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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 00:53:44 UTC
Update Date2023-02-21 17:16:45 UTC
HMDB IDHMDB0003585
Secondary Accession Numbers
  • HMDB0006337
  • HMDB03585
  • HMDB06337
Metabolite Identification
Common NameThiocysteine
DescriptionThe reactive species in the phosphofructokinase modulation system could be considered thiocysteine (R-S-S-) or cystine trisulfide (R-S-S-S-R) produced from cystine in the presence of gamma-Cystathionase (CST, EC 4.4.1.1). The desulfuration reaction of cystine in vivo produces thiocysteine containing a bound sulfur atom. Persulfide generated from L-cysteine inactivates tyrosine aminotransferase. Thiocysteine is the reactive (unstable) intermediate of thiocystine which functions as a persulfide in transferring its sulfane sulfur to thiophilic acceptors. Thiocystine conversion to unstable thiocysteine is accelerated by sulfhydryl compounds, or reagents that cleave sulfur-sulfur bonds to yield sulfhydryl groups. Thiocystine is proposed as the storage form of sulfane sulfur in biological systems. Liver cytosols contain factors that produce an inhibitor of tyrosine aminotransferase in 3 steps: initial oxidation of cysteine to form cystine; desulfurization of cystine catalyzed by cystathionase to form the persulfide, thiocysteine; and reaction of thiocysteine (or products of its decomposition) with proteins to form protein-bound sulfane. (PMID: 2903161 , 454618 , 7287665 ).
Structure
Thumb
Synonyms
ValueSource
3-(Thiosulfeno)-alanineHMDB
3-Disulfanyl-L-alanineHMDB
(2S)-2-Amino-3-disulfanylpropanoateHMDB
(2S)-2-Amino-3-disulphanylpropanoateHMDB
(2S)-2-Amino-3-disulphanylpropanoic acidHMDB
Chemical FormulaC3H7NO2S2
Average Molecular Weight153.223
Monoisotopic Molecular Weight152.991819853
IUPAC Name(2S)-2-amino-3-disulfanylpropanoic acid
Traditional Name(2S)-2-amino-3-disulfanylpropanoic acid
CAS Registry Number5652-32-4
SMILES
N[C@H](CSS)C(O)=O
InChI Identifier
InChI=1S/C3H7NO2S2/c4-2(1-8-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m1/s1
InChI KeyXBKONSCREBSMCS-UWTATZPHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCysteine and derivatives
Alternative Parents
Substituents
  • Cysteine or derivatives
  • Alpha-amino acid
  • D-alpha-amino acid
  • 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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.917Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023203
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC01962
BioCyc IDNot Available
BiGG ID38786
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439614
PDB IDNot Available
ChEBI ID28839
Food Biomarker OntologyNot Available
VMH IDTHCYS
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hargrove JL: Persulfide generated from L-cysteine inactivates tyrosine aminotransferase. Requirement for a protein with cysteine oxidase activity and gamma-cystathionase. J Biol Chem. 1988 Nov 25;263(33):17262-9. [PubMed:2903161 ]
  2. Abdolrasulnia R, Wood JL: Transfer of persulfide sulfur from thiocystine to rhodanese. Biochim Biophys Acta. 1979 Mar 16;567(1):135-43. [PubMed:454618 ]
  3. Yamanishi T, Tuboi S: The mechanism of the L-cystine cleavage reaction catalyzed by rat liver gamma-cystathionase. J Biochem. 1981 Jun;89(6):1913-21. [PubMed:7287665 ]

Enzymes

General function:
Involved in pyridoxal phosphate binding
Specific function:
Catalyzes the last step in the trans-sulfuration pathway from methionine to cysteine. Has broad substrate specificity. Converts cystathionine to cysteine, ammonia and 2-oxobutanoate. Converts two cysteine molecules to lanthionine and hydrogen sulfide. Can also accept homocysteine as substrate. Specificity depends on the levels of the endogenous substrates. Generates the endogenous signaling molecule hydrogen sulfide (H2S), and so contributes to the regulation of blood pressure. Acts as a cysteine-protein sulfhydrase by mediating sulfhydration of target proteins: sulfhydration consists of converting -SH groups into -SSH on specific cysteine residues of target proteins such as GAPDH, PTPN1 and NF-kappa-B subunit RELA, thereby regulating their function.
Gene Name:
CTH
Uniprot ID:
P32929
Molecular weight:
41259.91
Reactions
L-Cystine + Water → Pyruvic acid + Ammonia + Thiocysteinedetails