NP-MRD: Showing NP-Card for CL(20:4(5Z,8Z,11Z,14Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) (NP0338834)

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Record Information

Version

2.0

Created at

2024-09-11 18:09:00 UTC

Updated at

2024-09-11 18:09:00 UTC

NP-MRD ID

NP0338834

Secondary Accession Numbers

None

Natural Product Identification

Common Name

CL(20:4(5Z,8Z,11Z,14Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z))

Description

CL(20:4(5Z,8Z,11Z,14Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) 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(20:4(5Z,8Z,11Z,14Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) is an extremely weak basic (essentially neutral) compound (based on its pKa). CL(20:4(5Z,8Z,11Z,14Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) and cytidine monophosphate can be biosynthesized from PG(20:4(5Z,8Z,11Z,14Z)/20:1(11Z)) and CDP-DG(18:2(9Z,12Z)/18:2(9Z,12Z)) through its interaction with the enzyme cardiolipin synthase. In humans, CL(20:4(5Z,8Z,11Z,14Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) is involved in cardiolipin biosynthesis. They are highly abundant in metabolically active cells (heart, muscle) and play an important role in the blood clotting process. Cardiolipins (bisphosphatidyl glycerol) are an important component of the inner mitochondrial membrane, where they constitute about 20% of the total lipid. Cardiolipins are a "double" phospholipid because they have four fatty acid tails, instead of the usual two. CL(20:4(5Z,8Z,11Z,14Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) is a cardiolipin (CL). While most lipids are made in the endoplasmic reticulum, cardiolipin is synthesized on the matrix side of the inner mitochondrial membrane.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251203412D          

106105  0  0  1  0            999 V2000
    6.4551   10.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7613   11.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5778   11.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8840   12.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7006   12.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0068   13.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8233   13.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1295   13.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9461   14.0684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2523   14.8344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0688   14.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3750   15.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1915   15.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4977   16.6023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3143   16.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6205   17.4862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4370   17.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7432   18.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5598   18.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.9887   20.1380    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   16.6618   20.6684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1515   21.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4577   22.0826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3350   21.1987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8246   21.8469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1308   22.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9474   22.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2536   23.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7432   24.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0494   24.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8660   25.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1722   25.7951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9887   25.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4990   25.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3156   25.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8259   24.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5197   23.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0300   23.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7238   22.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2342   21.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9280   21.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4383   20.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8052   20.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3156   19.6076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1321   19.7255    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.2500   18.9090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0143   20.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9487   19.8434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   22.2755   19.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.7859   18.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6024   18.7826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1127   18.1344    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
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   24.7610   18.6448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6231   17.4862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4396   17.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9499   16.9559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.7665   17.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2768   16.4255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0934   16.5434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3996   17.3094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6037   15.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4202   16.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7264   16.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5430   16.8969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0533   16.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8699   16.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3802   15.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1967   15.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   36.7691   17.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   37.8918   17.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1980   18.7237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6437   16.1898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   21.4590   13.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1528   12.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   19.4176   10.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1114    9.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6218    8.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3156    8.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   25.9393   17.9460    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0  0  0  0
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M  END


  Mrv0541 02251203412D          

106105  0  0  1  0            999 V2000
    6.4551   10.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7613   11.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5778   11.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8840   12.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7006   12.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0068   13.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.0688   14.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.8660   25.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1722   25.7951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9887   25.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4990   25.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3156   25.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8259   24.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5197   23.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0300   23.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7238   22.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2342   21.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9280   21.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4383   20.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8052   20.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3156   19.6076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1321   19.7255    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.2500   18.9090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0143   20.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9487   19.8434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4590   19.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2755   19.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5817   20.0791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7859   18.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6024   18.7826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1127   18.1344    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.4645   17.6241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7610   18.6448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6231   17.4862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4396   17.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9499   16.9559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.7665   17.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2768   16.4255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0934   16.5434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3996   17.3094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6037   15.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4202   16.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7264   16.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5430   16.8969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0533   16.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8699   16.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3802   15.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1967   15.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7071   15.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5236   15.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8298   16.0719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6463   16.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9525   16.9559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7691   17.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0753   17.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8918   17.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1980   18.7237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6437   16.1898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8272   16.0719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3169   16.7201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5210   15.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7045   15.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3983   14.4219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5817   14.3041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2755   13.5380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4590   13.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1528   12.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3362   12.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0300   11.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2135   11.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9073   10.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4176   10.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1114    9.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6218    8.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3156    8.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8259    7.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5197    6.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3698   19.4021    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.9393   17.9460    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
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
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 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 30  1  4  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 34 33  1  4  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 37 36  1  4  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 40 39  1  4  0  0  0
 40 41  2  0  0  0  0
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 42 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
 23 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  2  0  0  0  0
 49 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  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 58 60  2  0  0  0  0
 58 61  1  0  0  0  0
 61 62  1  0  0  0  0
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 63 64  1  0  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
 66 67  2  0  0  0  0
 66 68  1  0  0  0  0
 68 69  1  0  0  0  0
 69 70  1  0  0  0  0
 70 71  1  0  0  0  0
 71 72  1  0  0  0  0
 72 73  1  0  0  0  0
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 75 74  1  4  0  0  0
 75 76  2  0  0  0  0
 76 77  1  0  0  0  0
 78 77  1  4  0  0  0
 78 79  2  0  0  0  0
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 92 93  1  0  0  0  0
 93 94  1  0  0  0  0
 95 94  1  4  0  0  0
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 98 99  2  0  0  0  0
 99100  1  0  0  0  0
100101  1  0  0  0  0
101102  1  0  0  0  0
102103  1  0  0  0  0
103104  1  0  0  0  0
 23105  1  1  0  0  0
 63106  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0338834

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C85H148O17P2/c1-5-9-13-17-21-25-29-33-37-39-43-46-50-54-58-62-66-70-83(88)96-76-81(102-85(90)72-68-64-60-56-52-48-44-40-38-34-30-26-22-18-14-10-6-2)78-100-104(93,94)98-74-79(86)73-97-103(91,92)99-77-80(101-84(89)71-67-63-59-55-51-47-42-36-32-28-24-20-16-12-8-4)75-95-82(87)69-65-61-57-53-49-45-41-35-31-27-23-19-15-11-7-3/h21,23-25,27-28,33-38,41-43,46,54,58,79-81,86H,5-20,22,26,29-32,39-40,44-45,47-53,55-57,59-78H2,1-4H3,(H,91,92)(H,93,94)/t79?,80-,81-/m1/s1

> <INCHI_KEY>
JICFHIJWQCVAHY-NYTMHASESA-N

> <FORMULA>
C85H148O17P2

> <MOLECULAR_WEIGHT>
1504.0219

> <EXACT_MASS>
1503.019176334

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
180.58446823831846

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[3-({[(2R)-2,3-bis(octadeca-9,12-dienoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-(icos-11-enoyloxy)-3-(icosa-5,8,11,14-tetraenoyloxy)propoxy]phosphinic acid

> <ALOGPS_LOGP>
9.31

> <JCHEM_LOGP>
25.790646131333325

> <ALOGPS_LOGS>
-7.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.191804358217161

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.589737614322165

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4105029523385797

> <JCHEM_POLAR_SURFACE_AREA>
236.94999999999993

> <JCHEM_REFRACTIVITY>
435.3630999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
81

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.74e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2R)-2,3-bis(octadeca-9,12-dienoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy(2R)-2-(icos-11-enoyloxy)-3-(icosa-5,8,11,14-tetraenoyloxy)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      12.050  19.661   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.621  21.091   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.145  21.311   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.717  22.741   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.241  22.961   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.813  24.391   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.337  24.611   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.908  26.041   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.433  26.261   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.004  27.691   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.528  27.911   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.100  29.341   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.624  29.561   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.196  30.991   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.720  31.211   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.292  32.641   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.816  32.861   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      29.387  34.291   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.912  34.511   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      31.483  35.941   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      30.530  37.151   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      33.007  36.161   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      33.579  37.591   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      32.626  38.801   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      31.102  38.581   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      30.149  39.791   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      30.721  41.221   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      28.625  39.571   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      27.673  40.781   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      28.244  42.211   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      29.768  42.431   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      30.340  43.861   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      29.387  45.071   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      29.959  46.501   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      31.483  46.721   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      32.055  48.151   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      33.579  48.371   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      34.531  47.161   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      36.056  47.381   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      37.008  46.171   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      36.437  44.741   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      37.389  43.531   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      36.818  42.101   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      37.771  40.891   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      37.199  39.461   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      38.151  38.251   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      35.103  37.811   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      36.056  36.601   0.000  0.00  0.00           O+0
HETATM   49  P   UNK     0      37.580  36.821   0.000  0.00  0.00           P+0
HETATM   50  O   UNK     0      37.800  35.297   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      37.360  38.345   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      39.104  37.041   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      40.057  35.831   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      41.581  36.051   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      42.153  37.481   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      42.534  34.841   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      44.058  35.061   0.000  0.00  0.00           O+0
HETATM   58  P   UNK     0      45.010  33.851   0.000  0.00  0.00           P+0
HETATM   59  O   UNK     0      43.800  32.898   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      46.221  34.804   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      45.963  32.641   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      47.487  32.861   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      48.440  31.651   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      49.964  31.871   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      50.917  30.661   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      52.441  30.881   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      53.013  32.311   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      53.394  29.671   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      54.918  29.891   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      55.489  31.321   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      57.014  31.541   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      57.966  30.331   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      59.490  30.551   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      60.443  29.341   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      61.967  29.561   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      62.920  28.351   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      64.444  28.571   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      65.016  30.001   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0      66.540  30.221   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0      67.111  31.651   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0      68.636  31.871   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0      69.207  33.301   0.000  0.00  0.00           C+0
HETATM   83  C   UNK     0      70.731  33.521   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0      71.303  34.951   0.000  0.00  0.00           C+0
HETATM   85  O   UNK     0      47.868  30.221   0.000  0.00  0.00           O+0
HETATM   86  C   UNK     0      46.344  30.001   0.000  0.00  0.00           C+0
HETATM   87  O   UNK     0      45.392  31.211   0.000  0.00  0.00           O+0
HETATM   88  C   UNK     0      45.773  28.571   0.000  0.00  0.00           C+0
HETATM   89  C   UNK     0      44.248  28.351   0.000  0.00  0.00           C+0
HETATM   90  C   UNK     0      43.677  26.921   0.000  0.00  0.00           C+0
HETATM   91  C   UNK     0      42.153  26.701   0.000  0.00  0.00           C+0
HETATM   92  C   UNK     0      41.581  25.271   0.000  0.00  0.00           C+0
HETATM   93  C   UNK     0      40.057  25.051   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0      39.485  23.621   0.000  0.00  0.00           C+0
HETATM   95  C   UNK     0      37.961  23.401   0.000  0.00  0.00           C+0
HETATM   96  C   UNK     0      37.389  21.971   0.000  0.00  0.00           C+0
HETATM   97  C   UNK     0      35.865  21.751   0.000  0.00  0.00           C+0
HETATM   98  C   UNK     0      35.294  20.321   0.000  0.00  0.00           C+0
HETATM   99  C   UNK     0      36.246  19.111   0.000  0.00  0.00           C+0
HETATM  100  C   UNK     0      35.675  17.681   0.000  0.00  0.00           C+0
HETATM  101  C   UNK     0      36.627  16.471   0.000  0.00  0.00           C+0
HETATM  102  C   UNK     0      36.056  15.041   0.000  0.00  0.00           C+0
HETATM  103  C   UNK     0      37.008  13.831   0.000  0.00  0.00           C+0
HETATM  104  C   UNK     0      36.437  12.401   0.000  0.00  0.00           C+0
HETATM  105  H   UNK     0      34.290  36.217   0.000  0.00  0.00           H+0
HETATM  106  H   UNK     0      48.420  33.499   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                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   47  105                                             
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   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   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45                                                            
CONECT   47   23   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50   51   52                                             
CONECT   50   49                                                            
CONECT   51   49                                                            
CONECT   52   49   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59   60   61                                             
CONECT   59   58                                                            
CONECT   60   58                                                            
CONECT   61   58   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   64   85  106                                             
CONECT   64   63   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65   67   68                                                  
CONECT   67   66                                                            
CONECT   68   66   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   83                                                       
CONECT   83   82   84                                                       
CONECT   84   83                                                            
CONECT   85   63   86                                                       
CONECT   86   85   87   88                                                  
CONECT   87   86                                                            
CONECT   88   86   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  103                                                       
CONECT  103  102  104                                                       
CONECT  104  103                                                            
CONECT  105   23                                                            
CONECT  106   63                                                            
MASTER        0    0    0    0    0    0    0    0  106    0  210    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₈₅H₁₄₈O₁₇P₂

Average Mass

1504.0219 Da

Monoisotopic Mass

1503.01918 Da

IUPAC Name

[3-({[(2R)-2,3-bis(octadeca-9,12-dienoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-(icos-11-enoyloxy)-3-(icosa-5,8,11,14-tetraenoyloxy)propoxy]phosphinic acid

Traditional Name

3-{[(2R)-2,3-bis(octadeca-9,12-dienoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy(2R)-2-(icos-11-enoyloxy)-3-(icosa-5,8,11,14-tetraenoyloxy)propoxyphosphinic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C85H148O17P2/c1-5-9-13-17-21-25-29-33-37-39-43-46-50-54-58-62-66-70-83(88)96-76-81(102-85(90)72-68-64-60-56-52-48-44-40-38-34-30-26-22-18-14-10-6-2)78-100-104(93,94)98-74-79(86)73-97-103(91,92)99-77-80(101-84(89)71-67-63-59-55-51-47-42-36-32-28-24-20-16-12-8-4)75-95-82(87)69-65-61-57-53-49-45-41-35-31-27-23-19-15-11-7-3/h21,23-25,27-28,33-38,41-43,46,54,58,79-81,86H,5-20,22,26,29-32,39-40,44-45,47-53,55-57,59-78H2,1-4H3,(H,91,92)(H,93,94)/t79?,80-,81-/m1/s1

InChI Key

JICFHIJWQCVAHY-NYTMHASESA-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	9.31	ALOGPS
logP	25.79	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	435.36 m³·mol⁻¹	ChemAxon
Polarizability	180.58 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

FDB027422

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(20:4(5Z,8Z,11Z,14Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)) (NP0338834)

MOL for NP0338834 (CL(20:4(5Z,8Z,11Z,14Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)))

3D MOL for NP0338834 (CL(20:4(5Z,8Z,11Z,14Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)))

3D SDF for NP0338834 (CL(20:4(5Z,8Z,11Z,14Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)))

3D-SDF for NP0338834 (CL(20:4(5Z,8Z,11Z,14Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)))

PDB for NP0338834 (CL(20:4(5Z,8Z,11Z,14Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)))

3D PDB for NP0338834 (CL(20:4(5Z,8Z,11Z,14Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)))

SMILES for NP0338834 (CL(20:4(5Z,8Z,11Z,14Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)))

INCHI for NP0338834 (CL(20:4(5Z,8Z,11Z,14Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)))

Structure for NP0338834 (CL(20:4(5Z,8Z,11Z,14Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)))

3D Structure for NP0338834 (CL(20:4(5Z,8Z,11Z,14Z)/20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)))