callyaerin E | 1243246-50-5

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: callyaerin E
• 英文别名: (2S)-N-[(2S,3S)-1-[[(2S,3S)-1-[(2-amino-2-oxoethyl)amino]-3-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]-1-[(3S,9S,12S,15S,21S,23Z,27S,30S)-9,12-dibenzyl-21-(2-methylpropyl)-2,8,11,14,20,26,29-heptaoxo-27-propan-2-yl-1,7,10,13,19,22,25,28-octazatetracyclo[28.3.0.03,7.015,19]tritriacont-23-ene-24-carbonyl]pyrrolidine-2-carboxamide
• CAS: 1243246-50-5
• 化学式: C₆₆H₉₅N₁₃O₁₂
• 分子量: 1262.56
• InChiKey: PWVGMUOAWMBHAU-KONYCJQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  91
• 可旋转键数：
  19
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  340
• 氢给体数：
  9
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  callyaerin E 在 盐酸 、 水 作用下， 反应 24.0h， 生成 L-亮氨酸
  参考文献：
  名称：

  Callyaerins A–F and H, new cytotoxic cyclic peptides from the Indonesian marine sponge Callyspongia aerizusa

  摘要：

  Bioassay guided fractionation of the EtOAc fraction of the sponge Callyspongia aerizusa yielded seven new cytotoxic cyclic peptides callyaerins A-F (1-6) and H (8). Their structures were determined using extensive 1D (H-1, C-13 and DEPT) and 2D (COSY, HMQC, HMBC, TOCSY, and ROESY) NMR and mass spectral (ESI and HRESI-TOF) data. All compounds were cyclic peptides containing ring systems of 5-9 amino acids and side chains of 2-5 amino acids in length. An unusual (Z)-2,3-diaminoacrylic acid unit provided the template for ring closure and afforded the linkage to the peptidic side chain which was always initiated with a proline moiety. All peptides contained three or more proline residues and the remaining residues were predominantly hydrophobic residues with all amino acids present in the L form. Callyaerins A-F (1-6) and H (8) showed biological activity in antibacterial assays and in various cytotoxicity assays employing different tumour cell-lines (L5178Y, HeLa, and PC12). Callyaerins E (5) and H (8) exhibited strong activity against the L5178Y cell line with ED50 values of 0.39 and 0.48 mu M, respectively. On the other hand, callyaerin A (1) showed strong inhibitory properties towards C. albicans. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.012