기본 정보
- CAS
1378-20-7- 표준 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- 분자식
- C18H20ClN3O6S2
- 평균 분자량
- 474 g/mol
- 단동위원소 질량
- 473.0482054
개요
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.
이름 및 식별자
- 우선 이름
- 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
이름 및 동의어
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
이름 더 보기
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
데이터베이스 식별자
- CAS
1378-20-7、1456-55-9- PubChem CID
물성
구조 계산 물성
- XLogP
- 0.2
- 극성 표면적
- 153 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 9
- 회전 가능 결합 수
- 2
- 무거운 원자 수
- 30
- 형식 전하
- 0
- 복잡도
- 825
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
유해성 정보
Regulatory InformationSporidesmin A: Does not have an individual approval but may be used under an appropriate group standard
독성 정보
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 ClassificationNot listed by IARC.
화학 및 산업
용도 및 제조
UsesSporidesmin is a mycotoxin found in the spores of the fungus Pithomyces chartarum. (A3095)
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