MiMeDB: Showing metabocard for PG(20:0/28:1(11Z)) (MMDBc0046863)

Microbial

Human

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 14:57:19 UTC

Update Date

2022-09-01 01:38:44 UTC

Metabolite ID

MMDBc0046863

Metabolite Identification

Common Name

PG(20:0/28:1(11Z))

Description

PG(20:0/28:1(11Z)) is a phosphatidylglycerol. Phosphatidylglycerols consist of a glycerol 3-phosphate backbone esterified to either saturated or unsaturated fatty acids on carbons 1 and 2. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PG(20:0/28:1(11Z)), in particular, consists of one eicosanoyl chain to the C-1 atom, and one 11Z-octocosanoyl to the C-2 atom. In E. coli glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes.

Structure

MOL SDF PDB SMILES InChI

PG(20:0/28:1(11Z))
  Mrv1652306231615502D          

 67 66  0  0  1  0            999 V2000
   14.0374  -24.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3624  -24.5493    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.6871  -24.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7126  -24.5493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0120  -24.5493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8354  -25.3289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3878  -24.1595    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.9979  -23.4844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7775  -24.8347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0628  -23.7697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7379  -24.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4131  -23.7697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.0883  -24.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9501  -25.3586    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.7261  -23.7330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9894  -23.0847    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.8011  -23.0847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2975  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2975  -23.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5834  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8693  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1551  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4410  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7268  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0127  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2985  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5844  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8703  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1561  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4420  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7279  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0137  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2996  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5854  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1287  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8428  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5570  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2711  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1210  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1210  -26.5128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4069  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6928  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9786  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2645  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5504  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8362  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1221  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4079  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6938  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9796  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2655  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4405  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7264  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0122  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2981  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1302  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8443  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5585  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2726  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9867  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7009  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4150  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1292  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8433  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5574  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2716  -25.7414    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 14  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
  5 18  1  0  0  0  0
  7  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 12 16  1  6  0  0  0
 12 17  1  0  0  0  0
 13 12  1  0  0  0  0
 13 15  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 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  1  0  0  0  0
 37 38  1  0  0  0  0
 39  6  1  0  0  0  0
 39 40  2  0  0  0  0
 39 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
 45 46  1  0  0  0  0
 46 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  2  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
 63 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
M  END

PG(20:0/28:1(11Z))
  Mrv1652306231615502D          

 67 66  0  0  1  0            999 V2000
   14.0374  -24.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3624  -24.5493    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.6871  -24.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7126  -24.5493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0120  -24.5493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8354  -25.3289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3878  -24.1595    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.9979  -23.4844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7775  -24.8347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0628  -23.7697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7379  -24.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4131  -23.7697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.0883  -24.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9501  -25.3586    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.7261  -23.7330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9894  -23.0847    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.8011  -23.0847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2975  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2975  -23.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5834  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8693  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1551  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4410  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7268  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0127  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2985  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5844  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8703  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1561  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4420  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7279  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0137  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2996  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5854  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1287  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8428  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5570  -24.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2711  -24.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1210  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1210  -26.5128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4069  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6928  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2645  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4079  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6938  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9796  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2655  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4405  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7264  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0122  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2981  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1302  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8443  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5585  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2726  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9867  -25.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7009  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.5574  -25.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2716  -25.7414    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 14  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
  5 18  1  0  0  0  0
  7  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 12 16  1  6  0  0  0
 12 17  1  0  0  0  0
 13 12  1  0  0  0  0
 13 15  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
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 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
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 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  1  0  0  0  0
 37 38  1  0  0  0  0
 39  6  1  0  0  0  0
 39 40  2  0  0  0  0
 39 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
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 46 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  2  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
 63 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
M  END
> <DATABASE_ID>
MMDBc0046863

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCC\C=C/CCCCCCCCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C54H105O10P/c1-3-5-7-9-11-13-15-17-19-21-22-23-24-25-26-27-28-30-32-34-36-38-40-42-44-46-54(58)64-52(50-63-65(59,60)62-48-51(56)47-55)49-61-53(57)45-43-41-39-37-35-33-31-29-20-18-16-14-12-10-8-6-4-2/h26-27,51-52,55-56H,3-25,28-50H2,1-2H3,(H,59,60)/b27-26-/t51-,52+/m0/s1

> <INCHI_KEY>
PWZQWKAFOOGPQO-NIUUQPPESA-N

> <FORMULA>
C54H105O10P

> <MOLECULAR_WEIGHT>
945.398

> <EXACT_MASS>
944.744536579

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
170

> <JCHEM_AVERAGE_POLARIZABILITY>
120.5180275813341

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S)-2,3-dihydroxypropoxy][(2R)-3-(icosanoyloxy)-2-[(12Z)-octacos-12-enoyloxy]propoxy]phosphinic acid

> <ALOGPS_LOGP>
9.86

> <JCHEM_LOGP>
17.688228502666668

> <ALOGPS_LOGS>
-7.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.641245576372423

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8907737771908404

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9689647678483633

> <JCHEM_POLAR_SURFACE_AREA>
148.82000000000002

> <JCHEM_REFRACTIVITY>
270.04150000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
55

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.22e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2,3-dihydroxypropoxy((2R)-3-(icosanoyloxy)-2-[(12Z)-octacos-12-enoyloxy]propoxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-JUN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PG(20:0/28:1(11Z))                                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JUN-16         0                                  
HETATM    1  C   UNK     0      26.203 -45.098   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.943 -45.825   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.683 -45.098   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      27.464 -45.825   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      22.422 -45.825   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      23.959 -47.281   0.000  0.00  0.00           O+0
HETATM    7  P   UNK     0      28.724 -45.098   0.000  0.00  0.00           P+0
HETATM    8  O   UNK     0      27.996 -43.837   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      29.451 -46.358   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      29.984 -44.370   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      31.244 -45.098   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      32.504 -44.370   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.765 -45.098   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0      26.040 -47.336   0.000  0.00  0.00           H+0
HETATM   15  O   UNK     0      34.955 -44.302   0.000  0.00  0.00           O+0
HETATM   16  H   UNK     0      33.580 -43.091   0.000  0.00  0.00           H+0
HETATM   17  O   UNK     0      31.362 -43.091   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      21.089 -45.055   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      21.089 -43.615   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      19.756 -45.827   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.423 -45.055   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.090 -45.827   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.756 -45.055   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.423 -45.827   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.090 -45.055   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.757 -45.827   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.424 -45.055   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.091 -45.827   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.758 -45.055   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.425 -45.827   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.092 -45.055   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.759 -45.827   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.426 -45.055   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.093 -45.827   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.240 -45.055   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.573 -45.827   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.906 -45.055   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -4.239 -45.827   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      22.626 -48.051   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      22.626 -49.491   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      21.293 -47.279   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      19.960 -48.051   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      18.627 -47.279   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      17.294 -48.051   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      15.961 -47.279   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      14.628 -48.051   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      13.295 -47.279   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      11.961 -48.051   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      10.628 -47.279   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       9.295 -48.051   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       7.962 -47.279   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       6.422 -47.279   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       5.089 -48.051   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       3.756 -47.279   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       2.423 -48.051   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       1.090 -47.279   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      -0.243 -48.051   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -1.576 -47.279   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      -2.909 -48.051   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      -4.242 -47.279   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      -5.575 -48.051   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      -6.908 -47.279   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      -8.241 -48.051   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      -9.574 -47.279   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0     -10.907 -48.051   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0     -12.240 -47.279   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0     -13.574 -48.051   0.000  0.00  0.00           C+0
CONECT    1    2    4                                                       
CONECT    2    1    6   14    3                                             
CONECT    3    2    5                                                       
CONECT    4    1    7                                                       
CONECT    5    3   18                                                       
CONECT    6    2   39                                                       
CONECT    7    4    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   16   17   13                                             
CONECT   13   12   15                                                       
CONECT   14    2                                                            
CONECT   15   13                                                            
CONECT   16   12                                                            
CONECT   17   12                                                            
CONECT   18    5   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39    6   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   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   64                                                       
CONECT   64   63   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65   67                                                       
CONECT   67   66                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  132    0
END

Synonyms

Value	Source
[(2S)-2,3-Dihydroxypropoxy][(2R)-3-(icosanoyloxy)-2-[(12Z)-octacos-12-enoyloxy]propoxy]phosphinate	Generator

Molecular Formula

C₅₄H₁₀₅O₁₀P

Average Mass

945.398

Monoisotopic Mass

944.744536579

IUPAC Name

[(2S)-2,3-dihydroxypropoxy][(2R)-3-(icosanoyloxy)-2-[(12Z)-octacos-12-enoyloxy]propoxy]phosphinic acid

Traditional Name

(2S)-2,3-dihydroxypropoxy((2R)-3-(icosanoyloxy)-2-[(12Z)-octacos-12-enoyloxy]propoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCC\C=C/CCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C54H105O10P/c1-3-5-7-9-11-13-15-17-19-21-22-23-24-25-26-27-28-30-32-34-36-38-40-42-44-46-54(58)64-52(50-63-65(59,60)62-48-51(56)47-55)49-61-53(57)45-43-41-39-37-35-33-31-29-20-18-16-14-12-10-8-6-4-2/h26-27,51-52,55-56H,3-25,28-50H2,1-2H3,(H,59,60)/b27-26-/t51-,52+/m0/s1

InChI Key

PWZQWKAFOOGPQO-NIUUQPPESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoglycerols

Direct Parent

Phosphatidylglycerols

Alternative Parents

Substituents

1,2-diacylglycerophosphoglycerol
Dialkyl phosphate
Fatty acid ester
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid ester
1,2-diol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
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	4.2e-05 g/L	ALOGPS
logP	9.86	ALOGPS
logP	17.69	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	1.89	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	148.82 Å²	ChemAxon
Rotatable Bond Count	55	ChemAxon
Refractivity	270.04 m³·mol⁻¹	ChemAxon
Polarizability	120.52 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	splash10-0229-0007943000-9e2863c299b86b518abc	2016-09-19	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (void)	2025-10-24	231.4
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	105.2
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	1417.5
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	1856.3
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	2296.0
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-24	694.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	7055.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	275.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	288.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	1618.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	922.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	267.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	470.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	10.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-24	887.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	1403.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	937.3
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	3805.4
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	4636.1

Retention Indices

Not Available

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0038082	PG(20:0/28:1(11Z))	Arachidic acid	Unknown Protein		RHEA	34755880

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

Other Exposures

Source Type	Data Source	Reference

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

CMMC Knowledgebase

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 PG(20:0/28:1(11Z)) (MMDBc0046863)

MOL for #<Metabolite:0x00007f2e3b5f8de8>

3D MOL for #<Metabolite:0x00007f2e3b5f8de8>

3D SDF for #<Metabolite:0x00007f2e3b5f8de8>

3D-SDF for #<Metabolite:0x00007f2e3b5f8de8>

PDB for #<Metabolite:0x00007f2e3b5f8de8>

3D PDB for #<Metabolite:0x00007f2e3b5f8de8>

SMILES for #<Metabolite:0x00007f2e3b5f8de8>

INCHI for #<Metabolite:0x00007f2e3b5f8de8>

Structure for #<Metabolite:0x00007f2e3b5f8de8>

3D Structure for #<Metabolite:0x00007f2e3b5f8de8>