CHEBI:61338 - bacillithiol

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ChEBI Name bacillithiol
ChEBI ID CHEBI:61338
Definition A thiol that is the α-anomeric glycoside of L-cysteinyl-D-glucosamine with L-malic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Midori Harris
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Formula C13H22N2O10S
Net Charge 0
Average Mass 398.38600
Monoisotopic Mass 398.100
InChI InChI=1S/C13H22N2O10S/c14-4(3-26)11(21)15-8-10(20)9(19)6(2-16)25-13(8)24-5(12(22)23)1-7(17)18/h4-6,8-10,13,16,19-20,26H,1-3,14H2,(H,15,21)(H,17,18)(H,22,23)/t4-,5-,6+,8+,9+,10+,13-/m0/s1
InChIKey UHNHELGKNQMNGF-AOQKXWSCSA-N
SMILES N[C@@H](CS)C(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H](CC(O)=O)C(O)=O
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): cofactor
An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group).
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
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ChEBI Ontology
Outgoing bacillithiol (CHEBI:61338) has role antioxidant (CHEBI:22586)
bacillithiol (CHEBI:61338) has role bacterial metabolite (CHEBI:76969)
bacillithiol (CHEBI:61338) has role cofactor (CHEBI:23357)
bacillithiol (CHEBI:61338) is a glycoside (CHEBI:24400)
bacillithiol (CHEBI:61338) is a monosaccharide derivative (CHEBI:63367)
bacillithiol (CHEBI:61338) is a thiol (CHEBI:29256)
bacillithiol (CHEBI:61338) is conjugate acid of bacillithiol(1−) (CHEBI:64876)
Incoming bacillithiol(1−) (CHEBI:64876) is conjugate base of bacillithiol (CHEBI:61338)
IUPAC Name
(2S)-2-{[2-(L-cysteinylamino)-2-deoxy-α-D-glucopyranosyl]oxy}butanedioic acid
Synonyms Sources
BSH ChEBI
Cys-GlcN-mal ChEBI
Database Links Databases
Bacillithiol Wikipedia
CPD8J2-3 MetaCyc
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Citations Waiting for Citations Types Sources
19578333 PubMed citation Europe PMC
20308541 PubMed citation SUBMITTER
20712413 PubMed citation Europe PMC
21751306 PubMed citation Europe PMC
22262099 PubMed citation Europe PMC
23030527 PubMed citation Europe PMC
23256780 PubMed citation Europe PMC
24115506 PubMed citation Europe PMC
24166956 PubMed citation Europe PMC
Last Modified
13 January 2014
General Comment
2011-02-22 Appears to participate in the sensing of peroxides by Bacillus.