25-epi-actinoramide A | 1816295-34-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: 25-epi-actinoramide A
• 英文别名: (3S)-N-[(2S,3S,4S)-5-[[(3R)-1-carbamoyl-2-oxopyrrolidin-3-yl]amino]-3-hydroxy-4-methyl-5-oxo-1-phenylpentan-2-yl]-2-[(2R,3R)-3-hydroxy-2-[(2-methoxyacetyl)amino]-4-methylpentanoyl]diazinane-3-carboxamide
• CAS: 1816295-34-7
• 化学式: C₃₁H₄₇N₇O₉
• 分子量: 661.756
• InChiKey: IAYPOIKGUHHBAU-DNMAVYRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  47
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  233
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  25-epi-actinoramide A 、 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 20.08h， 生成 、 、 、
  参考文献：
  名称：

  Actinoramide A Identified as a Potent Antimalarial from Titration-Based Screening of Marine Natural Product Extracts

  摘要：

  Methods to identify the bioactive diversity within natural product extracts (NPEs) continue to evolve. NPEs constitute complex mixtures of chemical substances varying in structure, composition, and abundance. NPEs can therefore be challenging to evaluate efficiently with high-throughput screening approaches designed to test pure substances. Here we facilitate the rapid identification and prioritization of antimalarial NPEs using a pharmacologically driven, quantitative high-throughput-screening (qHTS) paradigm. In qHTS each NPE is tested across a concentration range from which sigmoidal response, efficacy, and apparent EC(50)s can be used to rank order NPEs for subsequent organism reculture, extraction, and fractionation. Using an NPE library derived from diverse marine microorganisms we observed potent antimalarial activity from two Streptomyces sp. extracts identified from thousands tested using qHTS. Seven compounds were isolated from two phylogenetically related Streptomyces species: Streptomyces ballenaensis collected from Costa Rica and Streptomyces bangulaensis collected from Papua New Guinea. Among them we identified actinoramides A and B, belonging to the unusually elaborated nonproteinogenic amino-acid-containing tetrapeptide series of natural products. In addition, we characterized a series of new compounds, including an artifact, 25-epi-actinoramide A, and actinoramides D, E, and F, which are closely related biosynthetic congeners of the previously reported metabolites.

  DOI：

  10.1021/acs.jnatprod.5b00489
• 作为产物：
  描述：

  padanamide A 以 氘代吡啶 为溶剂， 以0.6 mg的产率得到25-epi-actinoramide A
  参考文献：
  名称：

  Actinoramide A Identified as a Potent Antimalarial from Titration-Based Screening of Marine Natural Product Extracts

  摘要：

  Methods to identify the bioactive diversity within natural product extracts (NPEs) continue to evolve. NPEs constitute complex mixtures of chemical substances varying in structure, composition, and abundance. NPEs can therefore be challenging to evaluate efficiently with high-throughput screening approaches designed to test pure substances. Here we facilitate the rapid identification and prioritization of antimalarial NPEs using a pharmacologically driven, quantitative high-throughput-screening (qHTS) paradigm. In qHTS each NPE is tested across a concentration range from which sigmoidal response, efficacy, and apparent EC(50)s can be used to rank order NPEs for subsequent organism reculture, extraction, and fractionation. Using an NPE library derived from diverse marine microorganisms we observed potent antimalarial activity from two Streptomyces sp. extracts identified from thousands tested using qHTS. Seven compounds were isolated from two phylogenetically related Streptomyces species: Streptomyces ballenaensis collected from Costa Rica and Streptomyces bangulaensis collected from Papua New Guinea. Among them we identified actinoramides A and B, belonging to the unusually elaborated nonproteinogenic amino-acid-containing tetrapeptide series of natural products. In addition, we characterized a series of new compounds, including an artifact, 25-epi-actinoramide A, and actinoramides D, E, and F, which are closely related biosynthetic congeners of the previously reported metabolites.

  DOI：

  10.1021/acs.jnatprod.5b00489

文献信息

• Actinoramide A Identified as a Potent Antimalarial from Titration-Based Screening of Marine Natural Product Extracts
  作者：Ken Chih-Chien Cheng、Shugeng Cao、Avi Raveh、Ryan MacArthur、Patricia Dranchak、George Chlipala、Matthew T. Okoneski、Rajarshi Guha、Richard T. Eastman、Jing Yuan、Pamela J. Schultz、Xin-zhuan Su、Giselle Tamayo-Castillo、Teatulohi Matainaho、Jon Clardy、David H. Sherman、James Inglese

  DOI：10.1021/acs.jnatprod.5b00489

  日期：2015.10.23

  Methods to identify the bioactive diversity within natural product extracts (NPEs) continue to evolve. NPEs constitute complex mixtures of chemical substances varying in structure, composition, and abundance. NPEs can therefore be challenging to evaluate efficiently with high-throughput screening approaches designed to test pure substances. Here we facilitate the rapid identification and prioritization of antimalarial NPEs using a pharmacologically driven, quantitative high-throughput-screening (qHTS) paradigm. In qHTS each NPE is tested across a concentration range from which sigmoidal response, efficacy, and apparent EC(50)s can be used to rank order NPEs for subsequent organism reculture, extraction, and fractionation. Using an NPE library derived from diverse marine microorganisms we observed potent antimalarial activity from two Streptomyces sp. extracts identified from thousands tested using qHTS. Seven compounds were isolated from two phylogenetically related Streptomyces species: Streptomyces ballenaensis collected from Costa Rica and Streptomyces bangulaensis collected from Papua New Guinea. Among them we identified actinoramides A and B, belonging to the unusually elaborated nonproteinogenic amino-acid-containing tetrapeptide series of natural products. In addition, we characterized a series of new compounds, including an artifact, 25-epi-actinoramide A, and actinoramides D, E, and F, which are closely related biosynthetic congeners of the previously reported metabolites.