(2E,8E,10E)-2,8,10-heptadecatrien-4,6-diyne-1,14-diol | 463-02-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E,8E,10E)-2,8,10-heptadecatrien-4,6-diyne-1,14-diol
• 英文别名: oenanthotoxin；all-trans-Oenanthotoxin；heptadeca-2t,8t,10t-triene-4,6-diyne-1,14-diol；(+/-)-Heptadeca-2t,8t,10t-trien-4,6-diin-1,14-diol；2,8,10-Heptadecatriene-4,6-diyne-1,14-diol；(2E,8E,10E)-heptadeca-2,8,10-trien-4,6-diyne-1,14-diol
• CAS: 463-02-5
• 化学式: C₁₇H₂₂O₂
• 分子量: 258.36
• InChiKey: UPXPHJXYZGEBCW-JHTNEVNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

ADMET

毒理性

• 毒性总结

Oenanthotoxin 是一种中枢神经系统毒物，作为一种非竞争性的γ-氨基丁酸拮抗剂发挥作用。

Oenanthotoxin is a central nervous system poison and acts as a non-competitive gamma-aminobutyric acid antagonist. (L1243)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

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

Oenanthotoxin破坏中枢神经系统，导致震颤、癫痫和死亡。

Oenanthotoxin disrupts the central nervous system, leading to tremors, seizures, and death. (L1232)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口服（摄入）（L1817）；皮肤（L1817）

Oral (ingestion) (L1817) ; dermal (L1817)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

蘑菇毒素会产生恶心、呕吐和腹痛，通常在摄入后60分钟内出现。

Oenanthotoxin produces nausea, emesis and abdominal pain, typically within 60 minutes of ingestion. (L1232)

来源:Toxin and Toxin Target Database (T3DB)

反应信息

• 作为反应物：
  描述：

  乙酸乙烯酯 、 (2E,8E,10E)-2,8,10-heptadecatrien-4,6-diyne-1,14-diol 在 novozyme435 作用下， 以 异丙醚 为溶剂， 反应 15.0h， 以18.4 mg的产率得到(2E,8E,10E,14S)-1,14-di-O-acetyl-2,8,10-heptadecatrien-4,6-diyne-1,14-diol
  参考文献：
  名称：

  Chemoenzymatic synthesis and cytotoxicity of oenanthotoxin and analogues

  摘要：

  We developed a synthetic scheme for the synthesis of naturally occurring (14R)-oenanthotoxin and several analogs. Key-steps of this synthesis were an efficient homo-coupling of alkynes and a chemoenzymatic resolution of racemic oenanthotoxin using novozyme 435 and vinyl acetate. The compounds were screened for their cytotoxic activity using a photometric sulforhodamine B assays and several human tumor cell lines. Oenanthotoxin and many derivatives thereof were cytotoxic to tumor cell lines as well as to non-malignant mouse fibroblasts. The highest activity was determined for human ovarian cancer cells A2780 with EC50 = 3.8 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.031
• 作为产物：
  描述：

  (7E,9E,15E)-17-hydroxy-7,9,15-heptadecatrien-11,13-diyn-4-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以82.6%的产率得到(2E,8E,10E)-2,8,10-heptadecatrien-4,6-diyne-1,14-diol
  参考文献：
  名称：

  Chemoenzymatic synthesis and cytotoxicity of oenanthotoxin and analogues

  摘要：

  We developed a synthetic scheme for the synthesis of naturally occurring (14R)-oenanthotoxin and several analogs. Key-steps of this synthesis were an efficient homo-coupling of alkynes and a chemoenzymatic resolution of racemic oenanthotoxin using novozyme 435 and vinyl acetate. The compounds were screened for their cytotoxic activity using a photometric sulforhodamine B assays and several human tumor cell lines. Oenanthotoxin and many derivatives thereof were cytotoxic to tumor cell lines as well as to non-malignant mouse fibroblasts. The highest activity was determined for human ovarian cancer cells A2780 with EC50 = 3.8 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.031

文献信息

• ENZYME INHIBITING COMPOUNDS AND METHODS
  申请人：The Board of Trustees of the University of Illinois

  公开号：US20140100198A1

  公开（公告）日：2014-04-10

  The invention provides compounds, compositions, and methods for studying the Rohmer pathway and for treating bacterial infections or parasitic infections. The parasitic infection can be a protozoan infection, such as malaria. The compounds and compositions can also be used as antibiotics, for example, to kill bacteria or parasites, or to inhibit bacterial or parasite growth. The invention further provides inhibitors of isoprenoid biosynthesis enzymes, and methods of inhibiting the activity of isoprenoid biosynthesis enzymes. The compounds can be, for example, alkynes or allenes that bind to a unique Fe of an Fe 4 S 4 cluster of an isoprenoid biosynthesis enzyme.

  本发明提供了化合物、组合物和方法，用于研究Rohmer途径和治疗细菌感染或寄生虫感染。寄生虫感染可以是原虫感染，例如疟疾。这些化合物和组合物也可以用作抗生素，例如杀死细菌或寄生虫，或抑制细菌或寄生虫的生长。本发明还提供异戊二烯生物合成酶的抑制剂，以及抑制异戊二烯生物合成酶活性的方法。这些化合物可以是例如炔烃或联烯，它们与异戊二烯生物合成酶的Fe4S4簇的独特Fe结合。
• GABA channel subunits of pollinator insects and their uses thereof
  申请人：Centre National de la Recherche Scientifique (CNRS)

  公开号：EP2975049A1

  公开（公告）日：2016-01-20

  The present invention relates to the cloning of the GABA-gated ion channel receptor subunits in pollinator insect such as Apis mellifera and their uses thereof.

  本发明涉及授粉昆虫（如蜜蜂）中 GABA 门控离子通道受体亚基的克隆及其用途。
• Methods for the selective sequestration of alkyne-presenting molecules and related compositions and methods
  申请人：LAWRENCE LIVERMORE NATIONAL SECURITY, LLC

  公开号：US10088491B2

  公开（公告）日：2018-10-02

  Provided herein are methods for sequestering an alkyne-presenting molecule in a sample and related sequestration reagents, compositions, methods and systems.

  本文提供了封存样品中含炔分子的方法以及相关的封存试剂、组合物、方法和系统。
• Methods for the selective detection of alkyne-presenting molecules and related compositions and systems
  申请人：LAWRENCE LIVERMORE NATIONAL SECURITY, LLC

  公开号：US10082514B2

  公开（公告）日：2018-09-25

  Provided herein are methods for selectively detecting an alkyne-presenting molecule in a sample and related detection reagents, compositions, methods and systems.

  本文提供了选择性检测样品中含炔分子的方法以及相关的检测试剂、组合物、方法和系统。
• Methods, compositions and kits for treating a subject using a recombinant neutralizing binding protein
  申请人：TUFTS UNIVERSITY

  公开号：US10202441B2

  公开（公告）日：2019-02-12

  Methods, compositions and kits are provided for treating a subject exposed to or at risk for exposure to a disease agent using a pharmaceutical composition including at least one recombinant binding protein or a source of expression of the binding protein, wherein the binding protein neutralizes a disease agent that is a toxin, for example a Clostridium difficile toxin, a Shiga toxin, a ricin toxin, or an anthrax toxin.

  提供了使用包括至少一种重组结合蛋白或结合蛋白表达源的药物组合物治疗暴露于或有暴露于疾病病原体风险的受试者的方法、组合物和试剂盒，其中结合蛋白可中和属于毒素的疾病病原体，例如艰难梭菌毒素、志贺毒素、蓖麻毒素或炭疽毒素。