NP-MRD: Showing NP-Card for CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(11Z)) (NP0338712)

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Record Information

Version

2.0

Created at

2024-09-11 17:13:12 UTC

Updated at

2024-09-11 17:13:12 UTC

NP-MRD ID

NP0338712

Secondary Accession Numbers

None

Natural Product Identification

Common Name

CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(11Z))

Description

CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/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(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(11Z)) is an extremely weak basic (essentially neutral) compound (based on its pKa). CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(11Z)) and cytidine monophosphate can be biosynthesized from PG(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)) and CDP-DG(18:2(9Z,12Z)/18:1(11Z)) through its interaction with the enzyme cardiolipin synthase. In humans, CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/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. 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. CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(11Z)) is a cardiolipin (CL). 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 02241223442D          

108107  0  0  1  0            999 V2000
    2.8342    6.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6444    6.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1845    5.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9946    5.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5347    5.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3448    5.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8849    4.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6950    4.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2351    4.3641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0453    4.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5854    3.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3955    4.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6655    4.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4757    4.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7457    5.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2056    6.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4757    7.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9356    7.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2056    8.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3153    9.6650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9651   10.1328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2351    8.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1550    7.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3448    7.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0748    6.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2646    6.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7246    7.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9144    7.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3743    7.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6444    8.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1043    9.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3743    9.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1845   10.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4545   10.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2646   11.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8047   10.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6149   10.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1550    9.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8849    9.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0748    9.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5347    9.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6655   11.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4757   11.5359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.5253   12.0455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   14.9862   15.1219    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.1422   14.3118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8303   15.9320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7964   15.2778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0664   16.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8766   16.2133    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   17.6867   18.5519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0369   18.0842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3070   18.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7669   19.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0369   20.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8471   20.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02241223442D          

108107  0  0  1  0            999 V2000
    2.8342    6.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6444    6.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1845    5.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9946    5.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5347    5.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3448    5.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8849    4.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6950    4.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2351    4.3641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0453    4.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5854    3.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.6655    9.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.9356    9.9768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3955   10.6005    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    8.5052    9.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0748    6.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2646    6.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7246    7.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1550    9.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.5558   14.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9061   14.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1761   14.9660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   15.1422   14.3118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8303   15.9320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   16.0664   16.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.2268   17.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6867   18.5519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0369   18.0842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3070   18.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7669   19.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0369   20.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8471   20.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.9272   21.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1973   22.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0074   22.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.7374   23.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0074   24.4765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4673   25.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7374   25.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1973   26.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4673   27.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9272   27.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4167   15.5896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1466   14.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3365   14.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6867   14.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4167   13.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9567   12.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6867   12.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2268   11.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9567   10.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4968    9.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2268    9.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7669    8.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4968    7.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0369    7.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7669    6.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3070    5.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1171    5.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6572    5.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4673    5.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0074    4.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1254    9.8210    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.6867   16.3692    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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102103  1  0  0  0  0
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 23107  1  1  0  0  0
 65108  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0338712

> <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)CCC=CCC=CCC=CCC=CCC=CCC=CCC)OC(=O)CCCC=CCC=CCC=CCCCCCCCC)OC(=O)CCCCCCCCCC=CCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C87H146O17P2/c1-5-9-13-17-21-25-29-33-37-39-40-42-45-48-52-56-60-64-68-72-85(90)98-78-83(104-87(92)74-70-66-62-58-54-50-46-41-38-34-30-26-22-18-14-10-6-2)80-102-106(95,96)100-76-81(88)75-99-105(93,94)101-79-82(103-86(91)73-69-65-61-57-53-49-44-36-32-28-24-20-16-12-8-4)77-97-84(89)71-67-63-59-55-51-47-43-35-31-27-23-19-15-11-7-3/h9,13,21,23,25,27-28,32-35,37-38,40,42-43,46,48,50,52,58,60,62,64,81-83,88H,5-8,10-12,14-20,22,24,26,29-31,36,39,41,44-45,47,49,51,53-57,59,61,63,65-80H2,1-4H3,(H,93,94)(H,95,96)/t81?,82-,83-/m1/s1

> <INCHI_KEY>
OEMLGHWAQMIXLT-XRQKZRKGSA-N

> <FORMULA>
C87H146O17P2

> <MOLECULAR_WEIGHT>
1526.0275

> <EXACT_MASS>
1525.00352627

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
179.8818054577619

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-3-(docosa-4,7,10,13,16,19-hexaenoyloxy)-2-(icosa-5,8,11-trienoyloxy)propoxy][2-hydroxy-3-({hydroxy[(2R)-2-(octadec-11-enoyloxy)-3-(octadeca-9,12-dienoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphinic acid

> <ALOGPS_LOGP>
9.26

> <JCHEM_LOGP>
25.594018491333337

> <ALOGPS_LOGS>
-7.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.1918043582150952

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5897376143161042

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4105029523385797

> <JCHEM_POLAR_SURFACE_AREA>
236.94999999999993

> <JCHEM_REFRACTIVITY>
447.9148999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
80

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.95e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-(docosa-4,7,10,13,16,19-hexaenoyloxy)-2-(icosa-5,8,11-trienoyloxy)propoxy(2-hydroxy-3-{[hydroxy(2R)-2-(octadec-11-enoyloxy)-3-(octadeca-9,12-dienoyloxy)propoxyphosphoryl]oxy}propoxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       5.291  11.639   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.803  11.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.811  10.766   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.323  11.057   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.331   9.892   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.844  10.183   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.852   9.019   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.364   9.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.372   8.146   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.885   8.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.893   7.273   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.405   7.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.909   9.019   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.421   9.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.925  10.766   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.917  11.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.421  13.385   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.413  14.549   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.917  16.004   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      19.909  17.168   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      18.397  16.877   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      20.413  18.623   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      19.405  19.788   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.893  19.497   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      17.389  18.041   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      15.876  17.750   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      14.868  18.915   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      15.372  16.295   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.860  16.004   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.356  14.549   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.844  14.258   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.340  12.803   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.827  12.512   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.819  13.676   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.307  13.385   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.299  14.549   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.803  16.004   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.795  17.168   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.299  18.623   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.811  18.915   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       8.315  20.370   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       9.827  20.661   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      10.835  19.497   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      12.348  19.788   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      13.356  18.623   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      12.852  17.168   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      11.340  16.877   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      10.331  18.041   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      19.909  21.243   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      21.421  21.534   0.000  0.00  0.00           O+0
HETATM   51  P   UNK     0      21.925  22.989   0.000  0.00  0.00           P+0
HETATM   52  O   UNK     0      23.381  22.485   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      20.470  23.493   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      22.429  24.444   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      23.942  24.735   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      24.446  26.190   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      23.437  27.355   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      25.958  26.481   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      26.462  27.937   0.000  0.00  0.00           O+0
HETATM   60  P   UNK     0      27.974  28.228   0.000  0.00  0.00           P+0
HETATM   61  O   UNK     0      28.265  26.715   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      27.683  29.740   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      29.487  28.519   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      29.991  29.974   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      31.503  30.265   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      32.007  31.720   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      33.519  32.011   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      34.023  33.466   0.000  0.00  0.00           C+0
HETATM   69  O   UNK     0      33.015  34.630   0.000  0.00  0.00           O+0
HETATM   70  C   UNK     0      35.536  33.757   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      36.040  35.212   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      35.032  36.376   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      35.536  37.832   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      37.048  38.123   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      37.552  39.578   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      39.064  39.869   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      39.568  41.324   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      41.080  41.615   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0      41.585  43.070   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0      40.576  44.234   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0      41.080  45.689   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0      40.072  46.854   0.000  0.00  0.00           C+0
HETATM   83  C   UNK     0      40.576  48.309   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0      39.568  49.473   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0      40.072  50.928   0.000  0.00  0.00           C+0
HETATM   86  C   UNK     0      39.064  52.092   0.000  0.00  0.00           C+0
HETATM   87  O   UNK     0      32.511  29.101   0.000  0.00  0.00           O+0
HETATM   88  C   UNK     0      32.007  27.646   0.000  0.00  0.00           C+0
HETATM   89  O   UNK     0      30.495  27.355   0.000  0.00  0.00           O+0
HETATM   90  C   UNK     0      33.015  26.481   0.000  0.00  0.00           C+0
HETATM   91  C   UNK     0      32.511  25.026   0.000  0.00  0.00           C+0
HETATM   92  C   UNK     0      33.519  23.862   0.000  0.00  0.00           C+0
HETATM   93  C   UNK     0      33.015  22.407   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0      34.023  21.243   0.000  0.00  0.00           C+0
HETATM   95  C   UNK     0      33.519  19.788   0.000  0.00  0.00           C+0
HETATM   96  C   UNK     0      34.527  18.623   0.000  0.00  0.00           C+0
HETATM   97  C   UNK     0      34.023  17.168   0.000  0.00  0.00           C+0
HETATM   98  C   UNK     0      35.032  16.004   0.000  0.00  0.00           C+0
HETATM   99  C   UNK     0      34.527  14.549   0.000  0.00  0.00           C+0
HETATM  100  C   UNK     0      35.536  13.385   0.000  0.00  0.00           C+0
HETATM  101  C   UNK     0      35.032  11.930   0.000  0.00  0.00           C+0
HETATM  102  C   UNK     0      36.040  10.766   0.000  0.00  0.00           C+0
HETATM  103  C   UNK     0      37.552  11.057   0.000  0.00  0.00           C+0
HETATM  104  C   UNK     0      38.560   9.892   0.000  0.00  0.00           C+0
HETATM  105  C   UNK     0      40.072  10.183   0.000  0.00  0.00           C+0
HETATM  106  C   UNK     0      41.080   9.019   0.000  0.00  0.00           C+0
HETATM  107  H   UNK     0      18.901  18.333   0.000  0.00  0.00           H+0
HETATM  108  H   UNK     0      33.015  30.556   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   49  107                                             
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47                                                            
CONECT   49   23   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52   53   54                                             
CONECT   52   51                                                            
CONECT   53   51                                                            
CONECT   54   51   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61   62   63                                             
CONECT   61   60                                                            
CONECT   62   60                                                            
CONECT   63   60   64                                                       
CONECT   64   63   65                                                       
CONECT   65   64   66   87  108                                             
CONECT   66   65   67                                                       
CONECT   67   66   68                                                       
CONECT   68   67   69   70                                                  
CONECT   69   68                                                            
CONECT   70   68   71                                                       
CONECT   71   70   72                                                       
CONECT   72   71   73                                                       
CONECT   73   72   74                                                       
CONECT   74   73   75                                                       
CONECT   75   74   76                                                       
CONECT   76   75   77                                                       
CONECT   77   76   78                                                       
CONECT   78   77   79                                                       
CONECT   79   78   80                                                       
CONECT   80   79   81                                                       
CONECT   81   80   82                                                       
CONECT   82   81   83                                                       
CONECT   83   82   84                                                       
CONECT   84   83   85                                                       
CONECT   85   84   86                                                       
CONECT   86   85                                                            
CONECT   87   65   88                                                       
CONECT   88   87   89   90                                                  
CONECT   89   88                                                            
CONECT   90   88   91                                                       
CONECT   91   90   92                                                       
CONECT   92   91   93                                                       
CONECT   93   92   94                                                       
CONECT   94   93   95                                                       
CONECT   95   94   96                                                       
CONECT   96   95   97                                                       
CONECT   97   96   98                                                       
CONECT   98   97   99                                                       
CONECT   99   98  100                                                       
CONECT  100   99  101                                                       
CONECT  101  100  102                                                       
CONECT  102  101  103                                                       
CONECT  103  102  104                                                       
CONECT  104  103  105                                                       
CONECT  105  104  106                                                       
CONECT  106  105                                                            
CONECT  107   23                                                            
CONECT  108   65                                                            
MASTER        0    0    0    0    0    0    0    0  108    0  214    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₈₇H₁₄₆O₁₇P₂

Average Mass

1526.0275 Da

Monoisotopic Mass

1525.00353 Da

IUPAC Name

[(2R)-3-(docosa-4,7,10,13,16,19-hexaenoyloxy)-2-(icosa-5,8,11-trienoyloxy)propoxy][2-hydroxy-3-({hydroxy[(2R)-2-(octadec-11-enoyloxy)-3-(octadeca-9,12-dienoyloxy)propoxy]phosphoryl}oxy)propoxy]phosphinic acid

Traditional Name

(2R)-3-(docosa-4,7,10,13,16,19-hexaenoyloxy)-2-(icosa-5,8,11-trienoyloxy)propoxy(2-hydroxy-3-{[hydroxy(2R)-2-(octadec-11-enoyloxy)-3-(octadeca-9,12-dienoyloxy)propoxyphosphoryl]oxy}propoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C87H146O17P2/c1-5-9-13-17-21-25-29-33-37-39-40-42-45-48-52-56-60-64-68-72-85(90)98-78-83(104-87(92)74-70-66-62-58-54-50-46-41-38-34-30-26-22-18-14-10-6-2)80-102-106(95,96)100-76-81(88)75-99-105(93,94)101-79-82(103-86(91)73-69-65-61-57-53-49-44-36-32-28-24-20-16-12-8-4)77-97-84(89)71-67-63-59-55-51-47-43-35-31-27-23-19-15-11-7-3/h9,13,21,23,25,27-28,32-35,37-38,40,42-43,46,48,50,52,58,60,62,64,81-83,88H,5-8,10-12,14-20,22,24,26,29-31,36,39,41,44-45,47,49,51,53-57,59,61,63,65-80H2,1-4H3,(H,93,94)(H,95,96)/t81?,82-,83-/m1/s1

InChI Key

OEMLGHWAQMIXLT-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	9.26	ALOGPS
logP	25.59	ChemAxon
logS	-7.3	ALOGPS
pKa (Strongest Acidic)	1.59	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	236.95 Å²	ChemAxon
Rotatable Bond Count	80	ChemAxon
Refractivity	447.91 m³·mol⁻¹	ChemAxon
Polarizability	179.88 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

FDB027454

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(11Z)) (NP0338712)

MOL for NP0338712 (CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(11Z)))

3D MOL for NP0338712 (CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(11Z)))

3D SDF for NP0338712 (CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(11Z)))

3D-SDF for NP0338712 (CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(11Z)))

PDB for NP0338712 (CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(11Z)))

3D PDB for NP0338712 (CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(11Z)))

SMILES for NP0338712 (CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(11Z)))

INCHI for NP0338712 (CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(11Z)))

Structure for NP0338712 (CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(11Z)))

3D Structure for NP0338712 (CL(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/18:1(11Z)))