(3S,4R,4aR,6aS,7aS,9aR,11R,13aS,13bR,15aS,15bR)-3,11-Diacetoxy-7a-hydroxy-4,6a,10,10,13a,15b-hexamethyl-docosahydro-cyclohepta[1,2-a;5,4-a']dinaphthalene-4-carboxylic acid | 448211-58-3

• 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: (3S,4R,4aR,6aS,7aS,9aR,11R,13aS,13bR,15aS,15bR)-3,11-Diacetoxy-7a-hydroxy-4,6a,10,10,13a,15b-hexamethyl-docosahydro-cyclohepta[1,2-a;5,4-a']dinaphthalene-4-carboxylic acid
• 英文别名: Lycernuic acid E diacetate；(1S,3S,6R,7R,8S,11R,12S,15R,16S,19R,21R)-8,19-diacetyloxy-1-hydroxy-3,7,11,16,20,20-hexamethylpentacyclo[13.8.0.03,12.06,11.016,21]tricosane-7-carboxylic acid
• CAS: 448211-58-3
• 化学式: C₃₄H₅₄O₇
• 分子量: 574.799
• InChiKey: ZTKNIOHKWFWGGH-DTQZJXPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  41
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3S,4R,4aR,6aS,7aS,9aR,11R,13aS,13bR,15aS,15bR)-3,11-Diacetoxy-7a-hydroxy-4,6a,10,10,13a,15b-hexamethyl-docosahydro-cyclohepta[1,2-a;5,4-a']dinaphthalene-4-carboxylic acid 在 吡啶 、 氯化亚砜 作用下， 反应 3.0h， 以1.5 mg的产率得到lycernuic acid A diacetate
  参考文献：
  名称：

  Natural Products Inhibiting Candida albicans Secreted Aspartic Proteases from Lycopodium cernuum

  摘要：

  Activity-guided fractionation of an ethanol extract of Lycopodium. cernuum. for Candida albicans secreted aspartic proteases (SAP) inhibition resulted in the identification of six new (1-6) and four known (7-10) serratene triterpenes, along with the known oipigenin-4'-O-(2",6"-di-O-p-coumaroyl)-beta-D-glucopyranoside (11). On the basis of spectroscopic analysis, the structures of 1-10 were established as 3beta,14alpha,15alpha,21beta,29-pentahydroxyserratane-24-oic acid (lycernuic acid C, 1), 3beta,14alpha,15alpha,21beta-tetrahydroxyserratane-24-oic acid (lycernuic acid D, 2), 3beta,14beta,21beta-trihydroxyserratane-24-oic acid (lycernuic acid E, 3), 3beta,21beta,29-trihydroxy-16-oxoserrat-14-en-24-methyl ester (lycernuic ketone A, 4), 3alpha,21beta,29-trihydroxy-16-oxoserrat-14-en-24-methyl ester (lycernuic ketone B, 5), 3alpha,21beta,29-trihydroxyserrat-14-en-16-one (lycernuic ketone C, 6), 3beta,21beta-dihydroxyserrat-14-en-24-oic acid (lycernuic acid A, 7) 3beta,21beta,29-trihydroxyserrat-14-en-24-oic acid (lycernuic acid B, 8), serrat-14-en-3beta,21beta-diol (9), and serrat-14-en-3beta,21alpha-diol (10). The C-13 NMR data for the known compounds 7 and 8 are reported for the first time. Compounds 1 and 11 showed inhibitory effects against C. albicans secreted aspartic proteases (SAP) with IC50 of 20 and 8.5 mug/mL, respectively, while the other compounds were inactive.

  DOI：

  10.1021/np0200616
• 作为产物：
  描述：

  乙酸酐 、 (3S,4R,4aR,6aS,7aS,9aR,11R,13aS,13bR,15aS,15bR)-3,7a,11-Trihydroxy-4,6a,10,10,13a,15b-hexamethyl-docosahydro-cyclohepta[1,2-a;5,4-a']dinaphthalene-4-carboxylic acid 在 吡啶 作用下， 反应 24.0h， 以2.0 mg的产率得到(3S,4R,4aR,6aS,7aS,9aR,11R,13aS,13bR,15aS,15bR)-3,11-Diacetoxy-7a-hydroxy-4,6a,10,10,13a,15b-hexamethyl-docosahydro-cyclohepta[1,2-a;5,4-a']dinaphthalene-4-carboxylic acid
  参考文献：
  名称：

  Natural Products Inhibiting Candida albicans Secreted Aspartic Proteases from Lycopodium cernuum

  摘要：

  Activity-guided fractionation of an ethanol extract of Lycopodium. cernuum. for Candida albicans secreted aspartic proteases (SAP) inhibition resulted in the identification of six new (1-6) and four known (7-10) serratene triterpenes, along with the known oipigenin-4'-O-(2",6"-di-O-p-coumaroyl)-beta-D-glucopyranoside (11). On the basis of spectroscopic analysis, the structures of 1-10 were established as 3beta,14alpha,15alpha,21beta,29-pentahydroxyserratane-24-oic acid (lycernuic acid C, 1), 3beta,14alpha,15alpha,21beta-tetrahydroxyserratane-24-oic acid (lycernuic acid D, 2), 3beta,14beta,21beta-trihydroxyserratane-24-oic acid (lycernuic acid E, 3), 3beta,21beta,29-trihydroxy-16-oxoserrat-14-en-24-methyl ester (lycernuic ketone A, 4), 3alpha,21beta,29-trihydroxy-16-oxoserrat-14-en-24-methyl ester (lycernuic ketone B, 5), 3alpha,21beta,29-trihydroxyserrat-14-en-16-one (lycernuic ketone C, 6), 3beta,21beta-dihydroxyserrat-14-en-24-oic acid (lycernuic acid A, 7) 3beta,21beta,29-trihydroxyserrat-14-en-24-oic acid (lycernuic acid B, 8), serrat-14-en-3beta,21beta-diol (9), and serrat-14-en-3beta,21alpha-diol (10). The C-13 NMR data for the known compounds 7 and 8 are reported for the first time. Compounds 1 and 11 showed inhibitory effects against C. albicans secreted aspartic proteases (SAP) with IC50 of 20 and 8.5 mug/mL, respectively, while the other compounds were inactive.

  DOI：

  10.1021/np0200616