(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

• ChemBase ID: 127563
• Molecular Formular: C13H14N2O4S2
• Molecular Mass: 326.39126
• Monoisotopic Mass: 326.03949894
• SMILES: O=C1N([C@@]2(SS[C@]31N(C2=O)[C@H]1C(=CC=C[C@@H]1O)C3)CO)C
• Canonical SMILES: OC[C@@]12SS[C@@]3(N(C1=O)[C@@H]1[C@@H](O)C=CC=C1C3)C(=O)N2C
• InChI: 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
• InChIKey: FIVPIPIDMRVLAY-RBJBARPLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,7S,8S,11R)-7-hydroxy-11-(hydroxymethyl)-15-methyl-12,13-dithia-9,15-diazatetracyclo[9.2.2.0^1,^9.0^3,^8]pentadeca-3,5-diene-10,14-dione
• IUPAC Traditional name: gliotoxin
• Synonyms: Gliotoxin from Gliocladium fimbriatum; Gliotoxin

Database IDs

• CAS Number: 67-99-2
• MDL Number: MFCD00058534
• Beilstein Number: 50675
• PubChem SID: 162221882; 24895384
• PubChem CID: 6223
• CHEMBL: 331627
• Chemspider ID: 5988
• Wikipedia Title: Gliotoxin

CALCULATED PROPERTIES

• Acid pKa: 13.807189
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.018463584
• LogD (pH = 7.4): -0.018463751
• Log P: -0.018463582
• Molar Refractivity: 81.6876 cm^3
• Polarizability: 31.235182 Å^3
• Polar Surface Area: 81.08 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: chloroform: soluble10 mg/mL, clear, colorless; soluble in DMSO
• Apperance: white to light yellow solid

Safety Information

• RTECS: KB4725000
• European Hazard Symbols: Toxic (T)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 36/37/39-45; R
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C13H14N2O4S2

DETAILS

Sigma Aldrich - G9893

Application
Noncompetitive inhibitor of the chymotrypsin-like activity of the 20S proteasome in vitro.
Biochem/physiol Actions
An antiphagocytic and immunomodulating agent that acts by blocking membrane thiol groups.

Sigma Aldrich - 48975

Application
Noncompetitive inhibitor of the chymotrypsin-like activity of the 20S proteasome in vitro.
Other Notes
Antiphagocytic and immunomodulating agent which acts by blocking membrane thiol groups1,2