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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-10-09 08:20:48 UTC

Update Date

2022-11-30 19:10:32 UTC

HMDB ID

HMDB0056519

Secondary Accession Numbers

HMDB56519

Metabolite Identification

Common Name

CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))

Description

CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z)) is a cardiolipin (CL). Cardiolipins are sometimes called 'double' phospholipids because they have four fatty acid tails, instead of the usual two. They are glycerophospholipids in which the O1 and O3 oxygen atoms of the central glycerol moiety are each linked to one 1,3-diacylglyerol 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(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z)) contains one chain of hexadecanoic acid at the C1 position, one chain of octadecanoic acid at the C2 position, two chains of (9Z,12Z-octadecadienoyl) at the C3 and C4 positions fatty acids. 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 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 ). Cardiolipins (bisphosphatidyl glycerol) are an important component of the inner mitochondrial membrane, where they constitute about 20% of the total lipid. While most lipids are made in the endoplasmic reticulum, cardiolipin is synthesized on the matrix side of the inner mitochondrial membrane and are important for mitochondrial respiratory capacity. They are highly abundant in metabolically active cells (heart, muscle) and play an important role in the blood clotting process. Tafazzin is an important enzyme in the remodeling of cardiolipins, and in contrast to cardiolipin synthase, it shows strong acyl specificity. This suggests that the specificity in cardiolipin composition is achieved through the remodeling steps. Mutation in the tafazzin gene disrupts the remodeling of cardiolipins and is the cause of Barth syndrome (BTHS), an X-linked human disease (PMID: 16973164 ). BTHS patients seem to lack acyl specificity. As a result, there are many potential cardiolipin species that can exist (PMID: 16226238 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))
  Mrv1652303302020162D          

101100  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
   24.8926   -6.0903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   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
   22.0574   -9.8262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1458  -10.6705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7327  -10.7128    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.1285   -9.3528    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   27.1285   -8.5278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7090  -10.4093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0617   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0617   -4.0901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3476   -5.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6335   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9194   -5.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2053   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4912   -5.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7770   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0629   -5.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3488   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6347   -5.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9205   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2064   -5.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4923   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7782   -5.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0641   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3500   -5.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1782   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1782   -7.2742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4641   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7500   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0358   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3217   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6076   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8935   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1794   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4653   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7512   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0371   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3229   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6088   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8947   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1806   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4665   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7524   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0383   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3430   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3430   -8.6423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6288   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9147   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2006   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4865   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7723   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0582   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3441   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6300   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8050   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0909   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3768   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5518   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8377   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1235   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4094   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6953   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9812   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4314  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4314  -11.8544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7173  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0032  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2890  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5749  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8608  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1467  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4326  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7185  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8935  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1794  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4653  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6403  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9261  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2120  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4979  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7838  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0697  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  1  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  9  8  1  0  0  0  0
  9 13  1  0  0  0  0
  9 14  1  1  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 12 10  1  0  0  0  0
 12 28  1  0  0  0  0
 13 45  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 15  5  1  0  0  0  0
 15 11  1  0  0  0  0
 19 18  1  0  0  0  0
 19 23  1  0  0  0  0
 19 24  1  1  0  0  0
 20 19  1  0  0  0  0
 21 18  1  0  0  0  0
 22 20  1  0  0  0  0
 22 64  1  0  0  0  0
 23 83  1  0  0  0  0
 25  4  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 25 21  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
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 45 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
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 64 66  1  0  0  0  0
 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
 68 69  1  0  0  0  0
 69 70  1  0  0  0  0
 70 71  1  0  0  0  0
 71 72  1  0  0  0  0
 72 73  1  0  0  0  0
 73 74  2  0  0  0  0
 74 75  1  0  0  0  0
 75 76  1  0  0  0  0
 76 77  2  0  0  0  0
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 78 79  1  0  0  0  0
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 95 96  2  0  0  0  0
 96 97  1  0  0  0  0
 97 98  1  0  0  0  0
 98 99  1  0  0  0  0
 99100  1  0  0  0  0
100101  1  0  0  0  0
M  END

HMDB0056519
     RDKit          3D
CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))
244243  0  0  0  0  0  0  0  0999 V2000
    0.8761    9.9954   -1.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4524    8.5511   -1.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2663    7.8710   -0.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1613    6.4445   -0.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4795    6.2579   -1.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8518    4.8573   -1.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0256    4.0973   -2.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8668    4.5298   -3.7274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8613    3.8966   -4.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0118    2.9851   -4.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2824    2.2415   -3.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7357    2.4578   -2.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1572    1.7274   -1.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3360    1.9357   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9022    1.3042    0.9785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1540   -0.1838    0.8861 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7268   -0.6088    2.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1424   -1.9795    2.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3763   -2.2408    2.0954 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3583   -3.0477    2.6798 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0118   -4.3233    2.7668 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1363   -5.4558    3.1355 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4828   -6.2306    2.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2898   -5.7446    1.5539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2483   -6.9030    0.4171 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.2875   -7.8135    1.0773 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0424   -7.9316   -0.0040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8328   -6.2050   -0.9564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2278   -6.2070   -1.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5107   -5.5577   -2.4321 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8628   -5.4519   -2.6849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7378   -4.2814   -2.5003 C   0  0  0  0  0  0  0  0  0  0  0  0
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CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))
  Mrv1652303302020162D          

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100101  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0056519

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C79H146O17P2/c1-5-9-13-17-21-25-29-33-36-40-44-48-52-56-60-64-77(82)90-70-75(96-79(84)66-62-58-54-50-46-42-38-35-31-27-23-19-15-11-7-3)72-94-98(87,88)92-68-73(80)67-91-97(85,86)93-71-74(69-89-76(81)63-59-55-51-47-43-39-32-28-24-20-16-12-8-4)95-78(83)65-61-57-53-49-45-41-37-34-30-26-22-18-14-10-6-2/h21,23,25,27,33,35-36,38,73-75,80H,5-20,22,24,26,28-32,34,37,39-72H2,1-4H3,(H,85,86)(H,87,88)/b25-21-,27-23-,36-33-,38-35-/t73-,74+,75+/m0/s1

> <INCHI_KEY>
UOAMDLHONFQUPT-QJCNJITASA-N

> <FORMULA>
C79H146O17P2

> <MOLECULAR_WEIGHT>
1429.968

> <EXACT_MASS>
1429.003527237

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
244

> <JCHEM_AVERAGE_POLARIZABILITY>
172.69812584980787

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy][(2S)-3-({[(2R)-3-(hexadecanoyloxy)-2-(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid

> <ALOGPS_LOGP>
9.09

> <JCHEM_LOGP>
24.932842424666664

> <ALOGPS_LOGS>
-7.29

> <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>
402.17409999999984

> <JCHEM_ROTATABLE_BOND_COUNT>
80

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.30e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy((2S)-3-{[(2R)-3-(hexadecanoyloxy)-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0056519
     RDKit          3D
CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))
244243  0  0  0  0  0  0  0  0999 V2000
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M  END

HEADER    PROTEIN                                 30-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-MAR-20         0                                  
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HETATM   40  C   UNK     0      28.385  -9.846   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      27.052  -9.075   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      25.719  -9.846   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      24.386  -9.075   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      23.053  -9.846   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      45.133 -12.139   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      45.133 -13.579   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      43.800 -11.367   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      42.467 -12.139   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      41.133 -11.367   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      39.801 -12.139   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      38.468 -11.367   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      37.135 -12.139   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      35.802 -11.367   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      34.469 -12.139   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      33.136 -11.367   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      31.803 -12.139   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      30.469 -11.367   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      29.136 -12.139   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      27.803 -11.367   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      26.470 -12.139   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      25.137 -11.367   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      23.804 -12.139   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      22.471 -11.367   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      39.840 -17.572   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      39.840 -16.132   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      38.507 -18.343   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      37.174 -17.572   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      35.841 -18.343   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      34.508 -17.572   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      33.175 -18.343   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      31.842 -17.572   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      30.509 -18.343   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      29.176 -17.572   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      27.636 -17.572   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      26.303 -18.343   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      24.970 -17.572   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      23.430 -17.572   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      22.097 -18.343   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0      20.764 -17.572   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0      19.431 -18.343   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0      18.098 -17.572   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0      16.765 -18.343   0.000  0.00  0.00           C+0
HETATM   83  C   UNK     0      41.872 -20.688   0.000  0.00  0.00           C+0
HETATM   84  O   UNK     0      41.872 -22.128   0.000  0.00  0.00           O+0
HETATM   85  C   UNK     0      40.539 -19.917   0.000  0.00  0.00           C+0
HETATM   86  C   UNK     0      39.206 -20.688   0.000  0.00  0.00           C+0
HETATM   87  C   UNK     0      37.873 -19.917   0.000  0.00  0.00           C+0
HETATM   88  C   UNK     0      36.540 -20.688   0.000  0.00  0.00           C+0
HETATM   89  C   UNK     0      35.207 -19.917   0.000  0.00  0.00           C+0
HETATM   90  C   UNK     0      33.874 -20.688   0.000  0.00  0.00           C+0
HETATM   91  C   UNK     0      32.541 -19.917   0.000  0.00  0.00           C+0
HETATM   92  C   UNK     0      31.208 -20.688   0.000  0.00  0.00           C+0
HETATM   93  C   UNK     0      29.668 -20.688   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0      28.335 -19.917   0.000  0.00  0.00           C+0
HETATM   95  C   UNK     0      27.002 -20.688   0.000  0.00  0.00           C+0
HETATM   96  C   UNK     0      25.462 -20.688   0.000  0.00  0.00           C+0
HETATM   97  C   UNK     0      24.129 -19.917   0.000  0.00  0.00           C+0
HETATM   98  C   UNK     0      22.796 -20.688   0.000  0.00  0.00           C+0
HETATM   99  C   UNK     0      21.463 -19.917   0.000  0.00  0.00           C+0
HETATM  100  C   UNK     0      20.130 -20.688   0.000  0.00  0.00           C+0
HETATM  101  C   UNK     0      18.797 -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   45                                                       
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   64                                                       
CONECT   23   19   83                                                       
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   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                                                            
CONECT   45   13   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62                                                            
CONECT   64   22   65   66                                                  
CONECT   65   64                                                            
CONECT   66   64   67                                                       
CONECT   67   66   68                                                       
CONECT   68   67   69                                                       
CONECT   69   68   70                                                       
CONECT   70   69   71                                                       
CONECT   71   70   72                                                       
CONECT   72   71   73                                                       
CONECT   73   72   74                                                       
CONECT   74   73   75                                                       
CONECT   75   74   76                                                       
CONECT   76   75   77                                                       
CONECT   77   76   78                                                       
CONECT   78   77   79                                                       
CONECT   79   78   80                                                       
CONECT   80   79   81                                                       
CONECT   81   80   82                                                       
CONECT   82   81                                                            
CONECT   83   23   84   85                                                  
CONECT   84   83                                                            
CONECT   85   83   86                                                       
CONECT   86   85   87                                                       
CONECT   87   86   88                                                       
CONECT   88   87   89                                                       
CONECT   89   88   90                                                       
CONECT   90   89   91                                                       
CONECT   91   90   92                                                       
CONECT   92   91   93                                                       
CONECT   93   92   94                                                       
CONECT   94   93   95                                                       
CONECT   95   94   96                                                       
CONECT   96   95   97                                                       
CONECT   97   96   98                                                       
CONECT   98   97   99                                                       
CONECT   99   98  100                                                       
CONECT  100   99  101                                                       
CONECT  101  100                                                            
MASTER        0    0    0    0    0    0    0    0  101    0  200    0
END

COMPND    HMDB0056519
HETATM    1  C1  UNL     1       0.876   9.995  -1.560  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.452   8.551  -1.873  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.266   7.871  -0.557  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.161   6.444  -0.615  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.480   6.258  -1.338  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.852   4.857  -1.333  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.026   4.097  -2.373  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.867   4.530  -3.727  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.861   3.897  -4.546  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.012   2.985  -4.355  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.282   2.241  -3.125  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.736   2.458  -2.686  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.157   1.727  -1.475  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.336   1.936  -0.245  1.00  0.00           C  
HETATM   15  C15 UNL     1       1.902   1.304   0.979  1.00  0.00           C  
HETATM   16  C16 UNL     1       2.154  -0.184   0.886  1.00  0.00           C  
HETATM   17  C17 UNL     1       2.727  -0.609   2.235  1.00  0.00           C  
HETATM   18  C18 UNL     1       3.142  -1.980   2.339  1.00  0.00           C  
HETATM   19  O1  UNL     1       4.376  -2.241   2.095  1.00  0.00           O  
HETATM   20  O2  UNL     1       2.358  -3.048   2.680  1.00  0.00           O  
HETATM   21  C19 UNL     1       3.012  -4.323   2.767  1.00  0.00           C  
HETATM   22  C20 UNL     1       2.136  -5.456   3.136  1.00  0.00           C  
HETATM   23  C21 UNL     1       1.483  -6.231   2.045  1.00  0.00           C  
HETATM   24  O3  UNL     1       0.290  -5.745   1.554  1.00  0.00           O  
HETATM   25  P1  UNL     1      -0.248  -6.903   0.417  1.00  0.00           P  
HETATM   26  O4  UNL     1      -1.287  -7.813   1.077  1.00  0.00           O  
HETATM   27  O5  UNL     1       1.042  -7.932  -0.004  1.00  0.00           O  
HETATM   28  O6  UNL     1      -0.833  -6.205  -0.956  1.00  0.00           O  
HETATM   29  C22 UNL     1      -2.228  -6.207  -1.075  1.00  0.00           C  
HETATM   30  C23 UNL     1      -2.511  -5.558  -2.432  1.00  0.00           C  
HETATM   31  O7  UNL     1      -3.863  -5.452  -2.685  1.00  0.00           O  
HETATM   32  C24 UNL     1      -1.738  -4.281  -2.500  1.00  0.00           C  
HETATM   33  O8  UNL     1      -0.379  -4.498  -2.200  1.00  0.00           O  
HETATM   34  P2  UNL     1       0.437  -2.982  -2.331  1.00  0.00           P  
HETATM   35  O9  UNL     1       1.902  -3.148  -2.019  1.00  0.00           O  
HETATM   36  O10 UNL     1      -0.255  -2.013  -1.146  1.00  0.00           O  
HETATM   37  O11 UNL     1       0.213  -2.403  -3.895  1.00  0.00           O  
HETATM   38  C25 UNL     1       1.415  -2.371  -4.581  1.00  0.00           C  
HETATM   39  C26 UNL     1       1.130  -2.000  -6.028  1.00  0.00           C  
HETATM   40  C27 UNL     1       0.124  -0.922  -6.127  1.00  0.00           C  
HETATM   41  O12 UNL     1      -0.763  -1.059  -5.061  1.00  0.00           O  
HETATM   42  C28 UNL     1      -1.914  -0.371  -4.752  1.00  0.00           C  
HETATM   43  O13 UNL     1      -2.276   0.505  -5.562  1.00  0.00           O  
HETATM   44  C29 UNL     1      -2.623  -0.716  -3.473  1.00  0.00           C  
HETATM   45  C30 UNL     1      -3.821   0.110  -3.272  1.00  0.00           C  
HETATM   46  C31 UNL     1      -4.401  -0.145  -1.839  1.00  0.00           C  
HETATM   47  C32 UNL     1      -3.377   0.248  -0.858  1.00  0.00           C  
HETATM   48  C33 UNL     1      -3.840   0.084   0.605  1.00  0.00           C  
HETATM   49  C34 UNL     1      -2.719   0.545   1.462  1.00  0.00           C  
HETATM   50  C35 UNL     1      -2.849   0.501   2.946  1.00  0.00           C  
HETATM   51  C36 UNL     1      -1.524   1.073   3.471  1.00  0.00           C  
HETATM   52  C37 UNL     1      -1.408   1.133   4.951  1.00  0.00           C  
HETATM   53  C38 UNL     1      -0.066   1.732   5.348  1.00  0.00           C  
HETATM   54  C39 UNL     1       0.100   1.816   6.823  1.00  0.00           C  
HETATM   55  C40 UNL     1       1.457   2.422   7.175  1.00  0.00           C  
HETATM   56  C41 UNL     1       2.574   1.601   6.614  1.00  0.00           C  
HETATM   57  C42 UNL     1       2.640   0.191   7.132  1.00  0.00           C  
HETATM   58  C43 UNL     1       2.870   0.127   8.608  1.00  0.00           C  
HETATM   59  O14 UNL     1       2.233  -2.011  -6.865  1.00  0.00           O  
HETATM   60  C44 UNL     1       2.507  -3.035  -7.763  1.00  0.00           C  
HETATM   61  O15 UNL     1       1.573  -3.952  -7.732  1.00  0.00           O  
HETATM   62  C45 UNL     1       3.573  -3.286  -8.675  1.00  0.00           C  
HETATM   63  C46 UNL     1       4.533  -2.384  -9.284  1.00  0.00           C  
HETATM   64  C47 UNL     1       4.124  -1.310 -10.177  1.00  0.00           C  
HETATM   65  C48 UNL     1       3.499  -0.056  -9.771  1.00  0.00           C  
HETATM   66  C49 UNL     1       4.439   0.910  -9.041  1.00  0.00           C  
HETATM   67  C50 UNL     1       3.632   2.178  -8.853  1.00  0.00           C  
HETATM   68  C51 UNL     1       4.349   3.356  -8.373  1.00  0.00           C  
HETATM   69  C52 UNL     1       5.034   3.367  -7.063  1.00  0.00           C  
HETATM   70  C53 UNL     1       4.134   3.198  -5.874  1.00  0.00           C  
HETATM   71  C54 UNL     1       4.961   3.402  -4.612  1.00  0.00           C  
HETATM   72  C55 UNL     1       6.049   2.407  -4.407  1.00  0.00           C  
HETATM   73  C56 UNL     1       6.825   2.778  -3.165  1.00  0.00           C  
HETATM   74  C57 UNL     1       5.954   2.786  -1.946  1.00  0.00           C  
HETATM   75  C58 UNL     1       6.717   3.204  -0.679  1.00  0.00           C  
HETATM   76  C59 UNL     1       7.832   2.251  -0.366  1.00  0.00           C  
HETATM   77  C60 UNL     1       8.604   2.651   0.871  1.00  0.00           C  
HETATM   78  C61 UNL     1       9.251   4.011   0.733  1.00  0.00           C  
HETATM   79  O16 UNL     1       1.360  -5.299   4.277  1.00  0.00           O  
HETATM   80  C62 UNL     1       1.455  -5.927   5.487  1.00  0.00           C  
HETATM   81  O17 UNL     1       2.321  -6.779   5.702  1.00  0.00           O  
HETATM   82  C63 UNL     1       0.481  -5.587   6.600  1.00  0.00           C  
HETATM   83  C64 UNL     1       0.054  -4.151   6.447  1.00  0.00           C  
HETATM   84  C65 UNL     1      -0.988  -3.789   7.445  1.00  0.00           C  
HETATM   85  C66 UNL     1      -1.398  -2.320   7.272  1.00  0.00           C  
HETATM   86  C67 UNL     1      -2.529  -2.100   8.251  1.00  0.00           C  
HETATM   87  C68 UNL     1      -3.027  -0.646   8.213  1.00  0.00           C  
HETATM   88  C69 UNL     1      -4.212  -0.623   9.170  1.00  0.00           C  
HETATM   89  C70 UNL     1      -4.807   0.696   9.317  1.00  0.00           C  
HETATM   90  C71 UNL     1      -6.034   0.968   8.958  1.00  0.00           C  
HETATM   91  C72 UNL     1      -7.023   0.045   8.345  1.00  0.00           C  
HETATM   92  C73 UNL     1      -7.421   0.652   7.040  1.00  0.00           C  
HETATM   93  C74 UNL     1      -7.263   0.147   5.854  1.00  0.00           C  
HETATM   94  C75 UNL     1      -6.643  -1.153   5.582  1.00  0.00           C  
HETATM   95  C76 UNL     1      -7.635  -2.066   4.849  1.00  0.00           C  
HETATM   96  C77 UNL     1      -8.068  -1.437   3.565  1.00  0.00           C  
HETATM   97  C78 UNL     1      -9.046  -2.324   2.826  1.00  0.00           C  
HETATM   98  C79 UNL     1      -8.416  -3.652   2.477  1.00  0.00           C  
HETATM   99  H1  UNL     1       0.509  10.308  -0.570  1.00  0.00           H  
HETATM  100  H2  UNL     1       0.568  10.687  -2.387  1.00  0.00           H  
HETATM  101  H3  UNL     1       1.973  10.005  -1.508  1.00  0.00           H  
HETATM  102  H4  UNL     1       1.259   8.130  -2.503  1.00  0.00           H  
HETATM  103  H5  UNL     1      -0.522   8.658  -2.414  1.00  0.00           H  
HETATM  104  H6  UNL     1      -0.446   8.501   0.049  1.00  0.00           H  
HETATM  105  H7  UNL     1       1.244   7.946   0.001  1.00  0.00           H  
HETATM  106  H8  UNL     1       0.640   5.827  -1.071  1.00  0.00           H  
HETATM  107  H9  UNL     1      -0.252   6.061   0.420  1.00  0.00           H  
HETATM  108  H10 UNL     1      -2.229   6.795  -0.655  1.00  0.00           H  
HETATM  109  H11 UNL     1      -1.541   6.813  -2.273  1.00  0.00           H  
HETATM  110  H12 UNL     1      -1.988   4.395  -0.339  1.00  0.00           H  
HETATM  111  H13 UNL     1      -2.379   3.053  -2.195  1.00  0.00           H  
HETATM  112  H14 UNL     1      -2.915   4.361  -4.227  1.00  0.00           H  
HETATM  113  H15 UNL     1      -1.697   5.642  -3.839  1.00  0.00           H  
HETATM  114  H16 UNL     1      -0.831   4.303  -5.635  1.00  0.00           H  
HETATM  115  H17 UNL     1       0.703   2.660  -5.219  1.00  0.00           H  
HETATM  116  H18 UNL     1      -0.297   2.596  -2.285  1.00  0.00           H  
HETATM  117  H19 UNL     1       0.114   1.164  -3.359  1.00  0.00           H  
HETATM  118  H20 UNL     1       2.336   2.099  -3.559  1.00  0.00           H  
HETATM  119  H21 UNL     1       1.956   3.535  -2.599  1.00  0.00           H  
HETATM  120  H22 UNL     1       2.225   0.631  -1.748  1.00  0.00           H  
HETATM  121  H23 UNL     1       3.199   2.057  -1.217  1.00  0.00           H  
HETATM  122  H24 UNL     1       1.166   3.008  -0.004  1.00  0.00           H  
HETATM  123  H25 UNL     1       0.333   1.445  -0.462  1.00  0.00           H  
HETATM  124  H26 UNL     1       1.228   1.480   1.870  1.00  0.00           H  
HETATM  125  H27 UNL     1       2.836   1.863   1.232  1.00  0.00           H  
HETATM  126  H28 UNL     1       1.208  -0.723   0.688  1.00  0.00           H  
HETATM  127  H29 UNL     1       2.879  -0.391   0.110  1.00  0.00           H  
HETATM  128  H30 UNL     1       3.598   0.092   2.395  1.00  0.00           H  
HETATM  129  H31 UNL     1       1.971  -0.314   3.013  1.00  0.00           H  
HETATM  130  H32 UNL     1       3.516  -4.507   1.775  1.00  0.00           H  
HETATM  131  H33 UNL     1       3.850  -4.139   3.493  1.00  0.00           H  
HETATM  132  H34 UNL     1       2.945  -6.255   3.516  1.00  0.00           H  
HETATM  133  H35 UNL     1       1.286  -7.298   2.378  1.00  0.00           H  
HETATM  134  H36 UNL     1       2.201  -6.292   1.191  1.00  0.00           H  
HETATM  135  H37 UNL     1       1.023  -8.203  -0.953  1.00  0.00           H  
HETATM  136  H38 UNL     1      -2.601  -7.255  -1.033  1.00  0.00           H  
HETATM  137  H39 UNL     1      -2.718  -5.582  -0.316  1.00  0.00           H  
HETATM  138  H40 UNL     1      -2.077  -6.322  -3.168  1.00  0.00           H  
HETATM  139  H41 UNL     1      -4.322  -5.986  -1.965  1.00  0.00           H  
HETATM  140  H42 UNL     1      -2.124  -3.564  -1.774  1.00  0.00           H  
HETATM  141  H43 UNL     1      -1.739  -3.903  -3.536  1.00  0.00           H  
HETATM  142  H44 UNL     1      -0.234  -2.566  -0.297  1.00  0.00           H  
HETATM  143  H45 UNL     1       1.827  -3.407  -4.517  1.00  0.00           H  
HETATM  144  H46 UNL     1       2.066  -1.605  -4.156  1.00  0.00           H  
HETATM  145  H47 UNL     1       0.521  -2.954  -6.352  1.00  0.00           H  
HETATM  146  H48 UNL     1       0.615   0.089  -6.140  1.00  0.00           H  
HETATM  147  H49 UNL     1      -0.453  -1.065  -7.092  1.00  0.00           H  
HETATM  148  H50 UNL     1      -2.916  -1.799  -3.494  1.00  0.00           H  
HETATM  149  H51 UNL     1      -1.852  -0.526  -2.691  1.00  0.00           H  
HETATM  150  H52 UNL     1      -3.647   1.185  -3.417  1.00  0.00           H  
HETATM  151  H53 UNL     1      -4.636  -0.193  -3.969  1.00  0.00           H  
HETATM  152  H54 UNL     1      -4.757  -1.182  -1.789  1.00  0.00           H  
HETATM  153  H55 UNL     1      -5.277   0.522  -1.773  1.00  0.00           H  
HETATM  154  H56 UNL     1      -2.412  -0.302  -0.901  1.00  0.00           H  
HETATM  155  H57 UNL     1      -3.105   1.333  -0.921  1.00  0.00           H  
HETATM  156  H58 UNL     1      -4.129  -0.949   0.819  1.00  0.00           H  
HETATM  157  H59 UNL     1      -4.741   0.721   0.697  1.00  0.00           H  
HETATM  158  H60 UNL     1      -2.526   1.640   1.214  1.00  0.00           H  
HETATM  159  H61 UNL     1      -1.783   0.016   1.134  1.00  0.00           H  
HETATM  160  H62 UNL     1      -3.046  -0.508   3.295  1.00  0.00           H  
HETATM  161  H63 UNL     1      -3.669   1.148   3.286  1.00  0.00           H  
HETATM  162  H64 UNL     1      -1.488   2.119   3.056  1.00  0.00           H  
HETATM  163  H65 UNL     1      -0.749   0.418   2.995  1.00  0.00           H  
HETATM  164  H66 UNL     1      -1.374   0.086   5.367  1.00  0.00           H  
HETATM  165  H67 UNL     1      -2.219   1.658   5.445  1.00  0.00           H  
HETATM  166  H68 UNL     1       0.732   1.084   4.900  1.00  0.00           H  
HETATM  167  H69 UNL     1       0.035   2.705   4.824  1.00  0.00           H  
HETATM  168  H70 UNL     1      -0.650   2.572   7.212  1.00  0.00           H  
HETATM  169  H71 UNL     1      -0.120   0.873   7.298  1.00  0.00           H  
HETATM  170  H72 UNL     1       1.494   3.426   6.690  1.00  0.00           H  
HETATM  171  H73 UNL     1       1.569   2.578   8.254  1.00  0.00           H  
HETATM  172  H74 UNL     1       3.533   2.105   6.920  1.00  0.00           H  
HETATM  173  H75 UNL     1       2.589   1.631   5.509  1.00  0.00           H  
HETATM  174  H76 UNL     1       3.488  -0.299   6.602  1.00  0.00           H  
HETATM  175  H77 UNL     1       1.729  -0.406   6.921  1.00  0.00           H  
HETATM  176  H78 UNL     1       2.816  -0.915   8.979  1.00  0.00           H  
HETATM  177  H79 UNL     1       2.216   0.807   9.187  1.00  0.00           H  
HETATM  178  H80 UNL     1       3.920   0.469   8.847  1.00  0.00           H  
HETATM  179  H81 UNL     1       3.161  -3.978  -9.537  1.00  0.00           H  
HETATM  180  H82 UNL     1       4.219  -4.115  -8.151  1.00  0.00           H  
HETATM  181  H83 UNL     1       5.234  -3.057  -9.900  1.00  0.00           H  
HETATM  182  H84 UNL     1       5.301  -2.002  -8.503  1.00  0.00           H  
HETATM  183  H85 UNL     1       4.974  -1.074 -10.932  1.00  0.00           H  
HETATM  184  H86 UNL     1       3.380  -1.793 -10.925  1.00  0.00           H  
HETATM  185  H87 UNL     1       2.602  -0.140  -9.141  1.00  0.00           H  
HETATM  186  H88 UNL     1       3.171   0.500 -10.668  1.00  0.00           H  
HETATM  187  H89 UNL     1       4.739   0.570  -8.048  1.00  0.00           H  
HETATM  188  H90 UNL     1       5.332   1.129  -9.637  1.00  0.00           H  
HETATM  189  H91 UNL     1       2.824   1.927  -8.089  1.00  0.00           H  
HETATM  190  H92 UNL     1       3.027   2.375  -9.786  1.00  0.00           H  
HETATM  191  H93 UNL     1       5.018   3.803  -9.186  1.00  0.00           H  
HETATM  192  H94 UNL     1       3.542   4.179  -8.291  1.00  0.00           H  
HETATM  193  H95 UNL     1       5.605   4.342  -6.947  1.00  0.00           H  
HETATM  194  H96 UNL     1       5.825   2.555  -7.039  1.00  0.00           H  
HETATM  195  H97 UNL     1       3.293   3.895  -5.815  1.00  0.00           H  
HETATM  196  H98 UNL     1       3.706   2.165  -5.811  1.00  0.00           H  
HETATM  197  H99 UNL     1       5.428   4.446  -4.674  1.00  0.00           H  
HETATM  198  HA0 UNL     1       4.248   3.462  -3.776  1.00  0.00           H  
HETATM  199  HA1 UNL     1       6.723   2.312  -5.284  1.00  0.00           H  
HETATM  200  HA2 UNL     1       5.595   1.399  -4.259  1.00  0.00           H  
HETATM  201  HA3 UNL     1       7.708   2.074  -3.029  1.00  0.00           H  
HETATM  202  HA4 UNL     1       7.290   3.793  -3.302  1.00  0.00           H  
HETATM  203  HA5 UNL     1       5.620   1.727  -1.728  1.00  0.00           H  
HETATM  204  HA6 UNL     1       5.114   3.480  -2.091  1.00  0.00           H  
HETATM  205  HA7 UNL     1       5.993   3.226   0.146  1.00  0.00           H  
HETATM  206  HA8 UNL     1       7.165   4.218  -0.849  1.00  0.00           H  
HETATM  207  HA9 UNL     1       8.540   2.111  -1.214  1.00  0.00           H  
HETATM  208  HB0 UNL     1       7.356   1.266  -0.145  1.00  0.00           H  
HETATM  209  HB1 UNL     1       9.430   1.914   1.039  1.00  0.00           H  
HETATM  210  HB2 UNL     1       7.931   2.590   1.745  1.00  0.00           H  
HETATM  211  HB3 UNL     1       8.404   4.761   0.670  1.00  0.00           H  
HETATM  212  HB4 UNL     1       9.862   4.287   1.592  1.00  0.00           H  
HETATM  213  HB5 UNL     1       9.847   4.092  -0.192  1.00  0.00           H  
HETATM  214  HB6 UNL     1       1.054  -5.690   7.536  1.00  0.00           H  
HETATM  215  HB7 UNL     1      -0.364  -6.268   6.612  1.00  0.00           H  
HETATM  216  HB8 UNL     1       0.953  -3.511   6.668  1.00  0.00           H  
HETATM  217  HB9 UNL     1      -0.338  -3.942   5.428  1.00  0.00           H  
HETATM  218  HC0 UNL     1      -0.692  -3.917   8.504  1.00  0.00           H  
HETATM  219  HC1 UNL     1      -1.897  -4.396   7.311  1.00  0.00           H  
HETATM  220  HC2 UNL     1      -1.725  -2.110   6.226  1.00  0.00           H  
HETATM  221  HC3 UNL     1      -0.535  -1.670   7.525  1.00  0.00           H  
HETATM  222  HC4 UNL     1      -3.387  -2.745   7.904  1.00  0.00           H  
HETATM  223  HC5 UNL     1      -2.222  -2.331   9.278  1.00  0.00           H  
HETATM  224  HC6 UNL     1      -2.293   0.059   8.617  1.00  0.00           H  
HETATM  225  HC7 UNL     1      -3.307  -0.338   7.192  1.00  0.00           H  
HETATM  226  HC8 UNL     1      -3.803  -1.018  10.159  1.00  0.00           H  
HETATM  227  HC9 UNL     1      -4.922  -1.371   8.815  1.00  0.00           H  
HETATM  228  HD0 UNL     1      -4.169   1.492   9.746  1.00  0.00           H  
HETATM  229  HD1 UNL     1      -6.370   2.017   9.138  1.00  0.00           H  
HETATM  230  HD2 UNL     1      -7.937   0.082   9.027  1.00  0.00           H  
HETATM  231  HD3 UNL     1      -6.691  -0.960   8.206  1.00  0.00           H  
HETATM  232  HD4 UNL     1      -7.908   1.647   7.106  1.00  0.00           H  
HETATM  233  HD5 UNL     1      -7.631   0.766   4.999  1.00  0.00           H  
HETATM  234  HD6 UNL     1      -6.297  -1.676   6.482  1.00  0.00           H  
HETATM  235  HD7 UNL     1      -5.730  -1.030   4.915  1.00  0.00           H  
HETATM  236  HD8 UNL     1      -7.163  -3.060   4.669  1.00  0.00           H  
HETATM  237  HD9 UNL     1      -8.488  -2.196   5.538  1.00  0.00           H  
HETATM  238  HE0 UNL     1      -8.531  -0.436   3.691  1.00  0.00           H  
HETATM  239  HE1 UNL     1      -7.184  -1.277   2.902  1.00  0.00           H  
HETATM  240  HE2 UNL     1      -9.468  -1.828   1.931  1.00  0.00           H  
HETATM  241  HE3 UNL     1      -9.938  -2.492   3.491  1.00  0.00           H  
HETATM  242  HE4 UNL     1      -8.556  -3.904   1.391  1.00  0.00           H  
HETATM  243  HE5 UNL     1      -8.885  -4.458   3.058  1.00  0.00           H  
HETATM  244  HE6 UNL     1      -7.314  -3.636   2.667  1.00  0.00           H  
CONECT    1    2   99  100  101
CONECT    2    3  102  103
CONECT    3    4  104  105
CONECT    4    5  106  107
CONECT    5    6  108  109
CONECT    6    7    7  110
CONECT    7    8  111
CONECT    8    9  112  113
CONECT    9   10   10  114
CONECT   10   11  115
CONECT   11   12  116  117
CONECT   12   13  118  119
CONECT   13   14  120  121
CONECT   14   15  122  123
CONECT   15   16  124  125
CONECT   16   17  126  127
CONECT   17   18  128  129
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22  130  131
CONECT   22   23   79  132
CONECT   23   24  133  134
CONECT   24   25
CONECT   25   26   26   27   28
CONECT   27  135
CONECT   28   29
CONECT   29   30  136  137
CONECT   30   31   32  138
CONECT   31  139
CONECT   32   33  140  141
CONECT   33   34
CONECT   34   35   35   36   37
CONECT   36  142
CONECT   37   38
CONECT   38   39  143  144
CONECT   39   40   59  145
CONECT   40   41  146  147
CONECT   41   42
CONECT   42   43   43   44
CONECT   44   45  148  149
CONECT   45   46  150  151
CONECT   46   47  152  153
CONECT   47   48  154  155
CONECT   48   49  156  157
CONECT   49   50  158  159
CONECT   50   51  160  161
CONECT   51   52  162  163
CONECT   52   53  164  165
CONECT   53   54  166  167
CONECT   54   55  168  169
CONECT   55   56  170  171
CONECT   56   57  172  173
CONECT   57   58  174  175
CONECT   58  176  177  178
CONECT   59   60
CONECT   60   61   61   62
CONECT   62   63  179  180
CONECT   63   64  181  182
CONECT   64   65  183  184
CONECT   65   66  185  186
CONECT   66   67  187  188
CONECT   67   68  189  190
CONECT   68   69  191  192
CONECT   69   70  193  194
CONECT   70   71  195  196
CONECT   71   72  197  198
CONECT   72   73  199  200
CONECT   73   74  201  202
CONECT   74   75  203  204
CONECT   75   76  205  206
CONECT   76   77  207  208
CONECT   77   78  209  210
CONECT   78  211  212  213
CONECT   79   80
CONECT   80   81   81   82
CONECT   82   83  214  215
CONECT   83   84  216  217
CONECT   84   85  218  219
CONECT   85   86  220  221
CONECT   86   87  222  223
CONECT   87   88  224  225
CONECT   88   89  226  227
CONECT   89   90   90  228
CONECT   90   91  229
CONECT   91   92  230  231
CONECT   92   93   93  232
CONECT   93   94  233
CONECT   94   95  234  235
CONECT   95   96  236  237
CONECT   96   97  238  239
CONECT   97   98  240  241
CONECT   98  242  243  244
END

HMDB0056519
     RDKit          3D
CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))
244243  0  0  0  0  0  0  0  0999 V2000
    0.8761    9.9954   -1.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4524    8.5511   -1.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2663    7.8710   -0.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1613    6.4445   -0.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4795    6.2579   -1.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8518    4.8573   -1.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0256    4.0973   -2.3731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8668    4.5298   -3.7274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8613    3.8966   -4.5465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0118    2.9851   -4.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2824    2.2415   -3.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7357    2.4578   -2.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1572    1.7274   -1.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3360    1.9357   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9022    1.3042    0.9785 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1540   -0.1838    0.8861 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7268   -0.6088    2.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1424   -1.9795    2.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3763   -2.2408    2.0954 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3583   -3.0477    2.6798 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0118   -4.3233    2.7668 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1363   -5.4558    3.1355 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4828   -6.2306    2.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2898   -5.7446    1.5539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2483   -6.9030    0.4171 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.2875   -7.8135    1.0773 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0424   -7.9316   -0.0040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8328   -6.2050   -0.9564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2278   -6.2070   -1.0749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5107   -5.5577   -2.4321 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8628   -5.4519   -2.6849 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7378   -4.2814   -2.5003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3794   -4.4975   -2.1996 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369   -2.9821   -2.3314 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.9023   -3.1481   -2.0195 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.8850   -4.4583    3.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3145   -3.6364    2.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cardiolipin(16:0/18:0/18:2/18:2)	HMDB
1'-[1-Palmitoyl-2-stearoyl-sn-glycero-3-phospho],3'-[1,2-dilinoleoyl-rac-glycero-3-phospho]-glycerol	HMDB
CL(70:4)	HMDB
CL(1'-[16:0/18:0],3'-[18:2(9Z,12Z)/18:2(9Z,12Z)])	HMDB
Cardiolipin(70:4)	HMDB
1'-[1-Hexadecanoyl-2-octadecanoyl-sn-glycero-3-phospho],3'-[1,2-di(9Z,12Z-octadecadienoyl)-rac-glycero-3-phospho]-glycerol	HMDB
CL(16:0/18:0/18:2/18:2)	HMDB
CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))	Lipid Annotator

Chemical Formula

C₇₉H₁₄₆O₁₇P₂

Average Molecular Weight

1429.968

Monoisotopic Molecular Weight

1429.003527237

IUPAC Name

[(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy][(2S)-3-({[(2R)-3-(hexadecanoyloxy)-2-(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid

Traditional Name

(2R)-2,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy((2S)-3-{[(2R)-3-(hexadecanoyloxy)-2-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

[H][C@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC

InChI Identifier

InChI=1S/C79H146O17P2/c1-5-9-13-17-21-25-29-33-36-40-44-48-52-56-60-64-77(82)90-70-75(96-79(84)66-62-58-54-50-46-42-38-35-31-27-23-19-15-11-7-3)72-94-98(87,88)92-68-73(80)67-91-97(85,86)93-71-74(69-89-76(81)63-59-55-51-47-43-39-32-28-24-20-16-12-8-4)95-78(83)65-61-57-53-49-45-41-37-34-30-26-22-18-14-10-6-2/h21,23,25,27,33,35-36,38,73-75,80H,5-20,22,24,26,28-32,34,37,39-72H2,1-4H3,(H,85,86)(H,87,88)/b25-21-,27-23-,36-33-,38-35-/t73-,74+,75+/m0/s1

InChI Key

UOAMDLHONFQUPT-QJCNJITASA-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.

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
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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Diabetic heart disease (PMID: 17487985)
Aging (PMID: 1629722)
Non-alcoholic fatty liver disease (PMID: 17900521)
Barth syndrome (PMID: 17082194)
Tangier disease (PMID: 11111099)

Organoleptic effect

Touch

Smooth (HMDB: HMDB0056519)

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0056519)

Organelle

Mitochondria

Inner mitochondrial membrane (PMID: 31315173)
Mitochondria (HMDB: HMDB0056519)

Cytoplasm (HMDB: HMDB0056519)
Endoplasmic reticulum (HMDB: HMDB0056519)
Inner mitochondrial membrane (HMDB: HMDB0056519)
Heart (HMDB: HMDB0056519)
Cell membrane (HMDB: HMDB0056519)
Intracellular membrane (HMDB: HMDB0056519)

Biofluid or Excreta

Blood (HMDB: HMDB0056519)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0056519)

Source

Endogenous

Endogenous (HMDB: HMDB0056519)

Animal

Animal (HMDB: HMDB0056519)

Exogenous

Food

Food (HMDB: HMDB0056519)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Fruit

Tropical fruit

Berry

Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)
Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)

Other fruit

Jujube (FooDB: FOOD00388)
Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)

Citrus

Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)
Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)

Drupe

Common chokecherry (FooDB: FOOD00562)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)

Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)
Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)

Other vegetable

Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)
Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)

Tuber

Leaf vegetable

Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)
Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)

Cabbage

Onion-family vegetable

Shoot vegetable

Stalk vegetable

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)

Nut

European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)
Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)

Pulse

Bean

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pea

Green lentil (FooDB: FOOD00970)

Lentil

Lentils (FooDB: FOOD00098)

Cereal and cereal product

Bulgur (FooDB: FOOD00741)
Semolina (FooDB: FOOD00745)
Flour (FooDB: FOOD00799)
Pasta (FooDB: FOOD00273)

Other bread

Potato bread (FooDB: FOOD00811)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Dough

Sourdough (FooDB: FOOD00275)

Gourd

Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)
Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)

Soy

Soy product

Soy sauce (FooDB: FOOD00694)
Miso (FooDB: FOOD00695)
Tofu (FooDB: FOOD00696)
Soy milk (FooDB: FOOD00736)
Soy cream (FooDB: FOOD00784)

Soy bean (FooDB: FOOD00085)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Dish

Other dish

Taco shell (FooDB: FOOD00991)
Tostada shell (FooDB: FOOD00992)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Process

Role

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.2e-05 g/L	ALOGPS
logP	9.09	ALOGPS
logP	24.93	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	402.17 m³·mol⁻¹	ChemAxon
Polarizability	172.7 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	386.818	30932474
DeepCCS	[M-H]-	384.075	30932474
DeepCCS	[M-2H]-	418.681	30932474
DeepCCS	[M+Na]+	393.828	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z)) 10V, Negative-QTOF	splash10-03di-0040000900-cf5f4adc5a3f90045e70	2017-10-05	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z)) 20V, Negative-QTOF	splash10-03di-0041310900-41e904f961ac632e810f	2017-10-05	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z)) 40V, Negative-QTOF	splash10-069u-0092400000-56ef6709b1608a8a7eec	2017-10-05	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z)) 10V, Positive-QTOF	splash10-029x-0890611231-27ca692b0c69f03c4b94	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z)) 20V, Positive-QTOF	splash10-02cf-0591202231-55ee613e3b08fb767efc	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z)) 40V, Positive-QTOF	splash10-0hk9-1398355500-2f0cebc6eb8b858e8377	2017-10-06	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Cardiolipin Biosynthesis CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z))		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB031545

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

118702554

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
Schlame M, Ren M, Xu Y, Greenberg ML, Haller I: Molecular symmetry in mitochondrial cardiolipins. Chem Phys Lipids. 2005 Dec;138(1-2):38-49. Epub 2005 Sep 7. [PubMed:16226238 ]
Schlame M, Ren M: Barth syndrome, a human disorder of cardiolipin metabolism. FEBS Lett. 2006 Oct 9;580(23):5450-5. Epub 2006 Jul 17. [PubMed:16973164 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
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 ]
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 ]
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 ]
Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
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 ]
Hauff KD, Hatch GM: Cardiolipin metabolism and Barth Syndrome. Prog Lipid Res. 2006 Mar;45(2):91-101. Epub 2006 Jan 18. [PubMed:16442164 ]
Schlame M, Rua D, Greenberg ML: The biosynthesis and functional role of cardiolipin. Prog Lipid Res. 2000 May;39(3):257-88. [PubMed:10799718 ]
McMillin JB, Dowhan W: Cardiolipin and apoptosis. Biochim Biophys Acta. 2002 Dec 30;1585(2-3):97-107. [PubMed:12531542 ]
Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z)) (HMDB0056519)

MOL for HMDB0056519 (CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z)))

3D MOL for HMDB0056519 (CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z)))

3D SDF for HMDB0056519 (CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z)))

3D-SDF for HMDB0056519 (CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z)))

PDB for HMDB0056519 (CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z)))

3D PDB for HMDB0056519 (CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z)))

SMILES for HMDB0056519 (CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z)))

INCHI for HMDB0056519 (CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z)))

Structure for HMDB0056519 (CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z)))

3D Structure for HMDB0056519 (CL(16:0/18:0/18:2(9Z,12Z)/18:2(9Z,12Z)))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra