NP-MRD: Showing NP-Card for dioleoyl phosphatidylcholine (NP0243095)

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Record Information

Version

2.0

Created at

2022-09-07 03:34:25 UTC

Updated at

2022-09-07 03:34:26 UTC

NP-MRD ID

NP0243095

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dioleoyl phosphatidylcholine

Description

1,2-Dioleoyl-sn-glycero-3-phosphocholine, also known as 1,2-dioleoyl-L-alpha-lecithin or dioleoyl lecithin, belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage. Thus, 1,2-dioleoyl-sn-glycero-3-phosphocholine is considered to be a glycerophosphocholine lipid molecule. 1,2-Dioleoyl-sn-glycero-3-phosphocholine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 1,2-Dioleoyl-sn-glycero-3-phosphocholine exists in all eukaryotes, ranging from yeast to humans. dioleoyl phosphatidylcholine is found in Trypanosoma brucei. A phosphatidylcholine 36:2 In which the phosphatidyl acyl groups at positions 1 and 2 are both oleoyl.

Structure

MOL 3D MOL SDF PDB SMILES InChI

PC(18:1(9Z)/18:1(9Z))
  Mrv1652303192020092D          

 55 54  0  0  0  0            999 V2000
   -3.8021    0.3608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591    0.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2447    0.7720    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6571    1.4866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1679    0.0575    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -3.0969    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3824    0.3590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6679    0.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9699   -0.3555    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7950   -0.3555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    1.1846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1844    0.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8988    1.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6132    0.7721    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.2007    0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2744    1.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3277    0.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5121    1.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2263    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9404    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6545    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3686    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0827    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7969    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5110    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2251    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0501    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7642    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4784    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1925    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9066    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.6207    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.3348    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.0490    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.7631    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5095   -1.5394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2237   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9378   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6519   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3660   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0801   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7943   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5084   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2225   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0475   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7616   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4758   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1899   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9040   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6181   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.3322   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.0464   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.7605   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  7  9  1  1  0  0  0
  6  1  1  0  0  0  0
  2  8  1  0  0  0  0
  7 10  1  6  0  0  0
  1 18  1  0  0  0  0
 10 37  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 11  3  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 37 38  2  0  0  0  0
 37 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  2  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
M  CHG  2   5  -1  14   1
M  END

     RDKit          3D

138137  0  0  0  0  0  0  0  0999 V2000
    0.1404   -3.6278    8.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5107   -2.5517    7.9819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4728   -1.4041    8.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1097   -0.3072    7.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1410    0.7682    7.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8821    1.9404    6.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4055    2.6576    6.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5374    3.8468    5.5955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7089    4.6049    5.9501 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7250    4.8943    5.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667    4.6620    3.9021 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6341    3.8779    2.8120 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6291    2.3762    2.9245 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1778    1.8068    1.6400 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    2.0297    1.1359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2667    1.4277    2.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0432   -0.0846    2.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1523   -0.7347    0.7940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7121   -0.2311   -0.2002 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4057   -1.9994    0.6244 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3132   -2.6820   -0.6165 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1126   -3.9487   -0.5413 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5965   -3.4720   -0.5863 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6253   -2.7411   -1.8016 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1582   -2.1233   -2.0441 P   0  0  1  0  0  5  0  0  0  0  0  0
    4.7324   -1.6560   -0.7383 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1666   -3.3273   -2.7081 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.0736   -0.7721   -3.0855 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9030   -0.8628   -3.8473 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8543    0.3558   -4.7503 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6753    0.3546   -5.5706 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.0359   -0.9501   -5.6007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8685    0.7840   -6.9198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7033    1.2559   -4.9561 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0162   -4.7136   -1.7238 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7308   -6.0444   -1.8302 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5247   -6.6872   -0.7903 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6998   -6.6051   -3.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0770   -5.6274   -4.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3578   -5.3705   -3.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0188   -4.3841   -4.6803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4342   -4.0863   -4.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7118   -3.5366   -3.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9716   -2.2180   -2.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3552   -1.7958   -1.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9516   -0.6803   -1.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3303    0.3294   -2.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5908    1.6012   -1.7854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9266    2.6636   -2.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1864    3.9734   -2.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5525    4.9524   -3.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0453    6.3313   -3.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5642    6.5229   -3.4089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9231    5.9207   -2.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7841   -4.5076    8.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9406   -3.9155    8.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2794   -3.2538   10.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5280   -2.2019    8.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5097   -2.9895    6.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5171   -1.7302    7.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3888   -0.9523    9.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0488   -0.7207    6.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8940    0.0622    7.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1846    1.1443    8.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1650    0.3672    6.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7125    2.6935    6.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8994    1.6468    5.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4458    3.0493    7.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2423    1.9694    6.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4722    3.4568    4.5787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4238    4.4143    5.7589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7238    4.9878    7.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4999    5.5360    5.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3114    4.3263    3.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4107    5.7371    3.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5442    4.1615    2.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1083    4.1307    1.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1062    2.0623    3.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7250    2.1064    3.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8848    2.1953    0.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4515    0.7059    1.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5612    3.1075    1.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6885    1.5875    0.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3807    1.9302    2.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2075    1.5576    1.4430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9720   -0.2327    2.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7480   -0.5243    2.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7806   -2.9765   -0.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5953   -1.9849   -1.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9281   -4.5096    0.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8127   -2.7827    0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2211   -4.3634   -0.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0666   -0.8718   -3.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0238   -1.7971   -4.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7618    0.3589   -5.3852 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8511    1.2305   -4.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6010   -1.2115   -4.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1750   -0.8658   -6.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7098   -1.7363   -5.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7290    0.3577   -7.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8378    1.8958   -6.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9536    0.4543   -7.4886 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2670    2.1268   -4.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1895    0.7757   -4.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0289    1.6592   -5.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1356   -7.5556   -3.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8893   -2.5269   -2.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
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 52132  1  0
 52133  1  0
 53134  1  0
 53135  1  0
 54136  1  0
 54137  1  0
 54138  1  0
M  CHG  2  27  -1  31   1
M  END

PC(18:1(9Z)/18:1(9Z))
  Mrv1652303192020092D          

 55 54  0  0  0  0            999 V2000
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  3  2  1  0  0  0  0
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  7  9  1  1  0  0  0
  6  1  1  0  0  0  0
  2  8  1  0  0  0  0
  7 10  1  6  0  0  0
  1 18  1  0  0  0  0
 10 37  1  0  0  0  0
 11 12  1  0  0  0  0
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 11  3  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
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 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 37 38  2  0  0  0  0
 37 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  2  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
M  CHG  2   5  -1  14   1
M  END
> <DATABASE_ID>
NP0243095

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C44H84NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h20-23,42H,6-19,24-41H2,1-5H3/b22-20-,23-21-/t42-/m1/s1

> <INCHI_KEY>
SNKAWJBJQDLSFF-NVKMUCNASA-N

> <FORMULA>
C44H84NO8P

> <MOLECULAR_WEIGHT>
786.1134

> <EXACT_MASS>
785.593455181

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
138

> <JCHEM_AVERAGE_POLARIZABILITY>
96.97129412589246

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
5.78

> <JCHEM_LOGP>
9.168227725861586

> <ALOGPS_LOGS>
-7.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8550572064469137

> <JCHEM_PKA_STRONGEST_BASIC>
-6.744159309169755

> <JCHEM_POLAR_SURFACE_AREA>
111.19

> <JCHEM_REFRACTIVITY>
236.50230000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
42

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.22e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PC(18:1(9Z)/18:1(9Z))                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  O   UNK     0      -7.097   0.673   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      -1.790   0.671   0.000  0.00  0.00           O+0
HETATM    3  P   UNK     0      -0.457   1.441   0.000  0.00  0.00           P+0
HETATM    4  O   UNK     0      -1.227   2.775   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.313   0.107   0.000  0.00  0.00           O-1
HETATM    6  C   UNK     0      -5.781   1.440   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.447   0.670   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.113   1.440   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0      -3.677  -0.664   0.000  0.00  0.00           H+0
HETATM   10  O   UNK     0      -5.217  -0.664   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.877   2.211   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.211   1.441   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.544   2.211   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       4.878   1.441   0.000  0.00  0.00           N+1
HETATM   15  C   UNK     0       4.108   0.108   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.112   3.054   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.212   0.671   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.423   1.436   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -8.423   2.876   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -9.756   0.665   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -11.089   1.436   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -12.422   0.665   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -13.755   1.436   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -15.088   0.665   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -16.421   1.436   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -17.754   0.665   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -19.087   1.436   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -20.627   1.436   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -21.960   0.665   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -23.293   1.436   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -24.626   0.665   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -25.959   1.436   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -27.292   0.665   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -28.625   1.436   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -29.958   0.665   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -31.291   1.436   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -6.551  -1.434   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -6.551  -2.874   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -7.884  -0.662   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -9.217  -1.434   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -10.550  -0.662   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -11.883  -1.434   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -13.216  -0.662   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -14.549  -1.434   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -15.882  -0.662   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -17.215  -1.434   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -18.755  -1.434   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -20.088  -0.662   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -21.421  -1.434   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -22.754  -0.662   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0     -24.087  -1.434   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0     -25.420  -0.662   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0     -26.754  -1.434   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0     -28.087  -0.662   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0     -29.420  -1.434   0.000  0.00  0.00           C+0
CONECT    1    6   18                                                       
CONECT    2    3    8                                                       
CONECT    3    2    4    5   11                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    7    1                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7    2                                                       
CONECT    9    7                                                            
CONECT   10    7   37                                                       
CONECT   11   12    3                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
CONECT   18    1   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   10   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   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                                                       
CONECT   55   54                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  108    0
END

View in JSmol

Synonyms

Value	Source
(R-(Z,Z))-(7-Oleoyl-4-oxido-10-oxo-3,5,9-trioxa-4-phosphaheptacos-18-enyl)trimethylammonium 4-oxide	ChEBI
1,2-Di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine	ChEBI
1,2-Dioleoyl-L-alpha-lecithin	ChEBI
1-(9Z)-Octadecenoyl-2-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine	ChEBI
1-C18:1(Omega-9)-2-C18:1(omega-9)-phosphatidylcholine	ChEBI
Dioleoyl lecithin	ChEBI
Dioleoyl phosphatidylcholine	ChEBI
PC 18:1	ChEBI
PC(18:1(9Z)/18:1(9Z))	ChEBI
PC(18:1/18:1)	ChEBI
Phosphatidylcholine 18:1	ChEBI
1,2-Dioleoyl-L-a-lecithin	Generator
1,2-Dioleoyl-L-α-lecithin	Generator
1,2-Di-(9Z)-octadecenoyl-sn-glycero-3-phosphocholine	HMDB
1,2-Dioleoyl-sn-glycerol-3-ethylphosphocholine	MeSH
Dioleylphosphatidylcholine	MeSH
1,2-Oleoylphosphatidylcholine, (L-alpha)-(R-(Z,Z))-isomer	MeSH
Dielaidoylphosphatidylcholine	MeSH
Dioleoylphosphatidylcholine	MeSH
1,2-Dioleoylglycerophosphocholine	MeSH
1,2-Oleoyl-sn-glycero-3-phosphocholine	MeSH
DOPC	MeSH
Dielaidinoyl lecithin	MeSH
1,2-DOCPC	MeSH
1,2-Dioleoyl glycerophosphocholine	MeSH
1,2-Dioleoyl-sn-glycero-3-phosphocholine	MeSH
1,2-Oleoylphosphatidylcholine	MeSH
1,2-Dioleoyl-GPC	HMDB
1,2-Dioleoyl-sn-glycero-phosphatidylcholine	HMDB
GPC(18:1(9Z)/18:1(9Z))	HMDB
GPC(18:1/18:1)	HMDB
GPC(18:1n9/18:1n9)	HMDB
GPC(18:1w9/18:1w9)	HMDB
GPC(36:2)	HMDB
GPCho(18:1(9Z)/18:1(9Z))	HMDB
GPCho(18:1/18:1)	HMDB
GPCho(18:1n9/18:1n9)	HMDB
GPCho(18:1w9/18:1w9)	HMDB
GPCho(36:2)	HMDB
PC(18:1n9/18:1n9)	HMDB
PC(18:1w9/18:1w9)	HMDB
PC(36:2)	HMDB
Phosphatidylcholine(18:1(9Z)/18:1(9Z))	HMDB
Phosphatidylcholine(18:1/18:1)	HMDB
Phosphatidylcholine(18:1n9/18:1n9)	HMDB
Phosphatidylcholine(18:1w9/18:1w9)	HMDB
Phosphatidylcholine(36:2)	HMDB
1,2-Dioleoyl-3-sn-phosphatidylcholine	HMDB
1,2-Dioleoyl-sn-glycero-3-phosphochline	HMDB
1,2-Dioleoyl-sn-glycero-3-phosphorylcholine	HMDB
1,2-Dioleoyl-sn-phosphatidylcholine	HMDB
1,2-Dioleoylphosphatidylcholine	HMDB
1,2-Dioleyl-L-lecithin	HMDB
Dioleoyl L-alpha-lecithin	HMDB
Dioleoyl L-α-lecithin	HMDB
Dioleoyl-3-sn-phosphatidylcholine	HMDB
Dioleoyl-L-alpha-glycerophosphocholine	HMDB
Dioleoyl-L-alpha-glycerophosphorylcholine	HMDB
Dioleoyl-L-alpha-phosphatidylcholine	HMDB
Dioleoyl-L-α-glycerophosphocholine	HMDB
Dioleoyl-L-α-glycerophosphorylcholine	HMDB
Dioleoyl-L-α-phosphatidylcholine	HMDB
Dioleoyllecithin	HMDB
L-Dioleoyl lecithin	HMDB
L-Dioleoylphosphatidylcholine	HMDB
L-alpha-Di(cis-9-octadecanoyl) lecithin	HMDB
L-alpha-Dioleoyl phosphatidylcholine	HMDB
L-alpha-Dioleoyllecithin	HMDB
L-alpha-Dioleylphosphatidylcholine	HMDB
L-α-Di(cis-9-octadecanoyl) lecithin	HMDB
L-α-Dioleoyl phosphatidylcholine	HMDB
L-α-Dioleoyllecithin	HMDB
L-α-Dioleylphosphatidylcholine	HMDB
sn-3-Dioleoyllecithin	HMDB
1,2-Dioleoylglycerol-3-phosphorylcholine	HMDB
1,2-Dioleoylglyceryl-3-phosphorylcholine	HMDB
1,2-Dioleoyllecithin	HMDB
Dioleoylglycerophosphocholine	HMDB
Dioleoylglycerophosphorylcholine	HMDB
Dioleoylglycerylphosphorylcholine	HMDB
Dioleyl lecithin	HMDB
Dioleyl phosphatidylcholine	HMDB

Chemical Formula

C₄₄H₈₄NO₈P

Average Mass

786.1134 Da

Monoisotopic Mass

785.59346 Da

IUPAC Name

(2-{[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-2,3-bis[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC

InChI Identifier

InChI=1S/C44H84NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h20-23,42H,6-19,24-41H2,1-5H3/b22-20-,23-21-/t42-/m1/s1

InChI Key

SNKAWJBJQDLSFF-NVKMUCNASA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

Phosphatidylcholines

Alternative Parents

Substituents

Diacylglycero-3-phosphocholine
Phosphocholine
Fatty acid ester
Dialkyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Amine
Organic salt
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

phosphatidylcholine 36:2 (CHEBI:74669 )
Diacylglycerophosphocholines (LMGP01010890 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	5.78	ALOGPS
logP	9.17	ChemAxon
logS	-7.6	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	111.19 Å²	ChemAxon
Rotatable Bond Count	42	ChemAxon
Refractivity	236.5 m³·mol⁻¹	ChemAxon
Polarizability	96.97 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

External Links

HMDB ID

HMDB0062690

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8525772

KEGG Compound ID

Not Available

BioCyc ID

CPD-2181

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10350317

PDB ID

Not Available

ChEBI ID

74669

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for dioleoyl phosphatidylcholine (NP0243095)

MOL for NP0243095 (dioleoyl phosphatidylcholine)

3D MOL for NP0243095 (dioleoyl phosphatidylcholine)

3D SDF for NP0243095 (dioleoyl phosphatidylcholine)

3D-SDF for NP0243095 (dioleoyl phosphatidylcholine)

PDB for NP0243095 (dioleoyl phosphatidylcholine)

3D PDB for NP0243095 (dioleoyl phosphatidylcholine)

SMILES for NP0243095 (dioleoyl phosphatidylcholine)

INCHI for NP0243095 (dioleoyl phosphatidylcholine)

Structure for NP0243095 (dioleoyl phosphatidylcholine)

3D Structure for NP0243095 (dioleoyl phosphatidylcholine)