NP-MRD: Showing NP-Card for CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (NP0338814)

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Record Information

Version

2.0

Created at

2024-09-11 17:59:05 UTC

Updated at

2024-09-11 17:59:05 UTC

NP-MRD ID

NP0338814

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) 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)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) is an extremely weak basic (essentially neutral) compound (based on its pKa). CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) and cytidine monophosphate can be biosynthesized from PG(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) and CDP-DG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) through the action of the enzyme cardiolipin synthase. In humans, CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) is involved in cardiolipin biosynthesis. CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) 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. Cardiolipins are a "double" phospholipid because they have four fatty acid tails, instead of the usual two. 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.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251203002D          

108107  0  0  1  0            999 V2000
   -0.2643    6.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5590    5.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    6.6752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8397    6.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2971    7.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1204    7.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5778    7.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4011    7.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8585    8.5766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4926    9.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5841   10.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0415   11.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6756   12.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1330   12.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7670   13.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2244   14.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8585   15.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3159   15.7066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2432   16.2348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.7984   14.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6217   14.6503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9876   13.9109    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.7270   14.2768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.3535   13.1715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1768   13.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.3660   12.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7319   11.5870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5553   11.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0126   12.2208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9212   10.7948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7445   10.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1104   10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9337    9.9498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.4199    9.8441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02251203002D          

108107  0  0  1  0            999 V2000
   -0.2643    6.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5590    5.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    6.6752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8397    6.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2971    7.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1204    7.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5778    7.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4011    7.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8585    8.5766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.4325   15.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8898   16.1292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7984   14.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6217   14.6503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.7270   14.2768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2482   13.5450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   13.7319   11.5870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5553   11.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0126   12.2208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9212   10.7948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7445   10.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1104   10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9337    9.9498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2996    9.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1229    9.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4888    8.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0314    7.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3974    6.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9400    6.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1167    6.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.8360    5.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4700    6.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6467    6.5168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2808    7.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4575    7.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0916    8.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5490    8.7350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0853   11.6927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2620   11.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8961   12.4849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8046   11.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9813   11.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5239   10.4251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7006   10.4779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2432    9.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4199    9.8441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9625    9.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3284    8.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8711    7.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2370    6.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0603    6.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4262    6.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2495    6.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7069    6.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5302    6.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9876    7.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8109    7.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2683    8.1012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9024    8.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0415   17.8721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2182   17.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7608   17.2383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8523   18.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0289   18.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630   19.4565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8397   19.5093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4738   20.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6505   20.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1931   19.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302   19.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0876   18.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7217   18.2418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1791   17.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8132   16.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0102   16.7629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3761   16.0235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1994   15.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5653   15.2313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3886   15.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7545   14.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5778   14.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8648   17.8192    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9086   11.6399    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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100101  2  0  0  0  0
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103104  1  0  0  0  0
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105106  1  0  0  0  0
 22107  1  6  0  0  0
 39108  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0338814

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

> <INCHI_IDENTIFIER>
InChI=1S/C87H142O17P2/c1-5-9-13-17-21-25-29-33-37-40-44-48-52-56-60-64-68-72-85(90)98-78-83(104-87(92)74-70-66-62-58-54-50-46-42-39-35-31-27-23-19-15-11-7-3)80-102-106(95,96)100-76-81(88)75-99-105(93,94)101-79-82(77-97-84(89)71-67-63-59-55-51-47-43-36-32-28-24-20-16-12-8-4)103-86(91)73-69-65-61-57-53-49-45-41-38-34-30-26-22-18-14-10-6-2/h21-28,33-39,43-46,48-50,56-58,60-62,81-83,88H,5-20,29-32,40-42,47,51-55,59,63-80H2,1-4H3,(H,93,94)(H,95,96)/t81?,82-,83-/m1/s1

> <INCHI_KEY>
MEFSWTNMBRIQIW-XRQKZRKGSA-N

> <FORMULA>
C87H142O17P2

> <MOLECULAR_WEIGHT>
1521.9957

> <EXACT_MASS>
1520.972226142

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
176.38795873484904

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
8.95

> <JCHEM_LOGP>
24.870175177999997

> <ALOGPS_LOGS>
-7.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.1918043582169613

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5897376143216926

> <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>
9.10e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2,3-bis(icosa-5,8,11,14-tetraenoyloxy)propoxy(2-hydroxy-3-{[hydroxy(2R)-2-(icosa-5,8,11,14-tetraenoyloxy)-3-(octadeca-9,12-dienoyloxy)propoxyphosphoryl]oxy}propoxy)phosphinic 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      -0.493  11.277   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.043  11.179   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.897  12.460   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.434  12.362   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.288  13.643   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.825  13.545   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.679  14.827   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.215  14.728   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.069  16.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.386  17.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.240  18.672   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.557  20.052   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.411  21.333   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.728  22.714   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.582  23.995   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.898  25.375   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.752  26.657   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.069  28.037   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.532  28.136   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.923  29.319   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.240  30.699   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.094  31.981   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.631  31.882   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.314  30.502   0.000  0.00  0.00           O+0
HETATM   25  P   UNK     0      13.850  30.404   0.000  0.00  0.00           P+0
HETATM   26  O   UNK     0      13.949  31.940   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      13.752  28.867   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      15.387  30.305   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      16.070  28.925   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.607  28.826   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      18.461  30.108   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      18.290  27.446   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      19.827  27.347   0.000  0.00  0.00           O+0
HETATM   34  P   UNK     0      20.510  25.967   0.000  0.00  0.00           P+0
HETATM   35  O   UNK     0      21.890  26.650   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      19.130  25.284   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      21.193  24.587   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      22.730  24.488   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      23.413  23.108   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      24.950  23.009   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      25.633  21.629   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      27.170  21.531   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      28.024  22.812   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      27.853  20.150   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      29.390  20.052   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      30.073  18.672   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      31.610  18.573   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      32.293  17.193   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      33.829  17.094   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      34.512  15.714   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      33.659  14.432   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      34.342  13.052   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      33.488  11.770   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      31.951  11.869   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      31.097  10.587   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      29.561  10.686   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      28.877  12.066   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      27.341  12.165   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      26.657  13.545   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      25.121  13.643   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      24.438  15.024   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      25.291  16.305   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      22.559  21.826   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      21.022  21.925   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      20.339  23.305   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      20.169  20.643   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      18.632  20.742   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      17.778  19.460   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      16.241  19.559   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      15.387  18.277   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      13.850  18.376   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      12.997  17.094   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      13.680  15.714   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      12.826  14.432   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      13.509  13.052   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      15.046  12.953   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      15.729  11.573   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      17.266  11.475   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0      18.120  12.756   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0      19.656  12.658   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0      20.510  13.939   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0      22.047  13.841   0.000  0.00  0.00           C+0
HETATM   83  C   UNK     0      22.901  15.122   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0      22.218  16.503   0.000  0.00  0.00           C+0
HETATM   85  O   UNK     0       9.411  33.361   0.000  0.00  0.00           O+0
HETATM   86  C   UNK     0       7.874  33.460   0.000  0.00  0.00           C+0
HETATM   87  O   UNK     0       7.020  32.178   0.000  0.00  0.00           O+0
HETATM   88  C   UNK     0       7.191  34.840   0.000  0.00  0.00           C+0
HETATM   89  C   UNK     0       5.654  34.939   0.000  0.00  0.00           C+0
HETATM   90  C   UNK     0       4.971  36.319   0.000  0.00  0.00           C+0
HETATM   91  C   UNK     0       3.434  36.417   0.000  0.00  0.00           C+0
HETATM   92  C   UNK     0       2.751  37.798   0.000  0.00  0.00           C+0
HETATM   93  C   UNK     0       1.214  37.896   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0       0.360  36.615   0.000  0.00  0.00           C+0
HETATM   95  C   UNK     0      -1.176  36.713   0.000  0.00  0.00           C+0
HETATM   96  C   UNK     0      -2.030  35.432   0.000  0.00  0.00           C+0
HETATM   97  C   UNK     0      -1.347  34.051   0.000  0.00  0.00           C+0
HETATM   98  C   UNK     0      -2.201  32.770   0.000  0.00  0.00           C+0
HETATM   99  C   UNK     0      -1.518  31.389   0.000  0.00  0.00           C+0
HETATM  100  C   UNK     0       0.019  31.291   0.000  0.00  0.00           C+0
HETATM  101  C   UNK     0       0.702  29.911   0.000  0.00  0.00           C+0
HETATM  102  C   UNK     0       2.239  29.812   0.000  0.00  0.00           C+0
HETATM  103  C   UNK     0       2.922  28.432   0.000  0.00  0.00           C+0
HETATM  104  C   UNK     0       4.459  28.333   0.000  0.00  0.00           C+0
HETATM  105  C   UNK     0       5.142  26.953   0.000  0.00  0.00           C+0
HETATM  106  C   UNK     0       6.679  26.854   0.000  0.00  0.00           C+0
HETATM  107  H   UNK     0      10.948  33.263   0.000  0.00  0.00           H+0
HETATM  108  H   UNK     0      24.096  21.728   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   85  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                                                            
CONECT   85   22   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  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

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

Traditional Name

(2R)-2,3-bis(icosa-5,8,11,14-tetraenoyloxy)propoxy(2-hydroxy-3-{[hydroxy(2R)-2-(icosa-5,8,11,14-tetraenoyloxy)-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)CCCC=CCC=CCC=CCC=CCCCCC)OC(=O)CCCC=CCC=CCC=CCC=CCCCCC)OC(=O)CCCC=CCC=CCC=CCC=CCCCCC

InChI Identifier

InChI=1S/C87H142O17P2/c1-5-9-13-17-21-25-29-33-37-40-44-48-52-56-60-64-68-72-85(90)98-78-83(104-87(92)74-70-66-62-58-54-50-46-42-39-35-31-27-23-19-15-11-7-3)80-102-106(95,96)100-76-81(88)75-99-105(93,94)101-79-82(77-97-84(89)71-67-63-59-55-51-47-43-36-32-28-24-20-16-12-8-4)103-86(91)73-69-65-61-57-53-49-45-41-38-34-30-26-22-18-14-10-6-2/h21-28,33-39,43-46,48-50,56-58,60-62,81-83,88H,5-20,29-32,40-42,47,51-55,59,63-80H2,1-4H3,(H,93,94)(H,95,96)/t81?,82-,83-/m1/s1

InChI Key

MEFSWTNMBRIQIW-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	8.95	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	176.39 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

FDB027404

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)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (NP0338814)

MOL for NP0338814 (CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)))

3D MOL for NP0338814 (CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)))

3D SDF for NP0338814 (CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)))

3D-SDF for NP0338814 (CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)))

PDB for NP0338814 (CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)))

3D PDB for NP0338814 (CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)))

SMILES for NP0338814 (CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)))

INCHI for NP0338814 (CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)))

Structure for NP0338814 (CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)))

3D Structure for NP0338814 (CL(18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)))