janadolide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: janadolide
• 英文别名: Janadolide；(3R,7E,9S,12S,15S,21S,24S)-9-tert-butyl-3,7,13,15,16-pentamethyl-12-(2-methylpropyl)-21-propan-2-yl-10-oxa-1,13,16,19,22-pentazabicyclo[22.3.0]heptacos-7-ene-2,11,14,17,20,23-hexone
• 化学式: C₃₇H₆₃N₅O₇
• 分子量: 689.937
• InChiKey: XXTPBUDGINBRRD-IQFPJXEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  49
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  145
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  janadolide 在 臭氧 、 甲酸 、 双氧水 、 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 2-methyl-5-oxohexanoic acid 、 (S)-(-)-2-羟基-3,3-二甲基丁酸
  参考文献：
  名称：

  Janadolide, a Cyclic Polyketide–Peptide Hybrid Possessing a tert-Butyl Group from an Okeania sp. Marine Cyanobacterium

  摘要：

  Janadolide, a new cyclic polyketide peptide hybrid possessing a tert-butyl group, was isolated from an Okeania sp. marine cyanobacterium. The gross structure was elucidated by spectroscopic analyses, and the absolute configurations of the amino acid moieties were determined by acid hydrolysis and chiral-phase HPLC analyses. The absolute configuration of the two stereogenic centers in the polyketide moiety was elucidated based on a combination of degradation reactions and spectroscopic analyses including the phenyl-glycine methyl ester method. Janadolide showed potent antitrypanosomal activity with an IC50 value of 47 nM without cytotoxicity against human cells at 10 mu M.

  DOI：

  10.1021/acs.jnatprod.6b00171

文献信息

• Janadolide, a Cyclic Polyketide–Peptide Hybrid Possessing a <i>tert</i>-Butyl Group from an <i>Okeania</i> sp. Marine Cyanobacterium
  作者：Hidetoshi Ogawa、Arihiro Iwasaki、Shinpei Sumimoto、Yuki Kanamori、Osamu Ohno、Masato Iwatsuki、Aki Ishiyama、Rei Hokari、Kazuhiko Otoguro、Satoshi O̅mura、Kiyotake Suenaga

  DOI：10.1021/acs.jnatprod.6b00171

  日期：2016.7.22

  Janadolide, a new cyclic polyketide peptide hybrid possessing a tert-butyl group, was isolated from an Okeania sp. marine cyanobacterium. The gross structure was elucidated by spectroscopic analyses, and the absolute configurations of the amino acid moieties were determined by acid hydrolysis and chiral-phase HPLC analyses. The absolute configuration of the two stereogenic centers in the polyketide moiety was elucidated based on a combination of degradation reactions and spectroscopic analyses including the phenyl-glycine methyl ester method. Janadolide showed potent antitrypanosomal activity with an IC50 value of 47 nM without cytotoxicity against human cells at 10 mu M.