5-OH-CMP | 51914-67-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: 5-OH-CMP
• 英文别名: 5-Hydroxycytidine 5'-(Dihydrogen Phosphate)；[(2R,3S,4R,5R)-5-(4-amino-5-hydroxy-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
• CAS: 51914-67-1
• 化学式: C₉H₁₄N₃O₉P
• 分子量: 339.199
• InChiKey: QONOHPMEMVHOPP-UAKXSSHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  195
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5'-胞苷酸 生成 5-OH-CMP
  参考文献：
  名称：

  BERNADOU, JEAN;GELAS, PASCALE;MEUNIER, BERNARD, TETRAHEDRON LETT., 29,(1988) N 50, C. 6615-6618

  摘要：

  DOI：

文献信息

• Novel Cytidine-Based Orotidine-5′-Monophosphate Decarboxylase Inhibitors with an Unusual Twist
  作者：Meena K. Purohit、Ewa Poduch、Lianhu William Wei、Ian Edward Crandall、Terrence To、Kevin C. Kain、Emil F. Pai、Lakshmi P. Kotra

  DOI：10.1021/jm301176r

  日期：2012.11.26

  Orotidine-5'-monophosphate decarboxylase (ODCase) is an interesting enzyme with an unusual catalytic activity and a potential drug target in Plasmodium falciparum, which causes malaria. ODCase has been shown to exhibit unusual and interesting interactions with a variety of nucleotide ligands. Cytidine-5'-monophosphate (CMP) is a poor ligand of ODCase, and CMP binds to the active site of ODCase with an unusual orientation and conformation. We designed N3- and N4-modified CMP derivatives as novel ligands to ODCase. These novel CMP derivatives and their corresponding nucleosides were evaluated against Plasmodium falciparum ODCase and parasitic cultures, respectively. These derivatives exhibited improved inhibition of the enzyme catalytic activity displayed interesting binding conformations and unusual molecular rearrangements of the ligands. These findings with the modified CMP nucleotides underscored the potential of transformation of poor ligands to ODCase into novel inhibitors of this drug target.
• BERNADOU, JEAN;GELAS, PASCALE;MEUNIER, BERNARD, TETRAHEDRON LETT., 29,(1988) N 50, C. 6615-6618
  作者：BERNADOU, JEAN、GELAS, PASCALE、MEUNIER, BERNARD

  DOI：——

  日期：——
• US3935185A
  申请人：——

  公开号：US3935185A

  公开（公告）日：1976-01-27
• US4151350A
  申请人：——

  公开号：US4151350A

  公开（公告）日：1979-04-24