Gliotoxin

Catalog Number

ACM67992

Product Name

Gliotoxin

Structure

CAS

67-99-2

Category

Inhibitors

Description

Gliotoxin is a secondary metabolite, the most abundant mycotoxin secreted by A. fumigatus, inhibits the phagocytosis of macrophages and the immune functions of other immune cells . Gliotoxin inhibits inducible NF-κB activity by preventing IκB degradation, which consequently induces host-cell apoptosis. Gliotoxin activates PKA and increases intracellular cAMP concentration; modulates actin cytoskeleton rearrangement to facilitate A. fumigatus internalization into lung epithelial cells.

Synonyms

Aspergillin

IUPAC Name

(1R,7S,8S,11R)-7-hydroxy-11-(hydroxymethyl)-15-methyl-12,13-dithia-9,15-diazatetracyclo[9.2.2.01,9.03,8]pentadeca-3,5-diene-10,14-dione

Molecular Weight

326.4

Molecular Formula

C13H14N2O4S2

Canonical SMILES

CN1C(=O)[C@]23CC4=CC=C[C@@H]([C@H]4N2C(=O)[C@]1(SS3)CO)O

InChI

FIVPIPIDMRVLAY-RBJBARPLSA-N

InChI Key

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

Boiling Point

699.7±55.0 °C(Predicted)

Solubility

Soluble in DMSO (up to 15 mg/ml)

Appearance

White lyophilized solid

Storage

Powder-20°C, 3 years; In solvent-80°C. 6 months; -20°C, 1 month.

Complexity

621

Defined Atom Stereocenter Count

4

Exact Mass

326.0394

Formal Charge

0

Heavy Atom Count

21

Hydrogen Bond Acceptor Count

6

Hydrogen Bond Donor Count

2

Isotope Atom Count

0

Monoisotopic Mass

326.0394

pKa

12.90±0.40(Predicted)

Rotatable Bond Count

1

Shipping

Room temperature

Source

Aspergillus fumigatus

Stability

Stable for 2 yeara as supplied. Solutions in DMSO may be stored at -20 °C for up to 1 month.

Storage Temperature

-20 °C

Topological Polar Surface Area

132 Ų

MSDS

COA

Spec Sheet