NP-MRD: Showing NP-Card for CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) (NP0338874)

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Record Information

Version

2.0

Created at

2024-09-11 18:25:57 UTC

Updated at

2024-09-11 18:25:58 UTC

NP-MRD ID

NP0338874

Secondary Accession Numbers

None

Natural Product Identification

Common Name

CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))

Description

CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) belongs to the class of organic compounds known as cardiolipins. These are glycerophospholipids in which the O1 and O3 oxygen atoms of the central glycerol moiety are each linked to one 1,2-diacylglycerol chain. Their general formula is OC(COP(O)(=O)OC[C@@H](CO[R1])O[R2])COP(O)(=O)OC[C@@H](CO[R3])O[R4], where R1-R4 are four fatty acyl chains. CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) is an extremely weak basic (essentially neutral) compound (based on its pKa). CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) and cytidine monophosphate can be biosynthesized from PG(20:2(11Z,14Z)/18:2(9Z,12Z)) and CDP-DG(18:2(9Z,12Z)/18:1(9Z)); which is mediated by the enzyme cardiolipin synthase. In humans, CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) is involved in cardiolipin biosynthesis. While most lipids are made in the endoplasmic reticulum, cardiolipin is synthesized on the matrix side of the inner mitochondrial membrane. They are highly abundant in metabolically active cells (heart, muscle) and play an important role in the blood clotting process. Cardiolipins are a "double" phospholipid because they have four fatty acid tails, instead of the usual two. CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) is a cardiolipin (CL). Cardiolipins (bisphosphatidyl glycerol) are an important component of the inner mitochondrial membrane, where they constitute about 20% of the total lipid.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251204332D          

104103  0  0  1  0            999 V2000
   21.7520    0.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7520    1.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4664    1.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4664    2.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1809    2.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1809    3.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8954    3.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8954    4.7210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6099    5.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6099    5.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3243    6.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3243    7.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0388    7.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0388    8.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7533    8.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7533    9.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4677   10.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4677   10.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7533   11.3210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.1822   11.3210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.1822   12.1460    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   27.4677   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7533   12.1460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0388   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0388   13.3835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3243   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6099   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8954   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1809   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4664   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7520   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0375   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3230   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3230   13.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6086   13.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6086   14.6210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3230   15.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3230   15.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0375   16.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0375   17.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7520   17.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7520   18.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8967   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6112   12.1460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3256   12.5585    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   30.7381   11.8440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9131   13.2730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0401   12.9710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7546   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4690   12.9710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4690   13.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.1835   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8980   12.9710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.6124   12.5585    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
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   35.3269   12.1460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   36.7559   12.1460    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   38.1848   12.1460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   38.8993   13.3835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.6137   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3282   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   41.7572   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4716   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1861   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9006   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6150   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.3295   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.0440   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   33.8980    7.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8980    6.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1835    5.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   32.4690    4.7210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4690    3.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1835    3.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1835    2.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8980    2.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8980    1.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   37.4704   11.7335    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
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M  END


  Mrv0541 02251204332D          

104103  0  0  1  0            999 V2000
   21.7520    0.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7520    1.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4664    1.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4664    2.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1809    2.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1809    3.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8954    3.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8954    4.7210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6099    5.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6099    5.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3243    6.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3243    7.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0388    7.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.3230   15.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.0375   16.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0375   17.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7520   17.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7520   18.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8967   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6112   12.1460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3256   12.5585    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   30.7381   11.8440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9131   13.2730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0401   12.9710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7546   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4690   12.9710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4690   13.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.1835   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8980   12.9710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.6124   12.5585    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   34.1999   11.8440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0249   13.2730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3269   12.1460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.0414   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7559   12.1460    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   37.4703   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1848   12.1460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.8993   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8993   13.3835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.6137   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3282   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0427   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7572   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4716   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1861   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9006   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6150   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.3295   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.0440   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.7585   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.4729   12.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.4729   13.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.1874   13.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.1874   14.6210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.9019   15.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.9019   15.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   49.6163   16.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   49.6163   17.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7559   11.3210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.0414   10.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3269   11.3210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.0414   10.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3269    9.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3269    8.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6124    8.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6124    7.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8980    7.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8980    6.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1835    5.9585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1835    5.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4690    4.7210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4690    3.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1835    3.4835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1835    2.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8980    2.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8980    1.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6124    1.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6124    0.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4677   11.7335    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   37.4704   11.7335    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
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 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
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 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 36 35  1  4  0  0  0
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 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
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 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 21 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  2  0  0  0  0
 45 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  2  0  0  0  0
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 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  2  0  0  0  0
 62 64  1  0  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
 68 69  1  0  0  0  0
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 70 71  1  0  0  0  0
 71 72  1  0  0  0  0
 73 72  1  4  0  0  0
 73 74  2  0  0  0  0
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 76 75  1  4  0  0  0
 76 77  2  0  0  0  0
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 87 88  1  0  0  0  0
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 90 91  1  0  0  0  0
 91 92  1  0  0  0  0
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 93 94  2  0  0  0  0
 94 95  1  0  0  0  0
 96 95  1  4  0  0  0
 96 97  2  0  0  0  0
 97 98  1  0  0  0  0
 98 99  1  0  0  0  0
 99100  1  0  0  0  0
100101  1  0  0  0  0
101102  1  0  0  0  0
 21103  1  1  0  0  0
 59104  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0338874

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](COC(=O)CCCCCCCCCC=CCC=CCCCCC)(COP(O)(=O)OCC(O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC=CCC=CCCCCC)OC(=O)CCCCCCCC=CCCCCCCCC)OC(=O)CCCCCCCC=CCC=CCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C83H148O17P2/c1-5-9-13-17-21-25-29-33-37-38-42-44-48-52-56-60-64-68-81(86)94-74-79(100-83(88)70-66-62-58-54-50-46-41-36-32-28-24-20-16-12-8-4)76-98-102(91,92)96-72-77(84)71-95-101(89,90)97-75-78(99-82(87)69-65-61-57-53-49-45-40-35-31-27-23-19-15-11-7-3)73-93-80(85)67-63-59-55-51-47-43-39-34-30-26-22-18-14-10-6-2/h21-22,24-26,28,33-37,39-41,77-79,84H,5-20,23,27,29-32,38,42-76H2,1-4H3,(H,89,90)(H,91,92)/t77?,78-,79-/m1/s1

> <INCHI_KEY>
FMZSACFMXWEBMY-FIDHOYNDSA-N

> <FORMULA>
C83H148O17P2

> <MOLECULAR_WEIGHT>
1480.0005

> <EXACT_MASS>
1479.019176334

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
179.41625308820986

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[2-hydroxy-3-({hydroxy[(2R)-3-(icosa-11,14-dienoyloxy)-2-(octadeca-9,12-dienoyloxy)propoxy]phosphoryl}oxy)propoxy][(2R)-2-(octadec-9-enoyloxy)-3-(octadeca-9,12-dienoyloxy)propoxy]phosphinic acid

> <ALOGPS_LOGP>
9.27

> <JCHEM_LOGP>
25.62535211466666

> <ALOGPS_LOGS>
-7.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.191804358217231

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.589737614322373

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4105029523385797

> <JCHEM_POLAR_SURFACE_AREA>
236.94999999999993

> <JCHEM_REFRACTIVITY>
423.9278999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
81

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.55e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-3-{[hydroxy(2R)-3-(icosa-11,14-dienoyloxy)-2-(octadeca-9,12-dienoyloxy)propoxyphosphoryl]oxy}propoxy(2R)-2-(octadec-9-enoyloxy)-3-(octadeca-9,12-dienoyloxy)propoxyphosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      40.604   0.343   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      40.604   1.883   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      41.937   2.653   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      41.937   4.193   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      43.271   4.963   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      43.271   6.503   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      44.605   7.273   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      44.605   8.813   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      45.938   9.583   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      45.938  11.123   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      47.272  11.893   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      47.272  13.433   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      48.606  14.203   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      48.606  15.743   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      49.939  16.513   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      49.939  18.053   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      51.273  18.823   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      51.273  20.363   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      49.939  21.133   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      52.607  21.133   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      52.607  22.673   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      51.273  23.443   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      49.939  22.673   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      48.606  23.443   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      48.606  24.983   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      47.272  22.673   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      45.938  23.443   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      44.605  22.673   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      43.271  23.443   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      41.937  22.673   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      40.604  23.443   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      39.270  22.673   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      37.936  23.443   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      37.936  24.983   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      36.603  25.753   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      36.603  27.293   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      37.936  28.063   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      37.936  29.603   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      39.270  30.373   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      39.270  31.913   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      40.604  32.683   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      40.604  34.223   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      53.941  23.443   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      55.274  22.673   0.000  0.00  0.00           O+0
HETATM   45  P   UNK     0      56.608  23.443   0.000  0.00  0.00           P+0
HETATM   46  O   UNK     0      57.378  22.109   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      55.838  24.776   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      57.942  24.213   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      59.275  23.443   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      60.609  24.213   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      60.609  25.753   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      61.943  23.443   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      63.276  24.213   0.000  0.00  0.00           O+0
HETATM   54  P   UNK     0      64.610  23.443   0.000  0.00  0.00           P+0
HETATM   55  O   UNK     0      63.840  22.109   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      65.380  24.776   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      65.944  22.673   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      67.277  23.443   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      68.611  22.673   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      69.945  23.443   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      71.278  22.673   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      72.612  23.443   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      72.612  24.983   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      73.946  22.673   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      75.279  23.443   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      76.613  22.673   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      77.947  23.443   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      79.280  22.673   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      80.614  23.443   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      81.948  22.673   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      83.281  23.443   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      84.615  22.673   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      85.949  23.443   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      87.283  22.673   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      88.616  23.443   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      88.616  24.983   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      89.950  25.753   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      89.950  27.293   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0      91.284  28.063   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0      91.284  29.603   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0      92.617  30.373   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0      92.617  31.913   0.000  0.00  0.00           C+0
HETATM   83  O   UNK     0      68.611  21.133   0.000  0.00  0.00           O+0
HETATM   84  C   UNK     0      67.277  20.363   0.000  0.00  0.00           C+0
HETATM   85  O   UNK     0      65.944  21.133   0.000  0.00  0.00           O+0
HETATM   86  C   UNK     0      67.277  18.823   0.000  0.00  0.00           C+0
HETATM   87  C   UNK     0      65.944  18.053   0.000  0.00  0.00           C+0
HETATM   88  C   UNK     0      65.944  16.513   0.000  0.00  0.00           C+0
HETATM   89  C   UNK     0      64.610  15.743   0.000  0.00  0.00           C+0
HETATM   90  C   UNK     0      64.610  14.203   0.000  0.00  0.00           C+0
HETATM   91  C   UNK     0      63.276  13.433   0.000  0.00  0.00           C+0
HETATM   92  C   UNK     0      63.276  11.893   0.000  0.00  0.00           C+0
HETATM   93  C   UNK     0      61.943  11.123   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0      61.943   9.583   0.000  0.00  0.00           C+0
HETATM   95  C   UNK     0      60.609   8.813   0.000  0.00  0.00           C+0
HETATM   96  C   UNK     0      60.609   7.273   0.000  0.00  0.00           C+0
HETATM   97  C   UNK     0      61.943   6.503   0.000  0.00  0.00           C+0
HETATM   98  C   UNK     0      61.943   4.963   0.000  0.00  0.00           C+0
HETATM   99  C   UNK     0      63.276   4.193   0.000  0.00  0.00           C+0
HETATM  100  C   UNK     0      63.276   2.653   0.000  0.00  0.00           C+0
HETATM  101  C   UNK     0      64.610   1.883   0.000  0.00  0.00           C+0
HETATM  102  C   UNK     0      64.610   0.343   0.000  0.00  0.00           C+0
HETATM  103  H   UNK     0      51.273  21.903   0.000  0.00  0.00           H+0
HETATM  104  H   UNK     0      69.945  21.903   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   43  103                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41                                                            
CONECT   43   21   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46   47   48                                             
CONECT   46   45                                                            
CONECT   47   45                                                            
CONECT   48   45   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55   56   57                                             
CONECT   55   54                                                            
CONECT   56   54                                                            
CONECT   57   54   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60   83  104                                             
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63   64                                                  
CONECT   63   62                                                            
CONECT   64   62   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65   67                                                       
CONECT   67   66   68                                                       
CONECT   68   67   69                                                       
CONECT   69   68   70                                                       
CONECT   70   69   71                                                       
CONECT   71   70   72                                                       
CONECT   72   71   73                                                       
CONECT   73   72   74                                                       
CONECT   74   73   75                                                       
CONECT   75   74   76                                                       
CONECT   76   75   77                                                       
CONECT   77   76   78                                                       
CONECT   78   77   79                                                       
CONECT   79   78   80                                                       
CONECT   80   79   81                                                       
CONECT   81   80   82                                                       
CONECT   82   81                                                            
CONECT   83   59   84                                                       
CONECT   84   83   85   86                                                  
CONECT   85   84                                                            
CONECT   86   84   87                                                       
CONECT   87   86   88                                                       
CONECT   88   87   89                                                       
CONECT   89   88   90                                                       
CONECT   90   89   91                                                       
CONECT   91   90   92                                                       
CONECT   92   91   93                                                       
CONECT   93   92   94                                                       
CONECT   94   93   95                                                       
CONECT   95   94   96                                                       
CONECT   96   95   97                                                       
CONECT   97   96   98                                                       
CONECT   98   97   99                                                       
CONECT   99   98  100                                                       
CONECT  100   99  101                                                       
CONECT  101  100  102                                                       
CONECT  102  101                                                            
CONECT  103   21                                                            
CONECT  104   59                                                            
MASTER        0    0    0    0    0    0    0    0  104    0  206    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₈₃H₁₄₈O₁₇P₂

Average Mass

1480.0005 Da

Monoisotopic Mass

1479.01918 Da

IUPAC Name

[2-hydroxy-3-({hydroxy[(2R)-3-(icosa-11,14-dienoyloxy)-2-(octadeca-9,12-dienoyloxy)propoxy]phosphoryl}oxy)propoxy][(2R)-2-(octadec-9-enoyloxy)-3-(octadeca-9,12-dienoyloxy)propoxy]phosphinic acid

Traditional Name

2-hydroxy-3-{[hydroxy(2R)-3-(icosa-11,14-dienoyloxy)-2-(octadeca-9,12-dienoyloxy)propoxyphosphoryl]oxy}propoxy(2R)-2-(octadec-9-enoyloxy)-3-(octadeca-9,12-dienoyloxy)propoxyphosphinic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](COC(=O)CCCCCCCCCC=CCC=CCCCCC)(COP(O)(=O)OCC(O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC=CCC=CCCCCC)OC(=O)CCCCCCCC=CCCCCCCCC)OC(=O)CCCCCCCC=CCC=CCCCCC

InChI Identifier

InChI=1S/C83H148O17P2/c1-5-9-13-17-21-25-29-33-37-38-42-44-48-52-56-60-64-68-81(86)94-74-79(100-83(88)70-66-62-58-54-50-46-41-36-32-28-24-20-16-12-8-4)76-98-102(91,92)96-72-77(84)71-95-101(89,90)97-75-78(99-82(87)69-65-61-57-53-49-45-40-35-31-27-23-19-15-11-7-3)73-93-80(85)67-63-59-55-51-47-43-39-34-30-26-22-18-14-10-6-2/h21-22,24-26,28,33-37,39-41,77-79,84H,5-20,23,27,29-32,38,42-76H2,1-4H3,(H,89,90)(H,91,92)/t77?,78-,79-/m1/s1

InChI Key

FMZSACFMXWEBMY-FIDHOYNDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cardiolipins. These are glycerophospholipids in which the O1 and O3 oxygen atoms of the central glycerol moiety are each linked to one 1,2-diacylglycerol chain. Their general formula is OC(COP(O)(=O)OC[C@@H](CO[R1])O[R2])COP(O)(=O)OC[C@@H](CO[R3])O[R4], where R1-R4 are four fatty acyl chains.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoglycerophosphoglycerols

Direct Parent

Cardiolipins

Alternative Parents

Substituents

Cardiolipin
Tetracarboxylic acid or derivatives
Dialkyl phosphate
Fatty acid ester
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	9.27	ALOGPS
logP	25.63	ChemAxon
logS	-7.3	ALOGPS
pKa (Strongest Acidic)	1.59	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	236.95 Å²	ChemAxon
Rotatable Bond Count	81	ChemAxon
Refractivity	423.93 m³·mol⁻¹	ChemAxon
Polarizability	179.42 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB027413

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) (NP0338874)

MOL for NP0338874 (CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)))

3D MOL for NP0338874 (CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)))

3D SDF for NP0338874 (CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)))

3D-SDF for NP0338874 (CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)))

PDB for NP0338874 (CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)))

3D PDB for NP0338874 (CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)))

SMILES for NP0338874 (CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)))

INCHI for NP0338874 (CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)))

Structure for NP0338874 (CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)))

3D Structure for NP0338874 (CL(20:2(11Z,14Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)))