CHEBI:28839 - 3-disulfanyl-L-alanine

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ChEBI Name 3-disulfanyl-L-alanine
ChEBI ID CHEBI:28839
ChEBI ASCII Name 3-disulfanyl-L-alanine
Definition An S-substituted L-cysteine where the S-substituent is specified as sulfanyl.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41743, CHEBI:41628, CHEBI:41711, CHEBI:41718, CHEBI:9551, CHEBI:21269
Supplier Information No supplier information found for this compound.
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Formula C3H7NO2S2
Net Charge 0
Average Mass 153.210
Monoisotopic Mass 152.99182
InChI InChI=1S/C3H7NO2S2/c4-2(1-8-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1
InChIKey XBKONSCREBSMCS-REOHCLBHSA-N
SMILES C([C@H](N)C(=O)O)SS
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 3-disulfanyl-L-alanine (CHEBI:28839) has role human metabolite (CHEBI:77746)
3-disulfanyl-L-alanine (CHEBI:28839) has role mouse metabolite (CHEBI:75771)
3-disulfanyl-L-alanine (CHEBI:28839) is a S-substituted L-cysteine (CHEBI:47910)
3-disulfanyl-L-alanine (CHEBI:28839) is tautomer of 3-disulfanyl-L-alanine zwitterion (CHEBI:58591)
Incoming 3-disulfanyl-L-alanine residue (CHEBI:61963) is substituent group from 3-disulfanyl-L-alanine (CHEBI:28839)
3-disulfanyl-L-alanine zwitterion (CHEBI:58591) is tautomer of 3-disulfanyl-L-alanine (CHEBI:28839)
IUPAC Name
3-disulfanyl-L-alanine
Synonyms Sources
(R)-2-amino-3-disulfanylpropanoic acid RESID
2-amino-3-disulfanylpropanoic acid RESID
2-amino-3-hydrodisulfidopropanoic acid RESID
2-amino-3-hydropersulfidopropanoic acid RESID
2-amino-3-persulfhydrylpropanoic acid RESID
3-(thiosulfeno)-alanine RESID
cysteine persulfide ChEBI
cysteine perthiol ChEBI
S-sulfanylcysteine RESID
Thiocysteine KEGG COMPOUND
thiocysteine RESID
Manual Xrefs Databases
AA0269 RESID
C01962 KEGG COMPOUND
CSS PDBeChem
DB02761 DrugBank
View more database links
Registry Numbers Types Sources
5652-32-4 CAS Registry Number KEGG COMPOUND
5652-32-4 CAS Registry Number ChemIDplus
6381723 Reaxys Registry Number Reaxys
Citations
Wright CM, Christman GD, Snellinger AM, Johnston MV, Mueller EG (2006)
Direct evidence for enzyme persulfide and disulfide intermediates during 4-thiouridine biosynthesis.
Chemical communications (Cambridge, England)3104-3106 [PubMed:16855700]
[show Abstract]
Kurihara T, Mihara H, Kato S, Yoshimura T, Esaki N (2003)
Assembly of iron-sulfur clusters mediated by cysteine desulfurases, IscS, CsdB and CSD, from Escherichia coli.
Biochimica et biophysica acta 1647, 303-309 [PubMed:12686149]
[show Abstract]
Ollagnier-de-Choudens S, Lascoux D, Loiseau L, Barras F, Forest E, Fontecave M (2003)
Mechanistic studies of the SufS-SufE cysteine desulfurase: evidence for sulfur transfer from SufS to SufE.
FEBS letters 555, 263-267 [PubMed:14644425]
[show Abstract]
Kaiser JT, Bruno S, Clausen T, Huber R, Schiaretti F, Mozzarelli A, Kessler D (2003)
Snapshots of the cystine lyase C-DES during catalysis. Studies in solution and in the crystalline state.
The Journal of biological chemistry 278, 357-365 [PubMed:12386155]
[show Abstract]
Mihara H, Esaki N (2002)
Bacterial cysteine desulfurases: their function and mechanisms.
Applied microbiology and biotechnology 60, 12-23 [PubMed:12382038]
[show Abstract]
Clausen T, Kaiser JT, Steegborn C, Huber R, Kessler D (2000)
Crystal structure of the cystine C-S lyase from Synechocystis: stabilization of cysteine persulfide for FeS cluster biosynthesis.
Proceedings of the National Academy of Sciences of the United States of America 97, 3856-3861 [PubMed:10760256]
[show Abstract]
Kambampati R, Lauhon CT (2000)
Evidence for the transfer of sulfane sulfur from IscS to ThiI during the in vitro biosynthesis of 4-thiouridine in Escherichia coli tRNA.
The Journal of biological chemistry 275, 10727-10730 [PubMed:10753862]
[show Abstract]
Lang T, Kessler D (1999)
Evidence for cysteine persulfide as reaction product of L-Cyst(e)ine C-S-lyase (C-DES) from Synechocystis. Analyses using cystine analogues and recombinant C-DES.
The Journal of biological chemistry 274, 189-195 [PubMed:9867829]
[show Abstract]
Leibrecht I, Kessler D (1997)
A novel L-cysteine/cystine C-S-lyase directing [2Fe-2S] cluster formation of Synechocystis ferredoxin.
The Journal of biological chemistry 272, 10442-10447 [PubMed:9099686]
[show Abstract]
Last Modified
31 January 2024