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Showing metabocard for CL(8:0/8:0/10:0/10:0) (HMDB0116832)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-09-11 02:15:20 UTC
Update Date2022-11-30 19:26:46 UTC
HMDB IDHMDB0116832
Secondary Accession NumbersNone
Metabolite Identification
Common NameCL(8:0/8:0/10:0/10:0)
DescriptionCL(8:0/8:0/10:0/10:0) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(8:0/8:0/10:0/10:0) contains two chains of octanoic acid at the C1 and C2 positions, two chains of decanoic acid at the C3 and C4 positions. Cardiolipins are known to be present in all mammalian cells especially cells with a high number of mitochondria. De novo synthesis of Cardiolipins begins with condensing phosphatidic acid (PA) with cytidine-5’-triphosphate (CTP) to form cytidine-diphosphate-1,2-diacyl-sn-glycerol (CDP- DG). Glycerol-3-phosphate is subsequently added to this newly formed CDP-DG molecule to form  phosphatidylglycerol phosphate (PGP), which is immediately dephosphorylated to form PG. The final step is the process of condensing the PG molecule with another CDP-DG molecule to form a new cardiolipin, which is catalyzed by cardiolipin synthase. All new cardiolipins will immediately undergo a series remodeling resulting in the common cardiolipin compositions. (PMID:16442164 ). Cardiolipin synthase shows no selectivity for fatty acyl chains used in the de novo synthesis of cardiolipin (PMID:16442164 ). Tafazzin is an important enzyme in the remodeling of cardiolipins, and opposite to cardiolipin synthase, it shows strong acyl specificity. This suggest that the specificity in cardiolipin composition is achieved through the remodeling steps. Mutation in the tafazzin gene disrupts the remodeling of cardiolipin and is the cause of Barth syndrome (BTHS), a X-linked human disease (PMID: 16973164 ). BTHS patients seems to lack acyl specificity and as a result, there are many potential cardiolipin species that can exists (PMID: 16226238 ). Common fatty acyl chains determined through methods such as gas chromatography and high-performance liquid chromatography are used to generate various cardiolipins and a representative molecule is chosen from each variation.
Structure
Data?1563873764
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0116832 (CL(8:0/8:0/10:0/10:0))

1'-[1,2-dioctanoyl-sn-glycero-3-phospho],3'-[1,2-didecanoyl-sn-glycero-3-phospho]-sn-glycerol CL(8:0/8:0/10:0/10:0)
  Mrv1652309111704152D          

 67 66  0  0  1  0            999 V2000
   28.9801   -8.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3984   -7.9046    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   28.9258   -6.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4528   -9.8262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3440   -5.9830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2253   -7.6197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5639   -7.5431    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.6598   -4.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6987   -5.2740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.7374   -4.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6210   -5.2740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7762   -5.2740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   26.4795   -6.1326    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.8473   -4.8685    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.9759   -5.1901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8473   -3.5722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9410   -9.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9798   -9.8262    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.0186   -9.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9022   -9.8262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
Download

3D MOL for HMDB0116832 (CL(8:0/8:0/10:0/10:0))

HMDB0116832
     RDKit          3D
CL(8:0/8:0/10:0/10:0)
150149  0  0  0  0  0  0  0  0999 V2000
    4.9916    6.9884    1.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8181    6.5948    2.9502 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4356    6.6130    3.5055 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4227    5.7114    2.9330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0849    5.8654    1.4781 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9852    4.8343    1.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5716    4.9013   -0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4902    3.8886   -0.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9814    3.8523   -1.9589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0312    2.7886   -2.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1479    2.9369   -1.4742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8261    1.5764   -2.7120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8428    0.5949   -2.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4524   -0.6252   -3.5030 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5542   -1.6989   -3.3902 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0823   -3.5950   -0.2015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9213   -4.6529    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.8953   -5.9798    1.7532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6980   -5.2018    2.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3237   -2.9101   -1.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6581   -2.1331   -4.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1623   -0.7711    3.3621 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8244    2.1421    3.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2908   -1.2583   -2.9894 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2623   -1.5822   -3.8592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4094   -1.3042   -5.0737 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9805   -2.2402   -3.3755 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1787   -2.1226   -1.9173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2525   -0.7995   -1.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3121    0.1593   -1.6000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4688    0.6595   -3.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6115    1.6843   -2.9365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9141    2.2701   -4.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7762    2.9943   -4.9259 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3247    4.1501   -4.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1953    7.6109    1.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2092    6.1135    0.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9286    7.6433    1.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3987    7.3563    3.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3356    5.6195    3.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0922    7.6848    3.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5343    6.3426    4.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7930    4.6485    3.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4762    5.7277    3.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6717    6.8709    1.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9368    5.6924    0.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3684    3.8633    1.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1249    5.1042    1.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4236    4.7741   -0.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1910    5.9489   -0.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
Download

3D SDF for HMDB0116832 (CL(8:0/8:0/10:0/10:0))

1'-[1,2-dioctanoyl-sn-glycero-3-phospho],3'-[1,2-didecanoyl-sn-glycero-3-phospho]-sn-glycerol CL(8:0/8:0/10:0/10:0)
  Mrv1652309111704152D          

 67 66  0  0  1  0            999 V2000
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 65 66  1  0  0  0  0
 66 67  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0116832

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC)OC(=O)CCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC)OC(=O)CCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C45H86O17P2/c1-5-9-13-17-19-23-26-30-43(48)56-36-41(62-45(50)32-28-24-20-18-14-10-6-2)38-60-64(53,54)58-34-39(46)33-57-63(51,52)59-37-40(61-44(49)31-27-22-16-12-8-4)35-55-42(47)29-25-21-15-11-7-3/h39-41,46H,5-38H2,1-4H3,(H,51,52)(H,53,54)/t39-,40+,41+/m0/s1

> <INCHI_KEY>
YAEVFMUDQXMEBM-NJZAESGASA-N

> <FORMULA>
C45H86O17P2

> <MOLECULAR_WEIGHT>
961.114

> <EXACT_MASS>
960.534025305

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
150

> <JCHEM_AVERAGE_POLARIZABILITY>
105.19974533035959

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-2,3-bis(decanoyloxy)propoxy][(2S)-3-({[(2R)-2,3-bis(octanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid

> <ALOGPS_LOGP>
6.10

> <JCHEM_LOGP>
11.26519444133333

> <ALOGPS_LOGS>
-5.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.191804358217231

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.589737614322373

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4105029523385797

> <JCHEM_POLAR_SURFACE_AREA>
236.94999999999996

> <JCHEM_REFRACTIVITY>
241.27370000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
50

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.07e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2,3-bis(decanoyloxy)propoxy((2S)-3-{[(2R)-2,3-bis(octanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0116832 (CL(8:0/8:0/10:0/10:0))

HMDB0116832
     RDKit          3D
CL(8:0/8:0/10:0/10:0)
150149  0  0  0  0  0  0  0  0999 V2000
    4.9916    6.9884    1.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
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 63 64  1  0
  1 65  1  0
  1 66  1  0
  1 67  1  0
  2 68  1  0
  2 69  1  0
  3 70  1  0
  3 71  1  0
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  4 73  1  0
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 64150  1  0
M  END
Download

PDB for HMDB0116832 (CL(8:0/8:0/10:0/10:0))

HEADER    PROTEIN                                 11-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1'-[1,2-dioctanoyl-sn-glycero-3-phospho],3'-[1,2-d
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-17         0                                  
HETATM    1  C   UNK     0      54.096 -16.519   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      53.010 -14.755   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      53.995 -12.932   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      53.112 -18.342   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      52.909 -11.168   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      54.554 -14.223   0.000  0.00  0.00           O+0
HETATM    7  H   UNK     0      51.453 -14.080   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0      49.765  -8.809   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      47.971  -9.845   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      46.177  -8.809   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      51.559  -9.845   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      44.382  -9.845   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      46.466 -11.369   0.000  0.00  0.00           O+0
HETATM   14  H   UNK     0      49.428 -11.448   0.000  0.00  0.00           H+0
HETATM   15  P   UNK     0      53.848  -9.088   0.000  0.00  0.00           P+0
HETATM   16  O   UNK     0      55.955  -9.688   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      53.848  -6.668   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      46.557 -17.306   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      44.762 -18.342   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      42.968 -17.306   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      48.351 -18.342   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      41.174 -18.342   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      43.206 -19.918   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0      46.168 -19.997   0.000  0.00  0.00           H+0
HETATM   25  P   UNK     0      50.640 -17.459   0.000  0.00  0.00           P+0
HETATM   26  O   UNK     0      50.640 -15.919   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      49.857 -19.431   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      43.049  -9.075   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      43.049  -7.635   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      41.716  -9.846   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      40.382  -9.075   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      39.049  -9.846   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      37.716  -9.075   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      36.384  -9.846   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      35.050  -9.075   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      33.717  -9.846   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      45.133 -12.139   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      45.133 -13.578   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      43.800 -11.367   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      42.467 -12.139   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      41.134 -11.367   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      39.801 -12.139   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      38.468 -11.367   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      37.135 -12.139   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      35.802 -11.367   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      39.840 -17.572   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      39.840 -16.132   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      38.507 -18.343   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      37.174 -17.572   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      35.841 -18.343   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      34.508 -17.572   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      33.175 -18.343   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      31.842 -17.572   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      30.509 -18.343   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      29.176 -17.572   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      27.843 -18.343   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      41.872 -20.688   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      41.872 -22.128   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      40.539 -19.917   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      39.206 -20.688   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      37.873 -19.917   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      36.540 -20.688   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      35.207 -19.917   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      33.874 -20.688   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      32.541 -19.917   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      31.208 -20.688   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      29.875 -19.917   0.000  0.00  0.00           C+0
CONECT    1    2    4                                                       
CONECT    2    1    6    7    3                                             
CONECT    3    2    5                                                       
CONECT    4    1   25                                                       
CONECT    5    3   15                                                       
CONECT    6    2                                                            
CONECT    7    2                                                            
CONECT    8    9   11                                                       
CONECT    9    8   13   14   10                                             
CONECT   10    9   12                                                       
CONECT   11    8   15                                                       
CONECT   12   10   28                                                       
CONECT   13    9   37                                                       
CONECT   14    9                                                            
CONECT   15   16   17    5   11                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   19   21                                                       
CONECT   19   18   23   24   20                                             
CONECT   20   19   22                                                       
CONECT   21   18   25                                                       
CONECT   22   20   46                                                       
CONECT   23   19   57                                                       
CONECT   24   19                                                            
CONECT   25    4   26   27   21                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   12   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   13   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44                                                            
CONECT   46   22   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55                                                            
CONECT   57   23   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   64                                                       
CONECT   64   63   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65   67                                                       
CONECT   67   66                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  132    0
END
Download

3D PDB for HMDB0116832 (CL(8:0/8:0/10:0/10:0))

COMPND    HMDB0116832
HETATM    1  C1  UNL     1       4.992   6.988   1.529  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.818   6.595   2.950  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.436   6.613   3.505  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.423   5.711   2.933  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.085   5.865   1.478  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.985   4.834   1.184  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.572   4.901  -0.268  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.490   3.889  -0.535  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.981   3.852  -1.959  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.031   2.789  -2.029  1.00  0.00           C  
HETATM   11  O1  UNL     1      -3.148   2.937  -1.474  1.00  0.00           O  
HETATM   12  O2  UNL     1      -1.826   1.576  -2.712  1.00  0.00           O  
HETATM   13  C11 UNL     1      -2.843   0.595  -2.746  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.452  -0.625  -3.503  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.554  -1.699  -3.390  1.00  0.00           C  
HETATM   16  O3  UNL     1      -3.711  -2.072  -2.079  1.00  0.00           O  
HETATM   17  P1  UNL     1      -4.884  -3.236  -1.822  1.00  0.00           P  
HETATM   18  O4  UNL     1      -6.208  -2.764  -2.387  1.00  0.00           O  
HETATM   19  O5  UNL     1      -4.448  -4.642  -2.666  1.00  0.00           O  
HETATM   20  O6  UNL     1      -5.082  -3.595  -0.201  1.00  0.00           O  
HETATM   21  C14 UNL     1      -5.921  -4.653   0.050  1.00  0.00           C  
HETATM   22  C15 UNL     1      -6.044  -4.909   1.551  1.00  0.00           C  
HETATM   23  O7  UNL     1      -6.895  -5.980   1.753  1.00  0.00           O  
HETATM   24  C16 UNL     1      -4.698  -5.202   2.157  1.00  0.00           C  
HETATM   25  O8  UNL     1      -4.777  -5.424   3.526  1.00  0.00           O  
HETATM   26  P2  UNL     1      -3.262  -5.750   4.189  1.00  0.00           P  
HETATM   27  O9  UNL     1      -3.286  -5.793   5.681  1.00  0.00           O  
HETATM   28  O10 UNL     1      -2.766  -7.296   3.651  1.00  0.00           O  
HETATM   29  O11 UNL     1      -2.093  -4.661   3.616  1.00  0.00           O  
HETATM   30  C17 UNL     1      -1.510  -3.968   4.664  1.00  0.00           C  
HETATM   31  C18 UNL     1      -0.469  -3.020   4.076  1.00  0.00           C  
HETATM   32  C19 UNL     1       0.513  -3.881   3.335  1.00  0.00           C  
HETATM   33  O12 UNL     1       1.541  -3.173   2.690  1.00  0.00           O  
HETATM   34  C20 UNL     1       2.495  -3.892   1.983  1.00  0.00           C  
HETATM   35  O13 UNL     1       2.360  -5.158   1.970  1.00  0.00           O  
HETATM   36  C21 UNL     1       3.629  -3.272   1.266  1.00  0.00           C  
HETATM   37  C22 UNL     1       4.443  -4.362   0.610  1.00  0.00           C  
HETATM   38  C23 UNL     1       5.634  -3.862  -0.136  1.00  0.00           C  
HETATM   39  C24 UNL     1       5.324  -2.910  -1.256  1.00  0.00           C  
HETATM   40  C25 UNL     1       6.655  -2.529  -1.879  1.00  0.00           C  
HETATM   41  C26 UNL     1       6.504  -1.569  -3.024  1.00  0.00           C  
HETATM   42  C27 UNL     1       5.658  -2.133  -4.145  1.00  0.00           C  
HETATM   43  O14 UNL     1      -1.114  -2.145   3.207  1.00  0.00           O  
HETATM   44  C28 UNL     1      -1.162  -0.771   3.362  1.00  0.00           C  
HETATM   45  O15 UNL     1      -0.576  -0.298   4.361  1.00  0.00           O  
HETATM   46  C29 UNL     1      -1.869   0.100   2.401  1.00  0.00           C  
HETATM   47  C30 UNL     1      -1.860   1.556   2.750  1.00  0.00           C  
HETATM   48  C31 UNL     1      -2.512   1.900   4.046  1.00  0.00           C  
HETATM   49  C32 UNL     1      -3.957   1.504   4.108  1.00  0.00           C  
HETATM   50  C33 UNL     1      -4.824   2.142   3.075  1.00  0.00           C  
HETATM   51  C34 UNL     1      -4.796   3.646   3.211  1.00  0.00           C  
HETATM   52  C35 UNL     1      -5.700   4.233   2.134  1.00  0.00           C  
HETATM   53  O16 UNL     1      -1.291  -1.258  -2.989  1.00  0.00           O  
HETATM   54  C36 UNL     1      -0.262  -1.582  -3.859  1.00  0.00           C  
HETATM   55  O17 UNL     1      -0.409  -1.304  -5.074  1.00  0.00           O  
HETATM   56  C37 UNL     1       0.980  -2.240  -3.375  1.00  0.00           C  
HETATM   57  C38 UNL     1       1.179  -2.123  -1.917  1.00  0.00           C  
HETATM   58  C39 UNL     1       1.252  -0.800  -1.287  1.00  0.00           C  
HETATM   59  C40 UNL     1       2.312   0.159  -1.600  1.00  0.00           C  
HETATM   60  C41 UNL     1       2.469   0.659  -3.002  1.00  0.00           C  
HETATM   61  C42 UNL     1       3.612   1.684  -2.937  1.00  0.00           C  
HETATM   62  C43 UNL     1       3.914   2.270  -4.267  1.00  0.00           C  
HETATM   63  C44 UNL     1       2.776   2.994  -4.926  1.00  0.00           C  
HETATM   64  C45 UNL     1       2.325   4.150  -4.054  1.00  0.00           C  
HETATM   65  H1  UNL     1       4.195   7.611   1.119  1.00  0.00           H  
HETATM   66  H2  UNL     1       5.209   6.113   0.880  1.00  0.00           H  
HETATM   67  H3  UNL     1       5.929   7.643   1.408  1.00  0.00           H  
HETATM   68  H4  UNL     1       5.399   7.356   3.562  1.00  0.00           H  
HETATM   69  H5  UNL     1       5.336   5.619   3.170  1.00  0.00           H  
HETATM   70  H6  UNL     1       3.092   7.685   3.555  1.00  0.00           H  
HETATM   71  H7  UNL     1       3.534   6.343   4.606  1.00  0.00           H  
HETATM   72  H8  UNL     1       2.793   4.648   3.126  1.00  0.00           H  
HETATM   73  H9  UNL     1       1.476   5.728   3.559  1.00  0.00           H  
HETATM   74  H10 UNL     1       1.672   6.871   1.287  1.00  0.00           H  
HETATM   75  H11 UNL     1       2.937   5.692   0.798  1.00  0.00           H  
HETATM   76  H12 UNL     1       1.368   3.863   1.504  1.00  0.00           H  
HETATM   77  H13 UNL     1       0.125   5.104   1.826  1.00  0.00           H  
HETATM   78  H14 UNL     1       1.424   4.774  -0.954  1.00  0.00           H  
HETATM   79  H15 UNL     1       0.191   5.949  -0.437  1.00  0.00           H  
HETATM   80  H16 UNL     1      -0.111   2.875  -0.301  1.00  0.00           H  
HETATM   81  H17 UNL     1      -1.379   4.145   0.096  1.00  0.00           H  
HETATM   82  H18 UNL     1      -1.445   4.822  -2.273  1.00  0.00           H  
HETATM   83  H19 UNL     1      -0.142   3.649  -2.622  1.00  0.00           H  
HETATM   84  H20 UNL     1      -3.737   1.026  -3.275  1.00  0.00           H  
HETATM   85  H21 UNL     1      -3.089   0.320  -1.701  1.00  0.00           H  
HETATM   86  H22 UNL     1      -2.402  -0.401  -4.581  1.00  0.00           H  
HETATM   87  H23 UNL     1      -4.472  -1.203  -3.770  1.00  0.00           H  
HETATM   88  H24 UNL     1      -3.270  -2.498  -4.075  1.00  0.00           H  
HETATM   89  H25 UNL     1      -3.518  -4.882  -2.355  1.00  0.00           H  
HETATM   90  H26 UNL     1      -5.499  -5.588  -0.396  1.00  0.00           H  
HETATM   91  H27 UNL     1      -6.937  -4.423  -0.335  1.00  0.00           H  
HETATM   92  H28 UNL     1      -6.524  -4.011   2.038  1.00  0.00           H  
HETATM   93  H29 UNL     1      -7.306  -5.983   2.665  1.00  0.00           H  
HETATM   94  H30 UNL     1      -4.291  -6.095   1.633  1.00  0.00           H  
HETATM   95  H31 UNL     1      -4.037  -4.329   1.998  1.00  0.00           H  
HETATM   96  H32 UNL     1      -1.977  -7.604   4.188  1.00  0.00           H  
HETATM   97  H33 UNL     1      -2.286  -3.358   5.176  1.00  0.00           H  
HETATM   98  H34 UNL     1      -1.060  -4.641   5.416  1.00  0.00           H  
HETATM   99  H35 UNL     1       0.004  -2.447   4.903  1.00  0.00           H  
HETATM  100  H36 UNL     1      -0.065  -4.439   2.564  1.00  0.00           H  
HETATM  101  H37 UNL     1       0.972  -4.602   4.064  1.00  0.00           H  
HETATM  102  H38 UNL     1       3.295  -2.578   0.468  1.00  0.00           H  
HETATM  103  H39 UNL     1       4.295  -2.711   1.975  1.00  0.00           H  
HETATM  104  H40 UNL     1       4.837  -5.029   1.428  1.00  0.00           H  
HETATM  105  H41 UNL     1       3.772  -4.987  -0.008  1.00  0.00           H  
HETATM  106  H42 UNL     1       6.325  -3.324   0.568  1.00  0.00           H  
HETATM  107  H43 UNL     1       6.246  -4.700  -0.548  1.00  0.00           H  
HETATM  108  H44 UNL     1       4.798  -2.015  -0.879  1.00  0.00           H  
HETATM  109  H45 UNL     1       4.681  -3.396  -2.034  1.00  0.00           H  
HETATM  110  H46 UNL     1       7.231  -3.404  -2.185  1.00  0.00           H  
HETATM  111  H47 UNL     1       7.258  -1.992  -1.099  1.00  0.00           H  
HETATM  112  H48 UNL     1       7.541  -1.445  -3.453  1.00  0.00           H  
HETATM  113  H49 UNL     1       6.187  -0.566  -2.735  1.00  0.00           H  
HETATM  114  H50 UNL     1       5.699  -1.406  -4.986  1.00  0.00           H  
HETATM  115  H51 UNL     1       4.598  -2.260  -3.857  1.00  0.00           H  
HETATM  116  H52 UNL     1       6.113  -3.068  -4.514  1.00  0.00           H  
HETATM  117  H53 UNL     1      -1.508  -0.094   1.371  1.00  0.00           H  
HETATM  118  H54 UNL     1      -2.957  -0.211   2.444  1.00  0.00           H  
HETATM  119  H55 UNL     1      -0.790   1.897   2.729  1.00  0.00           H  
HETATM  120  H56 UNL     1      -2.385   2.085   1.922  1.00  0.00           H  
HETATM  121  H57 UNL     1      -2.428   3.000   4.220  1.00  0.00           H  
HETATM  122  H58 UNL     1      -2.002   1.407   4.891  1.00  0.00           H  
HETATM  123  H59 UNL     1      -4.086   0.412   4.096  1.00  0.00           H  
HETATM  124  H60 UNL     1      -4.337   1.842   5.107  1.00  0.00           H  
HETATM  125  H61 UNL     1      -5.880   1.838   3.309  1.00  0.00           H  
HETATM  126  H62 UNL     1      -4.624   1.802   2.055  1.00  0.00           H  
HETATM  127  H63 UNL     1      -3.798   4.072   3.096  1.00  0.00           H  
HETATM  128  H64 UNL     1      -5.151   3.892   4.234  1.00  0.00           H  
HETATM  129  H65 UNL     1      -6.042   3.463   1.413  1.00  0.00           H  
HETATM  130  H66 UNL     1      -5.224   5.053   1.580  1.00  0.00           H  
HETATM  131  H67 UNL     1      -6.603   4.638   2.678  1.00  0.00           H  
HETATM  132  H68 UNL     1       0.813  -3.376  -3.555  1.00  0.00           H  
HETATM  133  H69 UNL     1       1.812  -2.010  -4.010  1.00  0.00           H  
HETATM  134  H70 UNL     1       0.461  -2.788  -1.334  1.00  0.00           H  
HETATM  135  H71 UNL     1       2.179  -2.636  -1.700  1.00  0.00           H  
HETATM  136  H72 UNL     1       0.271  -0.232  -1.353  1.00  0.00           H  
HETATM  137  H73 UNL     1       1.290  -1.003  -0.154  1.00  0.00           H  
HETATM  138  H74 UNL     1       3.318  -0.148  -1.170  1.00  0.00           H  
HETATM  139  H75 UNL     1       2.085   1.100  -0.986  1.00  0.00           H  
HETATM  140  H76 UNL     1       1.525   1.095  -3.340  1.00  0.00           H  
HETATM  141  H77 UNL     1       2.870  -0.159  -3.632  1.00  0.00           H  
HETATM  142  H78 UNL     1       4.496   1.120  -2.580  1.00  0.00           H  
HETATM  143  H79 UNL     1       3.342   2.408  -2.164  1.00  0.00           H  
HETATM  144  H80 UNL     1       4.770   2.977  -4.123  1.00  0.00           H  
HETATM  145  H81 UNL     1       4.291   1.503  -4.978  1.00  0.00           H  
HETATM  146  H82 UNL     1       3.093   3.444  -5.889  1.00  0.00           H  
HETATM  147  H83 UNL     1       1.912   2.356  -5.136  1.00  0.00           H  
HETATM  148  H84 UNL     1       2.224   3.877  -3.005  1.00  0.00           H  
HETATM  149  H85 UNL     1       3.060   4.995  -4.097  1.00  0.00           H  
HETATM  150  H86 UNL     1       1.351   4.559  -4.419  1.00  0.00           H  
CONECT    1    2   65   66   67
CONECT    2    3   68   69
CONECT    3    4   70   71
CONECT    4    5   72   73
CONECT    5    6   74   75
CONECT    6    7   76   77
CONECT    7    8   78   79
CONECT    8    9   80   81
CONECT    9   10   82   83
CONECT   10   11   11   12
CONECT   12   13
CONECT   13   14   84   85
CONECT   14   15   53   86
CONECT   15   16   87   88
CONECT   16   17
CONECT   17   18   18   19   20
CONECT   19   89
CONECT   20   21
CONECT   21   22   90   91
CONECT   22   23   24   92
CONECT   23   93
CONECT   24   25   94   95
CONECT   25   26
CONECT   26   27   27   28   29
CONECT   28   96
CONECT   29   30
CONECT   30   31   97   98
CONECT   31   32   43   99
CONECT   32   33  100  101
CONECT   33   34
CONECT   34   35   35   36
CONECT   36   37  102  103
CONECT   37   38  104  105
CONECT   38   39  106  107
CONECT   39   40  108  109
CONECT   40   41  110  111
CONECT   41   42  112  113
CONECT   42  114  115  116
CONECT   43   44
CONECT   44   45   45   46
CONECT   46   47  117  118
CONECT   47   48  119  120
CONECT   48   49  121  122
CONECT   49   50  123  124
CONECT   50   51  125  126
CONECT   51   52  127  128
CONECT   52  129  130  131
CONECT   53   54
CONECT   54   55   55   56
CONECT   56   57  132  133
CONECT   57   58  134  135
CONECT   58   59  136  137
CONECT   59   60  138  139
CONECT   60   61  140  141
CONECT   61   62  142  143
CONECT   62   63  144  145
CONECT   63   64  146  147
CONECT   64  148  149  150
END
Download

SMILES for HMDB0116832 (CL(8:0/8:0/10:0/10:0))

[H][C@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC)OC(=O)CCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC)OC(=O)CCCCCCCCC
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INCHI for HMDB0116832 (CL(8:0/8:0/10:0/10:0))

InChI=1S/C45H86O17P2/c1-5-9-13-17-19-23-26-30-43(48)56-36-41(62-45(50)32-28-24-20-18-14-10-6-2)38-60-64(53,54)58-34-39(46)33-57-63(51,52)59-37-40(61-44(49)31-27-22-16-12-8-4)35-55-42(47)29-25-21-15-11-7-3/h39-41,46H,5-38H2,1-4H3,(H,51,52)(H,53,54)/t39-,40+,41+/m0/s1
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View in JSmolView Stereo Labels
Synonyms
ValueSource
[(2R)-2,3-Bis(decanoyloxy)propoxy][(2S)-3-({[(2R)-2,3-bis(octanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinateGenerator
1'-[1,2-dicapryloyl-rac-glycero-3-phospho],3'-[1,2-dianimal fats-rac-glycero-3-phospho]-glycerolLipid Annotator, HMDB
1'-[1,2-dioctanoyl-rac-glycero-3-phospho],3'-[1,2-didecanoic acid-rac-glycero-3-phospho]-glycerolLipid Annotator, HMDB
Cardiolipin(8:0/8:0/10:0/10:0)Lipid Annotator, HMDB
Cardiolipin(36:0)Lipid Annotator, HMDB
CL(36:0)Lipid Annotator, HMDB
CL(8:0/8:0/10:0/10:0)Lipid Annotator
CL(1'-[8:0/8:0],3'-[10:0/10:0])Lipid Annotator, HMDB
Chemical FormulaC45H86O17P2
Average Molecular Weight961.114
Monoisotopic Molecular Weight960.534025305
IUPAC Name[(2R)-2,3-bis(decanoyloxy)propoxy][(2S)-3-({[(2R)-2,3-bis(octanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid
Traditional Name(2R)-2,3-bis(decanoyloxy)propoxy((2S)-3-{[(2R)-2,3-bis(octanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC)OC(=O)CCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC)OC(=O)CCCCCCCCC
InChI Identifier
InChI=1S/C45H86O17P2/c1-5-9-13-17-19-23-26-30-43(48)56-36-41(62-45(50)32-28-24-20-18-14-10-6-2)38-60-64(53,54)58-34-39(46)33-57-63(51,52)59-37-40(61-44(49)31-27-22-16-12-8-4)35-55-42(47)29-25-21-15-11-7-3/h39-41,46H,5-38H2,1-4H3,(H,51,52)(H,53,54)/t39-,40+,41+/m0/s1
InChI KeyYAEVFMUDQXMEBM-NJZAESGASA-N
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
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Health effect
Disposition
Biological location
Process
Naturally occurring process
Role
Biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP6.1ALOGPS
logP11.27ChemAxon
logS-5.5ALOGPS
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 Count50ChemAxon
Refractivity241.27 m³·mol⁻¹ChemAxon
Polarizability105.2 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+291.51730932474
DeepCCS[M-H]-288.38130932474
DeepCCS[M-2H]-322.98630932474
DeepCCS[M+Na]+298.83630932474
AllCCS[M+H]+313.132859911
AllCCS[M+H-H2O]+313.632859911
AllCCS[M+NH4]+312.632859911
AllCCS[M+Na]+312.532859911
AllCCS[M-H]-313.132859911
AllCCS[M+Na-2H]-319.132859911
AllCCS[M+HCOO]-325.732859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CL(8:0/8:0/10:0/10:0) 10V, Negative-QTOFsplash10-004i-0300900000-a4fabc2e4488f796e25f2017-10-05Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CL(8:0/8:0/10:0/10:0) 20V, Negative-QTOFsplash10-004i-0211900000-aa37e4d65ecef85a2eb82017-10-05Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CL(8:0/8:0/10:0/10:0) 40V, Negative-QTOFsplash10-05kf-0933100000-b2d27921c7a282d8a59f2017-10-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131823441
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Houtkooper RH, Vaz FM: Cardiolipin, the heart of mitochondrial metabolism. Cell Mol Life Sci. 2008 Aug;65(16):2493-506. doi: 10.1007/s00018-008-8030-5. [PubMed:18425414 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  7. Schlame M, Ren M: The role of cardiolipin in the structural organization of mitochondrial membranes. Biochim Biophys Acta. 2009 Oct;1788(10):2080-3. doi: 10.1016/j.bbamem.2009.04.019. Epub 2009 May 4. [PubMed:19413994 ]
  8. Schlame M, Rua D, Greenberg ML: The biosynthesis and functional role of cardiolipin. Prog Lipid Res. 2000 May;39(3):257-88. [PubMed:10799718 ]
  9. McMillin JB, Dowhan W: Cardiolipin and apoptosis. Biochim Biophys Acta. 2002 Dec 30;1585(2-3):97-107. [PubMed:12531542 ]
  10. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  11. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.