CHEBI:16768 - mycothiol

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ChEBI Name mycothiol
ChEBI ID CHEBI:16768
Definition A pseudodisaccharide, 1D-myo-inosityl-α-D-glucopyranoside, in which the hydroxy group at the 2-position of the glucose moiety is replaced by an (N-acetyl-L-cysteinyl)amido group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:7040, CHEBI:14626, CHEBI:25440
Supplier Information eMolecules:5851218, Selleckchem:nad
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Formula C17H30N2O12S
Net Charge 0
Average Mass 486.49238
Monoisotopic Mass 486.15195
InChI InChI=1S/C17H30N2O12S/c1-4(21)18-5(3-32)16(29)19-7-9(23)8(22)6(2-20)30-17(7)31-15-13(27)11(25)10(24)12(26)14(15)28/h5-15,17,20,22-28,32H,2-3H2,1H3,(H,18,21)(H,19,29)/t5-,6+,7+,8+,9+,10-,11-,12+,13+,14+,15-,17+/m0/s1
InChIKey MQBCDKMPXVYCGO-FQBKTPCVSA-N
SMILES CC(=O)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]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O
Roles Classification
Chemical Role(s): reducing agent
The element or compound in a reduction-oxidation (redox) reaction that donates an electron to another species.
Biological Role(s): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
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).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing mycothiol (CHEBI:16768) has functional parent myo-inositol (CHEBI:17268)
mycothiol (CHEBI:16768) has role bacterial metabolite (CHEBI:76969)
mycothiol (CHEBI:16768) has role cofactor (CHEBI:23357)
mycothiol (CHEBI:16768) has role reducing agent (CHEBI:63247)
mycothiol (CHEBI:16768) is a 2-deoxy-α-D-glucoside (CHEBI:37449)
mycothiol (CHEBI:16768) is a mycothiols (CHEBI:25441)
mycothiol (CHEBI:16768) is a thiol (CHEBI:29256)
Incoming S-(hydroxymethyl)mycothiol (CHEBI:61586) has functional parent mycothiol (CHEBI:16768)
S-formylmycothiol (CHEBI:15735) has functional parent mycothiol (CHEBI:16768)
S-nitrosomycothiol (CHEBI:59637) has functional parent mycothiol (CHEBI:16768)
mycothiol S-conjugate (CHEBI:59633) has functional parent mycothiol (CHEBI:16768)
mycothione (CHEBI:16086) has functional parent mycothiol (CHEBI:16768)
IUPAC Name
1-O-{2-[(N-acetyl-L-cysteinyl)amino]-2-deoxy-α-D-glucopyranosyl}-1D-myo-inositol
Synonyms Sources
(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl 2-[(N-acetyl-L-cysteinyl)amino]-2-deoxy-α-D-glucopyranoside IUPAC
1-D-myo-inositol-2-(N-acetyl-L-cysteinyl)amino-2-deoxy-alpha-D-glucopyranoside ChEBI
1-O-(2'-[N-acetyl-L-cysteinyl]amido-2'-deoxy-α-D-glucopyranosyl)-D-myo-inositol
Note: (2009-05-21) Cited in pmid:16768
 ChEBI
1-O-(2-[N-acetyl-L-cysteinyl]amido-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol IUBMB
1-O-[2-(N-acetyl-L-cysteinamido)-2-deoxy-α-D-glucopyranosyl]-D-myo-inositol IUBMB
1-O-[2-(N2-acetyl-L-cysteinamido)-2-deoxy-α-D-glucopyranosyl]-1D-myo-inositol MetaCyc
1-O-[2-[[(2R)-2-(acetylamino)-3-mercapto-1-oxopropyl]amino]-2-deoxy-α-D-glucopyranosyl]-D-myo-inositol ChEBI
1D-1-O-[2-(N-acetyl-L-cysteinamido)-2-deoxy-α-D-glucopyranosyl]-myo-inositol IUPAC
AcCys-GlcN-Ins ChemIDplus
MSH ChEBI
Mycothiol KEGG COMPOUND
mycothiol UniProt
Manual Xrefs Databases
C06717 KEGG COMPOUND
CPD1G-2 MetaCyc
G11174 KEGG GLYCAN
Mycothiol Wikipedia
View more database links
Registry Numbers Types Sources
192126-76-4 CAS Registry Number ChemIDplus
9308053 Beilstein Registry Number Beilstein
9308053 Reaxys Registry Number Reaxys
Citations Types Sources
11929223 PubMed citation Europe PMC
12809551 PubMed citation Europe PMC
14594852 PubMed citation Europe PMC
16768 PubMed citation Europe PMC
17428791 PubMed citation Europe PMC
17644601 PubMed citation Europe PMC
18772286 PubMed citation Europe PMC
19505149 PubMed citation Europe PMC
21919472 PubMed citation Europe PMC
22992771 PubMed citation Europe PMC
23428102 PubMed citation Europe PMC
23615850 PubMed citation Europe PMC
9804803 PubMed citation Europe PMC
Last Modified
28 January 2015