quinovic acid-3β-O-β-d-glucopyranosyl-(28→1)-β-d-glucopyranosyl ester | 104055-77-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: quinovic acid-3β-O-β-d-glucopyranosyl-(28→1)-β-d-glucopyranosyl ester
• 英文别名: 3-O-β-D-glucopyranosyl quinovic acid-28-β-D-glucopyranosyl ester；3-O-β-D-glucopyranosylquinovic acid 28-O-β-D-glucopyranosyl ester；(1S,2R,4aS,6aR,6bR,8aR,10S,12aR,12bR,14bS)-1,2,6b,9,9,12a-hexamethyl-10-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-4a-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)carbonyl)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-6a-carboxylic acid；(1S,2R,4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-1,2,6b,9,9,12a-hexamethyl-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-6a-carboxylic acid
• CAS: 104055-77-8
• 化学式: C₄₂H₆₆O₁₅
• 分子量: 810.977
• InChiKey: LDCLXZSKVDYDBF-DTJUAWDLSA-N

物化性质

• 熔点：
  210-213 °C
• 沸点：
  907.4±65.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  57
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  253
• 氢给体数：
  9
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  quinovic acid-3β-O-β-d-glucopyranosyl-(28→1)-β-d-glucopyranosyl ester 在 Nocardia sp. NRRL 5646 作用下， 以 乙醇 为溶剂， 反应 240.0h， 生成 鸡纳酸 、 cincholic acid
  参考文献：
  名称：

  Biotransformation of Quinovic Acid Glycosides by Microbes:  Direct Conversion of the Ursane to the Oleanane Triterpene Skeleton by Nocardia sp. NRRL 5646

  摘要：

  Quinovic acid glycosides were microbially deglycosylated by a Nocardia sp. to their aglycon quinovic acid and its biogenetic counterpart, cincholic acid (3), via an unprecedented carbon skeleton rearrangement involving a methyl group migration. The structures of the metabolites were established by ESI-LC/MS and 2D-NMR techniques.

  DOI：

  10.1021/ol048787b

文献信息

• ARRIAGA, F. JAVIER;, RUMBERO ANGEL;VAZQUEZ, PURIFICACION, PHYTOCHEMISTRY, 29,(1990) N, C. 209-213
  作者：ARRIAGA, F. JAVIER、, RUMBERO ANGEL、VAZQUEZ, PURIFICACION

  DOI：——

  日期：——
• Biotransformation of Quinovic Acid Glycosides by Microbes:  Direct Conversion of the Ursane to the Oleanane Triterpene Skeleton by <i>Nocardia </i>sp. NRRL 5646
  作者：Zhi-Hong Cheng、Bo-Yang Yu、Geoffrey A. Cordell、Sheng-Xiang Qiu

  DOI：10.1021/ol048787b

  日期：2004.9.1

  Quinovic acid glycosides were microbially deglycosylated by a Nocardia sp. to their aglycon quinovic acid and its biogenetic counterpart, cincholic acid (3), via an unprecedented carbon skeleton rearrangement involving a methyl group migration. The structures of the metabolites were established by ESI-LC/MS and 2D-NMR techniques.