Record Information
Version2.0
Creation Date2012-05-31 13:00:52 -0600
Update Date2015-09-13 12:56:09 -0600
Secondary Accession Numbers
  • ECMDB00731
Identification
Name:Cysteine-S-sulfate
DescriptionCysteine-S-sulfate (SSC) is produced by reaction of inorganic sulfite and cystine by a yet unknown pathway and is a very potent NMDA-receptor agonist. Electrophysiological studies have shown that SSC displays depolarizing properties similar to glutamate. It is an intermediate of cysteine and methionine metabolism.
Structure
Thumb
Synonyms:
  • Alaninethiosulfate
  • Alaninethiosulfurate
  • Alaninethiosulfuric acid
  • Alaninethiosulphate
  • Alaninethiosulphurate
  • Alaninethiosulphuric acid
  • Cysteine-S-sulfate
  • Cysteine-S-sulfonate
  • Cysteine-S-sulfonic acid
  • Cysteine-S-sulfuric acid
  • Cysteine-S-sulphate
  • Cysteine-S-sulphonate
  • Cysteine-S-sulphonic acid
  • Cysteine-S-sulphuric acid
  • Cysteinyl-S-sulfonate
  • Cysteinyl-S-sulfonic acid
  • Cysteinyl-S-sulphonate
  • Cysteinyl-S-sulphonic acid
  • L-Cysteine hydrogen sulfate (ester)
  • L-Cysteine hydrogen sulfuric acid (ester)
  • L-Cysteine hydrogen sulphate (ester)
  • L-Cysteine hydrogen sulphuric acid (ester)
  • L-Cysteine S-sulfate
  • L-Cysteine S-sulfuric acid
  • L-Cysteine S-sulphate
  • L-Cysteine S-sulphuric acid
  • L-Cysteine-S-sulfonate
  • L-Cysteine-S-sulfonic acid
  • L-Cysteine-S-sulphonate
  • L-Cysteine-S-sulphonic acid
  • L-Cysteinesulfonate
  • L-Cysteinesulfonic acid
  • L-Cysteinesulphonate
  • L-Cysteinesulphonic acid
  • S-Cysteinesulfonate
  • S-Cysteinesulfonic acid
  • S-Cysteinesulphonate
  • S-Cysteinesulphonic acid
  • S-Sulfo-L-cysteine
  • S-Sulfocysteine
  • S-Sulpho-L-cysteine
  • S-Sulphocysteine
Chemical Formula:C3H7NO5S2
Weight:Average: 201.221
Monoisotopic: 200.976563719
InChI Key:NOKPBJYHPHHWAN-REOHCLBHSA-N
InChI:InChI=1S/C3H7NO5S2/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)/t2-/m0/s1
CAS number:1637-71-4
IUPAC Name:(2R)-2-amino-3-(sulfosulfanyl)propanoic acid
Traditional IUPAC Name:S-sulphocysteine
SMILES:N[C@@H](CSS(O)(=O)=O)C(O)=O
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 nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:170-171 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility53.8 g/LALOGPS
logP-2.3ALOGPS
logP-2.3ChemAxon
logS-0.57ALOGPS
pKa (Strongest Acidic)-1.9ChemAxon
pKa (Strongest Basic)8.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area117.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.64 m³·mol⁻¹ChemAxon
Polarizability16.76 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
cysteine biosynthesisPW000800 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Cysteine and methionine metabolism ec00270
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-b41d65b938527c785175View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-5900000000-174ddc933fb4262b6c4bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0930000000-3a10270996044266f5ffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9100000000-d25cccbc09519d08f684View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-285ddd2bd242fb3f4f94View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0090000000-67fc3cbd5242cf8812ebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0080-6920000000-51297f61c1e507e4fc41View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0089-9200000000-a3bb8e3eaa57447953e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-9100000000-7709278c846451c0d981View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001i-9000000000-b8d9d78e8a4cb67d1d55View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-000i-2920000000-0b87083b8f086069245dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-8910000000-8731b3ae0d4eda8996c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-9400000000-54f0f85b487cc83c6b80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0abc-9200000000-7c97c65eb8848afdecb2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0udi-9500000000-a96d24f9946bb7c1a114View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0900000000-0f68d3c88020aecea493View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0a6r-9800000000-6d5b706f037dc2097042View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00dl-9000000000-41e2dd8cc34b88cf9a22View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-4910000000-371af0521b2bd90215c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-008j-7900000000-71cc4905c12f99250ba2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0090000000-67fc3cbd5242cf8812ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pc0-2920000000-f2d4cd6b66dfedcabbf4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-5900000000-4cfcbb384ce848a0a42bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-139770596676116aa83aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000t-4900000000-8b8f3384b567ae50c601View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0089-7900000000-b86202987a56dccfef99View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0089-9200000000-605200559d7d478c7e71View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Abbas AK, Xia W, Tranberg M, Wigstrom H, Weber SG, Sandberg M: S-sulfo-cysteine is an endogenous amino acid in neonatal rat brain but an unlikely mediator of cysteine neurotoxicity. Neurochem Res. 2008 Feb;33(2):301-7. Epub 2007 Sep 1. Pubmed: 17764028
  • Arnold GL, Greene CL, Stout JP, Goodman SI: Molybdenum cofactor deficiency. J Pediatr. 1993 Oct;123(4):595-8. Pubmed: 8410516
  • Beemer FA, Duran M, Wadman SK, Cats BP: Absence of hepatic molybdenum cofactor. An inborn error of metabolism associated with lens dislocation. Ophthalmic Paediatr Genet. 1985 Apr;5(3):191-5. Pubmed: 3877898
  • Duran M, Aarsen G, Fokkens RH, Nibbering NM, Cats BP, de Bree PK, Wadman SK: 2-Mercaptoethanesulfonate-cysteine disulfide excretion following the administration of 2-mercaptoethanesulfonate--a pitfall in the diagnosis of sulfite oxidase deficiency. Clin Chim Acta. 1981 Mar 19;111(1):47-53. Pubmed: 6784974
  • Graf WD, Oleinik OE, Jack RM, Weiss AH, Johnson JL: Ahomocysteinemia in molybdenum cofactor deficiency. Neurology. 1998 Sep;51(3):860-2. Pubmed: 9748040
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Rashed MS, Saadallah AA, Rahbeeni Z, Eyaid W, Seidahmed MZ, Al-Shahwan S, Salih MA, Osman ME, Al-Amoudi M, Al-Ahaidib L, Jacob M: Determination of urinary S-sulphocysteine, xanthine and hypoxanthine by liquid chromatography-electrospray tandem mass spectrometry. Biomed Chromatogr. 2005 Apr;19(3):223-30. Pubmed: 15558695
Synthesis Reference:Ubuka T; Kinuta M; Akagi R; Kiguchi S; Azumi M Reaction of S-(2-amino-2-carboxyethylsulfonyl)-L-cysteine with sulfite: synthesis of S-sulfo-L-cysteine and L-alanine 3-sulfinic acid and application to the determination of sulfite. Analytical biochemist
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID27891
HMDB IDHMDB00731
Pubchem Compound ID115015
Kegg IDC05824
ChemSpider ID102939
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand ExpoCSU

Enzymes

General function:
Involved in pyridoxal phosphate binding
Specific function:
O(4)-succinyl-L-homoserine + L-cysteine = L- cystathionine + succinate
Gene Name:
metB
Uniprot ID:
P00935
Molecular weight:
41550
Reactions
O(4)-succinyl-L-homoserine + L-cysteine = L-cystathionine + succinate.
General function:
Involved in cysteine biosynthetic process from serine
Specific function:
Two cysteine synthase enzymes are found. Both catalyze the same reaction. Cysteine synthase B can also use thiosulfate in place of sulfide to give cysteine thiosulfonate as a product
Gene Name:
cysM
Uniprot ID:
P16703
Molecular weight:
32664
Reactions
O(3)-acetyl-L-serine + H(2)S = L-cysteine + acetate.
General function:
Involved in transporter activity
Specific function:
Part of a binding-protein-dependent transport system for aliphatic sulfonates. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
ssuC
Uniprot ID:
P75851
Molecular weight:
28925
General function:
Involved in sulfur compound metabolic process
Specific function:
Part of a binding-protein-dependent transport system for aliphatic sulfonates. Putative binding protein
Gene Name:
ssuA
Uniprot ID:
P75853
Molecular weight:
34557
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex SsuABC involved in aliphatic sulfonates import. Responsible for energy coupling to the transport system (Probable)
Gene Name:
ssuB
Uniprot ID:
P0AAI1
Molecular weight:
27738

Transporters

General function:
Involved in transporter activity
Specific function:
Part of a binding-protein-dependent transport system for aliphatic sulfonates. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
ssuC
Uniprot ID:
P75851
Molecular weight:
28925
General function:
Involved in sulfur compound metabolic process
Specific function:
Part of a binding-protein-dependent transport system for aliphatic sulfonates. Putative binding protein
Gene Name:
ssuA
Uniprot ID:
P75853
Molecular weight:
34557
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex SsuABC involved in aliphatic sulfonates import. Responsible for energy coupling to the transport system (Probable)
Gene Name:
ssuB
Uniprot ID:
P0AAI1
Molecular weight:
27738