[[(3R)-4-[[3-[2-[2-[[(5S)-5-acetamido-6-[[6-[[(2R)-1-amino-1-oxo-3-sulfanylpropan-2-yl]amino]-6-oxohexyl]amino]-6-oxohexyl]amino]-2-oxoethyl]sulfanylethylamino]-3-oxopropyl]amino]-3-hydroxy-2,2-dimethyl-4-oxobutoxy]-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methyl hydrogen phosphate | 872702-43-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - S-烷基辅酶A
• 英文名称: [[(3R)-4-[[3-[2-[2-[[(5S)-5-acetamido-6-[[6-[[(2R)-1-amino-1-oxo-3-sulfanylpropan-2-yl]amino]-6-oxohexyl]amino]-6-oxohexyl]amino]-2-oxoethyl]sulfanylethylamino]-3-oxopropyl]amino]-3-hydroxy-2,2-dimethyl-4-oxobutoxy]-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methyl hydrogen phosphate
• CAS: 872702-43-7
• 化学式: C₄₀H₆₉N₁₂O₂₁P₃S₂
• 分子量: 1211.11
• InChiKey: HVQPDJKHXYNOPZ-USLPRILBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.7
• 重原子数：
  78
• 可旋转键数：
  37
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  532
• 氢给体数：
  15
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  [[(3R)-4-[[3-[2-[2-[[(5S)-5-acetamido-6-[[6-[[(2R)-1-amino-1-oxo-3-sulfanylpropan-2-yl]amino]-6-oxohexyl]amino]-6-oxohexyl]amino]-2-oxoethyl]sulfanylethylamino]-3-oxopropyl]amino]-3-hydroxy-2,2-dimethyl-4-oxobutoxy]-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methyl hydrogen phosphate 、 在 triethylammonium carbonate buffer 作用下， 以20%的产率得到(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-N-[3-[2-[2-[(5S)-6-[6-[(2R)-3-[[3-[6-[(2S)-5-carbamimidamido-1-[(2S)-5-carbamimidamido-1-[(2S)-5-carbamimidamido-1-[(2S)-5-carbamimidamido-1-[(2S)-5-carbamimidamido-1-[(2S)-5-carbamimidamido-1-[(2S)-5-carbamimidamido-1-[(2S)-5-carbamimidamido-1-[(2S)-5-carbamimidamido-1-[(2S)-5-carbamimidamido-1-hydroxy-1-iminopentan-2-yl]imino-1-hydroxypentan-2-yl]imino-1-hydroxypentan-2-yl]imino-1-hydroxypentan-2-yl]imino-1-hydroxypentan-2-yl]imino-1-hydroxypentan-2-yl]imino-1-hydroxypentan-2-yl]imino-1-hydroxypentan-2-yl]imino-1-hydroxypentan-2-yl]imino-1-hydroxypentan-2-yl]imino-6-hydroxyhexyl]imino-3-hydroxypropyl]disulfanyl]-1-hydroxy-1-iminopropan-2-yl]imino-6-hydroxyhexyl]imino-6-hydroxy-5-(1-hydroxyethylideneamino)hexyl]imino-2-hydroxyethyl]sulfanylethylimino]-3-hydroxypropyl]-2-hydroxy-3,3-dimethylbutanimidic acid
  参考文献：
  名称：

  Synthesis and Evaluation of a Potent and Selective Cell-Permeable p300 Histone Acetyltransferase Inhibitor

  摘要：

  This paper describes the first potent and selective p300 histone acetyltransferase (HAT) inhibitor which is effective in live cells. This compound 7 is a coenzyme A analogue conjugated to a cell permeabilizing oligoArg peptide via disulfide linkage. This compound was shown to block cellular histone acetylation and transcription using a p300-sensitive reporter. It should thus be broadly useful for dissecting the role of p300 HAT activity in physiologic and disease states.

  DOI：

  10.1021/ja0558544
• 作为产物：
  描述：

  芴甲氧羰酰基-6-氨基己酸 在 DL-dithiothreitol 、 triethylammonium carbonate buffer 、 三乙基碳酸氢铵缓冲液 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 [[(3R)-4-[[3-[2-[2-[[(5S)-5-acetamido-6-[[6-[[(2R)-1-amino-1-oxo-3-sulfanylpropan-2-yl]amino]-6-oxohexyl]amino]-6-oxohexyl]amino]-2-oxoethyl]sulfanylethylamino]-3-oxopropyl]amino]-3-hydroxy-2,2-dimethyl-4-oxobutoxy]-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methyl hydrogen phosphate
  参考文献：
  名称：

  Synthesis and Evaluation of a Potent and Selective Cell-Permeable p300 Histone Acetyltransferase Inhibitor

  摘要：

  This paper describes the first potent and selective p300 histone acetyltransferase (HAT) inhibitor which is effective in live cells. This compound 7 is a coenzyme A analogue conjugated to a cell permeabilizing oligoArg peptide via disulfide linkage. This compound was shown to block cellular histone acetylation and transcription using a p300-sensitive reporter. It should thus be broadly useful for dissecting the role of p300 HAT activity in physiologic and disease states.

  DOI：

  10.1021/ja0558544