S-sulfo-L-cysteine (CHEM042395)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 02:01:41 UTC
Update Date2016-11-09 01:22:40 UTC
Accession NumberCHEM042395
Identification
Common NameS-sulfo-L-cysteine
ClassSmall Molecule
DescriptionAn S-substituted L-cysteine where the S-substituent is specified as a sulfo group.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Cysteine-S-sulfonateChEBI
Cysteinyl-S-sulfonateChEBI
Cysteinyl-S-sulfonic acidChEBI
L-Cysteine hydrogen sulfateChEBI
L-Cysteine S-sulfateChEBI
S-SulfocysteineChEBI
S-SulphO-L-cysteineChEBI
S-SulphocysteineChEBI
Cysteine-S-sulfonic acidGenerator
Cysteine-S-sulphonateGenerator
Cysteine-S-sulphonic acidGenerator
Cysteinyl-S-sulphonateGenerator
Cysteinyl-S-sulphonic acidGenerator
L-Cysteine hydrogen sulfuric acidGenerator
L-Cysteine hydrogen sulphateGenerator
L-Cysteine hydrogen sulphuric acidGenerator
L-Cysteine S-sulfuric acidGenerator
L-Cysteine S-sulphateGenerator
L-Cysteine S-sulphuric acidGenerator
S-SulfO-L-cysteineGenerator
Cysteine-S-sulfuric acidGenerator
Cysteine-S-sulphateGenerator
Cysteine-S-sulphuric acidGenerator
Alaninethiosulfuric acidHMDB
L-Cysteine hydrogen sulfate (ester)HMDB
L-Cysteine hydrogen sulphate (ester)HMDB
L-Cysteine-S-sulfonateHMDB
L-Cysteinesulfonic acidHMDB
S-Cysteinesulfonic acidHMDB
S-Sulphocysteine, monosodium saltHMDB
S-Sulphocysteine ion (1-)HMDB
Chemical FormulaC3H7NO5S2
Average Molecular Mass201.221 g/mol
Monoisotopic Mass200.977 g/mol
CAS Registry NumberNot Available
IUPAC Name(2R)-2-amino-3-(sulfosulfanyl)propanoic acid
Traditional NameS-sulphocysteine
SMILESN[C@@H](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)/t2-/m0/s1
InChI KeyNOKPBJYHPHHWAN-REOHCLBHSA-N
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-b41d65b938527c785175Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-5900000000-174ddc933fb4262b6c4bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-0930000000-3a10270996044266f5ffSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9100000000-d25cccbc09519d08f684Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-285ddd2bd242fb3f4f94Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0090000000-67fc3cbd5242cf8812ebSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0080-6920000000-51297f61c1e507e4fc41Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0089-9200000000-a3bb8e3eaa57447953e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-9100000000-7709278c846451c0d981Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001i-9000000000-b8d9d78e8a4cb67d1d55Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-000i-2920000000-0b87083b8f086069245dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-8910000000-8731b3ae0d4eda8996c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-9400000000-54f0f85b487cc83c6b80Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0abc-9200000000-7c97c65eb8848afdecb2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0udi-9500000000-a96d24f9946bb7c1a114Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-0900000000-0f68d3c88020aecea493Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0a6r-9800000000-6d5b706f037dc2097042Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00dl-9000000000-41e2dd8cc34b88cf9a22Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-4910000000-371af0521b2bd90215c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-008j-7900000000-71cc4905c12f99250ba2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0090000000-67fc3cbd5242cf8812ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pc0-2920000000-f2d4cd6b66dfedcabbf4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-5900000000-4cfcbb384ce848a0a42bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-139770596676116aa83aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000t-4900000000-8b8f3384b567ae50c601Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0089-7900000000-b86202987a56dccfef99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0089-9200000000-605200559d7d478c7e71Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB04370
HMDB IDHMDB0000731
FooDB IDFDB022209
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID102939
ChEBI ID27891
PubChem Compound ID115015
Kegg Compound IDC05824
YMDB IDNot Available
ECMDB IDECMDB00731
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20179139
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23392866
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23430915
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24285094
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=962465
6. 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 biochemistry (1982), 126(2), 273-7.
7. Graf WD, Oleinik OE, Jack RM, Weiss AH, Johnson JL: Ahomocysteinemia in molybdenum cofactor deficiency. Neurology. 1998 Sep;51(3):860-2.
8. Arnold GL, Greene CL, Stout JP, Goodman SI: Molybdenum cofactor deficiency. J Pediatr. 1993 Oct;123(4):595-8.
9. 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.
10. 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.
11. 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.
12. 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.