Record Information
Version 1.0
Creation Date 2010-05-27 13:14:43 -0600
Update Date 2014-08-11 10:36:20 -0600
Accession Number T3D3776
Identification
Common Name Sporidesmin
Description Sporidesmin is a mycotoxin found in the spores of the fungus Pithomyces chartarum. It is a potent hepatotoxin and is known to cause pithomycotoxicosis (facial eczema, characterized by photosensitisation) in livestock. (A3095)
Compound Type
  • Organic Compound
  • Mycotoxin
Chemical Structure
Thumb
Synonyms
  1. Sporidesmin
  2. Sporidesmin A
  3. Hydroxysporidesmin B
  4. 3,11a-Epidithio-11aH-pyrazino(1',2':1,5)pyrrolo(2,3-b)indole-1,4-dione, 9-chloro-2,3,5a,6,10b,11-hexahydro-10b,11-dihydroxy-7,8-dimethoxy-2,3,6-trimethyl-, (3-alpha,5a-alpha,10b-alpha,11-beta,11a-alpha)-
Chemical Formula C18H20ClN3O6S2
Average Molecular Weight 473.951
Monoisotopic Molecular Weight 473.048204474
IUPAC Name
6-chloro-2,3-dihydroxy-7,8-dimethoxy-10,14,18-trimethyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0^{1,12}.0^{3,11}.0^{4,9}]octadeca-4,6,8-triene-13,17-dione
Traditional IUPAC Name
6-chloro-2,3-dihydroxy-7,8-dimethoxy-10,14,18-trimethyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0^{1,12}.0^{3,11}.0^{4,9}]octadeca-4,6,8-triene-13,17-dione
CAS Registry Number 1456-55-9
SMILES
COC1=C2N(C)C3N4C(=O)C5(C)SSC4(C(O)C3(O)C2=CC(Cl)=C1OC)C(=O)N5C
InChI Identifier
InChI=1S/C18H20ClN3O6S2/c1-16-14(24)22-13-17(26,12(23)18(22,30-29-16)15(25)21(16)3)7-6-8(19)10(27-4)11(28-5)9(7)20(13)2/h6,12-13,23,26H,1-5H3
InChI Key InChIKey=QTONANGUNATZOU-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Heterocyclic Compounds
Class Indoles and Derivatives
Sub Class Pyrroloindoles
Direct Parent Pyrroloindoles
Alternative Parents
  • Epipolythiodioxopiperazines
  • Indoles
  • Anisoles
  • Alkyl Aryl Ethers
  • Chlorobenzenes
  • Aryl Chlorides
  • Tertiary Carboxylic Acid Amides
  • Pyrrolidines
  • Lactams
  • Tertiary Alcohols
  • Pyrroles
  • 1,2-Diols
  • Secondary Alcohols
  • Aminals
  • Alkanolamines
  • Organosulfur Compounds
  • Diazinanes
Molecular Framework Aromatic Heteropolycyclic Compounds
Substituents
  • chlorobenzene
  • aryl chloride
  • organic halide
  • organochloride
  • benzene
  • organonitrogen compound
  • organosulfur compound
  • phenol ether
  • anisole
  • alkyl aryl ether
  • aminal
  • lactam
  • secondary alcohol
  • carboxamide group
  • polyol
  • 1,2-diol
  • alkanolamine
  • alcohol
  • tertiary alcohol
  • pyrrole
  • indole
  • pyrrolidine
  • tertiary carboxylic acid amide
  • 1,4-diazinane
  • dioxopiperazine
  • epipolythiodioxopiperazine
  • thiodioxopiperazine
External Descriptors Not Available
Biological Properties
Status Unknown/Not Detected
Origin Not Available
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Locations Not Available
Pathways Not Available
Physical Properties
State Not Available
Appearance Not Available
Experimental Properties
Property Value
Melting Point Not Available
Boiling Point Not Available
Solubility Not Available
LogP Not Available
Predicted Properties
PropertyValueSource
water solubility4.16e+00 g/lALOGPS
logP1.73ALOGPS
logP1.6ChemAxon
logS-2.1ALOGPS
pKa (strongest acidic)11.88ChemAxon
pKa (strongest basic)-3.9ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count7ChemAxon
hydrogen donor count2ChemAxon
polar surface area102.78ChemAxon
rotatable bond count2ChemAxon
refractivity112.73ChemAxon
polarizability45ChemAxon
Spectra
Spectra Not Available
Toxicity Profile
Route of Exposure Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Mechanism of Toxicity Sporidesmin and its reduced (dithiol) form undergo cyclic reduction/autoxidation reactions with glutathione and other thiols, generating toxic superoxide radicals, hydrogen peroxide, and hydroxy radicals. It targets the liver, causing pericholangitis and the occlusion of bile ducts, which leads to the accumulation of bile constitutents in the bloodstream. In livestock, this results in a build up of phylloerythrin, a photodyamic metabolite produced by the microbial degradation of chlorophyll in the rumen. High plasma levels of phylloerythrin cause the animals to become sensitive to sunlight. (A3097, A3098)
Metabolism Not Available
Toxicity Values Not Available
Lethal Dose Not Available
Carcinogenicity (IARC Classification) Not Available
Uses/Sources Sporidesmin is a mycotoxin found in the spores of the fungus Pithomyces chartarum. (A3095)
Minimum Risk Level Not Available
Health Effects Sporidesmin is a potent hepatotoxin, causing liver damage from pericholangitis and the occlusion of bile ducts, which results in the accumulation of bile constitutents in the bloodstream. This is known to lead to pithomycotoxicosis (facial eczema, characterized by photosensitisation) in livestock. Sporidesmin may also be carcinogenic in humans. (A3095, A3096)
Symptoms Sporidesmin causes diarrhea and lack of appetite. Pithomycotoxicosis is characterized by photosensitisation of the skin. (A3095)
Treatment Administration of zinc salts can protect against the effects of sporidesmin. Zinc forms a stable mercaptide with sporidesmin, preventing its autoxidation to toxic reactive oxygen species. (A3095)
Normal Concentrations
Not Available
DrugBank ID Not Available
HMDB ID Not Available
PubChem Compound ID 99596
ChEMBL ID Not Available
ChemSpider ID Not Available
KEGG ID Not Available
UniProt ID Not Available
OMIM ID Not Available
ChEBI ID Not Available
BioCyc ID Not Available
CTD ID Not Available
Stitch ID Not Available
PDB ID Not Available
ACToR ID Not Available
Wikipedia Link Not Available
References
General References
  • A3094 — Smith BL, Towers NR: Mycotoxicoses of grazing animals in New Zealand. N Z Vet J. 2002;50(3 Suppl):28-34. [16032233 ]
  • A3095 — Pinto C, Santos VM, Dinis J, Peleteiro MC, Fitzgerald JM, Hawkes AD, Smith BL: Pithomycotoxicosis (facial eczema) in ruminants in the Azores, Portugal. Vet Rec. 2005 Dec 17;157(25):805-10. [16361474 ]
  • A3096 — Ferguson LR: Natural and human-made mutagens and carcinogens in the human diet. Toxicology. 2002 Dec 27;181-182:79-82. [12505288 ]
  • A3097 — Munday R: Studies on the mechanism of toxicity of the mycotoxin, sporidesmin. I. Generation of superoxide radical by sporidesmin. Chem Biol Interact. 1982 Sep;41(3):361-74. [6286158 ]
  • A3098 — Munday R: Studies on the mechanism of toxicity of the mycotoxin, sporidesmin. V. Generation of hydroxyl radical by sporidesmin. J Appl Toxicol. 1987 Feb;7(1):17-22. [3611593 ]
  • A3101 — Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]

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