mycothiol

Mycothiol (MSH or AcCys-GlcN-Ins) is an unusual thiol compound found in the Actinomycetota. It is composed of a cysteine residue with an acetylated amino group linked to glucosamine, which is then linked to inositol. The oxidized, disulfide form of mycothiol (MSSM) is called mycothione, and is reduced to mycothiol by the flavoprotein mycothione reductase. Mycothiol biosynthesis and mycothiol-dependent enzymes such as mycothiol-dependent formaldehyde dehydrogenase and mycothione reductase have been proposed to be good drug targets for the development of treatments for tuberculosis.

In the Vinony graph

Vinony's link graph records 13 inbound references to mycothiol, and connects out to tuberculosis, digital object identifier and chemical formula.

It is catalogued under topics including Acetamides, Chembox image size set and Propionamides.

Vinony links it to 9 Wikipedia language editions.

Chemical data

Formula: C17H30N2O12S
Molecular weight: 486.5 g/mol
IUPAC name: (2R)-2-acetamido-N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(2R,3R,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyoxan-3-yl]-3-sulfanylpropanamide
SMILES: CC(=O)N[C@@H](CS)C(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1OC2[C@@H]([C@H](C([C@H]([C@H]2O)O)O)O)O)CO)O)O
InChIKey: MQBCDKMPXVYCGO-MGQAWMCHSA-N
XLogP: -5.6
Polar surface area: 240 Å²
H-bond donors: 11
H-bond acceptors: 13
Formal charge: 0

via PubChem

Wikidata facts

Subclass of: chemical compound
Mass: 486.151945

Show 4 more facts

chemical formula: C₁₇H₃₀N₂O₁₂S
canonical SMILES: CC(=O)NC(CS)C(=O)NC1C(C(C(OC1OC2C(C(C(C(C2O)O)O)O)O)CO)O)O
isomeric SMILES: CC(=O)N[C@@H](CS)C(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1OC2[C@@H]([C@H](C([C@H]([C@H]2O)O)O)O)O)CO)O)O
Commons category: Mycothiol

Sources (2)

via Wikidata · CC0

~1 min read