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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-09-09 08:24:01 UTC

Update Date

2022-11-30 19:26:39 UTC

HMDB ID

HMDB0116526

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PGP(a-13:0/i-20:0)

Description

PGP(a-13:0/i-20:0) 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(a-13:0/i-20:0), in particular, consists of one chain of anteisotridecanoic acid at the C-1 position and one chain of isoeicosanoic 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(a-13:0/i-20:0)
  Mrv1652309171703152D          

 56 55  0  0  1  0            999 V2000
    2.7850    0.9634    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3818    0.3608    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0920    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8022    0.3608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9714   -0.3495    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7924   -0.3495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6715    0.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9613    0.3608    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
    2.9276   -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    1.3958    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
    3.6379    0.3435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4301    0.5557    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.4301    1.3759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.3435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0200   -0.1546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5123    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5123    1.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2264    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9405    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6546    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3688    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0829    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7971    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5112    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2254    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9395    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6536    0.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6536   -0.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3677    0.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5362   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5362   -1.5406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2504   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9645   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6787   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3928   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1069   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8210   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5352   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2493   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9635   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6776   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3918   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1059   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8200   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5341   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2483   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.9624   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.6766   -0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.3907   -0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.3907    0.0559    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  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
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 36  6  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  1  0  0  0  0
M  END

HMDB0116526
     RDKit          3D
PGP(a-13:0/i-20:0)
132131  0  0  0  0  0  0  0  0999 V2000
   -2.3549    1.2728    0.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4725    0.9401    1.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5961    2.1293    1.9072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5393    3.2899    2.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292    1.9150    3.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2567    0.7498    2.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2070    0.4961    3.9903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567    1.7060    4.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8550    2.0447    2.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7426    3.2149    3.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5907    3.6761    2.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8781    4.0968    0.8164 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1905    3.0041    0.1395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7016    1.8291    0.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9651    3.1136   -0.4933 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2415    2.1336   -1.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7775    1.4777   -2.3404 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8601    2.4705   -3.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6600    3.3957   -3.4744 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6402    4.5558   -3.4229 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.2054    4.9146   -4.8310 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0548    6.0671   -2.8326 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0522    4.2268   -2.4753 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0279    5.1129   -2.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3245    4.9768   -2.1329 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1127    5.2102   -0.7689 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9435    3.6296   -2.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0847    2.6554   -1.7522 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8003    1.1163   -1.9090 P   0  0  0  0  0  5  0  0  0  0  0  0
    7.9797    0.3071   -2.8810 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3648    1.2567   -2.4923 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8117    0.3635   -0.3729 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8012    0.4958   -2.7229 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1616   -0.7571   -3.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3657   -1.0674   -3.2368 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1340   -1.7867   -3.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6369   -2.8704   -4.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4786   -3.8363   -4.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0718   -4.5404   -3.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1478   -5.4606   -3.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3176   -6.1382   -2.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5139   -7.0195   -2.1364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8107   -6.1986   -2.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8511   -5.1647   -1.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1126   -4.3497   -1.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0878   -3.2970   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3295   -2.4490   -0.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1287   -1.4597    1.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2780   -0.5448    1.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5353   -1.2813    1.6690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3489   -2.0914    2.9229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9423   -1.3390    4.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9274   -0.2932    4.5257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8980   -2.3644    5.2820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8328    1.9483   -0.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6324    0.3307   -0.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3083    1.7325    0.7551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8351    0.0960    1.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0975    0.6921    2.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0267    2.3116    1.0176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5617    2.9100    2.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1730    3.8305    3.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6699    3.9639    1.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9207    2.8495    3.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2659    1.7771    3.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8404    0.9328    1.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6685   -0.1828    2.6103 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8650   -0.3596    3.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6628    0.1662    4.9033 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7470    1.5134    5.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3915    2.5424    4.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3600    1.1227    2.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1366    2.3334    2.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1781    4.0732    3.6758 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4606    2.9106    4.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3140    2.8324    1.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2620    4.5258    2.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5665    4.6883    0.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1527    4.9019    1.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9122    1.3151   -0.4356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2688    2.6478   -1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7680    1.0559   -2.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0734    1.7567   -4.4323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7490    2.6668   -3.7322 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3291    5.9013   -2.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6320    6.1448   -2.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2107    5.0429   -3.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9994    5.7857   -2.5118 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6108    6.0807   -0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9255    3.6171   -1.7430 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1438    3.3885   -3.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4488    0.7529   -3.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2812    0.9360    0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8521   -2.2539   -2.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2066   -1.3343   -3.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5297   -3.3769   -4.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9083   -2.4294   -5.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7832   -4.6300   -5.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3782   -3.2998   -5.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8853   -5.2093   -3.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2676   -3.8176   -2.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9134   -6.2152   -4.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

PGP(a-13:0/i-20:0)
  Mrv1652309171703152D          

 56 55  0  0  1  0            999 V2000
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 10  9  1  0  0  0  0
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 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 36  6  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
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 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
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 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0116526

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC(C)CC)OC(=O)CCCCCCCCCCCCCCCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C39H78O13P2/c1-5-35(4)27-23-19-16-17-20-24-28-38(41)48-32-37(33-51-54(46,47)50-31-36(40)30-49-53(43,44)45)52-39(42)29-25-21-15-13-11-9-7-6-8-10-12-14-18-22-26-34(2)3/h34-37,40H,5-33H2,1-4H3,(H,46,47)(H2,43,44,45)/t35?,36-,37+/m0/s1

> <INCHI_KEY>
UGHKXGBVGBKZHB-AYZHLZKXSA-N

> <FORMULA>
C39H78O13P2

> <MOLECULAR_WEIGHT>
816.988

> <EXACT_MASS>
816.491766568

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
132

> <JCHEM_AVERAGE_POLARIZABILITY>
94.63250715479697

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S)-2-hydroxy-3-({hydroxy[(2R)-3-[(10-methyldodecanoyl)oxy]-2-[(18-methylnonadecanoyl)oxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid

> <ALOGPS_LOGP>
6.49

> <JCHEM_LOGP>
10.942955015666666

> <ALOGPS_LOGS>
-6.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.0402061436989327

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.354879296415124

> <JCHEM_PKA_STRONGEST_BASIC>
-3.410499386302644

> <JCHEM_POLAR_SURFACE_AREA>
195.34999999999997

> <JCHEM_REFRACTIVITY>
210.678

> <JCHEM_ROTATABLE_BOND_COUNT>
41

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.29e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-hydroxy-3-{[hydroxy((2R)-3-[(10-methyldodecanoyl)oxy]-2-[(18-methylnonadecanoyl)oxy]propoxy)phosphoryl]oxy}propoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0116526
     RDKit          3D
PGP(a-13:0/i-20:0)
132131  0  0  0  0  0  0  0  0999 V2000
   -2.3549    1.2728    0.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4725    0.9401    1.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5961    2.1293    1.9072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5393    3.2899    2.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292    1.9150    3.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2567    0.7498    2.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2070    0.4961    3.9903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567    1.7060    4.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8550    2.0447    2.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7426    3.2149    3.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5907    3.6761    2.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8781    4.0968    0.8164 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1905    3.0041    0.1395 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7775    1.4777   -2.3404 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8601    2.4705   -3.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6600    3.3957   -3.4744 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0548    6.0671   -2.8326 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0522    4.2268   -2.4753 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0279    5.1129   -2.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3245    4.9768   -2.1329 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1127    5.2102   -0.7689 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0847    2.6554   -1.7522 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.3648    1.2567   -2.4923 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HEADER    PROTEIN                                 17-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PGP(a-13:0/i-20:0)                                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-SEP-17         0                                  
HETATM    1  H   UNK     0       5.199   1.798   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      -4.446   0.673   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.772   1.437   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -7.097   0.673   0.000  0.00  0.00           O+0
HETATM    5  H   UNK     0      -3.680  -0.652   0.000  0.00  0.00           H+0
HETATM    6  O   UNK     0      -5.213  -0.652   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.120   1.439   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.794   0.673   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.487   0.642   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.813  -0.124   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.139   0.642   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.465  -0.124   0.000  0.00  0.00           C+0
HETATM   13  P   UNK     0       0.092   1.210   0.000  0.00  0.00           P+0
HETATM   14  O   UNK     0      -0.583   0.039   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.092   2.605   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       3.511   1.729   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.791   0.641   0.000  0.00  0.00           O+0
HETATM   18  P   UNK     0       8.270   1.037   0.000  0.00  0.00           P+0
HETATM   19  O   UNK     0       8.270   2.568   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.748   0.641   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       7.504  -0.289   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -8.423   1.437   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -8.423   2.877   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   1.437   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   1.437   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -15.088   0.665   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -16.421   1.437   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -17.754   0.665   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -19.087   1.437   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -20.420   0.665   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -21.753   1.437   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -21.753  -0.104   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -23.086   0.668   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -6.601  -1.436   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -6.601  -2.876   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -7.934  -0.665   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -9.267  -1.436   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -10.600  -0.665   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -11.933  -1.436   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -13.266  -0.665   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -14.599  -1.436   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -15.932  -0.665   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -17.265  -1.436   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -18.598  -0.665   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -19.931  -1.436   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -21.265  -0.665   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -22.598  -1.436   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -23.931  -0.665   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0     -25.264  -1.436   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0     -26.597  -0.665   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0     -27.930  -1.436   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0     -29.263  -0.665   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0     -30.596  -1.436   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0     -30.596   0.104   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   36                                                       
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   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34                                                            
CONECT   36    6   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   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   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  110    0
END

COMPND    HMDB0116526
HETATM    1  C1  UNL     1      -2.355   1.273   0.415  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.472   0.940   1.612  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.596   2.129   1.907  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.539   3.290   2.212  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.329   1.915   3.087  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.257   0.750   2.855  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.207   0.496   3.990  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.057   1.706   4.243  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.855   2.045   2.982  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.743   3.215   3.194  1.00  0.00           C  
HETATM   11  C11 UNL     1       5.591   3.676   2.071  1.00  0.00           C  
HETATM   12  C12 UNL     1       4.878   4.097   0.816  1.00  0.00           C  
HETATM   13  C13 UNL     1       4.191   3.004   0.139  1.00  0.00           C  
HETATM   14  O1  UNL     1       4.702   1.829   0.096  1.00  0.00           O  
HETATM   15  O2  UNL     1       2.965   3.114  -0.493  1.00  0.00           O  
HETATM   16  C14 UNL     1       2.242   2.134  -1.142  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.778   1.478  -2.340  1.00  0.00           C  
HETATM   18  C16 UNL     1       2.860   2.471  -3.546  1.00  0.00           C  
HETATM   19  O3  UNL     1       3.660   3.396  -3.474  1.00  0.00           O  
HETATM   20  P1  UNL     1       4.640   4.556  -3.423  1.00  0.00           P  
HETATM   21  O4  UNL     1       5.205   4.915  -4.831  1.00  0.00           O  
HETATM   22  O5  UNL     1       4.055   6.067  -2.833  1.00  0.00           O  
HETATM   23  O6  UNL     1       6.052   4.227  -2.475  1.00  0.00           O  
HETATM   24  C17 UNL     1       7.028   5.113  -2.888  1.00  0.00           C  
HETATM   25  C18 UNL     1       8.324   4.977  -2.133  1.00  0.00           C  
HETATM   26  O7  UNL     1       8.113   5.210  -0.769  1.00  0.00           O  
HETATM   27  C19 UNL     1       8.943   3.630  -2.283  1.00  0.00           C  
HETATM   28  O8  UNL     1       8.085   2.655  -1.752  1.00  0.00           O  
HETATM   29  P2  UNL     1       8.800   1.116  -1.909  1.00  0.00           P  
HETATM   30  O9  UNL     1       7.980   0.307  -2.881  1.00  0.00           O  
HETATM   31  O10 UNL     1      10.365   1.257  -2.492  1.00  0.00           O  
HETATM   32  O11 UNL     1       8.812   0.364  -0.373  1.00  0.00           O  
HETATM   33  O12 UNL     1       1.801   0.496  -2.723  1.00  0.00           O  
HETATM   34  C20 UNL     1       2.162  -0.757  -3.148  1.00  0.00           C  
HETATM   35  O13 UNL     1       3.366  -1.067  -3.237  1.00  0.00           O  
HETATM   36  C21 UNL     1       1.134  -1.787  -3.517  1.00  0.00           C  
HETATM   37  C22 UNL     1       1.637  -2.870  -4.409  1.00  0.00           C  
HETATM   38  C23 UNL     1       0.479  -3.836  -4.640  1.00  0.00           C  
HETATM   39  C24 UNL     1       0.072  -4.540  -3.394  1.00  0.00           C  
HETATM   40  C25 UNL     1      -1.148  -5.461  -3.587  1.00  0.00           C  
HETATM   41  C26 UNL     1      -1.318  -6.138  -2.244  1.00  0.00           C  
HETATM   42  C27 UNL     1      -2.514  -7.019  -2.136  1.00  0.00           C  
HETATM   43  C28 UNL     1      -3.811  -6.199  -2.276  1.00  0.00           C  
HETATM   44  C29 UNL     1      -3.851  -5.165  -1.199  1.00  0.00           C  
HETATM   45  C30 UNL     1      -5.113  -4.350  -1.256  1.00  0.00           C  
HETATM   46  C31 UNL     1      -5.088  -3.297  -0.151  1.00  0.00           C  
HETATM   47  C32 UNL     1      -6.330  -2.449  -0.095  1.00  0.00           C  
HETATM   48  C33 UNL     1      -6.129  -1.460   1.027  1.00  0.00           C  
HETATM   49  C34 UNL     1      -7.278  -0.545   1.275  1.00  0.00           C  
HETATM   50  C35 UNL     1      -8.535  -1.281   1.669  1.00  0.00           C  
HETATM   51  C36 UNL     1      -8.349  -2.091   2.923  1.00  0.00           C  
HETATM   52  C37 UNL     1      -7.942  -1.339   4.131  1.00  0.00           C  
HETATM   53  C38 UNL     1      -8.927  -0.293   4.526  1.00  0.00           C  
HETATM   54  C39 UNL     1      -7.898  -2.364   5.282  1.00  0.00           C  
HETATM   55  H1  UNL     1      -1.833   1.948  -0.269  1.00  0.00           H  
HETATM   56  H2  UNL     1      -2.632   0.331  -0.129  1.00  0.00           H  
HETATM   57  H3  UNL     1      -3.308   1.732   0.755  1.00  0.00           H  
HETATM   58  H4  UNL     1      -0.835   0.096   1.289  1.00  0.00           H  
HETATM   59  H5  UNL     1      -2.097   0.692   2.489  1.00  0.00           H  
HETATM   60  H6  UNL     1       0.027   2.312   1.018  1.00  0.00           H  
HETATM   61  H7  UNL     1      -2.562   2.910   2.484  1.00  0.00           H  
HETATM   62  H8  UNL     1      -1.173   3.830   3.103  1.00  0.00           H  
HETATM   63  H9  UNL     1      -1.670   3.964   1.342  1.00  0.00           H  
HETATM   64  H10 UNL     1       0.921   2.850   3.208  1.00  0.00           H  
HETATM   65  H11 UNL     1      -0.266   1.777   3.992  1.00  0.00           H  
HETATM   66  H12 UNL     1       1.840   0.933   1.938  1.00  0.00           H  
HETATM   67  H13 UNL     1       0.668  -0.183   2.610  1.00  0.00           H  
HETATM   68  H14 UNL     1       2.865  -0.360   3.636  1.00  0.00           H  
HETATM   69  H15 UNL     1       1.663   0.166   4.903  1.00  0.00           H  
HETATM   70  H16 UNL     1       3.747   1.513   5.096  1.00  0.00           H  
HETATM   71  H17 UNL     1       2.391   2.542   4.541  1.00  0.00           H  
HETATM   72  H18 UNL     1       4.360   1.123   2.674  1.00  0.00           H  
HETATM   73  H19 UNL     1       3.137   2.333   2.171  1.00  0.00           H  
HETATM   74  H20 UNL     1       4.178   4.073   3.676  1.00  0.00           H  
HETATM   75  H21 UNL     1       5.461   2.911   4.026  1.00  0.00           H  
HETATM   76  H22 UNL     1       6.314   2.832   1.845  1.00  0.00           H  
HETATM   77  H23 UNL     1       6.262   4.526   2.358  1.00  0.00           H  
HETATM   78  H24 UNL     1       5.567   4.688   0.142  1.00  0.00           H  
HETATM   79  H25 UNL     1       4.153   4.902   1.161  1.00  0.00           H  
HETATM   80  H26 UNL     1       1.912   1.315  -0.436  1.00  0.00           H  
HETATM   81  H27 UNL     1       1.269   2.648  -1.469  1.00  0.00           H  
HETATM   82  H28 UNL     1       3.768   1.056  -2.308  1.00  0.00           H  
HETATM   83  H29 UNL     1       3.073   1.757  -4.432  1.00  0.00           H  
HETATM   84  H30 UNL     1       1.749   2.667  -3.732  1.00  0.00           H  
HETATM   85  H31 UNL     1       3.329   5.901  -2.177  1.00  0.00           H  
HETATM   86  H32 UNL     1       6.632   6.145  -2.697  1.00  0.00           H  
HETATM   87  H33 UNL     1       7.211   5.043  -3.995  1.00  0.00           H  
HETATM   88  H34 UNL     1       8.999   5.786  -2.512  1.00  0.00           H  
HETATM   89  H35 UNL     1       7.611   6.081  -0.740  1.00  0.00           H  
HETATM   90  H36 UNL     1       9.925   3.617  -1.743  1.00  0.00           H  
HETATM   91  H37 UNL     1       9.144   3.388  -3.344  1.00  0.00           H  
HETATM   92  H38 UNL     1      10.449   0.753  -3.319  1.00  0.00           H  
HETATM   93  H39 UNL     1       8.281   0.936   0.266  1.00  0.00           H  
HETATM   94  H40 UNL     1       0.852  -2.254  -2.528  1.00  0.00           H  
HETATM   95  H41 UNL     1       0.207  -1.334  -3.906  1.00  0.00           H  
HETATM   96  H42 UNL     1       2.530  -3.377  -4.043  1.00  0.00           H  
HETATM   97  H43 UNL     1       1.908  -2.429  -5.402  1.00  0.00           H  
HETATM   98  H44 UNL     1       0.783  -4.630  -5.385  1.00  0.00           H  
HETATM   99  H45 UNL     1      -0.378  -3.300  -5.091  1.00  0.00           H  
HETATM  100  H46 UNL     1       0.885  -5.209  -3.039  1.00  0.00           H  
HETATM  101  H47 UNL     1      -0.268  -3.818  -2.631  1.00  0.00           H  
HETATM  102  H48 UNL     1      -0.913  -6.215  -4.341  1.00  0.00           H  
HETATM  103  H49 UNL     1      -2.027  -4.894  -3.906  1.00  0.00           H  
HETATM  104  H50 UNL     1      -0.420  -6.832  -2.166  1.00  0.00           H  
HETATM  105  H51 UNL     1      -1.180  -5.447  -1.388  1.00  0.00           H  
HETATM  106  H52 UNL     1      -2.568  -7.527  -1.164  1.00  0.00           H  
HETATM  107  H53 UNL     1      -2.536  -7.761  -2.943  1.00  0.00           H  
HETATM  108  H54 UNL     1      -4.634  -6.908  -2.076  1.00  0.00           H  
HETATM  109  H55 UNL     1      -3.932  -5.817  -3.300  1.00  0.00           H  
HETATM  110  H56 UNL     1      -3.844  -5.734  -0.223  1.00  0.00           H  
HETATM  111  H57 UNL     1      -2.947  -4.518  -1.149  1.00  0.00           H  
HETATM  112  H58 UNL     1      -5.248  -3.836  -2.218  1.00  0.00           H  
HETATM  113  H59 UNL     1      -5.969  -5.039  -1.120  1.00  0.00           H  
HETATM  114  H60 UNL     1      -5.062  -3.874   0.805  1.00  0.00           H  
HETATM  115  H61 UNL     1      -4.162  -2.704  -0.182  1.00  0.00           H  
HETATM  116  H62 UNL     1      -7.194  -3.095   0.005  1.00  0.00           H  
HETATM  117  H63 UNL     1      -6.422  -1.865  -1.035  1.00  0.00           H  
HETATM  118  H64 UNL     1      -5.187  -0.892   0.766  1.00  0.00           H  
HETATM  119  H65 UNL     1      -5.863  -1.988   1.964  1.00  0.00           H  
HETATM  120  H66 UNL     1      -7.503  -0.011   0.329  1.00  0.00           H  
HETATM  121  H67 UNL     1      -7.018   0.265   2.011  1.00  0.00           H  
HETATM  122  H68 UNL     1      -8.804  -1.920   0.802  1.00  0.00           H  
HETATM  123  H69 UNL     1      -9.385  -0.598   1.830  1.00  0.00           H  
HETATM  124  H70 UNL     1      -9.234  -2.704   3.187  1.00  0.00           H  
HETATM  125  H71 UNL     1      -7.557  -2.863   2.673  1.00  0.00           H  
HETATM  126  H72 UNL     1      -6.890  -0.953   4.094  1.00  0.00           H  
HETATM  127  H73 UNL     1      -9.633   0.018   3.732  1.00  0.00           H  
HETATM  128  H74 UNL     1      -8.428   0.614   4.964  1.00  0.00           H  
HETATM  129  H75 UNL     1      -9.599  -0.640   5.369  1.00  0.00           H  
HETATM  130  H76 UNL     1      -7.432  -1.892   6.147  1.00  0.00           H  
HETATM  131  H77 UNL     1      -7.190  -3.158   4.897  1.00  0.00           H  
HETATM  132  H78 UNL     1      -8.910  -2.745   5.412  1.00  0.00           H  
CONECT    1    2   55   56   57
CONECT    2    3   58   59
CONECT    3    4    5   60
CONECT    4   61   62   63
CONECT    5    6   64   65
CONECT    6    7   66   67
CONECT    7    8   68   69
CONECT    8    9   70   71
CONECT    9   10   72   73
CONECT   10   11   74   75
CONECT   11   12   76   77
CONECT   12   13   78   79
CONECT   13   14   14   15
CONECT   15   16
CONECT   16   17   80   81
CONECT   17   18   33   82
CONECT   18   19   83   84
CONECT   19   20
CONECT   20   21   21   22   23
CONECT   22   85
CONECT   23   24
CONECT   24   25   86   87
CONECT   25   26   27   88
CONECT   26   89
CONECT   27   28   90   91
CONECT   28   29
CONECT   29   30   30   31   32
CONECT   31   92
CONECT   32   93
CONECT   33   34
CONECT   34   35   35   36
CONECT   36   37   94   95
CONECT   37   38   96   97
CONECT   38   39   98   99
CONECT   39   40  100  101
CONECT   40   41  102  103
CONECT   41   42  104  105
CONECT   42   43  106  107
CONECT   43   44  108  109
CONECT   44   45  110  111
CONECT   45   46  112  113
CONECT   46   47  114  115
CONECT   47   48  116  117
CONECT   48   49  118  119
CONECT   49   50  120  121
CONECT   50   51  122  123
CONECT   51   52  124  125
CONECT   52   53   54  126
CONECT   53  127  128  129
CONECT   54  130  131  132
END

HMDB0116526
     RDKit          3D
PGP(a-13:0/i-20:0)
132131  0  0  0  0  0  0  0  0999 V2000
   -2.3549    1.2728    0.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4725    0.9401    1.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5961    2.1293    1.9072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5393    3.2899    2.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292    1.9150    3.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2567    0.7498    2.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2070    0.4961    3.9903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567    1.7060    4.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8550    2.0447    2.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7426    3.2149    3.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5907    3.6761    2.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8781    4.0968    0.8164 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1905    3.0041    0.1395 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7016    1.8291    0.0962 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9651    3.1136   -0.4933 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2415    2.1336   -1.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7775    1.4777   -2.3404 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8601    2.4705   -3.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6600    3.3957   -3.4744 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6402    4.5558   -3.4229 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.2054    4.9146   -4.8310 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0548    6.0671   -2.8326 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0522    4.2268   -2.4753 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0279    5.1129   -2.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3245    4.9768   -2.1329 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1127    5.2102   -0.7689 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9435    3.6296   -2.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0847    2.6554   -1.7522 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8003    1.1163   -1.9090 P   0  0  0  0  0  5  0  0  0  0  0  0
    7.9797    0.3071   -2.8810 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3648    1.2567   -2.4923 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8117    0.3635   -0.3729 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8012    0.4958   -2.7229 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1616   -0.7571   -3.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3657   -1.0674   -3.2368 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1340   -1.7867   -3.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6369   -2.8704   -4.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4786   -3.8363   -4.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0718   -4.5404   -3.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1478   -5.4606   -3.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3176   -6.1382   -2.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5139   -7.0195   -2.1364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8107   -6.1986   -2.2756 C   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-Anteisotridecanoyl-2-isoeicosanoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)	HMDB
PGP(33:0)	HMDB
3-sn-Phosphatidyl-1'-sn-glycerol 3'-phosphoric acid	HMDB
[(2S)-2-Hydroxy-3-({hydroxy[(2R)-3-[(10-methyldodecanoyl)oxy]-2-[(18-methylnonadecanoyl)oxy]propoxy]phosphoryl}oxy)propoxy]phosphonate	HMDB
PGP(a-13:0/i-20:0)	SMPDB

Chemical Formula

C₃₉H₇₈O₁₃P₂

Average Molecular Weight

816.988

Monoisotopic Molecular Weight

816.491766568

IUPAC Name

[(2S)-2-hydroxy-3-({hydroxy[(2R)-3-[(10-methyldodecanoyl)oxy]-2-[(18-methylnonadecanoyl)oxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid

Traditional Name

(2S)-2-hydroxy-3-{[hydroxy((2R)-3-[(10-methyldodecanoyl)oxy]-2-[(18-methylnonadecanoyl)oxy]propoxy)phosphoryl]oxy}propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC(C)CC)OC(=O)CCCCCCCCCCCCCCCCC(C)C

InChI Identifier

InChI=1S/C39H78O13P2/c1-5-35(4)27-23-19-16-17-20-24-28-38(41)48-32-37(33-51-54(46,47)50-31-36(40)30-49-53(43,44)45)52-39(42)29-25-21-15-13-11-9-7-6-8-10-12-14-18-22-26-34(2)3/h34-37,40H,5-33H2,1-4H3,(H,46,47)(H2,43,44,45)/t35?,36-,37+/m0/s1

InChI Key

UGHKXGBVGBKZHB-AYZHLZKXSA-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
logP	6.49	ALOGPS
logP	10.94	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	41	ChemAxon
Refractivity	210.68 m³·mol⁻¹	ChemAxon
Polarizability	94.63 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]+	299.243	31661259
DarkChem	[M-H]-	280.272	31661259
DeepCCS	[M+H]+	283.451	30932474
DeepCCS	[M-H]-	281.555	30932474
DeepCCS	[M-2H]-	314.796	30932474
DeepCCS	[M+Na]+	289.23	30932474
AllCCS	[M+H]+	288.9	32859911
AllCCS	[M+H-H2O]+	288.9	32859911
AllCCS	[M+NH4]+	288.9	32859911
AllCCS	[M+Na]+	288.9	32859911
AllCCS	[M-H]-	285.1	32859911
AllCCS	[M+Na-2H]-	291.7	32859911
AllCCS	[M+HCOO]-	298.9	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. Predicted by Afia on May 17, 2022.	10.87 minutes	32390414
Predicted by Siyang on May 30, 2022	23.1262 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.1 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	4485.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	187.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	308.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	170.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	897.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1396.2 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	1229.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	271.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2355.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	1040.8 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	2250.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	971.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	637.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	221.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	310.6 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	14.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
PGP(a-13:0/i-20:0)	[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC(C)CC)OC(=O)CCCCCCCCCCCCCCCCC(C)C	4915.4	Standard polar	33892256
PGP(a-13:0/i-20:0)	[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC(C)CC)OC(=O)CCCCCCCCCCCCCCCCC(C)C	4663.1	Standard non polar	33892256
PGP(a-13:0/i-20:0)	[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC(C)CC)OC(=O)CCCCCCCCCCCCCCCCC(C)C	5459.5	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(a-13:0/i-20:0) GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-19	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PGP(a-13:0/i-20:0) GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-19	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PGP(a-13:0/i-20:0) GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-19	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(a-13:0/i-20:0) 10V, Positive-QTOF	splash10-00kb-1892062730-f3ba31a34d2739b11197	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(a-13:0/i-20:0) 20V, Positive-QTOF	splash10-0002-5980023500-d9905fbb39d96df3b08e	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(a-13:0/i-20:0) 40V, Positive-QTOF	splash10-0a4i-9662120200-380c8ac15e4fd244d806	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(a-13:0/i-20:0) 10V, Negative-QTOF	splash10-03fs-6693032130-874280ad93a8483a5786	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(a-13:0/i-20:0) 20V, Negative-QTOF	splash10-004j-9140000000-05db9ceb8042b2a55e94	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(a-13:0/i-20:0) 40V, Negative-QTOF	splash10-004i-9000000000-47f3e36b6f0187bfe9df	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(a-13:0/i-20:0) 10V, Negative-QTOF	splash10-014i-0010000090-f8e939c9aa3f9f5b61f3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(a-13:0/i-20:0) 20V, Negative-QTOF	splash10-0gba-3091023160-8985320486ea67b68fc8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(a-13:0/i-20:0) 40V, Negative-QTOF	splash10-0gy2-6094622200-28db025e84b8bd19073c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(a-13:0/i-20:0) 10V, Positive-QTOF	splash10-014i-4100070690-88ebe55d4783f2777334	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(a-13:0/i-20:0) 20V, Positive-QTOF	splash10-066r-4500159500-5b4d7bdd1162b55c9288	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(a-13:0/i-20:0) 40V, Positive-QTOF	splash10-0zfr-8695551000-4fc7fed58d10902433af	2021-09-24	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(a-13:0/i-20:0/18:2(9Z,11Z)/18:2(9Z,11Z))		Not Available
Cardiolipin Biosynthesis CL(a-13:0/i-20:0/18:2(9Z,11Z)/a-13:0)		Not Available
Cardiolipin Biosynthesis CL(a-13:0/i-20:0/18:2(9Z,11Z)/a-15:0)		Not Available
Cardiolipin Biosynthesis CL(a-13:0/i-20:0/18:2(9Z,11Z)/a-17:0)		Not Available
Cardiolipin Biosynthesis CL(a-13:0/i-20:0/18:2(9Z,11Z)/a-21:0)		Not Available

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

74878238

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131823181

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(a-13:0/i-20:0) (HMDB0116526)

MOL for HMDB0116526 (PGP(a-13:0/i-20:0))

3D MOL for HMDB0116526 (PGP(a-13:0/i-20:0))

3D SDF for HMDB0116526 (PGP(a-13:0/i-20:0))

3D-SDF for HMDB0116526 (PGP(a-13:0/i-20:0))

PDB for HMDB0116526 (PGP(a-13:0/i-20:0))

3D PDB for HMDB0116526 (PGP(a-13:0/i-20:0))

SMILES for HMDB0116526 (PGP(a-13:0/i-20:0))

INCHI for HMDB0116526 (PGP(a-13:0/i-20:0))

Structure for HMDB0116526 (PGP(a-13:0/i-20:0))

3D Structure for HMDB0116526 (PGP(a-13:0/i-20:0))

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra