Gliotoxin - ≥99% , CAS No.67-99-2

CAS: 67-99-2 Cat. No.: G1421216 Molecular Weight: 326.39 Beilstein Registry Number: 50675 EC Number: 636-170-3 PubChem CID: 6223

GRADE & PURITY ≥99%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

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. Gliotoxinactivates PKA and increases intracellular cAMP concentration; modulates actin cytoskeleton rearrangement to facilitate A. fumigatus internalization into lung epithelial cells. Gliotoxin is a potent NOTCH2 transactivation inhibitor, can effectively induce apoptosis of chronic lymphocytic leukemia (CLL) cells.

Specifications

Specifications & Purity

≥99%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CN1C(=O)C23CC4=CC=CC(C4N2C(=O)C1(SS3)CO)O
• 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
• InChIKey: FIVPIPIDMRVLAY-RBJBARPLSA-N
• 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
• Isomeric SMILES: CN1C(=O)[C@]23CC4=CC=C[C@@H]([C@H]4N2C(=O)[C@]1(SS3)CO)O
• WGK Germany: 3
• RTECS: KB4725000
• PubChem CID: 6223
• Molecular Weight: 326.39
• Beilstein: 50675

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Diazinanes
      • Subclass Piperazines
        • Level5 Dioxopiperazines
          • Level6 2,5-dioxopiperazines
            • Level7 Thiodioxopiperazines
              • Level8 Epipolythiodioxopiperazines
                • Level9 Gliotoxins

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Diazinanes
• Subclass: Piperazines
• Intermediate Tree Nodes: Dioxopiperazines - 2,5-dioxopiperazines - Thiodioxopiperazines - Epipolythiodioxopiperazines
• Direct Parent: Gliotoxins
• Alternative Parents: Alpha amino acids and derivatives Indoles and derivatives N-methylpiperazines Dithiazinanes Tertiary carboxylic acid amides Pyrrolidines Secondary alcohols Organic disulfides Lactams Primary alcohols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Gliotoxin-skeleton - Alpha-amino acid or derivatives - Indole or derivatives - N-alkylpiperazine - N-methylpiperazine - Dithiazinane - Tertiary carboxylic acid amide - Pyrrolidine - Carboxamide group - Lactam - Organic disulfide - Secondary alcohol - Carboxylic acid derivative - Azacycle - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Alcohol - Organic oxygen compound - Carbonyl group - Organic nitrogen compound - Organooxygen compound - Primary alcohol - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as gliotoxins. These are polycyclic compounds containing the gliotoxin skeleton, which is structurally characterized by a epipolythiodioxopiperazine moiety fused to the pyrrolidine ring of an indol-7-ol derivative.
• External Descriptors: Mycotoxins

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y