Basic information
- CAS
1378-20-7- Standard SMILES
COc1c(Cl)cc2c(c1OC)N(C)[C@@H]1N3C(=O)[C@@]4(C)SS[C@@]3(C(=O)N4C)[C@H](O)[C@]21O- InChIKey
QTONANGUNATZOU-ICTVWZTPSA-N- Molecular formula
- C18H20ClN3O6S2
- Average molar mass
- 474 g/mol
- Monoisotopic mass
- 473.0482054
Overview
Sporidesmin A is an organic heteropentacyclic compound that has formula C18H20ClN3O6S2, produced by the saprophyte fungus Pithomyces chartarum. It is a mycotoxin responsible for the hepatogenous photosensitisation disease facial eczema in ruminants. It has a role as a Wnt signalling activator and a mycotoxin. It is a tertiary alcohol, an organic disulfide, an aromatic ether, a secondary alcohol, an organochlorine compound, an organic heteropentacyclic compound, a cyclic ketone, a diketone and a tertiary amino compound.
Names & identifiers
- Preferred name
- Sporidesmin
- IUPAC
- (1R,2R,3S,11R,14R)-6-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
Names & synonyms
SporidesminSporidesmin AHydroxysporidesmin B1456-55-9H70LC3H0RWCHEBI:9243DTXSID001030686NSC-246152(1R,2R,3S,11R,14R)-6-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(1R,2R,3S,11R,14R)-6-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-dioneRefChem:185019DTXCID101515768
Show more names
6-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(3r,5ar,10bs,11r,11ar)-9-chloro-10b,11-dihydroxy-7,8-dimethoxy-2,3,6-trimethyl-2,3,5a,6,10b,11-hexahydro-3,11a-epidithiopyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dioneCCRIS 5323SPORIDESMIN BENZENE SOLVATENSC 246152UNII-H70LC3H0RWSPORIDESMIN A [MI]Sporidesmin ADISCONTINUED
Database identifiers
- CAS
1378-20-7、1456-55-9
Properties
Computed structural properties
- XLogP
- 0.2
- Topological polar surface area
- 153 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 2
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 825
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory InformationSporidesmin A: Does not have an individual approval but may be used under an appropriate group standard
Toxicology
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. (A3095)
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)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary
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)
Signs and SymptomsSporidesmin causes diarrhea and lack of appetite. Pithomycotoxicosis is characterized by photosensitisation of the skin. (A3095)
Carcinogen Classification
Chemistry & industry
Uses & manufacturing
UsesSporidesmin is a mycotoxin found in the spores of the fungus Pithomyces chartarum. (A3095)
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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