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Substance Name: Gliotoxin
RN: 67-99-2
UNII: 5L648PH06K
InChIKey: FIVPIPIDMRVLAY-RBJBARPLSA-N

Note

  • A fungal toxin produced by various species of Trichoderma, Gladiocladium fimbriatum, Aspergillus fumigatus, and Penicillium. It is used as an immunosuppressive agent.

Molecular Formula

  • C13-H14-N2-O4-S2

Molecular Weight

  • 326.3956
 

Classification Codes

  • Agricultural Chemical
  • Drug / Therapeutic Agent
  • Fungicide, Bactericide, Wood Preservative
  • Immunologic Factors
  • Immunosuppressive Agents
  • Mutation Data
  • Natural Product
  • Out-Dated Pesticide
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Names and Synonyms

Name of Substance

  • Gliotoxin

MeSH Heading

  • Gliotoxin

Synonyms

  • 4-27-00-08902 (Beilstein Handbook Reference)
  • AI3-62383
  • Aspergillin
  • BRN 0050675
  • CCRIS 4025
  • Gliotoxin
  • NSC 102866
  • S.N. 12870
  • UNII-5L648PH06K

Systematic Names

  • 10H-3,10a-Epidithiopyrazino(1,2-a)indole-1,4-dione, 2,3,5a,6-hydroxy-3- (hydroxymethyl)-2-methyl-, (3R-(3-alpha,5a-beta,6-beta,10a-alpha))-
  • 10H-3,10a-Epidithiopyrazino(1,2-a)indole-1,4-dione, 2,3,5a,6-tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-
  • Gliotoxin

Registry Numbers

CAS Registry Number

  • 67-99-2

FDA UNII

  • 5L648PH06K

System Generated Number

  • 0000067992

Structure Descriptors

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

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
hamster LDLo oral 25mg/kg (25mg/kg)   Veterinary and Human Toxicology. Vol. 32(Suppl), Pg. 63, 1990.
mouse LD50 intraperitoneal 32mg/kg (32mg/kg)   Chemotherapia. Vol. 10, Pg. 12, 1965.
mouse LD50 intravenous 7800ug/kg (7.8mg/kg)   Chemotherapia. Vol. 10, Pg. 12, 1965.
mouse LD50 oral 67mg/kg (67mg/kg)   Chemotherapia. Vol. 10, Pg. 12, 1965.
mouse LD50 subcutaneous 25mg/kg (25mg/kg)   Chemotherapia. Vol. 10, Pg. 12, 1965.
rabbit LDLo intravenous 45mg/kg (45mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Journal of the American Chemical Society. Vol. 65, Pg. 2005, 1943.
rat LDLo intravenous 45mg/kg (45mg/kg)   Veterinary and Human Toxicology. Vol. 32(Suppl), Pg. 63, 1990.
rat LDLo unreported 50mg/kg (50mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) Journal of the American Chemical Society. Vol. 65, Pg. 2005, 1943.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 2.900 (none)   EST
Water Solubility 70 mg/L 30 EXP
Vapor Pressure 1.32E-14 mm Hg 25 EST
Henry's Law Constant 1.39E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 4.58E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.