NP-MRD: Showing NP-Card for CL(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z)) (NP0338875)

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Record Information

Version

2.0

Created at

2024-09-11 18:26:44 UTC

Updated at

2024-09-11 18:26:44 UTC

NP-MRD ID

NP0338875

Secondary Accession Numbers

None

Natural Product Identification

Common Name

CL(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z))

Description

CL(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(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(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z)) is an extremely weak basic (essentially neutral) compound (based on its pKa). CL(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z)) and cytidine monophosphate can be biosynthesized from PG(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)) and CDP-DG(18:2(9Z,12Z)/16:1(9Z)) through its interaction with the enzyme cardiolipin synthase. In humans, CL(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z)) 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. Cardiolipins are a "double" phospholipid because they have four fatty acid tails, instead of the usual two. CL(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(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. 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 02251204362D          

104103  0  0  1  0            999 V2000
   22.7048   -4.9942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4924   -4.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0765   -3.6144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8641   -2.8172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4483   -2.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2358   -1.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8200   -0.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6076   -0.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1918    0.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9793    1.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5635    1.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3511    2.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9352    3.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7228    4.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3070    4.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   23.0765    7.4848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   17.5535    6.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   26.0505    7.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8471    7.2089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   39.6457   11.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2298   12.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   40.6016   13.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3982   13.6477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   39.8050    2.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02251204362D          

104103  0  0  1  0            999 V2000
   22.7048   -4.9942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4924   -4.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   23.2358   -1.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8200   -0.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.2880    9.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8721   10.3670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6597   11.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0505    7.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8471    7.2089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4312    7.7914    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   28.0138    7.2073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8487    8.3756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0154    8.3740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8120    8.1594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3962    8.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1837    9.5391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1928    8.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7769    9.1099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5735    8.8952    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   31.3589    8.0986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.7881    9.6918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3701    8.6806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.9543    9.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7509    9.0485    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   34.3350    9.6311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1316    9.4165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   35.5034   10.7962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.5124    9.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0966   10.3670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8932   10.1523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4773   10.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2739   10.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8581   11.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6457   11.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2298   12.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0174   13.2797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6016   13.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3982   13.6477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9823   14.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7699   15.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3541   15.6100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1417   16.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7258   16.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5134   17.7869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0976   18.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8851   19.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9633    8.2514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.7599    8.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3441    8.6193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.9723    7.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7689    7.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9813    6.2277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7779    6.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9904    5.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7869    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9994    4.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7960    3.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0084    3.1923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8050    2.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3892    3.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1857    3.3456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7699    3.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5575    4.7253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1417    5.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9292    6.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5134    6.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3010    7.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8851    8.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8821    6.2584    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   34.5475    8.8339    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
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  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
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 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
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 22 24  1  0  0  0  0
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 37 38  1  0  0  0  0
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 48 50  1  0  0  0  0
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 55 56  1  0  0  0  0
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 59 60  1  0  0  0  0
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 60 62  1  0  0  0  0
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 63 64  1  0  0  0  0
 65 64  1  4  0  0  0
 65 66  2  0  0  0  0
 66 67  1  0  0  0  0
 68 67  1  4  0  0  0
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 98 99  1  0  0  0  0
 99100  1  0  0  0  0
100101  1  0  0  0  0
101102  1  0  0  0  0
 19103  1  1  0  0  0
 57104  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0338875

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

> <INCHI_IDENTIFIER>
InChI=1S/C83H142O17P2/c1-5-9-13-17-21-25-29-33-36-38-41-45-48-52-56-60-64-68-81(86)94-74-79(100-83(88)70-66-62-58-54-50-46-42-39-37-34-30-26-22-18-14-10-6-2)76-98-102(91,92)96-72-77(84)71-95-101(89,90)97-75-78(99-82(87)69-65-61-57-53-49-43-32-28-24-20-16-12-8-4)73-93-80(85)67-63-59-55-51-47-44-40-35-31-27-23-19-15-11-7-3/h21-23,25-28,32-37,40-42,45-46,52,56,77-79,84H,5-20,24,29-31,38-39,43-44,47-51,53-55,57-76H2,1-4H3,(H,89,90)(H,91,92)/t77?,78-,79-/m1/s1

> <INCHI_KEY>
DIARJYRNRUJHPN-FIDHOYNDSA-N

> <FORMULA>
C83H142O17P2

> <MOLECULAR_WEIGHT>
1473.9529

> <EXACT_MASS>
1472.972226142

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
174.40989022917702

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
9.18

> <JCHEM_LOGP>
24.53958714466667

> <ALOGPS_LOGS>
-7.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.191804358217161

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.589737614322165

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4105029523385797

> <JCHEM_POLAR_SURFACE_AREA>
236.94999999999993

> <JCHEM_REFRACTIVITY>
427.2776999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
78

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.11e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2R)-2-(hexadec-9-enoyloxy)-3-(octadeca-9,12-dienoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy(2R)-3-(icosa-5,8,11,14-tetraenoyloxy)-2-(icosa-8,11,14-trienoyloxy)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      42.382  -9.323   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      41.986  -7.834   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      43.076  -6.747   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      42.680  -5.259   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      43.770  -4.171   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      43.373  -2.683   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      44.464  -1.596   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      44.068  -0.108   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      45.158   0.980   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      44.761   2.468   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      45.852   3.555   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      45.455   5.043   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      46.546   6.131   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      46.149   7.619   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      47.240   8.706   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      46.843  10.194   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      45.356  10.595   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      47.934  11.282   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      47.537  12.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      46.050  13.170   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      44.960  12.083   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      43.473  12.484   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      43.076  13.972   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      42.382  11.396   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      40.895  11.797   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      39.805  10.709   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      38.318  11.110   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      37.227  10.023   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      35.741  10.423   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      34.650   9.336   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      33.163   9.736   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      32.767  11.224   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      31.280  11.625   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      30.883  13.113   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      31.973  14.201   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      31.577  15.689   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      32.667  16.776   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      32.271  18.264   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      33.361  19.352   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      32.965  20.840   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      48.628  13.857   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      50.115  13.457   0.000  0.00  0.00           O+0
HETATM   43  P   UNK     0      51.205  14.544   0.000  0.00  0.00           P+0
HETATM   44  O   UNK     0      52.292  13.454   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      50.118  15.634   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      52.295  15.631   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      53.782  15.231   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      54.873  16.318   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      54.476  17.806   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      56.360  15.918   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      57.450  17.005   0.000  0.00  0.00           O+0
HETATM   52  P   UNK     0      58.937  16.604   0.000  0.00  0.00           P+0
HETATM   53  O   UNK     0      58.537  15.117   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      59.338  18.091   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      60.424  16.204   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      61.515  17.291   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      63.002  16.891   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      64.092  17.978   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      65.579  17.577   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      66.669  18.665   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      66.273  20.153   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      68.156  18.264   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      69.247  19.352   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      70.734  18.951   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      71.824  20.038   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      73.311  19.638   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      74.402  20.725   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      74.005  22.213   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      75.096  23.301   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      74.699  24.789   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      75.790  25.876   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      77.277  25.476   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      78.367  26.563   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      77.970  28.051   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      79.061  29.139   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      78.665  30.627   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      79.755  31.714   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      79.358  33.202   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0      80.449  34.290   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0      80.052  35.778   0.000  0.00  0.00           C+0
HETATM   81  O   UNK     0      63.398  15.403   0.000  0.00  0.00           O+0
HETATM   82  C   UNK     0      64.885  15.002   0.000  0.00  0.00           C+0
HETATM   83  O   UNK     0      65.976  16.089   0.000  0.00  0.00           O+0
HETATM   84  C   UNK     0      65.282  13.514   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0      66.769  13.113   0.000  0.00  0.00           C+0
HETATM   86  C   UNK     0      67.165  11.625   0.000  0.00  0.00           C+0
HETATM   87  C   UNK     0      68.652  11.224   0.000  0.00  0.00           C+0
HETATM   88  C   UNK     0      69.049   9.736   0.000  0.00  0.00           C+0
HETATM   89  C   UNK     0      70.536   9.336   0.000  0.00  0.00           C+0
HETATM   90  C   UNK     0      70.932   7.848   0.000  0.00  0.00           C+0
HETATM   91  C   UNK     0      72.419   7.447   0.000  0.00  0.00           C+0
HETATM   92  C   UNK     0      72.816   5.959   0.000  0.00  0.00           C+0
HETATM   93  C   UNK     0      74.303   5.558   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0      75.393   6.646   0.000  0.00  0.00           C+0
HETATM   95  C   UNK     0      76.880   6.245   0.000  0.00  0.00           C+0
HETATM   96  C   UNK     0      77.970   7.333   0.000  0.00  0.00           C+0
HETATM   97  C   UNK     0      77.574   8.821   0.000  0.00  0.00           C+0
HETATM   98  C   UNK     0      78.665   9.908   0.000  0.00  0.00           C+0
HETATM   99  C   UNK     0      78.268  11.396   0.000  0.00  0.00           C+0
HETATM  100  C   UNK     0      79.358  12.484   0.000  0.00  0.00           C+0
HETATM  101  C   UNK     0      78.962  13.972   0.000  0.00  0.00           C+0
HETATM  102  C   UNK     0      80.052  15.059   0.000  0.00  0.00           C+0
HETATM  103  H   UNK     0      46.447  11.682   0.000  0.00  0.00           H+0
HETATM  104  H   UNK     0      64.489  16.490   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   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   41  103                                             
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   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                                                            
CONECT   41   19   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   45   46                                             
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46   43   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53   54   55                                             
CONECT   53   52                                                            
CONECT   54   52                                                            
CONECT   55   52   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58   81  104                                             
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60   63                                                       
CONECT   63   62   64                                                       
CONECT   64   63   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                                                            
CONECT   81   57   82                                                       
CONECT   82   81   83   84                                                  
CONECT   83   82                                                            
CONECT   84   82   85                                                       
CONECT   85   84   86                                                       
CONECT   86   85   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   19                                                            
CONECT  104   57                                                            
MASTER        0    0    0    0    0    0    0    0  104    0  206    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₈₃H₁₄₂O₁₇P₂

Average Mass

1473.9529 Da

Monoisotopic Mass

1472.97223 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C83H142O17P2/c1-5-9-13-17-21-25-29-33-36-38-41-45-48-52-56-60-64-68-81(86)94-74-79(100-83(88)70-66-62-58-54-50-46-42-39-37-34-30-26-22-18-14-10-6-2)76-98-102(91,92)96-72-77(84)71-95-101(89,90)97-75-78(99-82(87)69-65-61-57-53-49-43-32-28-24-20-16-12-8-4)73-93-80(85)67-63-59-55-51-47-44-40-35-31-27-23-19-15-11-7-3/h21-23,25-28,32-37,40-42,45-46,52,56,77-79,84H,5-20,24,29-31,38-39,43-44,47-51,53-55,57-76H2,1-4H3,(H,89,90)(H,91,92)/t77?,78-,79-/m1/s1

InChI Key

DIARJYRNRUJHPN-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	24.54	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	78	ChemAxon
Refractivity	427.28 m³·mol⁻¹	ChemAxon
Polarizability	174.41 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

FDB027844

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for CL(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z)) (NP0338875)

MOL for NP0338875 (CL(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z)))

3D MOL for NP0338875 (CL(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z)))

3D SDF for NP0338875 (CL(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z)))

3D-SDF for NP0338875 (CL(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z)))

PDB for NP0338875 (CL(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z)))

3D PDB for NP0338875 (CL(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z)))

SMILES for NP0338875 (CL(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z)))

INCHI for NP0338875 (CL(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z)))

Structure for NP0338875 (CL(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z)))

3D Structure for NP0338875 (CL(20:4(5Z,8Z,11Z,14Z)/20:3(8Z,11Z,14Z)/18:2(9Z,12Z)/16:1(9Z)))