1''-OH-cannabidiol | 2231221-49-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1''-OH-cannabidiol
• 英文别名: 1''-Hydroxycannabidiol；5-(1-hydroxypentyl)-2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]benzene-1,3-diol
• CAS: 2231221-49-9
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: OEWBQBNIVUMUKU-MYFVLZFPSA-N

物化性质

• 沸点：
  507.2±50.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  大麻二酚 在 cytochrome P₄₅₀ reductase 、 cytochrome P₄₅₀ 2J₂ 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.5h， 生成 1''-OH-cannabidiol
  参考文献：
  名称：

  Cross-talk of cannabinoid and endocannabinoid metabolism is mediated via human cardiac CYP2J2

  摘要：

  Phytocannabinoids have well-known cardiovascular implications. For instance, Delta 9-tetrahydrocannabinol (Delta 9-THC), the principal component of cannabis, induces tachycardia in humans. In order to understand the impact of phytocannabinoids on human cardiovascular health, there is a need to study the metabolism of phytocannabinoids by cardiac cytochromes p450 (CYPs). CYP2J2, the primary CYP of cardiomyocytes, is responsible for the metabolism of the endocannabinoid, anandamide (AEA), into cardioprotective epoxides (EET-EAs). Herein, we have investigated the kinetics of the direct metabolism of six phytocannabinoids (Delta 9-THC, Delta 8-tetra-hydrocannabinol, cannabinol, cannabidiol, cannabigerol, and cannabichromene) by CYP2J2. CYP2J2 mainly produces 1'/1 ''-OH metabolites of these phytocannabinoids. These phytocannabinoids are metabolized with greater catalytic efficiency compared to the metabolism of AEA by CYP2J2. We have also determined that the phytocannabinoids are potent inhibitors of CYP2J2-mediated AEA metabolism, with Delta 9-THC being the strongest inhibitor. Most of the inhibition of CYP2J2 by the phytocannabinoids follow a noncompetitive inhibition model, and therefore dramatically reduce the formation of EET-EAs by CYP2J2. Taken together, these data demonstrate that phytocannabinoids are directly metabolized by CYP2J2 and inhibit human cardiac CYP2J2, leading to a reduction in the formation of cardioprotective EET-EAs.

  DOI：

  10.1016/j.jinorgbio.2018.03.016