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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-09-09 08:13:22 UTC

Update Date

2022-11-30 19:26:37 UTC

HMDB ID

HMDB0116464

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))

Description

PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) is a phosphatidylglycerophosphate (PGP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site followed by another phosphate moiety. Phosphatidylglycerolphosphate is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant (up to 11% of the total). It is well established that the concentration of phosphatidylglycerolphosphate increases during fetal development. Phosphatidylglycerolphosphate may be present in animal tissues merely as a precursor for cardiolipin synthesis. As is the case with diacylglycerols, phosphatidylglycerophosphates can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of arachidonic acid at the C-1 position and one chain of arachidonic acid at the C-2 position. They are synthesized by the addition of glycerol 3-phosphate to a CDP-diacylglycerol. In turn, PGPs are dephosphorylated to phosphatidylglycerols (PGs). While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes.

Structure

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

PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))
  Mrv1652309171703182D          

 63 62  0  0  1  0            999 V2000
    2.7849    0.9634    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3818    0.3607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0919    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8021    0.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9713   -0.3494    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7924   -0.3494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6715    0.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9613    0.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7968    0.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5071   -0.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2174    0.3437    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9275   -0.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0493    0.6481    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3125    0.0209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0493    1.3957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8811    0.9262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6378    0.3434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4300    0.5557    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.4300    1.3758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2222    0.3434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0199   -0.1546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5122    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5122    1.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2263    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9404    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6545    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3686    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1936    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9077    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6219    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4469    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1610    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8751    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7001    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4142    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1283    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.9533    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.6674    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.3816    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.0957    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.8098    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.5240    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5361   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5361   -1.5406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2502   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9644   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6785   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3926   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2176   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9317   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6458   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4708   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1850   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8991   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7241   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4382   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1523   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9773   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.6915   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.4056   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.1197   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.8338   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.5480   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  2  5  1  1  0  0  0
  3  4  1  0  0  0  0
  4 22  1  0  0  0  0
  7  2  1  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 11 16  1  0  0  0  0
 11  1  1  6  0  0  0
 12 11  1  0  0  0  0
 12 17  1  0  0  0  0
 13  9  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 13  8  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 22 23  2  0  0  0  0
 22 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  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  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
 43  6  1  0  0  0  0
 43 44  2  0  0  0  0
 43 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  2  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  2  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  2  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
M  END

HMDB0116464
     RDKit          3D
PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))
137136  0  0  0  0  0  0  0  0999 V2000
   -0.0031    7.0109   -1.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0226    7.0761    0.4094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0147    6.0802    1.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9545    6.2257    2.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8975    5.2783    3.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    3.8868    2.9727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2826    3.0017    3.8539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1394    3.3487    5.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2419    3.0704    5.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5833    2.2481    6.6394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3042    1.4943    7.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3097    0.0644    7.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4148   -0.8067    6.9849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4510   -0.5667    5.9846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0775   -1.4875    4.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8901   -2.4685    4.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1424   -2.6276    5.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3972   -2.4918    4.3729 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7911   -3.4916    3.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0783   -3.8366    2.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4419   -4.9707    1.6085 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0574   -3.2269    1.4992 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5971   -3.8980    0.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4706   -3.2208   -0.3926 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9194   -1.9785   -1.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0593   -2.3249   -1.8446 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6390   -0.9700   -2.6855 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.0368   -1.2904   -3.1416 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6702    0.3858   -1.6983 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6939   -0.6991   -4.0748 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1091   -1.5158   -5.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2410   -1.2514   -6.3267 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9121   -1.5337   -5.9977 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108    0.1780   -6.7838 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5698    0.6047   -7.1494 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4295    2.2194   -7.6353 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.7789    2.8662   -7.7424 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6423    2.2298   -9.1479 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4824    3.0938   -6.5305 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3411   -3.0857    0.4211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7923   -3.9011    0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7225   -4.6674   -0.8115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9559   -3.7938    1.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9765   -4.8333    0.8207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8662   -4.8331   -0.3531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3749   -4.7712   -1.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7944   -3.8876   -2.5724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7773   -2.8160   -2.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3175   -1.4766   -2.8295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4624   -0.3971   -2.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0734   -0.0547   -0.8925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5960   -0.9869    0.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1728   -0.9485    1.3456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2076   -0.0033    1.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9828   -0.6555    2.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7719   -0.3076    1.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6105    0.7429    0.8855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0199    0.1825   -0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9622    1.3834   -1.3695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124    0.9691   -2.6964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3861    2.1641   -3.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8860    6.4417   -1.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0809    8.0108   -1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8775    6.4518   -1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3068    8.1017    0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0023    6.8975    0.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0065    6.3684    0.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8066    5.0656    0.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1564    7.2817    2.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0871    6.0059    2.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0263    5.6350    4.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9181    5.5122    2.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7080    3.5571    1.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0900    1.9528    3.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9032    2.7673    5.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4208    4.4109    5.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0653    3.5942    5.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7066    2.1596    6.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3838    1.8066    7.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2213    1.9690    8.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0736   -0.3790    8.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2791   -1.9151    7.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4753   -0.5892    6.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3448    0.4359    5.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1439   -1.3187    4.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5304   -3.0771    3.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1998   -2.2459    6.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1323   -3.7877    5.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3948   -1.4838    3.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2582   -2.3288    5.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))
  Mrv1652309171703182D          

 63 62  0  0  1  0            999 V2000
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 10  9  1  0  0  0  0
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 13  8  1  0  0  0  0
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 43  6  1  0  0  0  0
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 49 50  1  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0116464

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C46H76O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-45(48)55-41-44(42-58-61(53,54)57-40-43(47)39-56-60(50,51)52)59-46(49)38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11-14,17-20,23-26,29-32,43-44,47H,3-10,15-16,21-22,27-28,33-42H2,1-2H3,(H,53,54)(H2,50,51,52)/b13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,31-29-,32-30-/t43-,44+/m0/s1

> <INCHI_KEY>
DJKWAZSGTLJIDZ-MKYVJXLQSA-N

> <FORMULA>
C46H76O13P2

> <MOLECULAR_WEIGHT>
899.049

> <EXACT_MASS>
898.476116503

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
137

> <JCHEM_AVERAGE_POLARIZABILITY>
98.96438402605033

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S)-3-({[(2R)-2,3-bis[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid

> <ALOGPS_LOGP>
7.39

> <JCHEM_LOGP>
11.474661554666667

> <ALOGPS_LOGS>
-6.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.0402061436986916

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.354879296414361

> <JCHEM_PKA_STRONGEST_BASIC>
-3.410499386302644

> <JCHEM_POLAR_SURFACE_AREA>
195.34999999999997

> <JCHEM_REFRACTIVITY>
251.92260000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
42

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.72e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-{[(2R)-2,3-bis[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0116464
     RDKit          3D
PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))
137136  0  0  0  0  0  0  0  0999 V2000
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M  END

HEADER    PROTEIN                                 17-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-SEP-17         0                                  
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HETATM   23  O   UNK     0      -8.423   2.876   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -9.756   0.665   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -11.089   1.436   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -12.422   0.665   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -13.755   1.436   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -15.295   1.436   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -16.628   0.665   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -17.961   1.436   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -19.501   1.436   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -20.834   0.665   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -22.167   1.436   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -23.707   1.436   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -25.040   0.665   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -26.373   1.436   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -27.913   1.436   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -29.246   0.665   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -30.579   1.436   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -31.912   0.665   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -33.245   1.436   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -34.578   0.665   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -6.601  -1.436   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -6.601  -2.876   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -7.934  -0.665   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -9.267  -1.436   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -10.600  -0.665   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -11.933  -1.436   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -13.473  -1.436   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -14.806  -0.665   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0     -16.139  -1.436   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0     -17.679  -1.436   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0     -19.012  -0.665   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0     -20.345  -1.436   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0     -21.885  -1.436   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0     -23.218  -0.665   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0     -24.551  -1.436   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0     -26.091  -1.436   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0     -27.424  -0.665   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0     -28.757  -1.436   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0     -30.090  -0.665   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0     -31.423  -1.436   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0     -32.756  -0.665   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2    3    6    5    7                                             
CONECT    3    2    4                                                       
CONECT    4    3   22                                                       
CONECT    5    2                                                            
CONECT    6    2   43                                                       
CONECT    7    2    8                                                       
CONECT    8    7   13                                                       
CONECT    9   10   13                                                       
CONECT   10    9   11                                                       
CONECT   11   10   16    1   12                                             
CONECT   12   11   17                                                       
CONECT   13    9   14   15    8                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   11                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22    4   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   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   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41                                                            
CONECT   43    6   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   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                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  124    0
END

COMPND    HMDB0116464
HETATM    1  C1  UNL     1      -0.003   7.011  -1.082  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.023   7.076   0.409  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.015   6.080   1.021  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.955   6.226   2.507  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.897   5.278   3.239  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.620   3.887   2.973  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.283   3.002   3.854  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.139   3.349   5.294  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.242   3.070   5.681  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.583   2.248   6.639  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.304   1.494   7.458  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.310   0.064   7.582  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.415  -0.807   6.985  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.451  -0.567   5.985  1.00  0.00           C  
HETATM   15  C15 UNL     1       1.078  -1.487   4.831  1.00  0.00           C  
HETATM   16  C16 UNL     1       1.890  -2.469   4.433  1.00  0.00           C  
HETATM   17  C17 UNL     1       3.142  -2.628   5.140  1.00  0.00           C  
HETATM   18  C18 UNL     1       4.397  -2.492   4.373  1.00  0.00           C  
HETATM   19  C19 UNL     1       4.791  -3.492   3.375  1.00  0.00           C  
HETATM   20  C20 UNL     1       4.078  -3.837   2.195  1.00  0.00           C  
HETATM   21  O1  UNL     1       4.442  -4.971   1.609  1.00  0.00           O  
HETATM   22  O2  UNL     1       3.057  -3.227   1.499  1.00  0.00           O  
HETATM   23  C21 UNL     1       2.597  -3.898   0.322  1.00  0.00           C  
HETATM   24  C22 UNL     1       1.471  -3.221  -0.393  1.00  0.00           C  
HETATM   25  C23 UNL     1       1.919  -1.979  -1.091  1.00  0.00           C  
HETATM   26  O3  UNL     1       3.059  -2.325  -1.845  1.00  0.00           O  
HETATM   27  P1  UNL     1       3.639  -0.970  -2.686  1.00  0.00           P  
HETATM   28  O4  UNL     1       5.037  -1.290  -3.142  1.00  0.00           O  
HETATM   29  O5  UNL     1       3.670   0.386  -1.698  1.00  0.00           O  
HETATM   30  O6  UNL     1       2.694  -0.699  -4.075  1.00  0.00           O  
HETATM   31  C24 UNL     1       3.109  -1.516  -5.123  1.00  0.00           C  
HETATM   32  C25 UNL     1       2.241  -1.251  -6.327  1.00  0.00           C  
HETATM   33  O7  UNL     1       0.912  -1.534  -5.998  1.00  0.00           O  
HETATM   34  C26 UNL     1       2.311   0.178  -6.784  1.00  0.00           C  
HETATM   35  O8  UNL     1       3.570   0.605  -7.149  1.00  0.00           O  
HETATM   36  P2  UNL     1       3.430   2.219  -7.635  1.00  0.00           P  
HETATM   37  O9  UNL     1       4.779   2.866  -7.742  1.00  0.00           O  
HETATM   38  O10 UNL     1       2.642   2.230  -9.148  1.00  0.00           O  
HETATM   39  O11 UNL     1       2.482   3.094  -6.531  1.00  0.00           O  
HETATM   40  O12 UNL     1       0.341  -3.086   0.421  1.00  0.00           O  
HETATM   41  C27 UNL     1      -0.792  -3.901   0.145  1.00  0.00           C  
HETATM   42  O13 UNL     1      -0.722  -4.667  -0.811  1.00  0.00           O  
HETATM   43  C28 UNL     1      -1.956  -3.794   1.012  1.00  0.00           C  
HETATM   44  C29 UNL     1      -2.976  -4.833   0.821  1.00  0.00           C  
HETATM   45  C30 UNL     1      -3.866  -4.833  -0.353  1.00  0.00           C  
HETATM   46  C31 UNL     1      -3.375  -4.771  -1.704  1.00  0.00           C  
HETATM   47  C32 UNL     1      -3.794  -3.888  -2.572  1.00  0.00           C  
HETATM   48  C33 UNL     1      -4.777  -2.816  -2.494  1.00  0.00           C  
HETATM   49  C34 UNL     1      -4.318  -1.477  -2.829  1.00  0.00           C  
HETATM   50  C35 UNL     1      -4.462  -0.397  -2.152  1.00  0.00           C  
HETATM   51  C36 UNL     1      -5.073  -0.055  -0.892  1.00  0.00           C  
HETATM   52  C37 UNL     1      -5.596  -0.987   0.059  1.00  0.00           C  
HETATM   53  C38 UNL     1      -5.173  -0.949   1.346  1.00  0.00           C  
HETATM   54  C39 UNL     1      -4.208  -0.003   1.917  1.00  0.00           C  
HETATM   55  C40 UNL     1      -2.983  -0.656   2.371  1.00  0.00           C  
HETATM   56  C41 UNL     1      -1.772  -0.308   1.886  1.00  0.00           C  
HETATM   57  C42 UNL     1      -1.611   0.743   0.886  1.00  0.00           C  
HETATM   58  C43 UNL     1      -1.020   0.182  -0.420  1.00  0.00           C  
HETATM   59  C44 UNL     1      -0.962   1.383  -1.369  1.00  0.00           C  
HETATM   60  C45 UNL     1      -0.412   0.969  -2.696  1.00  0.00           C  
HETATM   61  C46 UNL     1      -0.386   2.164  -3.634  1.00  0.00           C  
HETATM   62  H1  UNL     1       0.886   6.442  -1.425  1.00  0.00           H  
HETATM   63  H2  UNL     1       0.081   8.011  -1.560  1.00  0.00           H  
HETATM   64  H3  UNL     1      -0.877   6.452  -1.497  1.00  0.00           H  
HETATM   65  H4  UNL     1      -0.307   8.102   0.728  1.00  0.00           H  
HETATM   66  H5  UNL     1       1.002   6.897   0.775  1.00  0.00           H  
HETATM   67  H6  UNL     1      -2.006   6.368   0.622  1.00  0.00           H  
HETATM   68  H7  UNL     1      -0.807   5.066   0.682  1.00  0.00           H  
HETATM   69  H8  UNL     1      -1.156   7.282   2.779  1.00  0.00           H  
HETATM   70  H9  UNL     1       0.087   6.006   2.864  1.00  0.00           H  
HETATM   71  H10 UNL     1      -2.026   5.635   4.255  1.00  0.00           H  
HETATM   72  H11 UNL     1      -2.918   5.512   2.754  1.00  0.00           H  
HETATM   73  H12 UNL     1      -1.708   3.557   1.916  1.00  0.00           H  
HETATM   74  H13 UNL     1      -1.090   1.953   3.559  1.00  0.00           H  
HETATM   75  H14 UNL     1      -1.903   2.767   5.855  1.00  0.00           H  
HETATM   76  H15 UNL     1      -1.421   4.411   5.463  1.00  0.00           H  
HETATM   77  H16 UNL     1       1.065   3.594   5.120  1.00  0.00           H  
HETATM   78  H17 UNL     1       1.707   2.160   6.850  1.00  0.00           H  
HETATM   79  H18 UNL     1      -1.384   1.807   7.251  1.00  0.00           H  
HETATM   80  H19 UNL     1      -0.221   1.969   8.537  1.00  0.00           H  
HETATM   81  H20 UNL     1      -1.074  -0.379   8.325  1.00  0.00           H  
HETATM   82  H21 UNL     1       0.279  -1.915   7.222  1.00  0.00           H  
HETATM   83  H22 UNL     1       2.475  -0.589   6.285  1.00  0.00           H  
HETATM   84  H23 UNL     1       1.345   0.436   5.446  1.00  0.00           H  
HETATM   85  H24 UNL     1       0.144  -1.319   4.357  1.00  0.00           H  
HETATM   86  H25 UNL     1       1.530  -3.077   3.623  1.00  0.00           H  
HETATM   87  H26 UNL     1       3.200  -2.246   6.179  1.00  0.00           H  
HETATM   88  H27 UNL     1       3.132  -3.788   5.397  1.00  0.00           H  
HETATM   89  H28 UNL     1       4.395  -1.484   3.820  1.00  0.00           H  
HETATM   90  H29 UNL     1       5.258  -2.329   5.105  1.00  0.00           H  
HETATM   91  H30 UNL     1       5.878  -3.252   3.065  1.00  0.00           H  
HETATM   92  H31 UNL     1       5.011  -4.491   3.955  1.00  0.00           H  
HETATM   93  H32 UNL     1       2.280  -4.943   0.582  1.00  0.00           H  
HETATM   94  H33 UNL     1       3.451  -3.992  -0.360  1.00  0.00           H  
HETATM   95  H34 UNL     1       1.210  -3.964  -1.224  1.00  0.00           H  
HETATM   96  H35 UNL     1       1.147  -1.591  -1.794  1.00  0.00           H  
HETATM   97  H36 UNL     1       2.156  -1.193  -0.359  1.00  0.00           H  
HETATM   98  H37 UNL     1       4.437   0.979  -1.919  1.00  0.00           H  
HETATM   99  H38 UNL     1       4.160  -1.250  -5.375  1.00  0.00           H  
HETATM  100  H39 UNL     1       3.013  -2.551  -4.782  1.00  0.00           H  
HETATM  101  H40 UNL     1       2.522  -1.911  -7.186  1.00  0.00           H  
HETATM  102  H41 UNL     1       0.845  -2.333  -5.429  1.00  0.00           H  
HETATM  103  H42 UNL     1       1.637   0.273  -7.673  1.00  0.00           H  
HETATM  104  H43 UNL     1       1.927   0.841  -5.955  1.00  0.00           H  
HETATM  105  H44 UNL     1       1.668   2.264  -9.046  1.00  0.00           H  
HETATM  106  H45 UNL     1       1.548   2.801  -6.535  1.00  0.00           H  
HETATM  107  H46 UNL     1      -2.470  -2.809   0.732  1.00  0.00           H  
HETATM  108  H47 UNL     1      -1.677  -3.653   2.094  1.00  0.00           H  
HETATM  109  H48 UNL     1      -3.677  -4.781   1.737  1.00  0.00           H  
HETATM  110  H49 UNL     1      -2.506  -5.877   0.956  1.00  0.00           H  
HETATM  111  H50 UNL     1      -4.631  -4.000  -0.196  1.00  0.00           H  
HETATM  112  H51 UNL     1      -4.564  -5.772  -0.279  1.00  0.00           H  
HETATM  113  H52 UNL     1      -2.647  -5.562  -2.021  1.00  0.00           H  
HETATM  114  H53 UNL     1      -3.292  -3.976  -3.576  1.00  0.00           H  
HETATM  115  H54 UNL     1      -5.251  -2.873  -1.496  1.00  0.00           H  
HETATM  116  H55 UNL     1      -5.609  -3.115  -3.251  1.00  0.00           H  
HETATM  117  H56 UNL     1      -3.753  -1.358  -3.823  1.00  0.00           H  
HETATM  118  H57 UNL     1      -3.999   0.526  -2.672  1.00  0.00           H  
HETATM  119  H58 UNL     1      -5.990   0.623  -1.186  1.00  0.00           H  
HETATM  120  H59 UNL     1      -4.431   0.701  -0.368  1.00  0.00           H  
HETATM  121  H60 UNL     1      -6.380  -1.750  -0.108  1.00  0.00           H  
HETATM  122  H61 UNL     1      -5.585  -1.694   2.030  1.00  0.00           H  
HETATM  123  H62 UNL     1      -4.716   0.325   2.938  1.00  0.00           H  
HETATM  124  H63 UNL     1      -4.116   0.965   1.440  1.00  0.00           H  
HETATM  125  H64 UNL     1      -2.979  -1.446   3.115  1.00  0.00           H  
HETATM  126  H65 UNL     1      -0.888  -0.836   2.257  1.00  0.00           H  
HETATM  127  H66 UNL     1      -0.823   1.481   1.261  1.00  0.00           H  
HETATM  128  H67 UNL     1      -2.452   1.361   0.621  1.00  0.00           H  
HETATM  129  H68 UNL     1      -0.016  -0.187  -0.223  1.00  0.00           H  
HETATM  130  H69 UNL     1      -1.700  -0.546  -0.851  1.00  0.00           H  
HETATM  131  H70 UNL     1      -2.018   1.719  -1.476  1.00  0.00           H  
HETATM  132  H71 UNL     1      -0.419   2.222  -0.914  1.00  0.00           H  
HETATM  133  H72 UNL     1       0.630   0.563  -2.561  1.00  0.00           H  
HETATM  134  H73 UNL     1      -1.047   0.188  -3.148  1.00  0.00           H  
HETATM  135  H74 UNL     1      -1.035   1.966  -4.526  1.00  0.00           H  
HETATM  136  H75 UNL     1      -0.803   3.041  -3.116  1.00  0.00           H  
HETATM  137  H76 UNL     1       0.625   2.371  -4.032  1.00  0.00           H  
CONECT    1    2   62   63   64
CONECT    2    3   65   66
CONECT    3    4   67   68
CONECT    4    5   69   70
CONECT    5    6   71   72
CONECT    6    7    7   73
CONECT    7    8   74
CONECT    8    9   75   76
CONECT    9   10   10   77
CONECT   10   11   78
CONECT   11   12   79   80
CONECT   12   13   13   81
CONECT   13   14   82
CONECT   14   15   83   84
CONECT   15   16   16   85
CONECT   16   17   86
CONECT   17   18   87   88
CONECT   18   19   89   90
CONECT   19   20   91   92
CONECT   20   21   21   22
CONECT   22   23
CONECT   23   24   93   94
CONECT   24   25   40   95
CONECT   25   26   96   97
CONECT   26   27
CONECT   27   28   28   29   30
CONECT   29   98
CONECT   30   31
CONECT   31   32   99  100
CONECT   32   33   34  101
CONECT   33  102
CONECT   34   35  103  104
CONECT   35   36
CONECT   36   37   37   38   39
CONECT   38  105
CONECT   39  106
CONECT   40   41
CONECT   41   42   42   43
CONECT   43   44  107  108
CONECT   44   45  109  110
CONECT   45   46  111  112
CONECT   46   47   47  113
CONECT   47   48  114
CONECT   48   49  115  116
CONECT   49   50   50  117
CONECT   50   51  118
CONECT   51   52  119  120
CONECT   52   53   53  121
CONECT   53   54  122
CONECT   54   55  123  124
CONECT   55   56   56  125
CONECT   56   57  126
CONECT   57   58  127  128
CONECT   58   59  129  130
CONECT   59   60  131  132
CONECT   60   61  133  134
CONECT   61  135  136  137
END

HMDB0116464
     RDKit          3D
PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))
137136  0  0  0  0  0  0  0  0999 V2000
   -0.0031    7.0109   -1.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0226    7.0761    0.4094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0147    6.0802    1.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9545    6.2257    2.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8975    5.2783    3.2389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    3.8868    2.9727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2826    3.0017    3.8539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1394    3.3487    5.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2419    3.0704    5.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5833    2.2481    6.6394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3042    1.4943    7.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3097    0.0644    7.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4148   -0.8067    6.9849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4510   -0.5667    5.9846 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0775   -1.4875    4.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8901   -2.4685    4.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1424   -2.6276    5.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3972   -2.4918    4.3729 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7911   -3.4916    3.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0783   -3.8366    2.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4419   -4.9707    1.6085 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0574   -3.2269    1.4992 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5971   -3.8980    0.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4706   -3.2208   -0.3926 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9194   -1.9785   -1.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0593   -2.3249   -1.8446 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6390   -0.9700   -2.6855 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.0368   -1.2904   -3.1416 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6702    0.3858   -1.6983 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6939   -0.6991   -4.0748 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1091   -1.5158   -5.1227 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2410   -1.2514   -6.3267 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9121   -1.5337   -5.9977 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108    0.1780   -6.7838 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5698    0.6047   -7.1494 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4295    2.2194   -7.6353 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.7789    2.8662   -7.7424 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6423    2.2298   -9.1479 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4824    3.0938   -6.5305 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3411   -3.0857    0.4211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7923   -3.9011    0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7225   -4.6674   -0.8115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9559   -3.7938    1.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9765   -4.8333    0.8207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8662   -4.8331   -0.3531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3749   -4.7712   -1.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7944   -3.8876   -2.5724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7773   -2.8160   -2.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3175   -1.4766   -2.8295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4624   -0.3971   -2.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0734   -0.0547   -0.8925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5960   -0.9869    0.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1728   -0.9485    1.3456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2076   -0.0033    1.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7719   -0.3076    1.8857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6105    0.7429    0.8855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0199    0.1825   -0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9622    1.3834   -1.3695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124    0.9691   -2.6964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3861    2.1641   -3.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8860    6.4417   -1.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3068    8.1017    0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0023    6.8975    0.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0263    5.6350    4.2549 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Arachidonoyl-2-arachidonoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)	HMDB
PGP(20:4/20:4)	HMDB
PGP(20:4n6/20:4n6)	HMDB
PGP(20:4W6/20:4W6)	HMDB
PGP(40:8)	HMDB
3-sn-Phosphatidyl-1'-sn-glycerol 3'-phosphoric acid	HMDB
1,2-Diarachidonoyl-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)	HMDB
1,2-Di(5Z,8Z,11Z,14Z-eicosatetraenoyl)-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)	HMDB
[(2S)-2-Hydroxy-3-({hydroxy[(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]-3-[(8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonate	HMDB
1-arachidonoyl-2-arachidonoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)	SMPDB, HMDB
PGP(20:4/20:4)	SMPDB, HMDB
PGP(20:4n6/20:4n6)	SMPDB, HMDB
PGP(20:4w6/20:4w6)	SMPDB, HMDB
PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))	SMPDB

Chemical Formula

C₄₆H₇₆O₁₃P₂

Average Molecular Weight

899.049

Monoisotopic Molecular Weight

898.476116503

IUPAC Name

[(2S)-3-({[(2R)-2,3-bis[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid

Traditional Name

(2S)-3-{[(2R)-2,3-bis[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC

InChI Identifier

InChI=1S/C46H76O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-37-45(48)55-41-44(42-58-61(53,54)57-40-43(47)39-56-60(50,51)52)59-46(49)38-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11-14,17-20,23-26,29-32,43-44,47H,3-10,15-16,21-22,27-28,33-42H2,1-2H3,(H,53,54)(H2,50,51,52)/b13-11-,14-12-,19-17-,20-18-,25-23-,26-24-,31-29-,32-30-/t43-,44+/m0/s1

InChI Key

DJKWAZSGTLJIDZ-MKYVJXLQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylglycerophosphates. These are glycerophosphoglycerophosphates in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoglycerophosphates

Direct Parent

Phosphatidylglycerophosphates

Alternative Parents

Substituents

Diacylglycerophosphoglycerophosphate
Sn-glycerol-3-phosphate
Fatty acid ester
Monoalkyl phosphate
Dialkyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0116464)

Process

Naturally occurring process

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	7.39	ALOGPS
logP	11.47	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	1.35	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	195.35 Å²	ChemAxon
Rotatable Bond Count	42	ChemAxon
Refractivity	251.92 m³·mol⁻¹	ChemAxon
Polarizability	98.96 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	275.771	30932474
DeepCCS	[M-H]-	273.375	30932474
DeepCCS	[M-2H]-	306.605	30932474
DeepCCS	[M+Na]+	281.683	30932474
AllCCS	[M+H]+	303.4	32859911
AllCCS	[M+H-H2O]+	303.5	32859911
AllCCS	[M+NH4]+	303.3	32859911
AllCCS	[M+Na]+	303.2	32859911
AllCCS	[M-H]-	300.7	32859911
AllCCS	[M+Na-2H]-	307.9	32859911
AllCCS	[M+HCOO]-	315.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	4.5 minutes	32390414
Predicted by Siyang on May 30, 2022	30.6244 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.52 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	5526.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	254.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	314.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	259.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	995.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1829.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	999.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	307.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	3171.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	1311.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2547.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	1280.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	715.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	316.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	520.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	11.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))	[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC	6293.1	Standard polar	33892256
PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))	[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC	4892.1	Standard non polar	33892256
PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))	[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC	6197.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) 10V, Positive-QTOF	splash10-0002-1362153290-390b31628b5dc3fa8fe6	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) 20V, Positive-QTOF	splash10-053b-4494134430-91a036dc1161ad8d6cc5	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) 40V, Positive-QTOF	splash10-0a4j-9346124510-a3f771c166a9e878b74f	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) 10V, Negative-QTOF	splash10-0ug1-7097022150-d3c1940cfbb3609078e6	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) 20V, Negative-QTOF	splash10-0fb9-9032000000-06aad147a315cc70c888	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) 40V, Negative-QTOF	splash10-004i-9000000000-8259c4cf6207672a3483	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) 10V, Positive-QTOF	splash10-0002-2000003190-b7f385ff573a7a6aa1a7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) 20V, Positive-QTOF	splash10-0pea-1200005920-fe4fcb10e4c3601062a3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) 40V, Positive-QTOF	splash10-0udj-0091002000-5ac97c068e0e3b90706a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) 10V, Negative-QTOF	splash10-0002-0010000090-03a190e1dcdd52224b21	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) 20V, Negative-QTOF	splash10-0f6t-3093182030-922922a14b2f90ba84f4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) 40V, Negative-QTOF	splash10-0fba-2091140000-01437e437b3297c96e04	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(11Z)/18:1(11Z))		Not Available
Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:1(9Z)/18:1(9Z))		Not Available
Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)/16:0)		Not Available
Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))		Not Available
Cardiolipin Biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/22:5(4Z,7Z,10Z,13Z,16Z))		Not Available