Gliotoxin

Gliotoxin is a sulfur-containing mycotoxin that belongs to a class of naturally occurring 2,5-diketopiperazines produced by several species of fungi, especially those of marine origin. It is the most prominent member of the epipolythiopiperazines, a large class of natural products featuring a diketopiperazine with di- or polysulfide linkage. These highly bioactive compounds have been the subject of numerous studies aimed at new therapeutics. Gliotoxin was originally isolated from Gliocladium fimbriatum, and was named accordingly. It is an epipolythiodioxopiperazine metabolite that is one of the most abundantly produced metabolites in human invasive Aspergillosis (IA).

Gliotoxin
Names
IUPAC name
(3R,6S,10aR)-6-Hydroxy-3-(hydroxymethyl)-2-methyl-2,3,6,10-tetrahydro-5aH-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.163.992
PubChem CID
UNII
  • InChI=1S/C13H14N2O4S2/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-20-12/h2-4,8-9,16-17H,5-6H2,1H3/t8-,9-,12+,13+/m0/s1 Y
    Key: FIVPIPIDMRVLAY-RBJBARPLSA-N Y
  • InChI=1S/C13H14N2O4S2/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-20-12/h2-4,8-9,16-17H,5-6H2,1H3/t8-,9-,12+,13+/m0/s1
    Key: FIVPIPIDMRVLAY-RBJBARPLBT
  • Key: FIVPIPIDMRVLAY-RBJBARPLSA-N
SMILES
  • O=C1N([C@@]2(SS[C@@]14N(C2=O)[C@H]3C(=C\C=C/[C@@H]3O)/C4)CO)C
Properties
C13H14N2O4S2
Molar mass 326.39 g·mol−1
Appearance White to light yellow solid
Density 1.75 g/ml
Solubility in DMSO soluble
Hazards
Safety data sheet (SDS) MSDS from Fermentek
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references
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