f9620c023173424ca78bSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityS-Sulfocysteine (SSC) is a very potent NMDA-receptor agonist. Electrophysiological studies have shown that SSC displays depolarizing properties similar to glutamate. Subcutaneous and intracerebral administration of SSC to infant rats induces brain damage. Apart from activating NMDA receptors, elevated SSC could also be neurotoxic by inhibition of the rate-limiting enzyme in glutathione synthesis (4), thereby reducing the intracellular levels of free radical scavengers. (3)
MetabolismS-Sulfocysteine is produced by reaction of inorganic sulfite and cystine by a yet unknown pathway (3). Sulfite is generated via the catabolism of sulfur-containing amino acids cysteine and methionine (1).
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesS-Sulfocysteine is produced by reaction of inorganic sulfite and cystine by a yet unknown pathway (3).
Minimum Risk LevelNot Available
Health EffectsNeurotoxicity.
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDSULFO-CYSTEINE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID62225
PubChem Compound ID6604702
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Pierre M. Bore, Jean-Claude Arnaud, “Keratin polymer containing S-sulphocysteine residues, process for its preparation and the compositions containing it.” U.S. Patent US4948876, issued May, 1981.

MSDSLink
General ReferencesNot Available