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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2010-05-13 16:09:00 UTC

Update Date

2022-11-30 19:04:12 UTC

HMDB ID

HMDB0013495

Secondary Accession Numbers

HMDB13495

Metabolite Identification

Common Name

PGP(16:1(9Z)/20:3(5Z,8Z,11Z))

Description

PGP(16:1(9Z)/20:3(5Z,8Z,11Z)) is a phosphatidylglycerolphosphate or glycerophospholipid (PGP or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site followed by another phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PGP(16:1(9Z)/20:3(5Z,8Z,11Z)), in particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of mead acid at the C-2 position. The palmitoleic acid moiety is derived from animal fats and vegetable oils, while the mead acid moiety is derived from fish oils, liver and kidney. 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 at 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 diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. 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. PGPs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PGP also serves as a precursor for the synthesis of cardiolipin. PGP is synthesized from CDP-diacylglycerol and glycerol-3-phosphate.

Structure

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


  Mrv1652303252017082D          

 59 58  0  0  1  0            999 V2000
   21.8881   -3.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2130   -3.5780    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.5379   -3.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5633   -3.5780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8627   -3.5780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6862   -4.3576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2383   -3.1883    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.8486   -2.5130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6282   -3.8633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9135   -2.7984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5886   -3.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2637   -2.7984    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.9389   -3.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8008   -4.3873    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.5767   -2.7617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8400   -2.1135    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.6517   -2.1135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4311   -3.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1456   -3.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8601   -3.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5745   -3.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2890   -3.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0035   -3.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7180   -3.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4325   -3.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1470   -3.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8614   -3.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5759   -3.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2904   -3.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0048   -3.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7193   -3.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4338   -3.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1482   -3.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1482   -2.3405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3966   -4.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1111   -4.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8255   -4.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5401   -4.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2545   -4.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9690   -4.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6835   -4.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3979   -4.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1124   -4.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8269   -4.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5414   -4.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2559   -4.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9703   -4.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6849   -4.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3993   -4.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1138   -4.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8283   -4.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5428   -4.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2572   -4.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9717   -4.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9717   -5.5951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3167   -3.1263    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   28.0568   -3.4910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6814   -2.3863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9521   -3.8664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  2  6  1  6  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
 13 12  1  0  0  0  0
  2 14  1  1  0  0  0
 13 15  1  0  0  0  0
 12 16  1  6  0  0  0
 12 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 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  2  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  5  1  0  0  0  0
 33 34  2  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  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  2  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  6  1  0  0  0  0
 54 55  2  0  0  0  0
 57 56  2  0  0  0  0
 58 56  1  0  0  0  0
 59 56  1  0  0  0  0
 15 56  1  0  0  0  0
M  END

HMDB0013495
     RDKit          3D
PGP(16:1(9Z)/20:3(5Z,8Z,11Z))
133132  0  0  0  0  0  0  0  0999 V2000
   -1.4277    7.2208   -5.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7274    6.5873   -4.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9375    7.4582   -2.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2866    6.8990   -1.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1883    6.7567   -1.9010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8766    6.2214   -0.6429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6640    7.0835    0.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1283    6.7232    1.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6466    5.3796    1.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8288    5.4588    2.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4370    4.1754    2.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3593    3.0735    1.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0761    3.4109    0.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1274    2.3934   -0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8706    1.1371   -0.4927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5263    0.2182    0.5849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2014    0.3025    1.6548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5274   -0.7399    0.5466 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1916   -1.6070    1.5863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3394   -2.4840    1.9931 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0603   -3.1993    3.3058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0827   -4.1814    3.1718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7675   -4.9745    4.6062 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.3463   -4.0339    5.7132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1106   -5.8364    5.1690 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4991   -6.0608    4.3626 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7898   -6.2890    3.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9307   -7.2800    2.9767 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3010   -7.5836    1.6690 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1136   -6.7876    3.7821 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6265   -5.6365    3.1638 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9457   -5.1117    4.0825 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.1332   -4.8108    3.1666 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4216   -6.3282    5.1682 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5356   -3.7368    4.9476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7892   -3.3777    1.0042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0440   -3.3158    0.4282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7530   -2.3190    0.8619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6019   -4.2337   -0.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1055   -4.1267   -1.9347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2227   -2.8000   -2.6292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8733   -2.9848   -4.0322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9527   -2.4777   -4.7465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9377   -1.4948   -4.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6329   -2.1335   -4.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3032   -2.3726   -3.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2682   -2.0478   -2.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4104   -3.2794   -1.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4478   -3.5087   -0.6838 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5653   -2.5625   -0.5638 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7049   -2.0698    0.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8538   -1.1457    1.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7211    0.0711    0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8184    1.0426    0.4148 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8022    2.1983   -0.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5842    3.0398   -0.5267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3172    2.4171   -0.9939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5858    6.4643   -6.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7691    8.0335   -5.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3680    7.7049   -5.0457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3475    6.4961   -4.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1357    5.5797   -3.9681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5311    8.4921   -3.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0235    7.6284   -2.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7160    5.8764   -1.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5714    7.5248   -0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3532    6.0178   -2.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203    7.7218   -2.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9809    6.2671   -0.8905 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5900    5.1811   -0.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9887    8.1325    0.4061 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0085    7.4714    2.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8772    4.5962    1.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1209    4.9948    2.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015    6.1803    3.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4074    5.8585    1.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9014    3.8279    3.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4943    4.2872    3.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6217    2.1537    2.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2612    2.9267    1.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0843    3.8745    0.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5049    4.2954   -0.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4891    2.8356   -1.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0584    2.1272   -0.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8081    0.5984   -1.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9826    1.3214   -0.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8147   -0.9893    2.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3926   -2.2870    1.1918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2357   -1.8280    2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9907   -3.6936    3.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7613   -2.4884    4.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8590   -6.4548    5.8987 H   0  0  0  0  0  0  0  0  0  0  0  0
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 57133  1  0
M  END


  Mrv1652303252017082D          

 59 58  0  0  1  0            999 V2000
   21.8881   -3.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2130   -3.5780    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   22.5633   -3.5780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   23.2383   -3.1883    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.8486   -2.5130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   18.4338   -3.5780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1482   -3.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1482   -2.3405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.3979   -4.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   13.5414   -4.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   19.9717   -5.5951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3167   -3.1263    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   28.0568   -3.4910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6814   -2.3863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9521   -3.8664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  2  6  1  6  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
 13 12  1  0  0  0  0
  2 14  1  1  0  0  0
 13 15  1  0  0  0  0
 12 16  1  6  0  0  0
 12 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
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 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  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  5  1  0  0  0  0
 33 34  2  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  2  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  2  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  6  1  0  0  0  0
 54 55  2  0  0  0  0
 57 56  2  0  0  0  0
 58 56  1  0  0  0  0
 59 56  1  0  0  0  0
 15 56  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013495

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C42H76O13P2/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-42(45)55-40(38-54-57(49,50)53-36-39(43)35-52-56(46,47)48)37-51-41(44)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h14,16-18,20,22,26,28,39-40,43H,3-13,15,19,21,23-25,27,29-38H2,1-2H3,(H,49,50)(H2,46,47,48)/b16-14-,18-17-,22-20-,28-26-/t39-,40+/m0/s1

> <INCHI_KEY>
JZUYPUNJRHZLJE-OILVUHFKSA-N

> <FORMULA>
C42H76O13P2

> <MOLECULAR_WEIGHT>
850.9926

> <EXACT_MASS>
850.476115542

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
133

> <JCHEM_AVERAGE_POLARIZABILITY>
94.88395659042806

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S)-3-({[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid

> <ALOGPS_LOGP>
7.33

> <JCHEM_LOGP>
11.144073521333333

> <ALOGPS_LOGS>
-6.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.040206143698788

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3548792964147385

> <JCHEM_PKA_STRONGEST_BASIC>
-3.410499386302644

> <JCHEM_POLAR_SURFACE_AREA>
195.35

> <JCHEM_REFRACTIVITY>
229.05220000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
42

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.97e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013495
     RDKit          3D
PGP(16:1(9Z)/20:3(5Z,8Z,11Z))
133132  0  0  0  0  0  0  0  0999 V2000
   -1.4277    7.2208   -5.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7274    6.5873   -4.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9375    7.4582   -2.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2866    6.8990   -1.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1883    6.7567   -1.9010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8766    6.2214   -0.6429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6640    7.0835    0.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1283    6.7232    1.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6466    5.3796    1.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8288    5.4588    2.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4370    4.1754    2.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3593    3.0735    1.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0761    3.4109    0.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1274    2.3934   -0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8706    1.1371   -0.4927 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HEADER    PROTEIN                                 25-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAR-20         0                                  
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HETATM   45  C   UNK     0      25.277  -8.134   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      26.611  -8.904   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      27.945  -8.904   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      29.278  -8.134   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      30.612  -8.904   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      31.946  -8.904   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      33.279  -8.134   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      34.613  -8.904   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      35.947  -8.134   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      37.281  -8.904   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      37.281 -10.444   0.000  0.00  0.00           O+0
HETATM   56  P   UNK     0      50.991  -5.836   0.000  0.00  0.00           P+0
HETATM   57  O   UNK     0      52.373  -6.517   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      51.672  -4.454   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      50.311  -7.217   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    3    6   14                                             
CONECT    3    2    5                                                       
CONECT    4    1    7                                                       
CONECT    5    3   33                                                       
CONECT    6    2   54                                                       
CONECT    7    4    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   16   17                                             
CONECT   13   12   15                                                       
CONECT   14    2                                                            
CONECT   15   13   56                                                       
CONECT   16   12                                                            
CONECT   17   12                                                            
CONECT   18   19                                                            
CONECT   19   18   20                                                       
CONECT   20   19   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    5   34                                                  
CONECT   34   33                                                            
CONECT   35   36                                                            
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   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    6   55                                                  
CONECT   55   54                                                            
CONECT   56   57   58   59   15                                             
CONECT   57   56                                                            
CONECT   58   56                                                            
CONECT   59   56                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  116    0
END

COMPND    HMDB0013495
HETATM    1  C1  UNL     1      -1.428   7.221  -5.373  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.727   6.587  -4.159  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.937   7.458  -2.966  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.287   6.899  -1.730  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.188   6.757  -1.901  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.877   6.221  -0.643  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.664   7.083   0.502  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.128   6.723   1.617  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.647   5.380   1.920  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.829   5.459   2.241  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.437   4.175   2.671  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.359   3.074   1.657  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.076   3.411   0.388  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.127   2.393  -0.674  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.871   1.137  -0.493  1.00  0.00           C  
HETATM   16  C16 UNL     1      -2.526   0.218   0.585  1.00  0.00           C  
HETATM   17  O1  UNL     1      -3.201   0.303   1.655  1.00  0.00           O  
HETATM   18  O2  UNL     1      -1.527  -0.740   0.547  1.00  0.00           O  
HETATM   19  C17 UNL     1      -1.192  -1.607   1.586  1.00  0.00           C  
HETATM   20  C18 UNL     1      -2.339  -2.484   1.993  1.00  0.00           C  
HETATM   21  C19 UNL     1      -2.060  -3.199   3.306  1.00  0.00           C  
HETATM   22  O3  UNL     1      -1.083  -4.181   3.172  1.00  0.00           O  
HETATM   23  P1  UNL     1      -0.768  -4.975   4.606  1.00  0.00           P  
HETATM   24  O4  UNL     1      -0.346  -4.034   5.713  1.00  0.00           O  
HETATM   25  O5  UNL     1      -2.111  -5.836   5.169  1.00  0.00           O  
HETATM   26  O6  UNL     1       0.499  -6.061   4.363  1.00  0.00           O  
HETATM   27  C20 UNL     1       0.790  -6.289   3.036  1.00  0.00           C  
HETATM   28  C21 UNL     1       1.931  -7.280   2.977  1.00  0.00           C  
HETATM   29  O7  UNL     1       2.301  -7.584   1.669  1.00  0.00           O  
HETATM   30  C22 UNL     1       3.114  -6.788   3.782  1.00  0.00           C  
HETATM   31  O8  UNL     1       3.626  -5.636   3.164  1.00  0.00           O  
HETATM   32  P2  UNL     1       4.946  -5.112   4.082  1.00  0.00           P  
HETATM   33  O9  UNL     1       6.133  -4.811   3.167  1.00  0.00           O  
HETATM   34  O10 UNL     1       5.422  -6.328   5.168  1.00  0.00           O  
HETATM   35  O11 UNL     1       4.536  -3.737   4.948  1.00  0.00           O  
HETATM   36  O12 UNL     1      -2.789  -3.378   1.004  1.00  0.00           O  
HETATM   37  C23 UNL     1      -4.044  -3.316   0.428  1.00  0.00           C  
HETATM   38  O13 UNL     1      -4.753  -2.319   0.862  1.00  0.00           O  
HETATM   39  C24 UNL     1      -4.602  -4.234  -0.563  1.00  0.00           C  
HETATM   40  C25 UNL     1      -4.105  -4.127  -1.935  1.00  0.00           C  
HETATM   41  C26 UNL     1      -4.223  -2.800  -2.629  1.00  0.00           C  
HETATM   42  C27 UNL     1      -3.873  -2.985  -4.032  1.00  0.00           C  
HETATM   43  C28 UNL     1      -2.953  -2.478  -4.746  1.00  0.00           C  
HETATM   44  C29 UNL     1      -1.938  -1.495  -4.238  1.00  0.00           C  
HETATM   45  C30 UNL     1      -0.633  -2.134  -4.529  1.00  0.00           C  
HETATM   46  C31 UNL     1       0.303  -2.373  -3.686  1.00  0.00           C  
HETATM   47  C32 UNL     1       0.268  -2.048  -2.252  1.00  0.00           C  
HETATM   48  C33 UNL     1       0.410  -3.279  -1.452  1.00  0.00           C  
HETATM   49  C34 UNL     1       1.448  -3.509  -0.684  1.00  0.00           C  
HETATM   50  C35 UNL     1       2.565  -2.563  -0.564  1.00  0.00           C  
HETATM   51  C36 UNL     1       2.705  -2.070   0.853  1.00  0.00           C  
HETATM   52  C37 UNL     1       3.854  -1.146   1.088  1.00  0.00           C  
HETATM   53  C38 UNL     1       3.721   0.071   0.170  1.00  0.00           C  
HETATM   54  C39 UNL     1       4.818   1.043   0.415  1.00  0.00           C  
HETATM   55  C40 UNL     1       4.802   2.198  -0.510  1.00  0.00           C  
HETATM   56  C41 UNL     1       3.584   3.040  -0.527  1.00  0.00           C  
HETATM   57  C42 UNL     1       2.317   2.417  -0.994  1.00  0.00           C  
HETATM   58  H1  UNL     1      -1.586   6.464  -6.146  1.00  0.00           H  
HETATM   59  H2  UNL     1      -0.769   8.033  -5.784  1.00  0.00           H  
HETATM   60  H3  UNL     1      -2.368   7.705  -5.046  1.00  0.00           H  
HETATM   61  H4  UNL     1       0.348   6.496  -4.400  1.00  0.00           H  
HETATM   62  H5  UNL     1      -1.136   5.580  -3.968  1.00  0.00           H  
HETATM   63  H6  UNL     1      -0.531   8.492  -3.138  1.00  0.00           H  
HETATM   64  H7  UNL     1      -2.024   7.628  -2.757  1.00  0.00           H  
HETATM   65  H8  UNL     1      -0.716   5.876  -1.596  1.00  0.00           H  
HETATM   66  H9  UNL     1      -0.571   7.525  -0.866  1.00  0.00           H  
HETATM   67  H10 UNL     1       1.353   6.018  -2.740  1.00  0.00           H  
HETATM   68  H11 UNL     1       1.620   7.722  -2.226  1.00  0.00           H  
HETATM   69  H12 UNL     1       2.981   6.267  -0.891  1.00  0.00           H  
HETATM   70  H13 UNL     1       1.590   5.181  -0.566  1.00  0.00           H  
HETATM   71  H14 UNL     1       1.989   8.132   0.406  1.00  0.00           H  
HETATM   72  H15 UNL     1       1.008   7.471   2.437  1.00  0.00           H  
HETATM   73  H16 UNL     1       0.877   4.596   1.187  1.00  0.00           H  
HETATM   74  H17 UNL     1       1.121   4.995   2.882  1.00  0.00           H  
HETATM   75  H18 UNL     1      -0.901   6.180   3.105  1.00  0.00           H  
HETATM   76  H19 UNL     1      -1.407   5.858   1.373  1.00  0.00           H  
HETATM   77  H20 UNL     1      -0.901   3.828   3.606  1.00  0.00           H  
HETATM   78  H21 UNL     1      -2.494   4.287   3.009  1.00  0.00           H  
HETATM   79  H22 UNL     1      -1.622   2.154   2.159  1.00  0.00           H  
HETATM   80  H23 UNL     1      -0.261   2.927   1.369  1.00  0.00           H  
HETATM   81  H24 UNL     1      -3.084   3.875   0.599  1.00  0.00           H  
HETATM   82  H25 UNL     1      -1.505   4.295  -0.044  1.00  0.00           H  
HETATM   83  H26 UNL     1      -2.489   2.836  -1.656  1.00  0.00           H  
HETATM   84  H27 UNL     1      -1.058   2.127  -0.927  1.00  0.00           H  
HETATM   85  H28 UNL     1      -2.808   0.598  -1.505  1.00  0.00           H  
HETATM   86  H29 UNL     1      -3.983   1.321  -0.418  1.00  0.00           H  
HETATM   87  H30 UNL     1      -0.815  -0.989   2.426  1.00  0.00           H  
HETATM   88  H31 UNL     1      -0.393  -2.287   1.192  1.00  0.00           H  
HETATM   89  H32 UNL     1      -3.236  -1.828   2.227  1.00  0.00           H  
HETATM   90  H33 UNL     1      -2.991  -3.694   3.650  1.00  0.00           H  
HETATM   91  H34 UNL     1      -1.761  -2.488   4.099  1.00  0.00           H  
HETATM   92  H35 UNL     1      -1.859  -6.455   5.899  1.00  0.00           H  
HETATM   93  H36 UNL     1       1.091  -5.302   2.601  1.00  0.00           H  
HETATM   94  H37 UNL     1      -0.067  -6.724   2.474  1.00  0.00           H  
HETATM   95  H38 UNL     1       1.539  -8.224   3.446  1.00  0.00           H  
HETATM   96  H39 UNL     1       3.272  -7.415   1.594  1.00  0.00           H  
HETATM   97  H40 UNL     1       2.788  -6.537   4.810  1.00  0.00           H  
HETATM   98  H41 UNL     1       3.857  -7.590   3.804  1.00  0.00           H  
HETATM   99  H42 UNL     1       6.365  -6.188   5.429  1.00  0.00           H  
HETATM  100  H43 UNL     1       5.121  -2.982   4.725  1.00  0.00           H  
HETATM  101  H44 UNL     1      -5.736  -4.048  -0.618  1.00  0.00           H  
HETATM  102  H45 UNL     1      -4.573  -5.299  -0.179  1.00  0.00           H  
HETATM  103  H46 UNL     1      -4.616  -4.936  -2.545  1.00  0.00           H  
HETATM  104  H47 UNL     1      -3.016  -4.463  -1.959  1.00  0.00           H  
HETATM  105  H48 UNL     1      -5.320  -2.529  -2.592  1.00  0.00           H  
HETATM  106  H49 UNL     1      -3.701  -1.990  -2.119  1.00  0.00           H  
HETATM  107  H50 UNL     1      -4.553  -3.714  -4.569  1.00  0.00           H  
HETATM  108  H51 UNL     1      -2.866  -2.766  -5.842  1.00  0.00           H  
HETATM  109  H52 UNL     1      -2.135  -1.236  -3.209  1.00  0.00           H  
HETATM  110  H53 UNL     1      -2.033  -0.529  -4.821  1.00  0.00           H  
HETATM  111  H54 UNL     1      -0.420  -2.450  -5.592  1.00  0.00           H  
HETATM  112  H55 UNL     1       1.261  -2.876  -4.018  1.00  0.00           H  
HETATM  113  H56 UNL     1      -0.743  -1.632  -1.950  1.00  0.00           H  
HETATM  114  H57 UNL     1       1.001  -1.258  -2.070  1.00  0.00           H  
HETATM  115  H58 UNL     1      -0.414  -4.005  -1.536  1.00  0.00           H  
HETATM  116  H59 UNL     1       1.473  -4.465  -0.102  1.00  0.00           H  
HETATM  117  H60 UNL     1       2.551  -1.702  -1.217  1.00  0.00           H  
HETATM  118  H61 UNL     1       3.511  -3.178  -0.732  1.00  0.00           H  
HETATM  119  H62 UNL     1       1.785  -1.516   1.150  1.00  0.00           H  
HETATM  120  H63 UNL     1       2.805  -2.915   1.566  1.00  0.00           H  
HETATM  121  H64 UNL     1       4.800  -1.687   0.899  1.00  0.00           H  
HETATM  122  H65 UNL     1       3.870  -0.754   2.108  1.00  0.00           H  
HETATM  123  H66 UNL     1       2.727   0.493   0.454  1.00  0.00           H  
HETATM  124  H67 UNL     1       3.805  -0.280  -0.858  1.00  0.00           H  
HETATM  125  H68 UNL     1       5.805   0.521   0.277  1.00  0.00           H  
HETATM  126  H69 UNL     1       4.815   1.435   1.471  1.00  0.00           H  
HETATM  127  H70 UNL     1       4.977   1.793  -1.555  1.00  0.00           H  
HETATM  128  H71 UNL     1       5.735   2.828  -0.348  1.00  0.00           H  
HETATM  129  H72 UNL     1       3.475   3.492   0.506  1.00  0.00           H  
HETATM  130  H73 UNL     1       3.794   3.914  -1.205  1.00  0.00           H  
HETATM  131  H74 UNL     1       1.572   2.366  -0.173  1.00  0.00           H  
HETATM  132  H75 UNL     1       1.791   3.128  -1.735  1.00  0.00           H  
HETATM  133  H76 UNL     1       2.416   1.500  -1.589  1.00  0.00           H  
CONECT    1    2   58   59   60
CONECT    2    3   61   62
CONECT    3    4   63   64
CONECT    4    5   65   66
CONECT    5    6   67   68
CONECT    6    7   69   70
CONECT    7    8    8   71
CONECT    8    9   72
CONECT    9   10   73   74
CONECT   10   11   75   76
CONECT   11   12   77   78
CONECT   12   13   79   80
CONECT   13   14   81   82
CONECT   14   15   83   84
CONECT   15   16   85   86
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   20   87   88
CONECT   20   21   36   89
CONECT   21   22   90   91
CONECT   22   23
CONECT   23   24   24   25   26
CONECT   25   92
CONECT   26   27
CONECT   27   28   93   94
CONECT   28   29   30   95
CONECT   29   96
CONECT   30   31   97   98
CONECT   31   32
CONECT   32   33   33   34   35
CONECT   34   99
CONECT   35  100
CONECT   36   37
CONECT   37   38   38   39
CONECT   39   40  101  102
CONECT   40   41  103  104
CONECT   41   42  105  106
CONECT   42   43   43  107
CONECT   43   44  108
CONECT   44   45  109  110
CONECT   45   46   46  111
CONECT   46   47  112
CONECT   47   48  113  114
CONECT   48   49   49  115
CONECT   49   50  116
CONECT   50   51  117  118
CONECT   51   52  119  120
CONECT   52   53  121  122
CONECT   53   54  123  124
CONECT   54   55  125  126
CONECT   55   56  127  128
CONECT   56   57  129  130
CONECT   57  131  132  133
END

HMDB0013495
     RDKit          3D
PGP(16:1(9Z)/20:3(5Z,8Z,11Z))
133132  0  0  0  0  0  0  0  0999 V2000
   -1.4277    7.2208   -5.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7274    6.5873   -4.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9375    7.4582   -2.9659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2866    6.8990   -1.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1883    6.7567   -1.9010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8766    6.2214   -0.6429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6640    7.0835    0.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1283    6.7232    1.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6466    5.3796    1.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8288    5.4588    2.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4370    4.1754    2.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3593    3.0735    1.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0761    3.4109    0.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1274    2.3934   -0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8706    1.1371   -0.4927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5263    0.2182    0.5849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2014    0.3025    1.6548 O   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
PGP(16:1(9Z)/20:3(5Z,8Z,11Z))	Lipid Annotator
3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid	Lipid Annotator, HMDB
PGP(16:1/20:3)	Lipid Annotator, HMDB
1-palmitoleoyl-2-meadoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)	Lipid Annotator, HMDB
1-(9Z-hexadecenoyl)-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)	Lipid Annotator, HMDB
PGP(36:4)	Lipid Annotator, HMDB
PGP(16:1n7/20:3n9)	HMDB
PGP(16:1W7/20:3W9)	HMDB

Chemical Formula

C₄₂H₇₆O₁₃P₂

Average Molecular Weight

850.9926

Monoisotopic Molecular Weight

850.476115542

IUPAC Name

[(2S)-3-({[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid

Traditional Name

(2S)-3-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C42H76O13P2/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-42(45)55-40(38-54-57(49,50)53-36-39(43)35-52-56(46,47)48)37-51-41(44)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h14,16-18,20,22,26,28,39-40,43H,3-13,15,19,21,23-25,27,29-38H2,1-2H3,(H,49,50)(H2,46,47,48)/b16-14-,18-17-,22-20-,28-26-/t39-,40+/m0/s1

InChI Key

JZUYPUNJRHZLJE-OILVUHFKSA-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

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0007 g/L	ALOGPS
logP	7.33	ALOGPS
logP	11.14	ChemAxon
logS	-6.1	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	229.05 m³·mol⁻¹	ChemAxon
Polarizability	94.88 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
DarkChem	[M+H]+	313.759	31661259
DarkChem	[M-H]-	299.23	31661259
DeepCCS	[M+H]+	284.935	30932474
DeepCCS	[M-H]-	282.702	30932474
DeepCCS	[M-2H]-	316.42	30932474
DeepCCS	[M+Na]+	290.739	30932474
AllCCS	[M+H]+	294.3	32859911
AllCCS	[M+H-H2O]+	294.4	32859911
AllCCS	[M+NH4]+	294.2	32859911
AllCCS	[M+Na]+	294.2	32859911
AllCCS	[M-H]-	286.3	32859911
AllCCS	[M+Na-2H]-	293.5	32859911
AllCCS	[M+HCOO]-	301.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
PGP(16:1(9Z)/20:3(5Z,8Z,11Z))	CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)COP(=O)(O)OC[C@@]([H])(O)COP(=O)(O)O	5483.8	Standard polar	33892256
PGP(16:1(9Z)/20:3(5Z,8Z,11Z))	CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)COP(=O)(O)OC[C@@]([H])(O)COP(=O)(O)O	4707.4	Standard non polar	33892256
PGP(16:1(9Z)/20:3(5Z,8Z,11Z))	CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)COP(=O)(O)OC[C@@]([H])(O)COP(=O)(O)O	5847.0	Semi standard non polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(16:1(9Z)/20:3(5Z,8Z,11Z)) 10V, Positive-QTOF	splash10-0k9j-1290060140-a15bbe1cb9c86da1fe02	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(16:1(9Z)/20:3(5Z,8Z,11Z)) 20V, Positive-QTOF	splash10-000b-2391031110-895e8adfe7577047bcb3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(16:1(9Z)/20:3(5Z,8Z,11Z)) 40V, Positive-QTOF	splash10-0a4s-6391021200-d533c8e181b48cc191be	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(16:1(9Z)/20:3(5Z,8Z,11Z)) 10V, Negative-QTOF	splash10-0kbs-3091021020-74356f9e346dc4a428fc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(16:1(9Z)/20:3(5Z,8Z,11Z)) 20V, Negative-QTOF	splash10-004i-9050000000-49145be7a0d48152a441	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(16:1(9Z)/20:3(5Z,8Z,11Z)) 40V, Negative-QTOF	splash10-004i-9000000000-4b2977d777bea260ca57	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(16:1(9Z)/20:3(5Z,8Z,11Z)) 10V, Negative-QTOF	splash10-0002-0000000090-40abed2e3880a3dd0c54	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(16:1(9Z)/20:3(5Z,8Z,11Z)) 20V, Negative-QTOF	splash10-0002-9041171060-abfbcbc89bafa285981b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(16:1(9Z)/20:3(5Z,8Z,11Z)) 40V, Negative-QTOF	splash10-0kdi-8096120000-d5e4d5423df361be75a7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(16:1(9Z)/20:3(5Z,8Z,11Z)) 10V, Positive-QTOF	splash10-0udj-3110090680-588e353cf7faf1c7a0e2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(16:1(9Z)/20:3(5Z,8Z,11Z)) 20V, Positive-QTOF	splash10-0k92-3410046900-a81def28f8590a24beba	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(16:1(9Z)/20:3(5Z,8Z,11Z)) 40V, Positive-QTOF	splash10-01p7-1101934100-a426d4ddec31a0b88f20	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

All Tissues

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029495

KNApSAcK ID

Not Available

Chemspider ID

35032673

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481814

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for PGP(16:1(9Z)/20:3(5Z,8Z,11Z)) (HMDB0013495)

MOL for HMDB0013495 (PGP(16:1(9Z)/20:3(5Z,8Z,11Z)))

3D MOL for HMDB0013495 (PGP(16:1(9Z)/20:3(5Z,8Z,11Z)))

3D SDF for HMDB0013495 (PGP(16:1(9Z)/20:3(5Z,8Z,11Z)))

3D-SDF for HMDB0013495 (PGP(16:1(9Z)/20:3(5Z,8Z,11Z)))

PDB for HMDB0013495 (PGP(16:1(9Z)/20:3(5Z,8Z,11Z)))

3D PDB for HMDB0013495 (PGP(16:1(9Z)/20:3(5Z,8Z,11Z)))

SMILES for HMDB0013495 (PGP(16:1(9Z)/20:3(5Z,8Z,11Z)))

INCHI for HMDB0013495 (PGP(16:1(9Z)/20:3(5Z,8Z,11Z)))

Structure for HMDB0013495 (PGP(16:1(9Z)/20:3(5Z,8Z,11Z)))

3D Structure for HMDB0013495 (PGP(16:1(9Z)/20:3(5Z,8Z,11Z)))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

MS/MS Spectra