Record Information
Version2.0 (beta)
Creation Date2010-05-27 13:14:43 -0600
Update Date2014-09-17 15:03:37 -0600
Accession NumberT3D3776
Identification
Common NameSporidesmin
ClassSmall Molecule
DescriptionSporidesmin 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. (2)
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 FormulaC18H20ClN3O6S2
Average Molecular Weight473.951 g/mol
CAS Registry Number1456-55-9
Monoisotopic Mass473.048204474 g/mol
IUPAC Name6-chloro-2,3-dihydroxy-7,8-dimethoxy-10,14,18-trimethyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁴,⁹]octadeca-4,6,8-triene-13,17-dione
Traditional IUPAC Name6-chloro-2,3-dihydroxy-7,8-dimethoxy-10,14,18-trimethyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁴,⁹]octadeca-4,6,8-triene-13,17-dione
SMILESCOC1=C2N(C)C3N4C(=O)C5(C)SSC4(C(O)C3(O)C2=CC(Cl)=C1OC)C(=O)N5C
InChI IdentifierInChI=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 KeyInChIKey=QTONANGUNATZOU-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassHeterocyclic Compounds
ClassIndoles and Derivatives
Sub ClassPyrroloindoles
Direct ParentPyrroloindoles
Alternative Parents
  • Epipolythiodioxopiperazines
  • Indoles
  • Anisoles
  • Dialkylarylamines
  • Chlorobenzenes
  • Alkyl Aryl Ethers
  • Aralkylamines
  • N-Methylpiperazines
  • Aryl Chlorides
  • Tertiary Carboxylic Acid Amides
  • Pyrroles
  • Pyrrolidines
  • Tertiary Alcohols
  • Secondary Alcohols
  • Organic Disulfides
  • Lactams
  • 1,2-Diols
  • Carboxylic Acids
  • Organochlorides
  • Carbonyl Compounds
Substituents
  • chlorobenzene
  • aryl chloride
  • organochloride
  • organonitrogen compound
  • anisole
  • alkyl aryl ether
  • lactam
  • secondary alcohol
  • carboxamide group
  • polyol
  • 1,2-diol
  • alcohol
  • tertiary alcohol
  • tertiary amine
  • carboxylic acid
  • pyrrole
  • indole
  • pyrrolidine
  • tertiary carboxylic acid amide
  • dioxopiperazine
  • epipolythiodioxopiperazine
  • thiodioxopiperazine
  • Benzenoid
  • Ether
  • Organooxygen Compound
  • Aromatic Heteropolycyclic Compound
  • Carbonyl Group
  • Carboxylic Acid Derivative
  • Halobenzene
  • Aryl Halide
  • Organohalogen Compound
  • Aralkylamine
  • Amine
  • Dialkylarylamine
  • Piperazine
  • Organic Disulfide
  • N-Alkylpiperazine
  • N-Methylpiperazine
  • Pyrroloindole
  • 2,5-Dioxopiperazine
External DescriptorsNot Available
Biological Properties
StatusDetected but not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot 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
SpectraNot Available
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (6)
Mechanism of ToxicitySporidesmin 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. (4, 5)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesSporidesmin is a mycotoxin found in the spores of the fungus Pithomyces chartarum. (2)
Minimum Risk LevelNot Available
Health EffectsSporidesmin 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. (2, 3)
SymptomsSporidesmin causes diarrhea and lack of appetite. Pithomycotoxicosis is characterized by photosensitisation of the skin. (2)
TreatmentAdministration 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. (2)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID99596
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDNot Available
UniProt IDNot Available
OMIM IDNot Available
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Smith BL, Towers NR: Mycotoxicoses of grazing animals in New Zealand. N Z Vet J. 2002;50(3 Suppl):28-34. [16032233 ]
  2. 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 ]
  3. Ferguson LR: Natural and human-made mutagens and carcinogens in the human diet. Toxicology. 2002 Dec 27;181-182:79-82. [12505288 ]
  4. 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 ]
  5. 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 ]
  6. Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Not Available