brachystemin I | 1312415-68-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: brachystemin I
• 英文别名: cyclo(Pro(1)-Ala(2)-Gly(3)-Phe(4)-Thr(5)-Thr(6)-Pro(7)-Trp(8))；(3S,6S,12S,15S,18S,24S,27S)-18-benzyl-12,15-bis[(1R)-1-hydroxyethyl]-3-(1H-indol-3-ylmethyl)-24-methyl-1,4,10,13,16,19,22,25-octazatricyclo[25.3.0.06,10]triacontane-2,5,11,14,17,20,23,26-octone
• CAS: 1312415-68-1
• 化学式: C₄₃H₅₅N₉O₁₀
• 分子量: 857.964
• InChiKey: KADRLXHCWSLEIB-HPAXBWHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  62
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  272
• 氢给体数：
  9
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  brachystemin I 、 N-A-(2,4-二硝基-5-氟苯基)-L-丙氨酸 在 盐酸 、 水 、 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 19.0h， 生成 (S)-2-(5-((S)-1-amino-1-oxopropan-2-ylamino)-2,4-dinitrophenylamino)propanoic acid 、 Gly-L-FDAA 、 L-FDAA-L-Thr 、 L-FDAA-L-Pro 、 L-Phe-L-FDAA
  参考文献：
  名称：

  Bioactive Compounds from the Aerial Parts of Brachystemma calycinum and Structural Revision of an Octacyclopeptide

  摘要：

  Four new cyclic peptides, brachystemins F-I (1-4), and 11 known compounds were isolated from the aerial parts of Brachystemma calycinim. The absolute configurations of compounds 1-4 were assigned using Marfey's method. The structure of compound 5 was revised from cyclo-(Pro(1)-Phe(2)-Leu(3)-Ala(4)-Thr(5)-Pro(6)-Ala(7)-Gly(8)) to cyclo-(Pro(1)-Pro(2)-Ala(3)-Gly(4)-Leu(5)-Ala(6)-Thr(7)-Phe(8)) with QTOF/MS and X-ray diffraction analysis. The N-containing compounds were assessed for their inhibitory effects on the secretion of monocyte chemokine ligand 2 (CCL-2), interleukin 6 (IL-6), and collagen IV against high-glucose-stimulated mesangial cells. Compound 5 was evaluated for its effects on collagen I, reactive oxygen species (ROS), superoxide anion (O(2)(center dot-)) production, and cell viability in mesangial cells, and on nitric oxide (NO) production in macrophage cells.

  DOI：

  10.1021/np200048u