MiMeDB: Showing metabocard for CL(16:0/16:1(9Z)/18:1(11Z)/22:0) (MMDBc0042911)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 11:49:02 UTC

Update Date

2022-08-31 23:59:30 UTC

Metabolite ID

MMDBc0042911

Metabolite Identification

Common Name

CL(16:0/16:1(9Z)/18:1(11Z)/22:0)

Description

CL(16:0/16:1(9Z)/18:1(11Z)/22:0) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(16:0/16:1(9Z)/18:1(11Z)/22:0) contains one chain of hexadecanoic acid at the C1 position, one chain of (9Z-hexadecenoyl) at the C2 position, one chain of (11Z-octadecenoyl) at the C3 position, one chain of docosanoic acid at the C4 position. While the theoretical charge of cardiolipins is -2, under normal physiological conditions (pH near 7), the molecule may carry only one negative charge. In prokaryotes such as E. coli, the enzyme known as diphosphatidylglycerol synthase catalyses the transfer of the phosphatidyl moiety of one phosphatidylglycerol to the free 3'-hydroxyl group of another, with the elimination of one molecule of glycerol. In E. coli, which acylates its glycerophospholipids with acyl chains ranging in length from 12 to 18 carbons and possibly containing an unsaturation, or a cyclopropane group more than 100 possible CL molecular species are theoretically possible, 53 of these species having been characterized. E. coli membranes consist of ~5% cardiolipin (CL), 20-25% phosphatidylglycerol (PG), and 70-80% phosphatidylethanolamine (PE) as well as smaller amounts of phosphatidylserine (PS). CL is distributed between the two leaflets of the bilayers and is located preferentially at the poles and septa in E. coli and other rod-shaped bacteria. It is known that the polar positioning of the proline transporter ProP and the mechanosensitive ion channel MscS in E. coli is dependent on CL. It is believed that cell shape may influence the localization of CL and the localization of certain membrane proteins.

Structure

MOL SDF PDB SMILES InChI

1'-[1-hexadecanoyl,2-(9Z-hexadecenoyl)-sn-glycero-3-phospho],3'-[1-(11Z-octadecenoyl),2-docosanoyl-sn-glycero-3-phospho]-sn-glycerol CL(16:0/16:1(9Z)/18:1(11Z)/22:0)
  Mrv1652307071617422D          

103102  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
   17.6403   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9262   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2121   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4979   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7838   -6.5028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0697   -6.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3556   -6.5028    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
   13.3768   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6627   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9485   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2344   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5203   -9.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8062   -9.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0921   -9.4137    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
   16.0044  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2903  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5761  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8620  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1479  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4338  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7197  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0056  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2915  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5774  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8632  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1491  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4350  -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 62  1  0  0  0  0
 23 81  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
 43 44  1  0  0  0  0
 45 46  2  0  0  0  0
 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  2  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
 62 63  2  0  0  0  0
 62 64  1  0  0  0  0
 64 65  1  0  0  0  0
 65 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  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
 81 82  2  0  0  0  0
 81 83  1  0  0  0  0
 83 84  1  0  0  0  0
 84 85  1  0  0  0  0
 85 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  1  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
100101  1  0  0  0  0
101102  1  0  0  0  0
102103  1  0  0  0  0
M  END

1'-[1-hexadecanoyl,2-(9Z-hexadecenoyl)-sn-glycero-3-phospho],3'-[1-(11Z-octadecenoyl),2-docosanoyl-sn-glycero-3-phospho]-sn-glycerol CL(16:0/16:1(9Z)/18:1(11Z)/22:0)
  Mrv1652307071617422D          

103102  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
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    9.5774  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8632  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1491  -11.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4350  -10.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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102103  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0042911

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C81H154O17P2/c1-5-9-13-17-21-25-29-33-35-36-37-38-40-44-48-52-56-60-64-68-81(86)98-77(72-92-79(84)66-62-58-54-50-46-43-39-34-30-26-22-18-14-10-6-2)74-96-100(89,90)94-70-75(82)69-93-99(87,88)95-73-76(97-80(85)67-63-59-55-51-47-42-32-28-24-20-16-12-8-4)71-91-78(83)65-61-57-53-49-45-41-31-27-23-19-15-11-7-3/h26,28,30,32,75-77,82H,5-25,27,29,31,33-74H2,1-4H3,(H,87,88)(H,89,90)/b30-26-,32-28-/t75-,76+,77+/m0/s1

> <INCHI_KEY>
DIRSFUVEBKGLHG-NDHLAWCTSA-N

> <FORMULA>
C81H154O17P2

> <MOLECULAR_WEIGHT>
1462.054

> <EXACT_MASS>
1461.066127495

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
254

> <JCHEM_AVERAGE_POLARIZABILITY>
177.51366504986277

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-3-({[(2R)-2-(docosanoyloxy)-3-[(11Z)-octadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(hexadecanoyloxy)propoxy]phosphinic acid

> <ALOGPS_LOGP>
9.07

> <JCHEM_LOGP>
26.545823067999994

> <ALOGPS_LOGS>
-7.32

> <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>
409.1429

> <JCHEM_ROTATABLE_BOND_COUNT>
84

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.00e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-3-{[(2R)-2-(docosanoyloxy)-3-[(11Z)-octadec-11-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy((2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(hexadecanoyloxy)propoxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-JUL-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1'-[1-hexadecanoyl,2-(9Z-hexadecenoyl)-sn-glycero-
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JUL-16         0                                  
HETATM    1  C   UNK     0      54.096 -16.519   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      53.010 -14.755   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      53.995 -12.932   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      53.112 -18.342   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      52.909 -11.168   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      54.554 -14.223   0.000  0.00  0.00           O+0
HETATM    7  H   UNK     0      51.453 -14.080   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0      49.765  -8.809   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      47.971  -9.845   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      46.177  -8.809   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      51.559  -9.845   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      44.382  -9.845   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      46.466 -11.369   0.000  0.00  0.00           O+0
HETATM   14  H   UNK     0      49.428 -11.448   0.000  0.00  0.00           H+0
HETATM   15  P   UNK     0      53.848  -9.088   0.000  0.00  0.00           P+0
HETATM   16  O   UNK     0      55.955  -9.688   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      53.848  -6.668   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      46.557 -17.306   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      44.762 -18.342   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      42.968 -17.306   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      48.351 -18.342   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      41.174 -18.342   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      43.206 -19.918   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0      46.168 -19.997   0.000  0.00  0.00           H+0
HETATM   25  P   UNK     0      50.640 -17.459   0.000  0.00  0.00           P+0
HETATM   26  O   UNK     0      50.640 -15.919   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      49.857 -19.431   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      43.049  -9.075   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      43.049  -7.635   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      41.716  -9.846   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      40.382  -9.075   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      39.049  -9.846   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      37.716  -9.075   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      36.384  -9.846   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      35.050  -9.075   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      33.717  -9.846   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      32.384  -9.075   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      31.051  -9.846   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      29.718  -9.075   0.000  0.00  0.00           C+0
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 -13.578   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      41.134 -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      32.929 -12.139   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      31.596 -11.367   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      30.263 -12.139   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      28.929 -11.367   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      27.596 -12.139   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      26.263 -11.367   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      24.930 -12.139   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      39.840 -17.572   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      39.840 -16.132   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      38.507 -18.343   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      37.174 -17.572   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      35.841 -18.343   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      34.508 -17.572   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      33.175 -18.343   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      31.842 -17.572   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      30.509 -18.343   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      29.176 -17.572   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      27.843 -18.343   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      26.510 -17.572   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      24.970 -17.572   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      23.637 -18.343   0.000  0.00  0.00           C+0
HETATM   76  C   UNK     0      22.304 -17.572   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0      20.971 -18.343   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0      19.638 -17.572   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0      18.305 -18.343   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0      16.972 -17.572   0.000  0.00  0.00           C+0
HETATM   81  C   UNK     0      41.872 -20.688   0.000  0.00  0.00           C+0
HETATM   82  O   UNK     0      41.872 -22.128   0.000  0.00  0.00           O+0
HETATM   83  C   UNK     0      40.539 -19.917   0.000  0.00  0.00           C+0
HETATM   84  C   UNK     0      39.206 -20.688   0.000  0.00  0.00           C+0
HETATM   85  C   UNK     0      37.873 -19.917   0.000  0.00  0.00           C+0
HETATM   86  C   UNK     0      36.540 -20.688   0.000  0.00  0.00           C+0
HETATM   87  C   UNK     0      35.207 -19.917   0.000  0.00  0.00           C+0
HETATM   88  C   UNK     0      33.874 -20.688   0.000  0.00  0.00           C+0
HETATM   89  C   UNK     0      32.541 -19.917   0.000  0.00  0.00           C+0
HETATM   90  C   UNK     0      31.208 -20.688   0.000  0.00  0.00           C+0
HETATM   91  C   UNK     0      29.875 -19.917   0.000  0.00  0.00           C+0
HETATM   92  C   UNK     0      28.542 -20.688   0.000  0.00  0.00           C+0
HETATM   93  C   UNK     0      27.209 -19.917   0.000  0.00  0.00           C+0
HETATM   94  C   UNK     0      25.876 -20.688   0.000  0.00  0.00           C+0
HETATM   95  C   UNK     0      24.543 -19.917   0.000  0.00  0.00           C+0
HETATM   96  C   UNK     0      23.210 -20.688   0.000  0.00  0.00           C+0
HETATM   97  C   UNK     0      21.877 -19.917   0.000  0.00  0.00           C+0
HETATM   98  C   UNK     0      20.544 -20.688   0.000  0.00  0.00           C+0
HETATM   99  C   UNK     0      19.211 -19.917   0.000  0.00  0.00           C+0
HETATM  100  C   UNK     0      17.878 -20.688   0.000  0.00  0.00           C+0
HETATM  101  C   UNK     0      16.545 -19.917   0.000  0.00  0.00           C+0
HETATM  102  C   UNK     0      15.212 -20.688   0.000  0.00  0.00           C+0
HETATM  103  C   UNK     0      13.879 -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   62                                                       
CONECT   23   19   81                                                       
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                                                            
CONECT   62   22   63   64                                                  
CONECT   63   62                                                            
CONECT   64   62   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65   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                                                            
CONECT   81   23   82   83                                                  
CONECT   82   81                                                            
CONECT   83   81   84                                                       
CONECT   84   83   85                                                       
CONECT   85   84   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  102                                                       
CONECT  102  101  103                                                       
CONECT  103  102                                                            
MASTER        0    0    0    0    0    0    0    0  103    0  204    0
END

Synonyms

Not Available

Molecular Formula

C₈₁H₁₅₄O₁₇P₂

Average Mass

1462.054

Monoisotopic Mass

1461.066127495

IUPAC Name

[(2R)-3-({[(2R)-2-(docosanoyloxy)-3-[(11Z)-octadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(hexadecanoyloxy)propoxy]phosphinic acid

Traditional Name

(2R)-3-{[(2R)-2-(docosanoyloxy)-3-[(11Z)-octadec-11-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy((2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-(hexadecanoyloxy)propoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC

InChI Identifier

InChI=1S/C81H154O17P2/c1-5-9-13-17-21-25-29-33-35-36-37-38-40-44-48-52-56-60-64-68-81(86)98-77(72-92-79(84)66-62-58-54-50-46-43-39-34-30-26-22-18-14-10-6-2)74-96-100(89,90)94-70-75(82)69-93-99(87,88)95-73-76(97-80(85)67-63-59-55-51-47-42-32-28-24-20-16-12-8-4)71-91-78(83)65-61-57-53-49-45-41-31-27-23-19-15-11-7-3/h26,28,30,32,75-77,82H,5-25,27,29,31,33-74H2,1-4H3,(H,87,88)(H,89,90)/b30-26-,32-28-/t75-,76+,77+/m0/s1

InChI Key

DIRSFUVEBKGLHG-NDHLAWCTSA-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
Dialkyl phosphate
Fatty acid ester
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	7.0e-05 g/L	ALOGPS
logP	9.07	ALOGPS
logP	26.55	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	84	ChemAxon
Refractivity	409.14 m³·mol⁻¹	ChemAxon
Polarizability	177.51 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ka9-0095311000-07f3b3445164dadeda31	2016-09-19	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Rattray JB, Schibeci A, Kidby DK: Lipids of yeasts. Bacteriol Rev. 1975 Sep;39(3):197-231. doi: 10.1128/br.39.3.197-231.1975. [PubMed:240350 ]

Showing metabocard for CL(16:0/16:1(9Z)/18:1(11Z)/22:0) (MMDBc0042911)

MOL for #<Metabolite:0x00007fdb7223e920>

3D MOL for #<Metabolite:0x00007fdb7223e920>

3D SDF for #<Metabolite:0x00007fdb7223e920>

3D-SDF for #<Metabolite:0x00007fdb7223e920>

PDB for #<Metabolite:0x00007fdb7223e920>

3D PDB for #<Metabolite:0x00007fdb7223e920>

SMILES for #<Metabolite:0x00007fdb7223e920>

INCHI for #<Metabolite:0x00007fdb7223e920>

Structure for #<Metabolite:0x00007fdb7223e920>

3D Structure for #<Metabolite:0x00007fdb7223e920>