[3R-(3α,3a&#x3B2,7&#x3B2,8aalpha)]-2,3,4,7,8,8a-六氢-3,8,8-三甲基-1H-3a,7-亚甲基薁-6-甲醛 | 28227-92-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: [3R-(3α,3a&amp#x3B2,7&amp#x3B2,8aalpha)]-2,3,4,7,8,8a-六氢-3,8,8-三甲基-1H-3a,7-亚甲基薁-6-甲醛
• 中文别名: 鬼笔素
• 英文名称: Phalloin
• 英文别名: 18-hydroxy-34-(1-hydroxyethyl)-28-(2-hydroxy-2-methylpropyl)-23,31-dimethyl-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-tetraene-15,21,24,26,29,32,35-heptone
• CAS: 28227-92-1
• 化学式: C₃₅H₄₈N₈O₁₀S
• 分子量: 772.9
• InChiKey: VVAHMTWEOWYEHQ-UHFFFAOYSA-N

物化性质

• 沸点：
  1314.6±65.0 °C(Predicted)
• 密度：
  1.1492 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  54
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  297
• 氢给体数：
  10
• 氢受体数：
  11

ADMET

代谢

在给予大鼠aMAnita phalloides提取物后，第一天检测到PHALLOIN和GAMMA-AMANITIN，第二天检测到PHALLOIDIN。

PHALLOIN AND GAMMA-AMANITIN WERE DETECTED WITHIN THE 1ST DAY AND PHALLOIDIN WITHIN THE 2ND DAY IN THE URINE OF RATS AFTER THE ADMINISTRATION OF AMANITA PHALLOIDES EXTRACTS.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

秋水仙素结合肌动蛋白，阻止其解聚并毒害细胞。它们特异性地结合在F-actin亚单位之间的界面上，将相邻的亚单位锁定在一起。这导致肌动蛋白亚单元从丝状末端解离的速率常数降低，实际上通过阻止丝状解聚来稳定肌动蛋白丝。此外，它们还抑制了F-actin的ATP水解活性。

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)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类无致癌性（未列入国际癌症研究机构IARC清单）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

肝脏病变，心动过速，低血糖，低血压和电解质失衡伴酸碱平衡紊乱。

Liver lesions, tachycardia, hypoglycemia, hypotension and electrolyte imbalance with acid- base disturbance (L1160).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服、皮肤、吸入和 parenteral（被污染的药物）。 (A3101)

Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

低血容量性休克；胃肠道症状在潜伏期后出现，包括腹痛、呕吐和水样腹泻。神经症状与肝衰竭有关，可能包括脑病、嗜睡、混乱、昏迷和癫痫发作（L1160）。

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).

来源:Toxin and Toxin Target Database (T3DB)