(2E,4E,8Z,11Z,14Z)-icosapentaenoyl-CoA(4-)

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E,4E,8Z,11Z,14Z)-icosapentaenoyl-CoA(4-)
• 英文别名: [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[[[[(3R)-3-hydroxy-4-[[3-[2-[(2E,4E,8Z,11Z,14Z)-icosa-2,4,8,11,14-pentaenoyl]sulfanylethylamino]-3-oxopropyl]amino]-2,2-dimethyl-4-oxobutoxy]-oxidophosphoryl]oxy-oxidophosphoryl]oxymethyl]oxolan-3-yl] phosphate
• 化学式: C41H60N7O17P3S-4
• 分子量: 1047.9
• InChiKey: VEOYVBZJFWTPAJ-AKGIYQAYSA-J

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  69
• 可旋转键数：
  32
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  400
• 氢给体数：
  5
• 氢受体数：
  22

反应信息

• 作为产物：
  描述：

  (3E,5Z,8Z,11Z,14Z)-icosapentaenoyl-CoA(4-) 生成 (2E,4E,8Z,11Z,14Z)-icosapentaenoyl-CoA(4-)
  参考文献：
  名称：

  Δ3,5-Δ2,4-Dienoyl-CoA Isomerase from Rat Liver

  摘要：

  rECH1, a recently identified rat cDNA (FitzPatrick, D. R., Germain-Lee, E., and Valle, D. (1995) Genomics 27, 457-466) encodes a polypeptide belonging to the hydratase/isomerase superfamily, We modeled the structure of rECH1 based on rat mitochondrial 2-enoyl-CoA hydratase 1, The model predicts that rECH1p has the hydratase fold in the core domain and two domains for interaction with other subunits. When we incubated 3,5,8,11,14-eicosapentaenoyl-CoA with purified rECH1p, the spectral data suggested a switching of the double bonds from the Delta(3)-Delta(5) to the Delta(2)-Delta(4) positions. This was confirmed by demonstrating that the product was a valid substrate for 2,4-dienoyl-CoA reductase, These results indicate that rECH1p is Delta(3,5)-Delta(2,4)-dienoyl-CoA isomerase, Subcellular fractionation and immunoelectron microscopy using antibodies to a synthetic polypeptide derived from the C terminus of rECH1p showed that rECH1p is located in the matrix of both mitochondria and peroxisomes in rat liver, Consistent with these observations, the 36,000-Da rECH1p has a potential N-terminal mitochondrial targeting signal as well as a C-terminal peroxisomal targeting signal type 1, Transport of the protein into the mitochondria with cleavage of the targeting signal results in a mature mitochondrial form with a molecular mass of 32,000 Da; transport to peroxisomes yields a protein of 36,000 Da.

  DOI：

  10.1074/jbc.273.1.349

文献信息

• Δ3,5-Δ2,4-Dienoyl-CoA Isomerase from Rat Liver
  作者：S.A. Filppula、A.I. Yagi、S.H. Kilpeläinen、D. Novikov、D.R. FitzPatrick、M. Vihinen、D. Valle、J.K. Hiltunen

  DOI：10.1074/jbc.273.1.349

  日期：1998.1

  rECH1, a recently identified rat cDNA (FitzPatrick, D. R., Germain-Lee, E., and Valle, D. (1995) Genomics 27, 457-466) encodes a polypeptide belonging to the hydratase/isomerase superfamily, We modeled the structure of rECH1 based on rat mitochondrial 2-enoyl-CoA hydratase 1, The model predicts that rECH1p has the hydratase fold in the core domain and two domains for interaction with other subunits. When we incubated 3,5,8,11,14-eicosapentaenoyl-CoA with purified rECH1p, the spectral data suggested a switching of the double bonds from the Delta(3)-Delta(5) to the Delta(2)-Delta(4) positions. This was confirmed by demonstrating that the product was a valid substrate for 2,4-dienoyl-CoA reductase, These results indicate that rECH1p is Delta(3,5)-Delta(2,4)-dienoyl-CoA isomerase, Subcellular fractionation and immunoelectron microscopy using antibodies to a synthetic polypeptide derived from the C terminus of rECH1p showed that rECH1p is located in the matrix of both mitochondria and peroxisomes in rat liver, Consistent with these observations, the 36,000-Da rECH1p has a potential N-terminal mitochondrial targeting signal as well as a C-terminal peroxisomal targeting signal type 1, Transport of the protein into the mitochondria with cleavage of the targeting signal results in a mature mitochondrial form with a molecular mass of 32,000 Da; transport to peroxisomes yields a protein of 36,000 Da.