Thiocysteine (BioCAD00000018506)

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Metabolite Card

Formula: C3H7NO2S2 (152.9918)
SMILES: N[C@H](CSS)C(O)=O

Synonyms [en]

Thiocysteine; 3-disulfanyl-L-alanine; L-Thiocysteine; S-Mercapto-L-cysteine; 2-amino-3-persulfhydrylpropanoic acid; (R)-2-amino-3-disulfanylpropanoic acid

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Thiocysteine. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000018506). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

The 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).

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 5652-32-4
  • CAS Registry Number: 6165-31-7
  • PubChem: 165331
  • PubChem: 439614
  • PubChem: 45266695
  • ChEBI: ChEBI:28839
  • ChEBI: ChEBI:58591
  • HMDB: HMDB0003585
  • HMDB: HMDB03585
  • KEGG: C01962
  • BioCyc: THIOCYSTEINE
  • NCBI MeSH: thiocysteine
  • DrugBank: DB02761
  • RefMet: RM0129940
  • Metlin: METLIN_58162
  • Coconut NaturalProduct: CNP0101794.1
  • Coconut NaturalProduct: CNP0101794.2

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02408 4.4.1.1 L-cystine thiocysteine-lyase (deaminating; pyruvate-forming)
BioCyc:CYSTHIOCYS-RXN 4.4.1.35 CYSTINE + WATER --> THIOCYSTEINE + PYRUVATE + AMMONIUM
BioCyc:RXN-15128 CYSTINE<=>2-AMINOACRYLATE + THIOCYSTEINE
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Organism Source

Taxonomy Source

Pathway Synthetic

pathway id name
WikiPathways:WP3604 Biochemical pathways: part I
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