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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-09-09 08:28:46 UTC

Update Date

2022-11-30 19:26:39 UTC

HMDB ID

HMDB0116555

Secondary Accession Numbers

None

Metabolite Identification

Common Name

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

Description

PGP(i-13:0/i-13:0) 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(i-13:0/i-13:0), in particular, consists of one chain of isotridecanoic acid at the C-1 position and one chain of isotridecanoic 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(i-13:0/i-13:0)
  Mrv1652309171703162D          

 49 48  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
  -12.3677    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3677    1.1814    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
  -11.3918   -1.1811    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
 33 34  1  0  0  0  0
 33 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
 47 49  1  0  0  0  0
M  END

HMDB0116555
     RDKit          3D
PGP(i-13:0/i-13:0)
111110  0  0  0  0  0  0  0  0999 V2000
  -10.5047   -3.3805   -0.4530 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0990   -3.0398   -1.8538 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2861   -2.4104   -2.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9251   -2.1693   -2.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6295   -2.6544   -1.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4742   -2.9654   -0.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0554   -3.3922    0.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0203   -2.3985   -0.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1461   -1.0759    0.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1062   -1.2193    2.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2470    0.1204    2.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1310    1.0373    2.3687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8439    0.5166    2.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7233   -0.4447    3.6248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6829    1.1386    2.3741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4600    0.6458    2.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7278    1.3635    2.2420 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7427    2.7845    2.6724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3237    3.5335    2.2453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1285    5.1057    2.8299 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.9097    5.2978    4.1296 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5229    5.3350    3.1388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7120    6.2601    1.7455 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3189    6.8076    0.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1812    7.8483    0.0127 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8077    8.9090    0.6840 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0572    8.3595   -0.7249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7071    9.3356   -1.6559 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0508    9.9089   -2.4707 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.0278    9.6124   -3.9438 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2110   11.5789   -2.1815 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4558    9.1840   -1.8371 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179    1.1891    0.8383 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7330    0.4850    0.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6306    0.0386    0.9357 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868    0.2583   -1.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9388   -0.6539   -1.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7826   -2.0062   -0.9690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9555   -2.9243   -1.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2433   -2.3216   -0.8053 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3659   -3.3006   -1.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6426   -2.6921   -0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8592   -3.5537   -0.9503 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6916   -4.8889   -0.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9178   -5.7453   -0.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1188   -5.0082   -0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0161   -5.9395   -2.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6535   -3.2768   -0.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3134   -4.4296   -0.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1169   -2.7099    0.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8906   -4.0227   -2.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5895   -1.5292   -1.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1030   -3.1486   -2.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9189   -2.0848   -3.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8826   -1.9066   -3.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1720   -1.1849   -1.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2838   -3.5562   -2.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8561   -1.8797   -1.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8314   -2.1421    0.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1348   -3.8570    0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8518   -4.3065   -0.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0270   -3.6965    1.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9510   -2.1686   -1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0260   -2.8137    0.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9482   -0.4286    0.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1823   -0.5389    0.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8856   -1.9451    2.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1510   -1.6799    2.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3278    0.0610    3.8968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1924    0.6315    2.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1570    1.2456    1.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2680    2.0645    2.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3905   -0.4234    2.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873    0.6111    3.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6303    0.8721    2.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6802    3.2856    2.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8199    2.7952    3.7943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6970    5.3850    4.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8705    6.0141    0.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0232    7.2727    1.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9242    7.4019   -0.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5018    8.9401    1.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115    8.8383    0.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5811    7.5063   -1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5863   11.8406   -1.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5570    9.4009   -0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8868    1.2062   -1.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8652   -0.3041   -1.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1479   -0.7062   -2.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8430   -0.1859   -1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8806   -2.5437   -1.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6921   -2.0291    0.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9450   -2.9980   -2.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7441   -3.9075   -0.8562 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2263   -2.1442    0.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4467   -1.3660   -1.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1580   -4.2680   -0.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3631   -3.5072   -2.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7575   -1.6823   -1.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5302   -2.5559    0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7360   -3.0345   -0.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0385   -3.6753   -2.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8267   -5.4229   -0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5629   -4.7563    0.8272 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8060   -6.6939   -0.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8646   -4.2365    0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6773   -4.5030   -0.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8339   -5.7288    0.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9996   -5.8151   -2.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6492   -5.1186   -2.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

PGP(i-13:0/i-13:0)
  Mrv1652309171703162D          

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 47 48  1  0  0  0  0
 47 49  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0116555

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCC(C)C)OC(=O)CCCCCCCCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C32H64O13P2/c1-27(2)19-15-11-7-5-9-13-17-21-31(34)41-25-30(26-44-47(39,40)43-24-29(33)23-42-46(36,37)38)45-32(35)22-18-14-10-6-8-12-16-20-28(3)4/h27-30,33H,5-26H2,1-4H3,(H,39,40)(H2,36,37,38)/t29-,30+/m0/s1

> <INCHI_KEY>
HKRQRTYPSBWPQM-XZWHSSHBSA-N

> <FORMULA>
C32H64O13P2

> <MOLECULAR_WEIGHT>
718.799

> <EXACT_MASS>
718.382216117

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
111

> <JCHEM_AVERAGE_POLARIZABILITY>
79.94769196217844

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S)-3-({[(2R)-2,3-bis[(11-methyldodecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid

> <ALOGPS_LOGP>
4.20

> <JCHEM_LOGP>
7.830974360666666

> <ALOGPS_LOGS>
-5.32

> <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>
178.471

> <JCHEM_ROTATABLE_BOND_COUNT>
34

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.48e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-{[(2R)-2,3-bis[(11-methyldodecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0116555
     RDKit          3D
PGP(i-13:0/i-13:0)
111110  0  0  0  0  0  0  0  0999 V2000
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    1.6802    3.2856    2.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8199    2.7952    3.7943 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8267   -5.4229   -0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5629   -4.7563    0.8272 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8060   -6.6939   -0.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8646   -4.2365    0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6773   -4.5030   -0.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8339   -5.7288    0.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9996   -5.8151   -2.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6492   -5.1186   -2.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4549   -6.9297   -2.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  2  4  1  0
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M  END

HEADER    PROTEIN                                 17-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PGP(i-13:0/i-13:0)                                
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     -23.086   0.665   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -23.086   2.205   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     -21.265  -2.205   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                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
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   49                                                  
CONECT   48   47                                                            
CONECT   49   47                                                            
MASTER        0    0    0    0    0    0    0    0   49    0   96    0
END

COMPND    HMDB0116555
HETATM    1  C1  UNL     1     -10.505  -3.381  -0.453  1.00  0.00           C  
HETATM    2  C2  UNL     1     -10.099  -3.040  -1.854  1.00  0.00           C  
HETATM    3  C3  UNL     1     -11.286  -2.410  -2.590  1.00  0.00           C  
HETATM    4  C4  UNL     1      -8.925  -2.169  -2.016  1.00  0.00           C  
HETATM    5  C5  UNL     1      -7.630  -2.654  -1.527  1.00  0.00           C  
HETATM    6  C6  UNL     1      -7.474  -2.965  -0.073  1.00  0.00           C  
HETATM    7  C7  UNL     1      -6.055  -3.392   0.239  1.00  0.00           C  
HETATM    8  C8  UNL     1      -5.020  -2.398  -0.071  1.00  0.00           C  
HETATM    9  C9  UNL     1      -5.146  -1.076   0.633  1.00  0.00           C  
HETATM   10  C10 UNL     1      -5.106  -1.219   2.158  1.00  0.00           C  
HETATM   11  C11 UNL     1      -5.247   0.120   2.783  1.00  0.00           C  
HETATM   12  C12 UNL     1      -4.131   1.037   2.369  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.844   0.517   2.838  1.00  0.00           C  
HETATM   14  O1  UNL     1      -2.723  -0.445   3.625  1.00  0.00           O  
HETATM   15  O2  UNL     1      -1.683   1.139   2.374  1.00  0.00           O  
HETATM   16  C14 UNL     1      -0.460   0.646   2.831  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.728   1.363   2.242  1.00  0.00           C  
HETATM   18  C16 UNL     1       0.743   2.784   2.672  1.00  0.00           C  
HETATM   19  O3  UNL     1      -0.324   3.533   2.245  1.00  0.00           O  
HETATM   20  P1  UNL     1      -0.129   5.106   2.830  1.00  0.00           P  
HETATM   21  O4  UNL     1      -0.910   5.298   4.130  1.00  0.00           O  
HETATM   22  O5  UNL     1       1.523   5.335   3.139  1.00  0.00           O  
HETATM   23  O6  UNL     1      -0.712   6.260   1.746  1.00  0.00           O  
HETATM   24  C17 UNL     1       0.319   6.808   0.983  1.00  0.00           C  
HETATM   25  C18 UNL     1      -0.181   7.848   0.013  1.00  0.00           C  
HETATM   26  O7  UNL     1      -0.808   8.909   0.684  1.00  0.00           O  
HETATM   27  C19 UNL     1       1.057   8.359  -0.725  1.00  0.00           C  
HETATM   28  O8  UNL     1       0.707   9.336  -1.656  1.00  0.00           O  
HETATM   29  P2  UNL     1       2.051   9.909  -2.471  1.00  0.00           P  
HETATM   30  O9  UNL     1       2.028   9.612  -3.944  1.00  0.00           O  
HETATM   31  O10 UNL     1       2.211  11.579  -2.181  1.00  0.00           O  
HETATM   32  O11 UNL     1       3.456   9.184  -1.837  1.00  0.00           O  
HETATM   33  O12 UNL     1       0.718   1.189   0.838  1.00  0.00           O  
HETATM   34  C20 UNL     1       1.733   0.485   0.184  1.00  0.00           C  
HETATM   35  O13 UNL     1       2.631   0.039   0.936  1.00  0.00           O  
HETATM   36  C21 UNL     1       1.787   0.258  -1.270  1.00  0.00           C  
HETATM   37  C22 UNL     1       2.939  -0.654  -1.593  1.00  0.00           C  
HETATM   38  C23 UNL     1       2.783  -2.006  -0.969  1.00  0.00           C  
HETATM   39  C24 UNL     1       3.955  -2.924  -1.308  1.00  0.00           C  
HETATM   40  C25 UNL     1       5.243  -2.322  -0.805  1.00  0.00           C  
HETATM   41  C26 UNL     1       6.366  -3.301  -1.166  1.00  0.00           C  
HETATM   42  C27 UNL     1       7.643  -2.692  -0.665  1.00  0.00           C  
HETATM   43  C28 UNL     1       8.859  -3.554  -0.950  1.00  0.00           C  
HETATM   44  C29 UNL     1       8.692  -4.889  -0.270  1.00  0.00           C  
HETATM   45  C30 UNL     1       9.918  -5.745  -0.560  1.00  0.00           C  
HETATM   46  C31 UNL     1      11.119  -5.008  -0.013  1.00  0.00           C  
HETATM   47  C32 UNL     1      10.016  -5.940  -2.055  1.00  0.00           C  
HETATM   48  H1  UNL     1     -11.654  -3.277  -0.389  1.00  0.00           H  
HETATM   49  H2  UNL     1     -10.313  -4.430  -0.171  1.00  0.00           H  
HETATM   50  H3  UNL     1     -10.117  -2.710   0.329  1.00  0.00           H  
HETATM   51  H4  UNL     1      -9.891  -4.023  -2.363  1.00  0.00           H  
HETATM   52  H5  UNL     1     -11.589  -1.529  -1.981  1.00  0.00           H  
HETATM   53  H6  UNL     1     -12.103  -3.149  -2.669  1.00  0.00           H  
HETATM   54  H7  UNL     1     -10.919  -2.085  -3.570  1.00  0.00           H  
HETATM   55  H8  UNL     1      -8.883  -1.907  -3.131  1.00  0.00           H  
HETATM   56  H9  UNL     1      -9.172  -1.185  -1.500  1.00  0.00           H  
HETATM   57  H10 UNL     1      -7.284  -3.556  -2.143  1.00  0.00           H  
HETATM   58  H11 UNL     1      -6.856  -1.880  -1.840  1.00  0.00           H  
HETATM   59  H12 UNL     1      -7.831  -2.142   0.525  1.00  0.00           H  
HETATM   60  H13 UNL     1      -8.135  -3.857   0.142  1.00  0.00           H  
HETATM   61  H14 UNL     1      -5.852  -4.306  -0.354  1.00  0.00           H  
HETATM   62  H15 UNL     1      -6.027  -3.697   1.306  1.00  0.00           H  
HETATM   63  H16 UNL     1      -4.951  -2.169  -1.155  1.00  0.00           H  
HETATM   64  H17 UNL     1      -4.026  -2.814   0.211  1.00  0.00           H  
HETATM   65  H18 UNL     1      -5.948  -0.429   0.286  1.00  0.00           H  
HETATM   66  H19 UNL     1      -4.182  -0.539   0.381  1.00  0.00           H  
HETATM   67  H20 UNL     1      -5.886  -1.945   2.493  1.00  0.00           H  
HETATM   68  H21 UNL     1      -4.151  -1.680   2.448  1.00  0.00           H  
HETATM   69  H22 UNL     1      -5.328   0.061   3.897  1.00  0.00           H  
HETATM   70  H23 UNL     1      -6.192   0.632   2.448  1.00  0.00           H  
HETATM   71  H24 UNL     1      -4.157   1.246   1.264  1.00  0.00           H  
HETATM   72  H25 UNL     1      -4.268   2.065   2.817  1.00  0.00           H  
HETATM   73  H26 UNL     1      -0.390  -0.423   2.489  1.00  0.00           H  
HETATM   74  H27 UNL     1      -0.387   0.611   3.947  1.00  0.00           H  
HETATM   75  H28 UNL     1       1.630   0.872   2.704  1.00  0.00           H  
HETATM   76  H29 UNL     1       1.680   3.286   2.310  1.00  0.00           H  
HETATM   77  H30 UNL     1       0.820   2.795   3.794  1.00  0.00           H  
HETATM   78  H31 UNL     1       1.697   5.385   4.112  1.00  0.00           H  
HETATM   79  H32 UNL     1       0.870   6.014   0.427  1.00  0.00           H  
HETATM   80  H33 UNL     1       1.023   7.273   1.688  1.00  0.00           H  
HETATM   81  H34 UNL     1      -0.924   7.402  -0.656  1.00  0.00           H  
HETATM   82  H35 UNL     1      -0.502   8.940   1.616  1.00  0.00           H  
HETATM   83  H36 UNL     1       1.712   8.838   0.029  1.00  0.00           H  
HETATM   84  H37 UNL     1       1.581   7.506  -1.171  1.00  0.00           H  
HETATM   85  H38 UNL     1       1.586  11.841  -1.460  1.00  0.00           H  
HETATM   86  H39 UNL     1       3.557   9.401  -0.864  1.00  0.00           H  
HETATM   87  H40 UNL     1       1.887   1.206  -1.842  1.00  0.00           H  
HETATM   88  H41 UNL     1       0.865  -0.304  -1.596  1.00  0.00           H  
HETATM   89  H42 UNL     1       3.148  -0.706  -2.678  1.00  0.00           H  
HETATM   90  H43 UNL     1       3.843  -0.186  -1.098  1.00  0.00           H  
HETATM   91  H44 UNL     1       1.881  -2.544  -1.353  1.00  0.00           H  
HETATM   92  H45 UNL     1       2.692  -2.029   0.121  1.00  0.00           H  
HETATM   93  H46 UNL     1       3.945  -2.998  -2.421  1.00  0.00           H  
HETATM   94  H47 UNL     1       3.744  -3.907  -0.856  1.00  0.00           H  
HETATM   95  H48 UNL     1       5.226  -2.144   0.283  1.00  0.00           H  
HETATM   96  H49 UNL     1       5.447  -1.366  -1.365  1.00  0.00           H  
HETATM   97  H50 UNL     1       6.158  -4.268  -0.631  1.00  0.00           H  
HETATM   98  H51 UNL     1       6.363  -3.507  -2.238  1.00  0.00           H  
HETATM   99  H52 UNL     1       7.758  -1.682  -1.104  1.00  0.00           H  
HETATM  100  H53 UNL     1       7.530  -2.556   0.443  1.00  0.00           H  
HETATM  101  H54 UNL     1       9.736  -3.034  -0.506  1.00  0.00           H  
HETATM  102  H55 UNL     1       9.038  -3.675  -2.025  1.00  0.00           H  
HETATM  103  H56 UNL     1       7.827  -5.423  -0.724  1.00  0.00           H  
HETATM  104  H57 UNL     1       8.563  -4.756   0.827  1.00  0.00           H  
HETATM  105  H58 UNL     1       9.806  -6.694  -0.013  1.00  0.00           H  
HETATM  106  H59 UNL     1      10.865  -4.236   0.731  1.00  0.00           H  
HETATM  107  H60 UNL     1      11.677  -4.503  -0.849  1.00  0.00           H  
HETATM  108  H61 UNL     1      11.834  -5.729   0.457  1.00  0.00           H  
HETATM  109  H62 UNL     1       9.000  -5.815  -2.488  1.00  0.00           H  
HETATM  110  H63 UNL     1      10.649  -5.119  -2.477  1.00  0.00           H  
HETATM  111  H64 UNL     1      10.455  -6.930  -2.311  1.00  0.00           H  
CONECT    1    2   48   49   50
CONECT    2    3    4   51
CONECT    3   52   53   54
CONECT    4    5   55   56
CONECT    5    6   57   58
CONECT    6    7   59   60
CONECT    7    8   61   62
CONECT    8    9   63   64
CONECT    9   10   65   66
CONECT   10   11   67   68
CONECT   11   12   69   70
CONECT   12   13   71   72
CONECT   13   14   14   15
CONECT   15   16
CONECT   16   17   73   74
CONECT   17   18   33   75
CONECT   18   19   76   77
CONECT   19   20
CONECT   20   21   21   22   23
CONECT   22   78
CONECT   23   24
CONECT   24   25   79   80
CONECT   25   26   27   81
CONECT   26   82
CONECT   27   28   83   84
CONECT   28   29
CONECT   29   30   30   31   32
CONECT   31   85
CONECT   32   86
CONECT   33   34
CONECT   34   35   35   36
CONECT   36   37   87   88
CONECT   37   38   89   90
CONECT   38   39   91   92
CONECT   39   40   93   94
CONECT   40   41   95   96
CONECT   41   42   97   98
CONECT   42   43   99  100
CONECT   43   44  101  102
CONECT   44   45  103  104
CONECT   45   46   47  105
CONECT   46  106  107  108
CONECT   47  109  110  111
END

HMDB0116555
     RDKit          3D
PGP(i-13:0/i-13:0)
111110  0  0  0  0  0  0  0  0999 V2000
  -10.5047   -3.3805   -0.4530 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0990   -3.0398   -1.8538 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2861   -2.4104   -2.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9251   -2.1693   -2.0163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6295   -2.6544   -1.5272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4742   -2.9654   -0.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0554   -3.3922    0.2392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0203   -2.3985   -0.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1461   -1.0759    0.6329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1062   -1.2193    2.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2470    0.1204    2.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1310    1.0373    2.3687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8439    0.5166    2.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7233   -0.4447    3.6248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6829    1.1386    2.3741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4600    0.6458    2.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7278    1.3635    2.2420 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7427    2.7845    2.6724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3237    3.5335    2.2453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1285    5.1057    2.8299 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.9097    5.2978    4.1296 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5229    5.3350    3.1388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7120    6.2601    1.7455 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3189    6.8076    0.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1812    7.8483    0.0127 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8077    8.9090    0.6840 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0572    8.3595   -0.7249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7071    9.3356   -1.6559 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0508    9.9089   -2.4707 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.0278    9.6124   -3.9438 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2110   11.5789   -2.1815 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4558    9.1840   -1.8371 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179    1.1891    0.8383 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7330    0.4850    0.1841 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6306    0.0386    0.9357 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868    0.2583   -1.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9388   -0.6539   -1.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7826   -2.0062   -0.9690 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9555   -2.9243   -1.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2433   -2.3216   -0.8053 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3659   -3.3006   -1.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6426   -2.6921   -0.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8592   -3.5537   -0.9503 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6916   -4.8889   -0.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9178   -5.7453   -0.5598 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1188   -5.0082   -0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0161   -5.9395   -2.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6535   -3.2768   -0.3887 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3134   -4.4296   -0.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1169   -2.7099    0.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8906   -4.0227   -2.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5895   -1.5292   -1.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1030   -3.1486   -2.6693 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9189   -2.0848   -3.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8826   -1.9066   -3.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1720   -1.1849   -1.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2838   -3.5562   -2.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8561   -1.8797   -1.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8314   -2.1421    0.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1348   -3.8570    0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8518   -4.3065   -0.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0270   -3.6965    1.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9510   -2.1686   -1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0260   -2.8137    0.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9482   -0.4286    0.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1823   -0.5389    0.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8856   -1.9451    2.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1510   -1.6799    2.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3278    0.0610    3.8968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1924    0.6315    2.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1570    1.2456    1.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2680    2.0645    2.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3905   -0.4234    2.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3873    0.6111    3.9466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6303    0.8721    2.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6802    3.2856    2.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8199    2.7952    3.7943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6970    5.3850    4.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8705    6.0141    0.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0232    7.2727    1.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9242    7.4019   -0.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5018    8.9401    1.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115    8.8383    0.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5811    7.5063   -1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5863   11.8406   -1.4596 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5570    9.4009   -0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8868    1.2062   -1.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8652   -0.3041   -1.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1479   -0.7062   -2.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8430   -0.1859   -1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8806   -2.5437   -1.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6921   -2.0291    0.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9450   -2.9980   -2.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7441   -3.9075   -0.8562 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2263   -2.1442    0.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4467   -1.3660   -1.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1580   -4.2680   -0.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3631   -3.5072   -2.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7575   -1.6823   -1.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5302   -2.5559    0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7360   -3.0345   -0.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0385   -3.6753   -2.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8267   -5.4229   -0.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5629   -4.7563    0.8272 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8060   -6.6939   -0.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8646   -4.2365    0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6773   -4.5030   -0.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8339   -5.7288    0.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9996   -5.8151   -2.4880 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6492   -5.1186   -2.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4549   -6.9297   -2.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 29 32  1  0
 17 33  1  0
 33 34  1  0
 34 35  2  0
 34 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 43 44  1  0
 44 45  1  0
 45 46  1  0
 45 47  1  0
  1 48  1  0
  1 49  1  0
  1 50  1  0
  2 51  1  0
  3 52  1  0
  3 53  1  0
  3 54  1  0
  4 55  1  0
  4 56  1  0
  5 57  1  0
  5 58  1  0
  6 59  1  0
  6 60  1  0
  7 61  1  0
  7 62  1  0
  8 63  1  0
  8 64  1  0
  9 65  1  0
  9 66  1  0
 10 67  1  0
 10 68  1  0
 11 69  1  0
 11 70  1  0
 12 71  1  0
 12 72  1  0
 16 73  1  0
 16 74  1  0
 17 75  1  1
 18 76  1  0
 18 77  1  0
 22 78  1  0
 24 79  1  0
 24 80  1  0
 25 81  1  6
 26 82  1  0
 27 83  1  0
 27 84  1  0
 31 85  1  0
 32 86  1  0
 36 87  1  0
 36 88  1  0
 37 89  1  0
 37 90  1  0
 38 91  1  0
 38 92  1  0
 39 93  1  0
 39 94  1  0
 40 95  1  0
 40 96  1  0
 41 97  1  0
 41 98  1  0
 42 99  1  0
 42100  1  0
 43101  1  0
 43102  1  0
 44103  1  0
 44104  1  0
 45105  1  0
 46106  1  0
 46107  1  0
 46108  1  0
 47109  1  0
 47110  1  0
 47111  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-isotridecanoyl-2-isotridecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)	SMPDB, HMDB
PGP(i-13:0/i-13:0)	SMPDB
PGP(26:0)	SMPDB, HMDB
1,2-diisotridecanoyl-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate)	Lipid Annotator, HMDB
3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid	Lipid Annotator, HMDB
[(2S)-3-({[(2R)-2,3-bis[(11-methyldodecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonate	Generator, HMDB

Chemical Formula

C₃₂H₆₄O₁₃P₂

Average Molecular Weight

718.799

Monoisotopic Molecular Weight

718.382216117

IUPAC Name

[(2S)-3-({[(2R)-2,3-bis[(11-methyldodecanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid

Traditional Name

(2S)-3-{[(2R)-2,3-bis[(11-methyldodecanoyl)oxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCC(C)C)OC(=O)CCCCCCCCCC(C)C

InChI Identifier

InChI=1S/C32H64O13P2/c1-27(2)19-15-11-7-5-9-13-17-21-31(34)41-25-30(26-44-47(39,40)43-24-29(33)23-42-46(36,37)38)45-32(35)22-18-14-10-6-8-12-16-20-28(3)4/h27-30,33H,5-26H2,1-4H3,(H,39,40)(H2,36,37,38)/t29-,30+/m0/s1

InChI Key

HKRQRTYPSBWPQM-XZWHSSHBSA-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

Physiological effect

Not Available

Disposition

Not Available

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(9Z,11Z)/18:2(9Z,11Z)) (PathBank: SMP0057207)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(9Z,11Z)/a-13:0) (PathBank: SMP0057208)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(9Z,11Z)/a-15:0) (PathBank: SMP0057209)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(9Z,11Z)/a-17:0) (PathBank: SMP0057210)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(9Z,11Z)/a-21:0) (PathBank: SMP0057211)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(9Z,11Z)/i-12:0) (PathBank: SMP0057212)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(9Z,11Z)/i-13:0) (PathBank: SMP0057213)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(9Z,11Z)/i-14:0) (PathBank: SMP0057214)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(9Z,11Z)/i-15:0) (PathBank: SMP0057215)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(9Z,11Z)/i-16:0) (PathBank: SMP0057216)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(9Z,11Z)/i-17:0) (PathBank: SMP0057217)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(9Z,11Z)/i-18:0) (PathBank: SMP0057218)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(9Z,11Z)/i-19:0) (PathBank: SMP0057219)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(9Z,11Z)/i-20:0) (PathBank: SMP0057220)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(9Z,11Z)/i-21:0) (PathBank: SMP0057221)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(9Z,11Z)/i-22:0) (PathBank: SMP0057222)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(9Z,11Z)/i-24:0) (PathBank: SMP0057223)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-13:0/18:2(9Z,11Z)) (PathBank: SMP0057224)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-13:0/a-13:0) (PathBank: SMP0057225)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-13:0/a-15:0) (PathBank: SMP0057226)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-13:0/a-17:0) (PathBank: SMP0057227)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-13:0/a-21:0) (PathBank: SMP0057228)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-13:0/a-25:0) (PathBank: SMP0057229)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-13:0/i-12:0) (PathBank: SMP0057230)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-13:0/i-13:0) (PathBank: SMP0057231)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-13:0/i-14:0) (PathBank: SMP0057232)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-13:0/i-15:0) (PathBank: SMP0057233)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-13:0/i-16:0) (PathBank: SMP0057234)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-13:0/i-17:0) (PathBank: SMP0057235)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-13:0/i-18:0) (PathBank: SMP0057236)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-13:0/i-19:0) (PathBank: SMP0057237)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-13:0/i-20:0) (PathBank: SMP0057238)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-13:0/i-21:0) (PathBank: SMP0057239)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-13:0/i-22:0) (PathBank: SMP0057240)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-13:0/i-24:0) (PathBank: SMP0057241)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-15:0/18:2(9Z,11Z)) (PathBank: SMP0057242)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-15:0/a-13:0) (PathBank: SMP0057243)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-15:0/a-15:0) (PathBank: SMP0057244)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-15:0/a-17:0) (PathBank: SMP0057245)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-15:0/a-21:0) (PathBank: SMP0057246)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-15:0/a-25:0) (PathBank: SMP0057247)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-15:0/i-12:0) (PathBank: SMP0057248)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-15:0/i-13:0) (PathBank: SMP0057249)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-15:0/i-14:0) (PathBank: SMP0057250)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-15:0/i-15:0) (PathBank: SMP0057251)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-15:0/i-16:0) (PathBank: SMP0057252)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-15:0/i-17:0) (PathBank: SMP0057253)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-15:0/i-18:0) (PathBank: SMP0057254)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-15:0/i-19:0) (PathBank: SMP0057255)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-15:0/i-20:0) (PathBank: SMP0057256)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-15:0/i-21:0) (PathBank: SMP0057257)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-15:0/i-22:0) (PathBank: SMP0057258)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-15:0/i-24:0) (PathBank: SMP0057259)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-17:0/18:2(9Z,11Z)) (PathBank: SMP0057260)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-17:0/a-13:0) (PathBank: SMP0057261)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-17:0/a-15:0) (PathBank: SMP0057262)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-17:0/a-17:0) (PathBank: SMP0057263)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-17:0/a-21:0) (PathBank: SMP0057264)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-17:0/a-25:0) (PathBank: SMP0057265)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-17:0/i-12:0) (PathBank: SMP0057266)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-17:0/i-13:0) (PathBank: SMP0057267)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-17:0/i-14:0) (PathBank: SMP0057268)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-17:0/i-15:0) (PathBank: SMP0057269)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-17:0/i-16:0) (PathBank: SMP0057270)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-17:0/i-17:0) (PathBank: SMP0057271)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-17:0/i-18:0) (PathBank: SMP0057272)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-17:0/i-19:0) (PathBank: SMP0057273)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-17:0/i-20:0) (PathBank: SMP0057274)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-17:0/i-21:0) (PathBank: SMP0057275)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-17:0/i-22:0) (PathBank: SMP0057276)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-17:0/i-24:0) (PathBank: SMP0057277)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-21:0/18:2(9Z,11Z)) (PathBank: SMP0057278)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-21:0/a-13:0) (PathBank: SMP0057279)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-21:0/a-15:0) (PathBank: SMP0057280)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-21:0/a-17:0) (PathBank: SMP0057281)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-21:0/a-21:0) (PathBank: SMP0057282)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-21:0/a-25:0) (PathBank: SMP0057283)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-21:0/i-12:0) (PathBank: SMP0057284)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-21:0/i-13:0) (PathBank: SMP0057285)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-21:0/i-14:0) (PathBank: SMP0057286)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-21:0/i-15:0) (PathBank: SMP0057287)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-21:0/i-16:0) (PathBank: SMP0057288)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-21:0/i-17:0) (PathBank: SMP0057289)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-21:0/i-18:0) (PathBank: SMP0057290)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-21:0/i-19:0) (PathBank: SMP0057291)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-21:0/i-20:0) (PathBank: SMP0057292)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-21:0/i-21:0) (PathBank: SMP0057293)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-21:0/i-22:0) (PathBank: SMP0057294)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-21:0/i-24:0) (PathBank: SMP0057295)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-25:0/18:2(9Z,11Z)) (PathBank: SMP0057296)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-25:0/a-13:0) (PathBank: SMP0057297)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-25:0/a-15:0) (PathBank: SMP0057298)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-25:0/a-17:0) (PathBank: SMP0057299)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-25:0/a-21:0) (PathBank: SMP0057300)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-25:0/a-25:0) (PathBank: SMP0057301)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-25:0/i-12:0) (PathBank: SMP0057302)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-25:0/i-13:0) (PathBank: SMP0057303)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-25:0/i-14:0) (PathBank: SMP0057304)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-25:0/i-15:0) (PathBank: SMP0057305)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-25:0/i-16:0) (PathBank: SMP0057306)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-25:0/i-17:0) (PathBank: SMP0057307)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-25:0/i-18:0) (PathBank: SMP0057308)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-25:0/i-19:0) (PathBank: SMP0057309)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-25:0/i-20:0) (PathBank: SMP0057310)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-25:0/i-21:0) (PathBank: SMP0057311)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-25:0/i-22:0) (PathBank: SMP0057312)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/a-25:0/i-24:0) (PathBank: SMP0057313)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-12:0/18:2(9Z,11Z)) (PathBank: SMP0057314)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-12:0/a-13:0) (PathBank: SMP0057315)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-12:0/a-15:0) (PathBank: SMP0057316)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-12:0/a-17:0) (PathBank: SMP0057317)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-12:0/a-21:0) (PathBank: SMP0057318)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-12:0/a-25:0) (PathBank: SMP0057319)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-12:0/i-12:0) (PathBank: SMP0057320)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-12:0/i-13:0) (PathBank: SMP0057321)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-12:0/i-14:0) (PathBank: SMP0057322)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-12:0/i-15:0) (PathBank: SMP0057323)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-12:0/i-16:0) (PathBank: SMP0057324)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-12:0/i-17:0) (PathBank: SMP0057325)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-12:0/i-18:0) (PathBank: SMP0057326)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-12:0/i-19:0) (PathBank: SMP0057327)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-12:0/i-20:0) (PathBank: SMP0057328)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-12:0/i-21:0) (PathBank: SMP0057329)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-12:0/i-22:0) (PathBank: SMP0057330)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-12:0/i-24:0) (PathBank: SMP0057331)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-13:0/18:2(9Z,11Z)) (PathBank: SMP0057332)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-13:0/a-13:0) (PathBank: SMP0057333)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-13:0/a-15:0) (PathBank: SMP0057334)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-13:0/a-17:0) (PathBank: SMP0057335)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-13:0/a-21:0) (PathBank: SMP0057336)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-13:0/a-25:0) (PathBank: SMP0057337)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-13:0/i-12:0) (PathBank: SMP0057338)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-13:0/i-13:0) (PathBank: SMP0057339)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-13:0/i-14:0) (PathBank: SMP0057340)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-13:0/i-15:0) (PathBank: SMP0057341)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-13:0/i-16:0) (PathBank: SMP0057342)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-13:0/i-17:0) (PathBank: SMP0057343)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-13:0/i-18:0) (PathBank: SMP0057344)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-13:0/i-19:0) (PathBank: SMP0057345)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-13:0/i-20:0) (PathBank: SMP0057346)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-13:0/i-21:0) (PathBank: SMP0057347)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-13:0/i-22:0) (PathBank: SMP0057348)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-13:0/i-24:0) (PathBank: SMP0057349)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-14:0/18:2(9Z,11Z)) (PathBank: SMP0057350)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-14:0/a-13:0) (PathBank: SMP0057351)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-14:0/a-15:0) (PathBank: SMP0057352)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-14:0/a-17:0) (PathBank: SMP0057353)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-14:0/a-21:0) (PathBank: SMP0057354)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-14:0/a-25:0) (PathBank: SMP0057355)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-14:0/i-12:0) (PathBank: SMP0057356)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-14:0/i-13:0) (PathBank: SMP0057357)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-14:0/i-14:0) (PathBank: SMP0057358)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-14:0/i-15:0) (PathBank: SMP0057359)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-14:0/i-16:0) (PathBank: SMP0057360)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-14:0/i-17:0) (PathBank: SMP0057361)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-14:0/i-18:0) (PathBank: SMP0057362)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-14:0/i-19:0) (PathBank: SMP0057363)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-14:0/i-20:0) (PathBank: SMP0057364)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-14:0/i-21:0) (PathBank: SMP0057365)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-14:0/i-22:0) (PathBank: SMP0057366)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-14:0/i-24:0) (PathBank: SMP0057367)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-15:0/18:2(9Z,11Z)) (PathBank: SMP0057368)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-15:0/a-13:0) (PathBank: SMP0057369)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-15:0/a-15:0) (PathBank: SMP0057370)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-15:0/a-17:0) (PathBank: SMP0057371)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-15:0/a-21:0) (PathBank: SMP0057372)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-15:0/a-25:0) (PathBank: SMP0057373)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-15:0/i-12:0) (PathBank: SMP0057374)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-15:0/i-13:0) (PathBank: SMP0057375)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-15:0/i-14:0) (PathBank: SMP0057376)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-15:0/i-15:0) (PathBank: SMP0057377)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-15:0/i-16:0) (PathBank: SMP0057378)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-15:0/i-17:0) (PathBank: SMP0057379)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-15:0/i-18:0) (PathBank: SMP0057380)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-15:0/i-19:0) (PathBank: SMP0057381)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-15:0/i-20:0) (PathBank: SMP0057382)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-15:0/i-21:0) (PathBank: SMP0057383)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-15:0/i-22:0) (PathBank: SMP0057384)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-15:0/i-24:0) (PathBank: SMP0057385)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-16:0/18:2(9Z,11Z)) (PathBank: SMP0057386)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-16:0/a-13:0) (PathBank: SMP0057387)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-16:0/a-15:0) (PathBank: SMP0057388)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-16:0/a-17:0) (PathBank: SMP0057389)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-16:0/a-21:0) (PathBank: SMP0057390)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-16:0/a-25:0) (PathBank: SMP0057391)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-16:0/i-12:0) (PathBank: SMP0057392)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-16:0/i-13:0) (PathBank: SMP0057393)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-16:0/i-14:0) (PathBank: SMP0057394)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-16:0/i-15:0) (PathBank: SMP0057395)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-16:0/i-16:0) (PathBank: SMP0057396)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-16:0/i-17:0) (PathBank: SMP0057397)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-16:0/i-18:0) (PathBank: SMP0057398)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-16:0/i-19:0) (PathBank: SMP0057399)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-16:0/i-20:0) (PathBank: SMP0057400)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-16:0/i-21:0) (PathBank: SMP0057401)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-16:0/i-22:0) (PathBank: SMP0057402)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-16:0/i-24:0) (PathBank: SMP0057403)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-17:0/18:2(9Z,11Z)) (PathBank: SMP0057404)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-17:0/a-13:0) (PathBank: SMP0057405)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-17:0/a-15:0) (PathBank: SMP0057406)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-17:0/a-17:0) (PathBank: SMP0057407)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-17:0/a-21:0) (PathBank: SMP0057408)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-17:0/a-25:0) (PathBank: SMP0057409)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-17:0/i-12:0) (PathBank: SMP0057410)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-17:0/i-13:0) (PathBank: SMP0057411)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-17:0/i-14:0) (PathBank: SMP0057412)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-17:0/i-15:0) (PathBank: SMP0057413)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-17:0/i-16:0) (PathBank: SMP0057414)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-17:0/i-17:0) (PathBank: SMP0057415)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-17:0/i-18:0) (PathBank: SMP0057416)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-17:0/i-19:0) (PathBank: SMP0057417)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-17:0/i-20:0) (PathBank: SMP0057418)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-17:0/i-21:0) (PathBank: SMP0057419)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-17:0/i-22:0) (PathBank: SMP0057420)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-17:0/i-24:0) (PathBank: SMP0057421)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-18:0/18:2(9Z,11Z)) (PathBank: SMP0057422)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-18:0/a-13:0) (PathBank: SMP0057423)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-18:0/a-15:0) (PathBank: SMP0057424)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-18:0/a-17:0) (PathBank: SMP0057425)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-18:0/a-21:0) (PathBank: SMP0057426)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-18:0/a-25:0) (PathBank: SMP0057427)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-18:0/i-12:0) (PathBank: SMP0057428)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-18:0/i-13:0) (PathBank: SMP0057429)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-18:0/i-14:0) (PathBank: SMP0057430)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-18:0/i-15:0) (PathBank: SMP0057431)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-18:0/i-16:0) (PathBank: SMP0057432)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-18:0/i-17:0) (PathBank: SMP0057433)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-18:0/i-18:0) (PathBank: SMP0057434)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-18:0/i-19:0) (PathBank: SMP0057435)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-18:0/i-20:0) (PathBank: SMP0057436)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-18:0/i-21:0) (PathBank: SMP0057437)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-18:0/i-22:0) (PathBank: SMP0057438)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-18:0/i-24:0) (PathBank: SMP0057439)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-19:0/18:2(9Z,11Z)) (PathBank: SMP0057440)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-19:0/a-13:0) (PathBank: SMP0057441)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-19:0/a-15:0) (PathBank: SMP0057442)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-19:0/a-17:0) (PathBank: SMP0057443)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-19:0/a-21:0) (PathBank: SMP0057444)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-19:0/a-25:0) (PathBank: SMP0057445)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-19:0/i-12:0) (PathBank: SMP0057446)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-19:0/i-13:0) (PathBank: SMP0057447)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-19:0/i-14:0) (PathBank: SMP0057448)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-19:0/i-15:0) (PathBank: SMP0057449)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-19:0/i-16:0) (PathBank: SMP0057450)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-19:0/i-17:0) (PathBank: SMP0057451)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-19:0/i-18:0) (PathBank: SMP0057452)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-19:0/i-19:0) (PathBank: SMP0057453)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-19:0/i-20:0) (PathBank: SMP0057454)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-19:0/i-21:0) (PathBank: SMP0057455)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-19:0/i-22:0) (PathBank: SMP0057456)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-19:0/i-24:0) (PathBank: SMP0057457)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-20:0/18:2(9Z,11Z)) (PathBank: SMP0057458)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-20:0/a-13:0) (PathBank: SMP0057459)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-20:0/a-15:0) (PathBank: SMP0057460)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-20:0/a-17:0) (PathBank: SMP0057461)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-20:0/a-21:0) (PathBank: SMP0057462)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-20:0/a-25:0) (PathBank: SMP0057463)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-20:0/i-12:0) (PathBank: SMP0057464)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-20:0/i-13:0) (PathBank: SMP0057465)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-20:0/i-14:0) (PathBank: SMP0057466)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-20:0/i-15:0) (PathBank: SMP0057467)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-20:0/i-16:0) (PathBank: SMP0057468)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-20:0/i-17:0) (PathBank: SMP0057469)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-20:0/i-18:0) (PathBank: SMP0057470)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-20:0/i-19:0) (PathBank: SMP0057471)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-20:0/i-20:0) (PathBank: SMP0057472)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-20:0/i-21:0) (PathBank: SMP0057473)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-20:0/i-22:0) (PathBank: SMP0057474)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-20:0/i-24:0) (PathBank: SMP0057475)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-21:0/18:2(9Z,11Z)) (PathBank: SMP0057476)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-21:0/a-13:0) (PathBank: SMP0057477)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-21:0/a-15:0) (PathBank: SMP0057478)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-21:0/a-17:0) (PathBank: SMP0057479)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-21:0/a-21:0) (PathBank: SMP0057480)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-21:0/a-25:0) (PathBank: SMP0057481)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-21:0/i-12:0) (PathBank: SMP0057482)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-21:0/i-13:0) (PathBank: SMP0057483)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-21:0/i-14:0) (PathBank: SMP0057484)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-21:0/i-15:0) (PathBank: SMP0057485)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-21:0/i-16:0) (PathBank: SMP0057486)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-21:0/i-17:0) (PathBank: SMP0057487)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-21:0/i-18:0) (PathBank: SMP0057488)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-21:0/i-19:0) (PathBank: SMP0057489)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-21:0/i-20:0) (PathBank: SMP0057490)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-21:0/i-21:0) (PathBank: SMP0057491)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-21:0/i-22:0) (PathBank: SMP0057492)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-21:0/i-24:0) (PathBank: SMP0057493)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-22:0/18:2(9Z,11Z)) (PathBank: SMP0057494)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-22:0/a-13:0) (PathBank: SMP0057495)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-22:0/a-15:0) (PathBank: SMP0057496)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-22:0/a-17:0) (PathBank: SMP0057497)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-22:0/a-21:0) (PathBank: SMP0057498)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-22:0/a-25:0) (PathBank: SMP0057499)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-22:0/i-12:0) (PathBank: SMP0057500)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-22:0/i-13:0) (PathBank: SMP0057501)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-22:0/i-14:0) (PathBank: SMP0057502)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-22:0/i-15:0) (PathBank: SMP0057503)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-22:0/i-16:0) (PathBank: SMP0057504)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-22:0/i-17:0) (PathBank: SMP0057505)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-22:0/i-18:0) (PathBank: SMP0057506)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-22:0/i-19:0) (PathBank: SMP0057507)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-22:0/i-20:0) (PathBank: SMP0057508)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-22:0/i-21:0) (PathBank: SMP0057509)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-22:0/i-22:0) (PathBank: SMP0057510)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-22:0/i-24:0) (PathBank: SMP0057511)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-24:0/18:2(9Z,11Z)) (PathBank: SMP0057512)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-24:0/a-13:0) (PathBank: SMP0057513)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-24:0/a-15:0) (PathBank: SMP0057514)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-24:0/a-17:0) (PathBank: SMP0057515)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-24:0/a-21:0) (PathBank: SMP0057516)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-24:0/a-25:0) (PathBank: SMP0057517)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-24:0/i-12:0) (PathBank: SMP0057518)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-24:0/i-13:0) (PathBank: SMP0057519)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-24:0/i-14:0) (PathBank: SMP0057520)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-24:0/i-15:0) (PathBank: SMP0057521)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-24:0/i-16:0) (PathBank: SMP0057522)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-24:0/i-17:0) (PathBank: SMP0057523)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-24:0/i-18:0) (PathBank: SMP0057524)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-24:0/i-19:0) (PathBank: SMP0057525)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-24:0/i-20:0) (PathBank: SMP0057526)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-24:0/i-21:0) (PathBank: SMP0057527)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-24:0/i-22:0) (PathBank: SMP0057528)
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/i-24:0/i-24:0) (PathBank: SMP0057529)

Role

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	4.2	ALOGPS
logP	7.83	ChemAxon
logS	-5.3	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	34	ChemAxon
Refractivity	178.47 m³·mol⁻¹	ChemAxon
Polarizability	79.95 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]+	260.625	31661259
DarkChem	[M-H]-	245.468	31661259
DeepCCS	[M+H]+	249.036	30932474
DeepCCS	[M-H]-	247.14	30932474
DeepCCS	[M-2H]-	280.379	30932474
DeepCCS	[M+Na]+	254.708	30932474
AllCCS	[M+H]+	270.8	32859911
AllCCS	[M+H-H2O]+	270.6	32859911
AllCCS	[M+NH4]+	271.0	32859911
AllCCS	[M+Na]+	271.0	32859911
AllCCS	[M-H]-	253.1	32859911
AllCCS	[M+Na-2H]-	258.5	32859911
AllCCS	[M+HCOO]-	264.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
PGP(i-13:0/i-13:0)	[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCC(C)C)OC(=O)CCCCCCCCCC(C)C	4513.0	Standard polar	33892256
PGP(i-13:0/i-13:0)	[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCC(C)C)OC(=O)CCCCCCCCCC(C)C	4076.7	Standard non polar	33892256
PGP(i-13:0/i-13:0)	[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCC(C)C)OC(=O)CCCCCCCCCC(C)C	4762.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
PGP(i-13:0/i-13:0),2TMS,isomer #1	CC(C)CCCCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](COP(=O)(O)O)O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCC(C)C	4775.5	Semi standard non polar	33892256
PGP(i-13:0/i-13:0),2TMS,isomer #1	CC(C)CCCCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](COP(=O)(O)O)O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCC(C)C	3977.6	Standard non polar	33892256
PGP(i-13:0/i-13:0),2TMS,isomer #1	CC(C)CCCCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@H](COP(=O)(O)O)O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCC(C)C	6310.1	Standard polar	33892256
PGP(i-13:0/i-13:0),2TMS,isomer #2	CC(C)CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCC(C)C	4804.2	Semi standard non polar	33892256
PGP(i-13:0/i-13:0),2TMS,isomer #2	CC(C)CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCC(C)C	3991.4	Standard non polar	33892256
PGP(i-13:0/i-13:0),2TMS,isomer #2	CC(C)CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCC(C)C	6402.8	Standard polar	33892256
PGP(i-13:0/i-13:0),2TMS,isomer #3	CC(C)CCCCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@@H](O)COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCC(C)C	4800.4	Semi standard non polar	33892256
PGP(i-13:0/i-13:0),2TMS,isomer #3	CC(C)CCCCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@@H](O)COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCC(C)C	4004.2	Standard non polar	33892256
PGP(i-13:0/i-13:0),2TMS,isomer #3	CC(C)CCCCCCCCCC(=O)OC[C@H](COP(=O)(OC[C@@H](O)COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCC(C)C	5961.8	Standard polar	33892256
PGP(i-13:0/i-13:0),2TMS,isomer #4	CC(C)CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCC(C)C	4807.4	Semi standard non polar	33892256
PGP(i-13:0/i-13:0),2TMS,isomer #4	CC(C)CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCC(C)C	4005.0	Standard non polar	33892256
PGP(i-13:0/i-13:0),2TMS,isomer #4	CC(C)CCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)OC(=O)CCCCCCCCCC(C)C	6061.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - PGP(i-13:0/i-13:0) GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PGP(i-13:0/i-13:0) GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PGP(i-13:0/i-13:0) GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PGP(i-13:0/i-13:0) GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PGP(i-13:0/i-13:0) GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PGP(i-13:0/i-13:0) GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - PGP(i-13:0/i-13:0) GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-18	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(i-13:0/i-13:0) 10V, Positive-QTOF	splash10-0pvi-1940374800-9ea1cae1c47907e42a43	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(i-13:0/i-13:0) 20V, Positive-QTOF	splash10-0a4j-4941242200-9565a88bdd187267949e	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(i-13:0/i-13:0) 40V, Positive-QTOF	splash10-0a4i-9860713000-d335de02ed4f7c6c5d69	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(i-13:0/i-13:0) 10V, Negative-QTOF	splash10-01r2-7790061300-16cfa76cf9e1983937e4	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(i-13:0/i-13:0) 20V, Negative-QTOF	splash10-004j-9130000000-c02d031bee6ca400a53a	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(i-13:0/i-13:0) 40V, Negative-QTOF	splash10-004i-9000000000-d7fac0f775d0fbb70ee2	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(i-13:0/i-13:0) 10V, Negative-QTOF	splash10-014i-0010000900-541bb93e530e505f5b8c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(i-13:0/i-13:0) 20V, Negative-QTOF	splash10-0gba-3091050600-1f27ab7c88567c9dd0eb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(i-13:0/i-13:0) 40V, Negative-QTOF	splash10-0gw1-5093731000-5142a6ad6290cfe402f8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(i-13:0/i-13:0) 10V, Positive-QTOF	splash10-014i-2110515900-87adf7376d41f1dc0385	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(i-13:0/i-13:0) 20V, Positive-QTOF	splash10-0600-7600796000-eabf9145a673d53d7a5c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - PGP(i-13:0/i-13:0) 40V, Positive-QTOF	splash10-0zfs-6696500000-dea60c06180ed18315be	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(i-13:0/i-13:0/18:2(9Z,11Z)/18:2(9Z,11Z))		Not Available
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(9Z,11Z)/a-13:0)		Not Available
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(9Z,11Z)/a-15:0)		Not Available
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(9Z,11Z)/a-17:0)		Not Available
Cardiolipin Biosynthesis CL(i-13:0/i-13:0/18:2(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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131823210

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(i-13:0/i-13:0) (HMDB0116555)

MOL for HMDB0116555 (PGP(i-13:0/i-13:0))

3D MOL for HMDB0116555 (PGP(i-13:0/i-13:0))

3D SDF for HMDB0116555 (PGP(i-13:0/i-13:0))

3D-SDF for HMDB0116555 (PGP(i-13:0/i-13:0))

PDB for HMDB0116555 (PGP(i-13:0/i-13:0))

3D PDB for HMDB0116555 (PGP(i-13:0/i-13:0))

SMILES for HMDB0116555 (PGP(i-13:0/i-13:0))

INCHI for HMDB0116555 (PGP(i-13:0/i-13:0))

Structure for HMDB0116555 (PGP(i-13:0/i-13:0))

3D Structure for HMDB0116555 (PGP(i-13:0/i-13:0))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra