NP-MRD: Showing NP-Card for CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (NP0338902)

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Record Information

Version

2.0

Created at

2024-09-11 18:38:38 UTC

Updated at

2024-09-11 18:38:39 UTC

NP-MRD ID

NP0338902

Secondary Accession Numbers

None

Natural Product Identification

Common Name

CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))

Description

CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 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(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is an extremely weak basic (essentially neutral) compound (based on its pKa). CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) and cytidine monophosphate can be biosynthesized from PG(18:2(9Z,12Z)/18:2(9Z,12Z)) and CDP-DG(20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) through its interaction with the enzyme cardiolipin synthase. In humans, CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is involved in cardiolipin biosynthesis. CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a cardiolipin (CL). They are highly abundant in metabolically active cells (heart, muscle) and play an important role in the blood clotting process. While most lipids are made in the endoplasmic reticulum, cardiolipin is synthesized on the matrix side of the inner mitochondrial membrane. 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.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251205072D          

108107  0  0  1  0            999 V2000
   16.7654   11.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9333   11.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3177   10.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4856    9.7545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8700    9.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0379    8.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4223    7.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5902    7.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3737    6.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5415    5.9742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3250    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9406    6.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7240    6.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3396    6.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1231    6.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7387    6.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5221    6.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1377    7.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9698    7.9451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9212    6.8789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5367    7.4282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3202    7.1697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.9358    7.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7193    7.4605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3348    8.0097    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   26.8841    7.3942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7856    8.6253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9504    8.5590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7339    8.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3495    8.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1816    9.6575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1329    8.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7485    9.1406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5320    8.8821    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   30.2735    8.0986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7904    9.6656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3154    8.6236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9310    9.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7145    8.9144    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   32.8823    8.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6658    7.8482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8337    7.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2181    6.4912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.6172    6.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7850    5.9742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5685    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7364    4.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5199    4.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6877    3.8418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4712    3.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0868    4.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8702    3.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4858    4.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3179    5.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9335    5.7804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7656    6.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9822    6.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8143    7.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0308    7.9128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8629    8.7206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0795    8.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4639    8.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3300    9.4637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.1135    9.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2814    8.3975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   35.5125    9.4960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1281   10.0452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9116    9.7868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5272   10.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3106   10.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4785    9.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2620    9.0113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8776    9.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6610    9.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2766    9.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1087   10.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7243   11.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5564   12.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7729   12.2746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6051   13.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8216   13.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2060   12.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4226   13.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8070   12.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0235   12.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4881    6.3620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8725    5.8127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0891    6.0712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0404    5.0050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4248    4.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5927    3.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9771    3.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1450    2.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5294    1.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6973    0.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0817    0.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2496   -0.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6340   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8019   -1.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5854   -2.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7533   -2.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5367   -3.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7046   -3.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4881   -4.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6560   -4.9787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1037    6.9112    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   33.4980    8.6559    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
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  7  8  1  0  0  0  0
  9  8  1  4  0  0  0
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105106  1  0  0  0  0
 22107  1  1  0  0  0
 39108  1  1  0  0  0
M  END


  Mrv0541 02251205072D          

108107  0  0  1  0            999 V2000
   16.7654   11.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9333   11.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3177   10.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4856    9.7545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8700    9.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0379    8.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4223    7.8482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5902    7.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3737    6.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5415    5.9742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3250    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9406    6.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7240    6.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3396    6.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1231    6.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7387    6.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5221    6.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1377    7.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9698    7.9451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9212    6.8789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5367    7.4282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3202    7.1697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.9358    7.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7193    7.4605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3348    8.0097    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   26.8841    7.3942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7856    8.6253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9504    8.5590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7339    8.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3495    8.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1816    9.6575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1329    8.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   37.0795    8.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   33.3300    9.4637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   36.1281   10.0452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   37.5272   10.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3106   10.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4785    9.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2620    9.0113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8776    9.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   41.2766    9.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1087   10.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7243   11.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5564   12.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7729   12.2746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6051   13.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8216   13.3408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2060   12.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4226   13.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8070   12.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0235   12.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4881    6.3620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8725    5.8127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0891    6.0712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0404    5.0050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4248    4.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5927    3.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9771    3.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1450    2.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5294    1.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6973    0.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0817    0.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2496   -0.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6340   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8019   -1.7800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5854   -2.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7533   -2.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5367   -3.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7046   -3.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4881   -4.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6560   -4.9787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1037    6.9112    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   33.4980    8.6559    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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102103  1  0  0  0  0
103104  1  0  0  0  0
104105  1  0  0  0  0
105106  1  0  0  0  0
 22107  1  1  0  0  0
 39108  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0338902

> <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)CCC=CCC=CCC=CCC=CCC=CCC=CCC)OC(=O)CCCCCCCC=CCC=CCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C87H142O17P2/c1-5-9-13-17-21-25-29-33-37-39-40-42-46-50-54-58-62-66-70-74-87(92)104-83(78-98-85(90)72-68-64-60-56-52-48-45-41-38-34-30-26-22-18-14-10-6-2)80-102-106(95,96)100-76-81(88)75-99-105(93,94)101-79-82(103-86(91)73-69-65-61-57-53-49-44-36-32-28-24-20-16-12-8-4)77-97-84(89)71-67-63-59-55-51-47-43-35-31-27-23-19-15-11-7-3/h9,13,21-28,33-38,40,42-45,48,50,54,56,60,62,66,81-83,88H,5-8,10-12,14-20,29-32,39,41,46-47,49,51-53,55,57-59,61,63-65,67-80H2,1-4H3,(H,93,94)(H,95,96)/t81?,82-,83-/m1/s1

> <INCHI_KEY>
YAFUBRKZBHXFPH-XRQKZRKGSA-N

> <FORMULA>
C87H142O17P2

> <MOLECULAR_WEIGHT>
1521.9957

> <EXACT_MASS>
1520.972226142

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
175.93899058206665

> <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-(docosa-4,7,10,13,16,19-hexaenoyloxy)-3-(icosa-5,8,11,14-tetraenoyloxy)propoxy]phosphinic acid

> <ALOGPS_LOGP>
8.93

> <JCHEM_LOGP>
24.870175177999997

> <ALOGPS_LOGS>
-7.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.1918043581923543

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5897376142934831

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4105029523385797

> <JCHEM_POLAR_SURFACE_AREA>
236.94999999999996

> <JCHEM_REFRACTIVITY>
450.1480999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
78

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.19e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2R)-2,3-bis(octadeca-9,12-dienoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy(2R)-2-(docosa-4,7,10,13,16,19-hexaenoyloxy)-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      31.295  22.249   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      31.609  20.741   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      30.460  19.716   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.773  18.208   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.624  17.183   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.937  15.675   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.788  14.650   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.102  13.142   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      30.564  12.660   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      30.877  11.152   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      32.340  10.669   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      33.489  11.695   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      34.951  11.212   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      36.101  12.237   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      37.563  11.755   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      38.712  12.780   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      40.175  12.298   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      41.324  13.323   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      41.010  14.831   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      42.786  12.841   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      43.935  13.866   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      45.398  13.383   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      46.547  14.409   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      48.009  13.926   0.000  0.00  0.00           O+0
HETATM   25  P   UNK     0      49.158  14.951   0.000  0.00  0.00           P+0
HETATM   26  O   UNK     0      50.184  13.803   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      48.133  16.101   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      50.307  15.977   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      51.770  15.494   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      52.919  16.520   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      52.606  18.027   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      54.381  16.037   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      55.531  17.062   0.000  0.00  0.00           O+0
HETATM   34  P   UNK     0      56.993  16.580   0.000  0.00  0.00           P+0
HETATM   35  O   UNK     0      56.511  15.117   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      57.475  18.042   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      58.455  16.097   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      59.605  17.123   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      61.067  16.640   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      61.380  15.133   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      62.843  14.650   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      63.156  13.142   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      62.007  12.117   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      64.619  12.660   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      64.932  11.152   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      66.395  10.669   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      66.708   9.162   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      68.170   8.679   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      68.484   7.171   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      69.946   6.689   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      71.095   7.714   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      72.558   7.232   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      73.707   8.257   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      73.393   9.765   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      74.543  10.790   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      74.229  12.298   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      72.767  12.780   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      72.453  14.288   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      70.991  14.771   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      70.677  16.278   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      69.215  16.761   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      68.066  15.736   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      62.216  17.666   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      63.679  17.183   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      63.992  15.675   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      64.828  18.208   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      66.290  17.726   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      67.439  18.751   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      68.902  18.269   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      70.051  19.294   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      71.513  18.811   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      71.827  17.304   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      73.289  16.821   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      74.438  17.846   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      75.901  17.364   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      77.050  18.389   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      76.736  19.897   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      77.885  20.922   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0      77.572  22.430   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0      76.109  22.913   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0      75.796  24.420   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0      74.334  24.903   0.000  0.00  0.00           C+0
HETATM   83  C   UNK     0      73.185  23.877   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0      71.722  24.360   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0      70.573  23.335   0.000  0.00  0.00           C+0
HETATM   86  C   UNK     0      69.111  23.817   0.000  0.00  0.00           C+0
HETATM   87  O   UNK     0      45.711  11.876   0.000  0.00  0.00           O+0
HETATM   88  C   UNK     0      44.562  10.850   0.000  0.00  0.00           C+0
HETATM   89  O   UNK     0      43.100  11.333   0.000  0.00  0.00           O+0
HETATM   90  C   UNK     0      44.875   9.343   0.000  0.00  0.00           C+0
HETATM   91  C   UNK     0      43.726   8.317   0.000  0.00  0.00           C+0
HETATM   92  C   UNK     0      44.040   6.810   0.000  0.00  0.00           C+0
HETATM   93  C   UNK     0      42.891   5.784   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0      43.204   4.277   0.000  0.00  0.00           C+0
HETATM   95  C   UNK     0      42.055   3.251   0.000  0.00  0.00           C+0
HETATM   96  C   UNK     0      42.368   1.743   0.000  0.00  0.00           C+0
HETATM   97  C   UNK     0      41.219   0.718   0.000  0.00  0.00           C+0
HETATM   98  C   UNK     0      41.533  -0.790   0.000  0.00  0.00           C+0
HETATM   99  C   UNK     0      40.383  -1.815   0.000  0.00  0.00           C+0
HETATM  100  C   UNK     0      40.697  -3.323   0.000  0.00  0.00           C+0
HETATM  101  C   UNK     0      42.159  -3.805   0.000  0.00  0.00           C+0
HETATM  102  C   UNK     0      42.473  -5.313   0.000  0.00  0.00           C+0
HETATM  103  C   UNK     0      43.935  -5.795   0.000  0.00  0.00           C+0
HETATM  104  C   UNK     0      44.249  -7.303   0.000  0.00  0.00           C+0
HETATM  105  C   UNK     0      45.711  -7.786   0.000  0.00  0.00           C+0
HETATM  106  C   UNK     0      46.025  -9.294   0.000  0.00  0.00           C+0
HETATM  107  H   UNK     0      46.860  12.901   0.000  0.00  0.00           H+0
HETATM  108  H   UNK     0      62.530  16.158   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                                                       
CONECT   22   21   23   87  107                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36   37                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   34   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   63  108                                             
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61                                                            
CONECT   63   39   64                                                       
CONECT   64   63   65   66                                                  
CONECT   65   64                                                            
CONECT   66   64   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   83                                                       
CONECT   83   82   84                                                       
CONECT   84   83   85                                                       
CONECT   85   84   86                                                       
CONECT   86   85                                                            
CONECT   87   22   88                                                       
CONECT   88   87   89   90                                                  
CONECT   89   88                                                            
CONECT   90   88   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  105                                                       
CONECT  105  104  106                                                       
CONECT  106  105                                                            
CONECT  107   22                                                            
CONECT  108   39                                                            
MASTER        0    0    0    0    0    0    0    0  108    0  214    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₈₇H₁₄₂O₁₇P₂

Average Mass

1521.9957 Da

Monoisotopic Mass

1520.97223 Da

IUPAC Name

[3-({[(2R)-2,3-bis(octadeca-9,12-dienoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-(docosa-4,7,10,13,16,19-hexaenoyloxy)-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-(docosa-4,7,10,13,16,19-hexaenoyloxy)-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)CCC=CCC=CCC=CCC=CCC=CCC=CCC)OC(=O)CCCCCCCC=CCC=CCCCCC

InChI Identifier

InChI=1S/C87H142O17P2/c1-5-9-13-17-21-25-29-33-37-39-40-42-46-50-54-58-62-66-70-74-87(92)104-83(78-98-85(90)72-68-64-60-56-52-48-45-41-38-34-30-26-22-18-14-10-6-2)80-102-106(95,96)100-76-81(88)75-99-105(93,94)101-79-82(103-86(91)73-69-65-61-57-53-49-44-36-32-28-24-20-16-12-8-4)77-97-84(89)71-67-63-59-55-51-47-43-35-31-27-23-19-15-11-7-3/h9,13,21-28,33-38,40,42-45,48,50,54,56,60,62,66,81-83,88H,5-8,10-12,14-20,29-32,39,41,46-47,49,51-53,55,57-59,61,63-65,67-80H2,1-4H3,(H,93,94)(H,95,96)/t81?,82-,83-/m1/s1

InChI Key

YAFUBRKZBHXFPH-XRQKZRKGSA-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	8.93	ALOGPS
logP	24.87	ChemAxon
logS	-7.2	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	78	ChemAxon
Refractivity	450.15 m³·mol⁻¹	ChemAxon
Polarizability	175.94 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

FDB027402

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(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (NP0338902)

MOL for NP0338902 (CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D MOL for NP0338902 (CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D SDF for NP0338902 (CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D-SDF for NP0338902 (CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

PDB for NP0338902 (CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D PDB for NP0338902 (CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

SMILES for NP0338902 (CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

INCHI for NP0338902 (CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

Structure for NP0338902 (CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D Structure for NP0338902 (CL(18:2(9Z,12Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))