ECMDB: Cysteine-S-sulfate (ECMDB00731) (M2MDB000180)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (5)Transporters (3)XML

Proteins (117)

Record Information

Version

2.0

Creation Date

2012-05-31 13:00:52 -0600

Update Date

2015-09-13 12:56:09 -0600

Secondary Accession Numbers

ECMDB00731

Identification

Name:

Cysteine-S-sulfate

Description

Cysteine-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

MOL SDF PDB SMILES InChI

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

S-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 Framework

Aliphatic acyclic compounds

External Descriptors

S-substituted L-cysteine (CHEBI:27891 )
organic thiosulfate (CHEBI:27891 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

170-171 °C

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	53.8 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-2.3	ChemAxon
logS	-0.57	ALOGPS
pKa (Strongest Acidic)	-1.9	ChemAxon
pKa (Strongest Basic)	8.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	117.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	38.64 m³·mol⁻¹	ChemAxon
Polarizability	16.76 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

O-Acetylserine + Thiosulfate <> Cysteine-S-sulfate + Acetic acid
O-Acetylserine + Thiosulfate + Thiosulfate > Cysteine-S-sulfate + Acetic acid
Cysteine-S-sulfate + Adenosine triphosphate + Water > Cysteine-S-sulfate + Adenosine diphosphate + Phosphate + Hydrogen ion + ADP
Cysteine-S-sulfate + Adenosine triphosphate + Water > Cysteine-S-sulfate + Adenosine diphosphate + Phosphate + Hydrogen ion + ADP

SMPDB Pathways:

cysteine biosynthesis

PW000800

KEGG Pathways:

Cysteine and methionine metabolism ec00270

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-b41d65b938527c785175	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-5900000000-174ddc933fb4262b6c4b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-0930000000-3a10270996044266f5ff	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9100000000-d25cccbc09519d08f684	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00di-9000000000-285ddd2bd242fb3f4f94	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0090000000-67fc3cbd5242cf8812eb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0080-6920000000-51297f61c1e507e4fc41	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0089-9200000000-a3bb8e3eaa57447953e8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-001i-9100000000-7709278c846451c0d981	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-001i-9000000000-b8d9d78e8a4cb67d1d55	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-000i-2920000000-0b87083b8f086069245d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00di-8910000000-8731b3ae0d4eda8996c3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00di-9400000000-54f0f85b487cc83c6b80	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0abc-9200000000-7c97c65eb8848afdecb2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0udi-9500000000-a96d24f9946bb7c1a114	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-00di-0900000000-0f68d3c88020aecea493	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0a6r-9800000000-6d5b706f037dc2097042	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-00dl-9000000000-41e2dd8cc34b88cf9a22	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-4910000000-371af0521b2bd90215c3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-008j-7900000000-71cc4905c12f99250ba2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0090000000-67fc3cbd5242cf8812eb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0pc0-2920000000-f2d4cd6b66dfedcabbf4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-5900000000-4cfcbb384ce848a0a42b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9300000000-139770596676116aa83a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000t-4900000000-8b8f3384b567ae50c601	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0089-7900000000-b86202987a56dccfef99	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0089-9200000000-605200559d7d478c7e71	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View 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)

Links

External Links:

Resource	Link
CHEBI ID	27891
HMDB ID	HMDB00731
Pubchem Compound ID	115015
Kegg ID	C05824
ChemSpider ID	102939
Wikipedia ID	Not Available
BioCyc ID	Not Available
Ligand Expo	CSU

Enzymes

Protein Details

1. Cystathionine gamma-synthase

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.

Protein Details

2. Cysteine synthase B

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.

Protein Details

3. Putative aliphatic sulfonates transport permease protein ssuC

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

Protein Details

4. Putative aliphatic sulfonates-binding protein

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

Protein Details

5. Aliphatic sulfonates import ATP-binding protein SsuB

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

Protein Details

1. Putative aliphatic sulfonates transport permease protein ssuC

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

Protein Details

2. Putative aliphatic sulfonates-binding protein

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

Protein Details

3. Aliphatic sulfonates import ATP-binding protein SsuB

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

Cysteine-S-sulfate (ECMDB00731) (M2MDB000180)

Structure for #<Compound:0xa44286b0>

Enzymes

Reactions

Reactions

Transporters