Np mrd loader

Showing NP-Card for CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z)) (NP0338963)

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Record Information
Version2.0
Created at2024-09-11 18:58:01 UTC
Updated at2024-09-11 18:58:01 UTC
NP-MRD IDNP0338963
Secondary Accession NumbersNone
Natural Product Identification
Common NameCL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z))
DescriptionCL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/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(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z)) is an extremely weak basic (essentially neutral) compound (based on its pKa). CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z)) and cytidine monophosphate can be biosynthesized from PG(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)) and CDP-DG(18:2(9Z,12Z)/16:1(9Z)); which is mediated by the enzyme cardiolipin synthase. In humans, CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z)) is involved in cardiolipin biosynthesis. 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(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z)) is a cardiolipin (CL). They are highly abundant in metabolically active cells (heart, muscle) and play an important role in the blood clotting process. While most lipids are made in the endoplasmic reticulum, cardiolipin is synthesized on the matrix side of the inner mitochondrial membrane.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0338963 (CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z)))


  Mrv0541 02251206532D          

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M  END
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3D MOL for NP0338963 (CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z)))

Download
3D SDF for NP0338963 (CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z)))

  Mrv0541 02251206532D          

104103  0  0  1  0            999 V2000
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   23.7684   11.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4570   11.0056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1948   11.3747    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   24.8256   12.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   27.4082   12.4822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   28.7854   11.5735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   29.9284   11.8078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0196   10.4306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1626   10.6648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.9004   11.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5890   10.5796    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   32.3268   10.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0154   10.4944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   33.8024   11.6871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.4418   10.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1796   10.7784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2288   11.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   36.6552   11.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3930   11.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   39.5080   11.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2458   11.7155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9344   11.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6722   11.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3608   11.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3116   10.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0002    9.8981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9510    9.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6396    8.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5398    9.7561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8020    9.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1134    9.8413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7528    8.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0150    8.1942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9659    7.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2281    7.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1789    6.1780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4411    5.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3919    4.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6541    4.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6049    3.7926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2935    3.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2443    2.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9329    2.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8838    1.2368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5724    0.7824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5232   -0.0411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2928   10.7216    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   32.2776   10.1252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0338963

> <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)CCCCCCC=CCC=CCC=CCC=CCC)OC(=O)CCCC=CCC=CCC=CCCCCCCCC)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/h9,13,21,23,25,27-28,32-37,40-42,45-46,54,58,77-79,84H,5-8,10-12,14-20,22,24,26,29-31,38-39,43-44,47-53,55-57,59-76H2,1-4H3,(H,89,90)(H,91,92)/t77?,78-,79-/m1/s1

> <INCHI_KEY>
NHLLXZNSQVSIFB-FIDHOYNDSA-N

> <FORMULA>
C83H142O17P2

> <MOLECULAR_WEIGHT>
1473.9529

> <EXACT_MASS>
1472.972226142

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
174.39368913694358

> <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)-2-(icosa-5,8,11-trienoyloxy)-3-(icosa-8,11,14,17-tetraenoyloxy)propoxy]phosphinic acid

> <ALOGPS_LOGP>
9.20

> <JCHEM_LOGP>
24.53958714466667

> <ALOGPS_LOGS>
-7.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.1918043582171283

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5897376143221367

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4105029523385797

> <JCHEM_POLAR_SURFACE_AREA>
236.94999999999993

> <JCHEM_REFRACTIVITY>
427.2776999999998

> <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)-2-(icosa-5,8,11-trienoyloxy)-3-(icosa-8,11,14,17-tetraenoyloxy)propoxyphosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0338963 (CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z)))
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PDB for NP0338963 (CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z)))
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      30.871  -3.257   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      30.963  -1.720   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      32.340  -1.031   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      32.432   0.506   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      33.809   1.195   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.901   2.733   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      35.278   3.422   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      35.370   4.959   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      36.747   5.648   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      36.839   7.186   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      38.216   7.875   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      38.308   9.412   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      37.023  10.260   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      37.114  11.797   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      38.492  12.486   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      38.583  14.024   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      39.961  14.713   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      40.052  16.250   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      41.430  16.939   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      41.521  18.476   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      40.236  19.324   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      42.899  19.165   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      42.990  20.703   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      41.705  21.551   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      40.328  20.862   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      39.042  21.710   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      39.134  23.247   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      37.665  21.021   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      36.380  21.869   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      35.003  21.180   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      33.717  22.028   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      32.340  21.339   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      31.055  22.187   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      29.677  21.498   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      28.392  22.346   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      27.015  21.657   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      25.729  22.505   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      24.352  21.816   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      23.067  22.664   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      23.159  24.201   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      24.536  24.891   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      24.628  26.428   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      26.005  27.117   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      27.290  26.269   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      28.668  26.958   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      29.953  26.110   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      44.368  21.392   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      45.653  20.544   0.000  0.00  0.00           O+0
HETATM   49  P   UNK     0      47.030  21.233   0.000  0.00  0.00           P+0
HETATM   50  O   UNK     0      46.341  22.610   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      47.719  19.856   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      48.408  21.922   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      49.693  21.074   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      51.070  21.763   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      51.162  23.300   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      52.356  20.915   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      53.733  21.604   0.000  0.00  0.00           O+0
HETATM   58  P   UNK     0      55.018  20.756   0.000  0.00  0.00           P+0
HETATM   59  O   UNK     0      55.866  22.041   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      54.170  19.470   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      56.304  19.908   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      57.681  20.597   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      58.966  19.749   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      60.343  20.438   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      61.629  19.590   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      63.006  20.279   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      63.098  21.816   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      64.291  19.431   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      65.669  20.120   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      65.760  21.657   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      67.138  22.346   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      68.423  21.498   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      69.800  22.187   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      71.086  21.339   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      72.463  22.028   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      73.748  21.180   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      75.125  21.869   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      76.411  21.021   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0      77.788  21.710   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0      79.073  20.862   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0      78.982  19.324   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0      80.267  18.476   0.000  0.00  0.00           C+0
HETATM   83  C   UNK     0      80.175  16.939   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0      81.461  16.091   0.000  0.00  0.00           C+0
HETATM   85  O   UNK     0      58.874  18.211   0.000  0.00  0.00           O+0
HETATM   86  C   UNK     0      57.497  17.522   0.000  0.00  0.00           C+0
HETATM   87  O   UNK     0      56.212  18.370   0.000  0.00  0.00           O+0
HETATM   88  C   UNK     0      57.405  15.985   0.000  0.00  0.00           C+0
HETATM   89  C   UNK     0      56.028  15.296   0.000  0.00  0.00           C+0
HETATM   90  C   UNK     0      55.936  13.759   0.000  0.00  0.00           C+0
HETATM   91  C   UNK     0      54.559  13.069   0.000  0.00  0.00           C+0
HETATM   92  C   UNK     0      54.467  11.532   0.000  0.00  0.00           C+0
HETATM   93  C   UNK     0      53.090  10.843   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0      52.998   9.306   0.000  0.00  0.00           C+0
HETATM   95  C   UNK     0      51.621   8.617   0.000  0.00  0.00           C+0
HETATM   96  C   UNK     0      51.529   7.080   0.000  0.00  0.00           C+0
HETATM   97  C   UNK     0      52.815   6.231   0.000  0.00  0.00           C+0
HETATM   98  C   UNK     0      52.723   4.694   0.000  0.00  0.00           C+0
HETATM   99  C   UNK     0      54.008   3.846   0.000  0.00  0.00           C+0
HETATM  100  C   UNK     0      53.916   2.309   0.000  0.00  0.00           C+0
HETATM  101  C   UNK     0      55.202   1.460   0.000  0.00  0.00           C+0
HETATM  102  C   UNK     0      55.110  -0.077   0.000  0.00  0.00           C+0
HETATM  103  H   UNK     0      41.613  20.014   0.000  0.00  0.00           H+0
HETATM  104  H   UNK     0      60.252  18.900   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   47  103                                             
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                                                            
CONECT   47   23   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50   51   52                                             
CONECT   50   49                                                            
CONECT   51   49                                                            
CONECT   52   49   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59   60   61                                             
CONECT   59   58                                                            
CONECT   60   58                                                            
CONECT   61   58   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   64   85  104                                             
CONECT   64   63   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65   67   68                                                  
CONECT   67   66                                                            
CONECT   68   66   69                                                       
CONECT   69   68   70                                                       
CONECT   70   69   71                                                       
CONECT   71   70   72                                                       
CONECT   72   71   73                                                       
CONECT   73   72   74                                                       
CONECT   74   73   75                                                       
CONECT   75   74   76                                                       
CONECT   76   75   77                                                       
CONECT   77   76   78                                                       
CONECT   78   77   79                                                       
CONECT   79   78   80                                                       
CONECT   80   79   81                                                       
CONECT   81   80   82                                                       
CONECT   82   81   83                                                       
CONECT   83   82   84                                                       
CONECT   84   83                                                            
CONECT   85   63   86                                                       
CONECT   86   85   87   88                                                  
CONECT   87   86                                                            
CONECT   88   86   89                                                       
CONECT   89   88   90                                                       
CONECT   90   89   91                                                       
CONECT   91   90   92                                                       
CONECT   92   91   93                                                       
CONECT   93   92   94                                                       
CONECT   94   93   95                                                       
CONECT   95   94   96                                                       
CONECT   96   95   97                                                       
CONECT   97   96   98                                                       
CONECT   98   97   99                                                       
CONECT   99   98  100                                                       
CONECT  100   99  101                                                       
CONECT  101  100  102                                                       
CONECT  102  101                                                            
CONECT  103   23                                                            
CONECT  104   63                                                            
MASTER        0    0    0    0    0    0    0    0  104    0  206    0
END

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3D PDB for NP0338963 (CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z)))
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SMILES for NP0338963 (CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z)))
[H][C@@](COC(=O)CCCCCCCC=CCC=CCCCCC)(COP(O)(=O)OCC(O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC=CCC=CCC=CCC=CCC)OC(=O)CCCC=CCC=CCC=CCCCCCCCC)OC(=O)CCCCCCCC=CCCCCCC
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INCHI for NP0338963 (CL(20:4(8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)/18:2(9Z,12Z)/16:1(9Z)))
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/h9,13,21,23,25,27-28,32-37,40-42,45-46,54,58,77-79,84H,5-8,10-12,14-20,22,24,26,29-31,38-39,43-44,47-53,55-57,59-76H2,1-4H3,(H,89,90)(H,91,92)/t77?,78-,79-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC83H142O17P2
Average Mass1473.9529 Da
Monoisotopic Mass1472.97223 Da
IUPAC Name[3-({[(2R)-2-(hexadec-9-enoyloxy)-3-(octadeca-9,12-dienoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-(icosa-5,8,11-trienoyloxy)-3-(icosa-8,11,14,17-tetraenoyloxy)propoxy]phosphinic acid
Traditional Name3-{[(2R)-2-(hexadec-9-enoyloxy)-3-(octadeca-9,12-dienoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy(2R)-2-(icosa-5,8,11-trienoyloxy)-3-(icosa-8,11,14,17-tetraenoyloxy)propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCC=CCC=CCCCCC)(COP(O)(=O)OCC(O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC=CCC=CCC=CCC=CCC)OC(=O)CCCC=CCC=CCC=CCCCCCCCC)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/h9,13,21,23,25,27-28,32-37,40-42,45-46,54,58,77-79,84H,5-8,10-12,14-20,22,24,26,29-31,38-39,43-44,47-53,55-57,59-76H2,1-4H3,(H,89,90)(H,91,92)/t77?,78-,79-/m1/s1
InChI KeyNHLLXZNSQVSIFB-FIDHOYNDSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot 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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassGlycerophospholipids  
Sub ClassGlycerophosphoglycerophosphoglycerols  
Direct ParentCardiolipins  
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 FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP9.2ALOGPS
logP24.54ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)1.59ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area236.95 ŲChemAxon
Rotatable Bond Count78ChemAxon
Refractivity427.28 m³·mol⁻¹ChemAxon
Polarizability174.39 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB027845  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available