3-O-<β-D-glucopyranosyl>-quinovic acid | 79955-41-2

• 物质功能分类: 天然产物 - 萜类
• 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: 3-O-<β-D-glucopyranosyl>-quinovic acid
• 英文别名: quinovic acid 3β-O-β-D-glucopyranoside；quinovic acid-3β-O-β-D-glucopyranoside；quinovic acid-3β-O-β-D-glycopyranoside；3-O-[β-D-glucopyranosyl]-quinovic acid；3-O-[β-D-glucopyranosyl]quinovic acid；quinovic acid-3-O-β-D-glucopyranoside；Quinovic acid 3-O-beta-D-glucoside；(1S,2R,4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-1,2,6b,9,9,12a-hexamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a,6a-dicarboxylic acid
• CAS: 79955-41-2
• 化学式: C₃₆H₅₆O₁₀
• 分子量: 648.835
• InChiKey: AXNXSFBKZQIMPF-ZZZTYRQWSA-N

物化性质

• 熔点：
  245-247 °C
• 沸点：
  787.8±60.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  46
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  174
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-O-<β-D-glucopyranosyl>-quinovic acid 在 Nocardia sp. NRRL 5646 作用下， 以 乙醇 为溶剂， 反应 120.0h， 生成 鸡纳酸
  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
• 作为产物：
  描述：

  quinovic acid-3β-O-β-d-glucopyranosyl-(28→1)-β-d-glucopyranosyl ester 、 氢氧化钾 、 甲醇 生成 3-O-<β-D-glucopyranosyl>-quinovic acid
  参考文献：
  名称：

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

  摘要：

  DOI：

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.