NP-MRD: Showing NP-Card for CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) (NP0338710)

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Record Information

Version

2.0

Created at

2024-09-11 17:12:08 UTC

Updated at

2024-09-11 17:12:08 UTC

NP-MRD ID

NP0338710

Secondary Accession Numbers

None

Natural Product Identification

Common Name

CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z))

Description

CL(22:5(4Z,7Z,10Z,13Z,16Z)/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(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) is an extremely weak basic (essentially neutral) compound (based on its pKa). CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) and cytidine monophosphate can be biosynthesized from PG(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)) and CDP-DG(18:2(9Z,12Z)/18:1(9Z)); which is catalyzed by the enzyme cardiolipin synthase. In humans, CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) is involved in cardiolipin biosynthesis. Cardiolipins are a "double" phospholipid because they have four fatty acid tails, instead of the usual two. CL(22:5(4Z,7Z,10Z,13Z,16Z)/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. 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.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241223422D          

106105  0  0  1  0            999 V2000
   11.8048    1.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4303    1.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8797    2.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5052    3.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9546    3.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5801    4.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0295    5.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6550    6.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1044    6.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7299    7.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1793    8.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8048    8.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2541    9.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8797   10.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3290   11.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9546   11.8433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4039   12.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0295   13.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2056   13.3135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4788   13.9622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1044   14.6973    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.2805   14.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8311   14.0486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0072   14.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6328   14.8270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5579   13.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7340   13.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2846   12.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4607   12.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0114   12.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7381   11.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9143   11.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5398   12.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7159   12.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3414   13.0108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7908   13.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4163   14.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8657   15.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4912   15.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9406   16.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5661   17.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5537   15.3891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3776   15.3459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8270   16.0378    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.5189   15.5884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1351   16.4871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2764   16.7296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1002   16.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5496   17.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1751   18.1134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3735   17.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8229   18.0269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6467   17.9836    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.6035   17.1598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6900   18.8075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4706   17.9404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9200   18.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7438   18.5890    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.1932   19.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0171   19.2377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4665   19.9295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0920   20.6646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2903   19.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7397   20.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5636   20.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0130   21.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8368   21.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2113   20.4484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7619   19.7566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1364   19.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9603   18.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3348   18.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1586   18.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6080   18.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4319   18.8485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8813   19.5403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5068   20.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   28.5817   21.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7578   21.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3833   22.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5595   22.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1850   23.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1183   17.8539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   18.8451   17.2053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   19.5940   15.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9685   15.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5191   14.3081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8936   13.5730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4443   12.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8187   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3694   11.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7438   10.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2945   10.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6689    9.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4928    9.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8673    8.5137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6912    8.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0656    7.7353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.6550   14.0054    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.5677   18.5458    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
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M  END


  Mrv0541 02241223422D          

106105  0  0  1  0            999 V2000
   11.8048    1.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4303    1.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8797    2.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5052    3.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9546    3.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5801    4.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0295    5.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6550    6.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1044    6.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7299    7.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1793    8.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8048    8.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2541    9.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8797   10.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3290   11.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.0295   13.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2056   13.3135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4788   13.9622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.2805   14.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8311   14.0486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0072   14.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6328   14.8270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5579   13.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.4607   12.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1875   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9143   11.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5398   12.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7159   12.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3414   13.0108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4163   14.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8657   15.1297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4912   15.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9406   16.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5661   17.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5537   15.3891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3776   15.3459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8270   16.0378    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.5189   15.5884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1351   16.4871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2764   16.7296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1002   16.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5496   17.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1751   18.1134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   16.8229   18.0269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6467   17.9836    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.6035   17.1598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6900   18.8075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4706   17.9404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9200   18.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7438   18.5890    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.1932   19.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0171   19.2377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   21.0920   20.6646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2903   19.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7397   20.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5636   20.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0130   21.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8368   21.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2113   20.4484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7619   19.7566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1364   19.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9603   18.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   27.1586   18.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6080   18.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4319   18.8485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8813   19.5403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5068   20.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9562   20.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5817   21.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7578   21.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3833   22.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5595   22.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1850   23.2591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1183   17.8539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6689   17.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8451   17.2053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0434   16.4269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5940   15.7351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9685   15.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5191   14.3081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8936   13.5730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4443   12.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8187   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3694   11.4541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7438   10.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2945   10.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6689    9.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4928    9.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8673    8.5137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6912    8.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0656    7.7353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8895    7.6921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2640    6.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6550   14.0054    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.5677   18.5458    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
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  9  8  1  4  0  0  0
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 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
 21105  1  1  0  0  0
 59106  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0338710

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

> <INCHI_IDENTIFIER>
InChI=1S/C85H146O17P2/c1-5-9-13-17-21-25-29-33-37-38-39-40-44-46-50-54-58-62-66-70-83(88)96-76-81(102-85(90)72-68-64-60-56-52-48-43-36-32-28-24-20-16-12-8-4)78-100-104(93,94)98-74-79(86)73-97-103(91,92)99-77-80(101-84(89)71-67-63-59-55-51-47-42-35-31-27-23-19-15-11-7-3)75-95-82(87)69-65-61-57-53-49-45-41-34-30-26-22-18-14-10-6-2/h9,13,21-22,24-26,28,33-37,39-43,46,50,79-81,86H,5-8,10-12,14-20,23,27,29-32,38,44-45,47-49,51-78H2,1-4H3,(H,91,92)(H,93,94)/t79?,80-,81-/m1/s1

> <INCHI_KEY>
JNNDHTRZWPJCBR-NYTMHASESA-N

> <FORMULA>
C85H146O17P2

> <MOLECULAR_WEIGHT>
1502.0061

> <EXACT_MASS>
1501.00352627

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
178.25876316187328

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-3-(docosa-7,10,13,16,19-pentaenoyloxy)-2-(octadeca-9,12-dienoyloxy)propoxy][2-hydroxy-3-({hydroxy[(2R)-2-(octadec-9-enoyloxy)-3-(octadeca-9,12-dienoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphinic acid

> <ALOGPS_LOGP>
9.23

> <JCHEM_LOGP>
25.428724474666666

> <ALOGPS_LOGS>
-7.27

> <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>
436.47969999999964

> <JCHEM_ROTATABLE_BOND_COUNT>
80

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.13e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-(docosa-7,10,13,16,19-pentaenoyloxy)-2-(octadeca-9,12-dienoyloxy)propoxy(2-hydroxy-3-{[hydroxy(2R)-2-(octadec-9-enoyloxy)-3-(octadeca-9,12-dienoyloxy)propoxyphosphoryl]oxy}propoxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      22.036   2.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.337   3.462   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.175   4.753   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.476   6.125   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.315   7.417   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.616   8.789   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.455  10.081   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.756  11.453   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.595  12.744   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.896  14.116   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.735  15.408   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.036  16.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.874  18.072   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.175  19.444   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.014  20.735   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.315  22.107   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.154  23.399   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.455  24.771   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      20.917  24.852   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      23.294  26.063   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      22.595  27.435   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.057  27.516   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      20.218  26.224   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      18.680  26.305   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      17.981  27.677   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      17.841  25.013   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.303  25.094   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.465  23.803   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.927  23.883   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.088  22.592   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.550  22.673   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.711  21.381   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.173  21.462   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.474  22.834   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.936  22.915   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.237  24.287   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.076  25.578   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.377  26.951   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.216  28.242   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.517  29.614   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       7.356  30.906   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       6.657  32.278   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      23.434  28.726   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      24.972  28.646   0.000  0.00  0.00           O+0
HETATM   45  P   UNK     0      25.810  29.937   0.000  0.00  0.00           P+0
HETATM   46  O   UNK     0      27.102  29.098   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      24.519  30.776   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      26.649  31.229   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      28.187  31.148   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      29.026  32.439   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      28.327  33.812   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      30.564  32.359   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      31.403  33.650   0.000  0.00  0.00           O+0
HETATM   54  P   UNK     0      32.941  33.569   0.000  0.00  0.00           P+0
HETATM   55  O   UNK     0      32.860  32.032   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      33.021  35.107   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      34.478  33.489   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      35.317  34.780   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      36.855  34.699   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      37.694  35.991   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      39.232  35.910   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      40.071  37.202   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      39.372  38.574   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      41.609  37.121   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      42.447  38.412   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      43.985  38.332   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      44.824  39.623   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      46.362  39.543   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      47.061  38.170   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      46.222  36.879   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      46.921  35.507   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      48.459  35.426   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      49.158  34.054   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      50.696  33.973   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      51.535  35.265   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      53.073  35.184   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      53.912  36.475   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      53.213  37.848   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0      54.052  39.139   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0      53.353  40.511   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0      51.815  40.592   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0      51.115  41.964   0.000  0.00  0.00           C+0
HETATM   83  C   UNK     0      49.578  42.045   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0      48.879  43.417   0.000  0.00  0.00           C+0
HETATM   85  O   UNK     0      37.554  33.327   0.000  0.00  0.00           O+0
HETATM   86  C   UNK     0      36.715  32.036   0.000  0.00  0.00           C+0
HETATM   87  O   UNK     0      35.178  32.117   0.000  0.00  0.00           O+0
HETATM   88  C   UNK     0      37.414  30.664   0.000  0.00  0.00           C+0
HETATM   89  C   UNK     0      36.575  29.372   0.000  0.00  0.00           C+0
HETATM   90  C   UNK     0      37.275  28.000   0.000  0.00  0.00           C+0
HETATM   91  C   UNK     0      36.436  26.708   0.000  0.00  0.00           C+0
HETATM   92  C   UNK     0      37.135  25.336   0.000  0.00  0.00           C+0
HETATM   93  C   UNK     0      36.296  24.045   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0      36.995  22.673   0.000  0.00  0.00           C+0
HETATM   95  C   UNK     0      36.156  21.381   0.000  0.00  0.00           C+0
HETATM   96  C   UNK     0      36.855  20.009   0.000  0.00  0.00           C+0
HETATM   97  C   UNK     0      36.016  18.717   0.000  0.00  0.00           C+0
HETATM   98  C   UNK     0      36.715  17.345   0.000  0.00  0.00           C+0
HETATM   99  C   UNK     0      38.253  17.264   0.000  0.00  0.00           C+0
HETATM  100  C   UNK     0      38.952  15.892   0.000  0.00  0.00           C+0
HETATM  101  C   UNK     0      40.490  15.812   0.000  0.00  0.00           C+0
HETATM  102  C   UNK     0      41.189  14.439   0.000  0.00  0.00           C+0
HETATM  103  C   UNK     0      42.727  14.359   0.000  0.00  0.00           C+0
HETATM  104  C   UNK     0      43.426  12.986   0.000  0.00  0.00           C+0
HETATM  105  H   UNK     0      21.756  26.143   0.000  0.00  0.00           H+0
HETATM  106  H   UNK     0      38.393  34.619   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  105                                             
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   85  106                                             
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   83                                                       
CONECT   83   82   84                                                       
CONECT   84   83                                                            
CONECT   85   59   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   21                                                            
CONECT  106   59                                                            
MASTER        0    0    0    0    0    0    0    0  106    0  210    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₈₅H₁₄₆O₁₇P₂

Average Mass

1502.0061 Da

Monoisotopic Mass

1501.00353 Da

IUPAC Name

[(2R)-3-(docosa-7,10,13,16,19-pentaenoyloxy)-2-(octadeca-9,12-dienoyloxy)propoxy][2-hydroxy-3-({hydroxy[(2R)-2-(octadec-9-enoyloxy)-3-(octadeca-9,12-dienoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphinic acid

Traditional Name

(2R)-3-(docosa-7,10,13,16,19-pentaenoyloxy)-2-(octadeca-9,12-dienoyloxy)propoxy(2-hydroxy-3-{[hydroxy(2R)-2-(octadec-9-enoyloxy)-3-(octadeca-9,12-dienoyloxy)propoxyphosphoryl]oxy}propoxy)phosphinic 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)CCCCCC=CCC=CCC=CCC=CCC=CCC)OC(=O)CCCCCCCC=CCC=CCCCCC)OC(=O)CCCCCCCC=CCCCCCCCC

InChI Identifier

InChI=1S/C85H146O17P2/c1-5-9-13-17-21-25-29-33-37-38-39-40-44-46-50-54-58-62-66-70-83(88)96-76-81(102-85(90)72-68-64-60-56-52-48-43-36-32-28-24-20-16-12-8-4)78-100-104(93,94)98-74-79(86)73-97-103(91,92)99-77-80(101-84(89)71-67-63-59-55-51-47-42-35-31-27-23-19-15-11-7-3)75-95-82(87)69-65-61-57-53-49-45-41-34-30-26-22-18-14-10-6-2/h9,13,21-22,24-26,28,33-37,39-43,46,50,79-81,86H,5-8,10-12,14-20,23,27,29-32,38,44-45,47-49,51-78H2,1-4H3,(H,91,92)(H,93,94)/t79?,80-,81-/m1/s1

InChI Key

JNNDHTRZWPJCBR-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	9.23	ALOGPS
logP	25.43	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	80	ChemAxon
Refractivity	436.48 m³·mol⁻¹	ChemAxon
Polarizability	178.26 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

FDB027440

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(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)) (NP0338710)

MOL for NP0338710 (CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)))

3D MOL for NP0338710 (CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)))

3D SDF for NP0338710 (CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)))

3D-SDF for NP0338710 (CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)))

PDB for NP0338710 (CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)))

3D PDB for NP0338710 (CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)))

SMILES for NP0338710 (CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)))

INCHI for NP0338710 (CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)))

Structure for NP0338710 (CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)))

3D Structure for NP0338710 (CL(22:5(4Z,7Z,10Z,13Z,16Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(9Z)))