NP-MRD: Showing NP-Card for CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)) (NP0338784)

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Record Information

Version

2.0

Created at

2024-09-11 17:44:52 UTC

Updated at

2024-09-11 17:44:52 UTC

NP-MRD ID

NP0338784

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

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

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251201592D          

104103  0  0  1  0            999 V2000
    0.8250   15.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   14.2894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   14.2894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   13.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   13.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750   12.8605    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
    7.0125   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2500   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.2000   15.7184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   16.8020   17.4493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   17.3250   18.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7375   19.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3250   20.0052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   18.9750   20.0052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02251201592D          

104103  0  0  1  0            999 V2000
    0.8250   15.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   14.2894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   14.2894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125   13.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   13.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   12.8605    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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   21.0375   20.7197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8625   20.7197    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.2750   21.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1000   21.4341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5125   22.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1000   22.8631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3375   22.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7500   22.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5750   22.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9875   23.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8125   23.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2250   24.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0500   24.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4625   25.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2875   25.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7000   25.7210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2875   26.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7000   27.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2875   27.8644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7000   28.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2875   29.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7000   30.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2875   30.7223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2750   20.0052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8625   19.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0375   19.2907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2750   18.5762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8625   17.8618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2750   17.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8625   16.4328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2750   15.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8625   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2750   14.2894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8625   13.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2750   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8625   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2750   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8625   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0375   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6250   10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8000   10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3875    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5625    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8500   15.7184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4375   15.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6125   15.0039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8500   14.2894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4375   13.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8500   12.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4375   12.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8500   11.4315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4375   10.7171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8500   10.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4375    9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8500    8.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4375    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8500    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6750    7.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0875    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9125    6.4302    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
   18.1500    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5625    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2625   16.4328    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.6875   20.7197    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
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 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 36 39  1  0  0  0  0
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 41 42  1  0  0  0  0
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 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 53 52  1  4  0  0  0
 53 54  2  0  0  0  0
 54 55  1  0  0  0  0
 56 55  1  4  0  0  0
 56 57  2  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 41 63  1  1  0  0  0
 63 64  1  0  0  0  0
 64 65  2  0  0  0  0
 64 66  1  0  0  0  0
 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
 68 69  1  0  0  0  0
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 70 71  1  0  0  0  0
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 72 73  1  0  0  0  0
 73 74  1  0  0  0  0
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 84 86  1  0  0  0  0
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 90 91  1  0  0  0  0
 91 92  1  0  0  0  0
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 93 94  2  0  0  0  0
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 96 95  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
 24103  1  1  0  0  0
 41104  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0338784

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

> <INCHI_IDENTIFIER>
InChI=1S/C83H150O17P2/c1-5-9-13-17-21-25-29-33-37-38-42-44-48-52-56-60-64-68-81(86)94-74-79(100-83(88)70-66-62-58-54-50-46-41-36-32-28-24-20-16-12-8-4)76-98-102(91,92)96-72-77(84)71-95-101(89,90)97-75-78(99-82(87)69-65-61-57-53-49-45-40-35-31-27-23-19-15-11-7-3)73-93-80(85)67-63-59-55-51-47-43-39-34-30-26-22-18-14-10-6-2/h22,24,26-28,31,33-34,36-37,39,41,77-79,84H,5-21,23,25,29-30,32,35,38,40,42-76H2,1-4H3,(H,89,90)(H,91,92)/t77?,78-,79-/m1/s1

> <INCHI_KEY>
AQSFNERDFJAYEP-FIDHOYNDSA-N

> <FORMULA>
C83H150O17P2

> <MOLECULAR_WEIGHT>
1482.0164

> <EXACT_MASS>
1481.034826398

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
179.23457292281253

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
9.18

> <JCHEM_LOGP>
25.98727377133333

> <ALOGPS_LOGS>
-7.30

> <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>
236.94999999999996

> <JCHEM_REFRACTIVITY>
422.8112999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
82

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.47e-05 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0       1.540  29.341   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310  28.007   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.850  28.007   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.620  26.674   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.160  26.674   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.930  25.340   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.470  25.340   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.240  24.006   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.780  24.006   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.550  22.673   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.090  22.673   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.860  24.006   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.400  24.006   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.170  25.340   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.710  25.340   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.480  26.674   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.020  26.674   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.790  28.007   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.330  28.007   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      23.100  29.341   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      22.330  30.675   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      24.640  29.341   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      25.410  30.675   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      26.950  30.675   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      27.720  32.008   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      29.260  32.008   0.000  0.00  0.00           O+0
HETATM   27  P   UNK     0      30.030  33.342   0.000  0.00  0.00           P+0
HETATM   28  O   UNK     0      31.364  32.572   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      28.696  34.112   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      30.800  34.676   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      32.340  34.676   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      33.110  36.009   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      32.340  37.343   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      34.650  36.009   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      35.420  37.343   0.000  0.00  0.00           O+0
HETATM   36  P   UNK     0      36.960  37.343   0.000  0.00  0.00           P+0
HETATM   37  O   UNK     0      36.960  35.803   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      36.960  38.883   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      38.500  37.343   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      39.270  38.677   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      40.810  38.677   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      41.580  40.010   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      43.120  40.010   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      43.890  41.344   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      43.120  42.678   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      45.430  41.344   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      46.200  42.678   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      47.740  42.678   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      48.510  44.011   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      50.050  44.011   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      50.820  45.345   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      52.360  45.345   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      53.130  46.679   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      54.670  46.679   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      55.440  48.013   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      54.670  49.346   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      55.440  50.680   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      54.670  52.014   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      55.440  53.347   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      54.670  54.681   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      55.440  56.015   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      54.670  57.348   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      41.580  37.343   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      40.810  36.009   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      39.270  36.009   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      41.580  34.676   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      40.810  33.342   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      41.580  32.008   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      40.810  30.675   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      41.580  29.341   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      40.810  28.007   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      41.580  26.674   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      40.810  25.340   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      41.580  24.006   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      40.810  22.673   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      41.580  21.339   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      40.810  20.005   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      39.270  20.005   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0      38.500  18.672   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0      36.960  18.672   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0      36.190  17.338   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0      34.650  17.338   0.000  0.00  0.00           C+0
HETATM   83  O   UNK     0      27.720  29.341   0.000  0.00  0.00           O+0
HETATM   84  C   UNK     0      26.950  28.007   0.000  0.00  0.00           C+0
HETATM   85  O   UNK     0      25.410  28.007   0.000  0.00  0.00           O+0
HETATM   86  C   UNK     0      27.720  26.674   0.000  0.00  0.00           C+0
HETATM   87  C   UNK     0      26.950  25.340   0.000  0.00  0.00           C+0
HETATM   88  C   UNK     0      27.720  24.006   0.000  0.00  0.00           C+0
HETATM   89  C   UNK     0      26.950  22.673   0.000  0.00  0.00           C+0
HETATM   90  C   UNK     0      27.720  21.339   0.000  0.00  0.00           C+0
HETATM   91  C   UNK     0      26.950  20.005   0.000  0.00  0.00           C+0
HETATM   92  C   UNK     0      27.720  18.672   0.000  0.00  0.00           C+0
HETATM   93  C   UNK     0      26.950  17.338   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0      27.720  16.004   0.000  0.00  0.00           C+0
HETATM   95  C   UNK     0      26.950  14.671   0.000  0.00  0.00           C+0
HETATM   96  C   UNK     0      27.720  13.337   0.000  0.00  0.00           C+0
HETATM   97  C   UNK     0      29.260  13.337   0.000  0.00  0.00           C+0
HETATM   98  C   UNK     0      30.030  12.003   0.000  0.00  0.00           C+0
HETATM   99  C   UNK     0      31.570  12.003   0.000  0.00  0.00           C+0
HETATM  100  C   UNK     0      32.340  10.669   0.000  0.00  0.00           C+0
HETATM  101  C   UNK     0      33.880  10.669   0.000  0.00  0.00           C+0
HETATM  102  C   UNK     0      34.650   9.336   0.000  0.00  0.00           C+0
HETATM  103  H   UNK     0      28.490  30.675   0.000  0.00  0.00           H+0
HETATM  104  H   UNK     0      42.350  38.677   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   83  103                                             
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38   39                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   36   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42   63  104                                             
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   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   41   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                                                            
CONECT   83   24   84                                                       
CONECT   84   83   85   86                                                  
CONECT   85   84                                                            
CONECT   86   84   87                                                       
CONECT   87   86   88                                                       
CONECT   88   87   89                                                       
CONECT   89   88   90                                                       
CONECT   90   89   91                                                       
CONECT   91   90   92                                                       
CONECT   92   91   93                                                       
CONECT   93   92   94                                                       
CONECT   94   93   95                                                       
CONECT   95   94   96                                                       
CONECT   96   95   97                                                       
CONECT   97   96   98                                                       
CONECT   98   97   99                                                       
CONECT   99   98  100                                                       
CONECT  100   99  101                                                       
CONECT  101  100  102                                                       
CONECT  102  101                                                            
CONECT  103   24                                                            
CONECT  104   41                                                            
MASTER        0    0    0    0    0    0    0    0  104    0  206    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₈₃H₁₅₀O₁₇P₂

Average Mass

1482.0164 Da

Monoisotopic Mass

1481.03483 Da

IUPAC Name

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

Traditional Name

2-hydroxy-3-{[hydroxy(2R)-2-(octadec-11-enoyloxy)-3-(octadeca-9,12-dienoyloxy)propoxyphosphoryl]oxy}propoxy(2R)-3-(icos-11-enoyloxy)-2-(octadeca-9,12-dienoyloxy)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)CCCCCCCCCC=CCCCCCCCC)OC(=O)CCCCCCCC=CCC=CCCCCC)OC(=O)CCCCCCCCCC=CCCCCCC

InChI Identifier

InChI=1S/C83H150O17P2/c1-5-9-13-17-21-25-29-33-37-38-42-44-48-52-56-60-64-68-81(86)94-74-79(100-83(88)70-66-62-58-54-50-46-41-36-32-28-24-20-16-12-8-4)76-98-102(91,92)96-72-77(84)71-95-101(89,90)97-75-78(99-82(87)69-65-61-57-53-49-45-40-35-31-27-23-19-15-11-7-3)73-93-80(85)67-63-59-55-51-47-43-39-34-30-26-22-18-14-10-6-2/h22,24,26-28,31,33-34,36-37,39,41,77-79,84H,5-21,23,25,29-30,32,35,38,40,42-76H2,1-4H3,(H,89,90)(H,91,92)/t77?,78-,79-/m1/s1

InChI Key

AQSFNERDFJAYEP-FIDHOYNDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoglycerophosphoglycerols

Direct Parent

Cardiolipins

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	9.18	ALOGPS
logP	25.99	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	82	ChemAxon
Refractivity	422.81 m³·mol⁻¹	ChemAxon
Polarizability	179.23 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

FDB027410

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)) (NP0338784)

MOL for NP0338784 (CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)))

3D MOL for NP0338784 (CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)))

3D SDF for NP0338784 (CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)))

3D-SDF for NP0338784 (CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)))

PDB for NP0338784 (CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)))

3D PDB for NP0338784 (CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)))

SMILES for NP0338784 (CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)))

INCHI for NP0338784 (CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)))

Structure for NP0338784 (CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)))

3D Structure for NP0338784 (CL(20:1(11Z)/18:2(9Z,12Z)/18:2(9Z,12Z)/18:1(11Z)))