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Record Information

Version

5.0

Status

Predicted

Creation Date

2021-12-21 04:32:17 UTC

Update Date

2022-11-30 20:17:05 UTC

HMDB ID

HMDB0316846

Secondary Accession Numbers

None

Metabolite Identification

Common Name

CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14:0/16:1(9Z))

Description

CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14:0/16:1(9Z)) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14:0/16:1(9Z)) contains one chain of (9Z-octadecenoyl) at the C1 position, one chain of (4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl) at the C2 position, one chain of tetradecanoic acid at the C3 position, one chain of (9Z-hexadecenoyl) at the C4 position 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 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), an 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

MOL SDF PDB SMILES InChI

CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14:0/16:1(9Z))
  Mrv1652312212105402D          

100 99  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  1  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
   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
   27.5639   -7.5431    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
   16.5238   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8097   -5.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0956   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3815   -5.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6674   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9532   -5.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2391   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5250   -5.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8109   -4.8616    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
   21.2108   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4967   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7826   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9576   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2435   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5294   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7044   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9903   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2762   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4512   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7371   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0229   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1980   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4839   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7698   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9448   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2307   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5165   -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
   14.9159   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2018   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4877   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7735   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0594   -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
   13.7511  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0370  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3229  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6088  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  2 26  1  6  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  1  0  0  0
  8  7  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 10 27  1  0  0  0  0
 11 46  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 13  5  1  0  0  0  0
 13  9  1  0  0  0  0
 17 16  1  0  0  0  0
 17 21  1  0  0  0  0
 17 22  1  1  0  0  0
 18 17  1  0  0  0  0
 19 16  1  0  0  0  0
 20 18  1  0  0  0  0
 20 69  1  0  0  0  0
 21 84  1  0  0  0  0
 23  4  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 23 19  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 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  2  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
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 46 47  2  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  2  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  2  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  2  0  0  0  0
 63 64  1  0  0  0  0
 64 65  1  0  0  0  0
 65 66  2  0  0  0  0
 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
 69 70  2  0  0  0  0
 69 71  1  0  0  0  0
 71 72  1  0  0  0  0
 72 73  1  0  0  0  0
 73 74  1  0  0  0  0
 74 75  1  0  0  0  0
 75 76  1  0  0  0  0
 76 77  1  0  0  0  0
 77 78  1  0  0  0  0
 78 79  1  0  0  0  0
 79 80  1  0  0  0  0
 80 81  1  0  0  0  0
 81 82  1  0  0  0  0
 82 83  1  0  0  0  0
 84 85  2  0  0  0  0
 84 86  1  0  0  0  0
 86 87  1  0  0  0  0
 87 88  1  0  0  0  0
 88 89  1  0  0  0  0
 89 90  1  0  0  0  0
 90 91  1  0  0  0  0
 91 92  1  0  0  0  0
 92 93  1  0  0  0  0
 93 94  2  0  0  0  0
 94 95  1  0  0  0  0
 95 96  1  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
M  END

CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14:0/16:1(9Z))
  Mrv1652312212105402D          

100 99  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  1  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
   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
   27.5639   -7.5431    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
   16.5238   -4.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0316846

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@](COC(=O)CCCCCCCCCCCCC)(COP(O)(=O)OC[C@H](O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCC\C=C/CCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C79H138O17P2/c1-5-9-13-17-21-25-29-32-34-35-36-37-39-42-46-50-54-58-62-66-79(84)96-75(70-90-77(82)64-60-56-52-48-44-41-38-33-30-26-22-18-14-10-6-2)72-94-98(87,88)92-68-73(80)67-91-97(85,86)93-71-74(69-89-76(81)63-59-55-51-47-43-28-24-20-16-12-8-4)95-78(83)65-61-57-53-49-45-40-31-27-23-19-15-11-7-3/h9,13,21,25,27,31-34,36-38,42,46,54,58,73-75,80H,5-8,10-12,14-20,22-24,26,28-30,35,39-41,43-45,47-53,55-57,59-72H2,1-4H3,(H,85,86)(H,87,88)/b13-9-,25-21-,31-27-,34-32-,37-36-,38-33-,46-42-,58-54-/t73-,74+,75+/m0/s1

> <INCHI_KEY>
YNUCRSWWHYISEO-XZABBVHSSA-N

> <FORMULA>
C79H138O17P2

> <MOLECULAR_WEIGHT>
1421.904

> <EXACT_MASS>
1420.94092698

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
236

> <JCHEM_AVERAGE_POLARIZABILITY>
167.76761456933275

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy][(2S)-3-({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid

> <ALOGPS_LOGP>
9.23

> <JCHEM_LOGP>
23.485155798

> <ALOGPS_LOGS>
-7.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.19180435819243

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.589737614293691

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4105029523385797

> <JCHEM_POLAR_SURFACE_AREA>
236.95

> <JCHEM_REFRACTIVITY>
406.6405

> <JCHEM_ROTATABLE_BOND_COUNT>
76

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.47e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy((2S)-3-{[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-DEC-21   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14:0/16:1(
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-DEC-21         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  C   UNK     0      49.765  -8.809   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      47.971  -9.845   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      46.177  -8.809   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      51.559  -9.845   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      44.382  -9.845   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      46.466 -11.369   0.000  0.00  0.00           O+0
HETATM   12  H   UNK     0      49.428 -11.448   0.000  0.00  0.00           H+0
HETATM   13  P   UNK     0      53.848  -9.088   0.000  0.00  0.00           P+0
HETATM   14  O   UNK     0      55.955  -9.688   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      53.848  -6.668   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      46.557 -17.306   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      44.762 -18.342   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      42.968 -17.306   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      48.351 -18.342   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      41.174 -18.342   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      43.206 -19.918   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0      46.168 -19.997   0.000  0.00  0.00           H+0
HETATM   23  P   UNK     0      50.640 -17.459   0.000  0.00  0.00           P+0
HETATM   24  O   UNK     0      50.640 -15.919   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      49.857 -19.431   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      51.453 -14.080   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      43.049  -9.075   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      43.049  -7.635   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      41.716  -9.846   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      40.382  -9.075   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      39.049  -9.846   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      37.716  -9.075   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      36.384  -9.846   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      35.050  -9.075   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      33.717  -9.846   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      32.384  -9.075   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      30.844  -9.075   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      29.511  -9.846   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      28.178  -9.075   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      26.845  -9.846   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      25.512  -9.075   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      24.179  -9.846   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      22.846  -9.075   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      21.513  -9.846   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      20.180  -9.075   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      45.133 -12.139   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      45.133 -13.578   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      43.800 -11.367   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      42.467 -12.139   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      41.134 -11.367   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      39.594 -11.367   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      38.261 -12.139   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      36.928 -11.367   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      35.388 -11.367   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      34.055 -12.139   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      32.722 -11.367   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      31.182 -11.367   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      29.849 -12.139   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      28.516 -11.367   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      26.976 -11.367   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      25.643 -12.139   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      24.310 -11.367   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      22.770 -11.367   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      21.437 -12.139   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      20.104 -11.367   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      18.564 -11.367   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      17.231 -12.139   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      15.897 -11.367   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      39.840 -17.572   0.000  0.00  0.00           C+0
HETATM   70  O   UNK     0      39.840 -16.132   0.000  0.00  0.00           O+0
HETATM   71  C   UNK     0      38.507 -18.343   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      37.174 -17.572   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      35.841 -18.343   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      34.508 -17.572   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      33.175 -18.343   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      31.842 -17.572   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      30.509 -18.343   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      29.176 -17.572   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0      27.843 -18.343   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0      26.510 -17.572   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0      25.177 -18.343   0.000  0.00  0.00           C+0
HETATM   82  C   UNK     0      23.844 -17.572   0.000  0.00  0.00           C+0
HETATM   83  C   UNK     0      22.511 -18.343   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0      41.872 -20.688   0.000  0.00  0.00           C+0
HETATM   85  O   UNK     0      41.872 -22.128   0.000  0.00  0.00           O+0
HETATM   86  C   UNK     0      40.539 -19.917   0.000  0.00  0.00           C+0
HETATM   87  C   UNK     0      39.206 -20.688   0.000  0.00  0.00           C+0
HETATM   88  C   UNK     0      37.873 -19.917   0.000  0.00  0.00           C+0
HETATM   89  C   UNK     0      36.540 -20.688   0.000  0.00  0.00           C+0
HETATM   90  C   UNK     0      35.207 -19.917   0.000  0.00  0.00           C+0
HETATM   91  C   UNK     0      33.874 -20.688   0.000  0.00  0.00           C+0
HETATM   92  C   UNK     0      32.541 -19.917   0.000  0.00  0.00           C+0
HETATM   93  C   UNK     0      31.208 -20.688   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0      29.668 -20.688   0.000  0.00  0.00           C+0
HETATM   95  C   UNK     0      28.335 -19.917   0.000  0.00  0.00           C+0
HETATM   96  C   UNK     0      27.002 -20.688   0.000  0.00  0.00           C+0
HETATM   97  C   UNK     0      25.669 -19.917   0.000  0.00  0.00           C+0
HETATM   98  C   UNK     0      24.336 -20.688   0.000  0.00  0.00           C+0
HETATM   99  C   UNK     0      23.003 -19.917   0.000  0.00  0.00           C+0
HETATM  100  C   UNK     0      21.670 -20.688   0.000  0.00  0.00           C+0
CONECT    1    2    4                                                       
CONECT    2    1   26    3                                                  
CONECT    3    2    5                                                       
CONECT    4    1   23                                                       
CONECT    5    3   13                                                       
CONECT    6    7    9                                                       
CONECT    7    6   11   12    8                                             
CONECT    8    7   10                                                       
CONECT    9    6   13                                                       
CONECT   10    8   27                                                       
CONECT   11    7   46                                                       
CONECT   12    7                                                            
CONECT   13   14   15    5    9                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   17   19                                                       
CONECT   17   16   21   22   18                                             
CONECT   18   17   20                                                       
CONECT   19   16   23                                                       
CONECT   20   18   69                                                       
CONECT   21   17   84                                                       
CONECT   22   17                                                            
CONECT   23    4   24   25   19                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26    2                                                            
CONECT   27   10   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44                                                            
CONECT   46   11   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   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   64                                                       
CONECT   64   63   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65   67                                                       
CONECT   67   66   68                                                       
CONECT   68   67                                                            
CONECT   69   20   70   71                                                  
CONECT   70   69                                                            
CONECT   71   69   72                                                       
CONECT   72   71   73                                                       
CONECT   73   72   74                                                       
CONECT   74   73   75                                                       
CONECT   75   74   76                                                       
CONECT   76   75   77                                                       
CONECT   77   76   78                                                       
CONECT   78   77   79                                                       
CONECT   79   78   80                                                       
CONECT   80   79   81                                                       
CONECT   81   80   82                                                       
CONECT   82   81   83                                                       
CONECT   83   82                                                            
CONECT   84   21   85   86                                                  
CONECT   85   84                                                            
CONECT   86   84   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                                                            
MASTER        0    0    0    0    0    0    0    0  100    0  198    0
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₇₉H₁₃₈O₁₇P₂

Average Molecular Weight

1421.904

Monoisotopic Molecular Weight

1420.94092698

IUPAC Name

[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy][(2S)-3-({[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphinic acid

Traditional Name

(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy((2S)-3-{[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(tetradecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](COC(=O)CCCCCCCCCCCCC)(COP(O)(=O)OC[C@H](O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCC\C=C/CCCCCC

InChI Identifier

InChI=1S/C79H138O17P2/c1-5-9-13-17-21-25-29-32-34-35-36-37-39-42-46-50-54-58-62-66-79(84)96-75(70-90-77(82)64-60-56-52-48-44-41-38-33-30-26-22-18-14-10-6-2)72-94-98(87,88)92-68-73(80)67-91-97(85,86)93-71-74(69-89-76(81)63-59-55-51-47-43-28-24-20-16-12-8-4)95-78(83)65-61-57-53-49-45-40-31-27-23-19-15-11-7-3/h9,13,21,25,27,31-34,36-38,42,46,54,58,73-75,80H,5-8,10-12,14-20,22-24,26,28-30,35,39-41,43-45,47-53,55-57,59-72H2,1-4H3,(H,85,86)(H,87,88)/b13-9-,25-21-,31-27-,34-32-,37-36-,38-33-,46-42-,58-54-/t73-,74+,75+/m0/s1

InChI Key

YNUCRSWWHYISEO-XZABBVHSSA-N

Chemical Taxonomy

Classification

Not classified

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)

Disposition

Biological location

Cellular substructure

Organelle

Mitochondria

Inner mitochondrial membrane (PMID: 31315173)

Process

Naturally occurring process

Biological process

Cellular process

Apoptosis (PMID: 19368971)

Biochemical pathway

Signaling pathway

Apoptosis (PMID: 19368971)

Biochemical process

Proton trap for oxidative phosphorylation (PMID: 12297275)

Role

Biological role

Stabilizing agent

Stabilizing cytochrome oxidase (PMID: 10413476)
Proton trap for oxidative phosphorylation (PMID: 12297275)
Stabilizing mitochondrial structure (PMID: 10413476;)

Molecular messenger

Apoptosis (PMID: 19368971)

Transporter

Cholesterol translocation (PMID: 11111099)

Physical Properties

State

Not Available

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
logP	9.23	ALOGPS
logP	23.49	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	76	ChemAxon
Refractivity	406.64 m³·mol⁻¹	ChemAxon
Polarizability	167.77 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 Kovats Retention Indices

Not Available

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
Hauff KD, Hatch GM: Cardiolipin metabolism and Barth Syndrome. Prog Lipid Res. 2006 Mar;45(2):91-101. Epub 2006 Jan 18. [PubMed:16442164 ]

Showing metabocard for CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14:0/16:1(9Z)) (HMDB0316846)

MOL for HMDB0316846 (CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14:0/16:1(9Z)))

3D MOL for HMDB0316846 (CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14:0/16:1(9Z)))

3D SDF for HMDB0316846 (CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14:0/16:1(9Z)))

3D-SDF for HMDB0316846 (CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14:0/16:1(9Z)))

PDB for HMDB0316846 (CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14:0/16:1(9Z)))

3D PDB for HMDB0316846 (CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14:0/16:1(9Z)))

SMILES for HMDB0316846 (CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14:0/16:1(9Z)))

INCHI for HMDB0316846 (CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14:0/16:1(9Z)))

Structure for HMDB0316846 (CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14:0/16:1(9Z)))

3D Structure for HMDB0316846 (CL(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14:0/16:1(9Z)))

Predicted Kovats Retention Indices