(2S,3R,26S,27S)-2,27-diamino-1,3,26-trihydroxynonacosan-18-one-1-β-D-glucoside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: (2S,3R,26S,27S)-2,27-diamino-1,3,26-trihydroxynonacosan-18-one-1-β-D-glucoside
• 英文别名: calyxoside；(2S,3S,26R,27S)-2,27-diamino-3,26-dihydroxy-28-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctacosan-11-one
• 化学式: C₃₄H₆₈N₂O₉
• 分子量: 648.922
• InChiKey: DVBWWNHCQFZFCN-LQQLXRTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  45
• 可旋转键数：
  29
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  209
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2S,3R,26S,27S)-2,27-diamino-1,3,26-trihydroxynonacosan-18-one-1-β-D-glucoside 在 盐酸 、 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 calyxinin pentabenzoate
  参考文献：
  名称：

  Structure and stereochemistry of a novel bioactive sphingolipid from a Calyx sp.

  摘要：

  Bioassay-directed fractionation of a sponge of the genus Calyx using a yeast bioassay for DNA-damaging agents yielded the novel sphingolipid calyxoside (1) as the major bioactive constituent. The structure of 1 was assigned as 1,3,26-trihydroxy-2,27-diaminooctacosan-18-one-1-beta -D-glucoside by H-1- and C-13 NMR, DEPT, DQCOSY, HMQC, and HMBC spectra. The carbonyl group was located at C-18 by analysis of the EI-MS fragmentation of the amino derivative of its aglycone pentaacetate. Its absolute configuration was determined as 2S,3R,26S,27S by analysis of the H-1 NMR and CD spectra of its aglycone pentabenzoate. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(01)00958-9

文献信息

• Structure and stereochemistry of a novel bioactive sphingolipid from a Calyx sp.
  作者：Bing-Nan Zhou、Michael P Mattern、Randall K Johnson、David G.I Kingston

  DOI：10.1016/s0040-4020(01)00958-9

  日期：2001.11

  Bioassay-directed fractionation of a sponge of the genus Calyx using a yeast bioassay for DNA-damaging agents yielded the novel sphingolipid calyxoside (1) as the major bioactive constituent. The structure of 1 was assigned as 1,3,26-trihydroxy-2,27-diaminooctacosan-18-one-1-beta -D-glucoside by H-1- and C-13 NMR, DEPT, DQCOSY, HMQC, and HMBC spectra. The carbonyl group was located at C-18 by analysis of the EI-MS fragmentation of the amino derivative of its aglycone pentaacetate. Its absolute configuration was determined as 2S,3R,26S,27S by analysis of the H-1 NMR and CD spectra of its aglycone pentabenzoate. (C) 2001 Published by Elsevier Science Ltd.