기본 정보
- CAS
26645-35-2- 표준 SMILES
CC1NC(=O)C2CC(O)CN2C(=O)C2CSc3[nH]c4ccccc4c3CC(NC1=O)C(=O)NC(CC(C)(O)CO)C(=O)NC(C(C)C)C(=O)NC(C(O)C(=O)O)C(=O)N2- InChIKey
KUBDTFZQCYLLGC-UHFFFAOYSA-N- 분자식
- C37H50N8O13S
- 평균 분자량
- 846.9 g/mol
- 단동위원소 질량
- 846.32180485
개요
Phallacidin has been reported in Amanita phalloides, Amanita bisporigera, and other organisms with data available.
이름 및 식별자
- 우선 이름
- Phallacidin
- IUPAC
- 2-[28-(2,3-dihydroxy-2-methylpropyl)-18-hydroxy-23-methyl-15,21,24,26,29,32,35-heptaoxo-31-propan-2-yl-12-thia-10,16,22,25,27,30,33,36-octazapentacyclo[12.11.11.03,11.04,9.016,20]hexatriaconta-3(11),4,6,8-tetraen-34-yl]-2-hydroxyacetic acid
- 현지명
- 팔라시딘
- 영어명
- Phallacidin
- 분자식
- C37H50N8O13S
- 분자량
- 846.91
이름 및 동의어
Phallacidin26645-35-2DTXSID001046316CHEBI:52732RefChem:172410DTXCID001528146cyclic(L-Alanyl-2-mercapto-L-tryptophyl-4,5-dihydroxy-L-leucyl-L-valyl-erythro-3-hydroxy-D-alpha-aspartyl-L-cysteinyl-cis-4-hydroxy-L-prolyl) cyclic (2-6)-sulfideBRN 0604129SCHEMBL3507281MSK72182-[28-(2,3-dihydroxy-2-methylpropyl)-18-hydroxy-23-methyl-15,21,24,26,29,32,35-heptaoxo-31-propan-2-yl-12-thia-10,16,22,25,27,30,33,36-octazapentacyclo[12.11.11.03,11.04,9.016,20]hexatriaconta-3(11),4,6,8-tetraen-34-yl]-2-hydroxyacetic acidPhallacidin from Amanita phalloides, >=85%
이름 더 보기
팔라시딘PHALLICIDINPhallacidin DISCONTINUEDCYCLO(ALA-2-MERCAPTO-TRP-4phallacidin from amanita phalloidesPhallacidin from Amanita phalloidesCyclo(Ala-2-Mercapto-Trp-45-DIHYDROXY-LEU-VAL-ERYTHRO-3-HYDROXY-D-ASP-CYS-CIS-4-HYDROXY-PRO)-3-hydroxy-d-alpha-aspartyl-l-cysteinyl-cis-4-hydroxy-l-prolyl)cyclic(2-6)-s
물성
구조 계산 물성
- XLogP
- -1.5
- 극성 표면적
- 354 Ų
- 수소 결합 공여자 수
- 12
- 수소 결합 수용자 수
- 14
- 회전 가능 결합 수
- 6
- 무거운 원자 수
- 59
- 형식 전하
- 0
- 복잡도
- 1,660
물리화학적 성질
- 끓는 점
- 1435.246 · 1435.246±65.00 °C(Press: 760.00 Torr)(predicted)
- 밀도
- 1.1678 · 1.1678 (rough estimate)
- 굴절률
- 1.74 · 1.7400 (estimate)
- 용해도
- DMF: Soluble; DMSO: Soluble; Methanol: Soluble; Water: Soluble
- 물리적 상태
- 백색 내지 회백색 분말.
- 산도 계수 (pKa)
- 3.129 · 3.129±0.11(predicted)
- 색상
- White to off-white
- 생물학적 소스
- Amanita phalloides
- InChIKey
- KUBDTFZQCYLLGC-UHFFFAOYSA-N
- SMILES
- CC(C)C1NC(=O)C(CC(C)(O)CO)NC(=O)C2Cc3c(SCC(NC(=O)C(NC1=O)C(O)C(O)=O)C(=O)N4CC(O)CC4C(=O)NC(C)C(=O)N2)[nH]c5ccccc35
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
독성 정보
TreatmentConsider gastric lavage and activated charcoal. (A678)
Health EffectsLiver lesions, tachycardia, hypoglycemia, hypotension and electrolyte imbalance with acid- base disturbance (L1160).
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary
Phallotoxins bind actin, preventing its depolymerization and poisoning the cell. They bind specifically at the interface between F-actin subunits, locking adjacent subunits together. This leads to a decrease in the rate constant for the dissociation of actin subunits from filament ends, which essentially stabilizes actin filaments through the prevention of filament depolymerization. Moreover, they inhibit the ATP hydrolysis activity of F-actin. (L1183, A2465)
Signs and Symptoms
Hypovolemic shock; Gastrointestinal symptoms occur after a latent period and include abdominal pain, vomiting, and watery diarrhea. Neurologic symptoms are related to hepatic failure and may include encephalopathy, somnolence, confusion, coma and seizures (L1160).
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Toxicity DataLD50: 1.5 mg/kg (Mouse) (T258)
안전 데이터
- wgk
- 3
- rtecs
- GT8943000
- ridadr
- 1544
- HS 번호
- 2934999090
- risk_code
- 26/27/28
- hazard_code
- T+
화학 및 산업
약리 정보
Metabolism/Metabolites
Free toxin may be removed by opsonization via the reticuloendothelial system (primarily the liver and kidneys) or it may be degraded through cellular internalization via the lysosomes. Lysosomes are membrane-enclosed organelles that contain an array of digestive enzymes, including several proteases.
용도 및 제조
UsesPhallisin is one of a group of toxins from the death cap (Amanita phalloides) known as phallotoxins. (L996)
응용 분야
개요Phallacidin is a natural mycotoxin first isolated from the death cap mushroom, A. phalloides. It binds filamentous actin (F-actin) like phalloidin , but contains a carboxyl group for coupling reactions.
용도Toxin Phallacidin is a weak fluorescent bicyclic peptide probe in aquous solution, Which is isolated from Amanita phalloides mushroom and could be used for blocking F-actin staining by labeled phallotoxins, which promotes actin polymerization.
추가 설명
정의ChEBI: A homodetic bicyclic heptapeptide having a sulfide bridge.
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