NP-MRD: Showing NP-Card for (2-{[(2r)-2-[(9z)-hexadec-9-enoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium (NP0172987)

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Record Information

Version

2.0

Created at

2022-09-03 10:02:51 UTC

Updated at

2022-09-03 10:02:51 UTC

NP-MRD ID

NP0172987

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2-{[(2r)-2-[(9z)-hexadec-9-enoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

Description

PC(18:2(9Z,12Z)/16:1(9Z)), also known as lecithin or PC(18:2/16:1), 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, PC(18:2(9Z,12Z)/16:1(9Z)) is considered to be a glycerophosphocholine lipid molecule. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. PC(18:2(9Z,12Z)/16:1(9Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:2(9Z,12Z)/16:1(9Z)), in particular, consists of one chain of linoleic acid at the C-1 position and one chain of palmitoleic acid at the C-2 position. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PC(18:2(9Z,12Z)/16:1(9Z)) exists in all eukaryotes, ranging from yeast to humans. The linoleic acid moiety is derived from seed oils, while the palmitoleic acid moiety is derived from animal fats and vegetable oils. A third route to PC synthesis involves the conversion of either PS or PE to PC. Within humans, PC(18:2(9Z,12Z)/16:1(9Z)) participates in a number of enzymatic reactions. In particular, S-adenosylhomocysteine and PC(18:2(9Z,12Z)/16:1(9Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:2(9Z,12Z)/16:1(9Z)); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. In addition, cytidine monophosphate and PC(18:2(9Z,12Z)/16:1(9Z)) can be biosynthesized from CDP-choline and DG(18:2(9Z,12Z)/16:1(9Z)/0:0); Which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. PCs can be synthesized via three different routes. In humans, PC(18:2(9Z,12Z)/16:1(9Z)) is involved in phosphatidylcholine biosynthesis. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Fatty acids containing 16, 18 and 20 carbons are the most common. 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. It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. (2-{[(2r)-2-[(9z)-hexadec-9-enoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium is found in Aphis gossypii. PC(18:2(9Z,12Z)/16:1(9Z)) is a phosphatidylcholine (PC or GPCho).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231222062D          

 53 52  0  0  1  0            999 V2000
   20.3252  -10.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6200  -10.7149    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.9148  -10.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0304  -10.7149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2097  -10.7149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6200  -11.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7355  -10.3078    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.1427  -11.0129    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   21.3284   -9.6025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4407   -9.9006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1459  -10.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8511   -9.9006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5563  -10.3078    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   24.1491  -11.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2089   -9.4552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2614  -10.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3491  -10.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0636  -10.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7780  -10.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4925  -10.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2070  -10.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9215  -10.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6360  -10.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3504  -10.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0649  -10.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7794  -10.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4938  -10.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2083  -10.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9228  -10.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6373  -10.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3518  -10.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0662  -10.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7807  -10.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4952  -10.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4952   -9.4774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1885  -11.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9029  -11.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6174  -11.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3319  -11.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0464  -11.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7608  -11.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4753  -11.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1898  -11.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9042  -11.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6187  -11.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3332  -11.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0476  -11.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7621  -11.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4766  -11.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1910  -11.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9055  -11.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9055  -12.7666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5073  -11.2653    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  1  4  1  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  6  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 10  1  0  0  0  0
 10 11  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
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  2  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
 26 25  2  0  0  0  0
 27 26  1  0  0  0  0
 28 27  1  0  0  0  0
 29 28  1  0  0  0  0
 30 29  1  0  0  0  0
 31 30  1  0  0  0  0
 32 31  1  0  0  0  0
 33 32  1  0  0  0  0
 34 33  1  0  0  0  0
 35 34  2  0  0  0  0
  5 34  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51  6  1  0  0  0  0
 51 52  2  0  0  0  0
  2 53  1  1  0  0  0
M  CHG  2   8  -1  13   1
M  END

     RDKit          3D

130129  0  0  0  0  0  0  0  0999 V2000
   -2.3102   -2.8783   -0.7208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0839   -1.6220    0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9786   -0.4711   -0.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4178   -0.8150   -0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2566    0.4015   -0.6944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9726    1.5668    0.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5945    2.7217   -0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3298    3.2779   -1.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4519    2.5359   -2.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4881    2.3424   -3.6585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1441    2.8689   -3.5213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1352    1.7129   -3.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2539    2.3551   -3.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3544    1.3607   -3.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2739    0.5591   -2.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3996    1.5120   -0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3444    0.8405    0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4104   -0.1704    0.7303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5217    0.1946    1.1837 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2202   -1.5075    0.4602 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2015   -2.5174    0.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6225   -3.8781    0.2634 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5639   -3.9634   -1.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1908   -5.2702   -1.5799 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1620   -5.3211   -3.2974 P   0  0  2  0  0  5  0  0  0  0  0  0
    0.9548   -4.5836   -3.7913 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0746   -6.9028   -3.8547 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.5282   -4.5095   -3.8292 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2626   -3.6231   -4.8581 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5405   -2.9176   -5.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3223   -1.9876   -6.3477 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.0621   -0.6441   -5.8548 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5543   -1.9252   -7.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2649   -2.3731   -7.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4559   -4.1414    0.9622 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2839   -5.1002    1.9317 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2383   -5.8455    2.2492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0534   -5.2435    2.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0906   -4.3044    3.8105 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9285   -4.6419    4.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9370   -3.6497    5.9990 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3928   -2.3245    5.4893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4321   -1.2165    6.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0519   -0.8893    7.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8070   -0.5143    5.9367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3533    0.6541    5.7964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1694    1.7449    6.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4991    2.8885    6.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2608    3.3889    4.8339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6214    3.9330    5.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3222    4.4054    3.8629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5671    5.4863    3.1415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7665   -3.6589   -0.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3247   -3.3000   -1.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9442   -2.6590   -1.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0363   -1.2712   -0.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1515   -1.7740    1.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6873    0.4175    0.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7716   -0.3104   -1.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7374   -1.6752   -0.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6880   -1.0149    0.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9041    0.5323   -1.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3271    0.0861   -0.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1134    1.3966    1.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4332    3.4626    0.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0576    4.1936   -1.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3524    3.8884   -1.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4393    2.1058   -3.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6706    1.7392   -4.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8692    3.3799   -4.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9267    3.5409   -2.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2328    1.0816   -4.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3182    1.1969   -2.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3201    2.9084   -4.3984 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2391    3.1198   -2.6364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3124    0.6866   -4.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3089    1.9246   -3.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3856   -0.0651   -1.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1737   -0.0849   -1.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2590    2.1888   -0.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4835    2.1680   -0.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4683    1.6733    1.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3268    0.4701    0.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4976   -2.5752    1.7405 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1101   -2.2848    0.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4058   -4.6090    0.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651   -3.2376   -1.6751 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5506   -3.7761   -1.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5542   -2.8678   -4.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8466   -4.2348   -5.6968 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  CHG  2  27  -1  31   1
M  END


  Mrv0541 02231222062D          

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 50 51  1  0  0  0  0
 51  6  1  0  0  0  0
 51 52  2  0  0  0  0
  2 53  1  1  0  0  0
M  CHG  2   8  -1  13   1
M  END
> <DATABASE_ID>
NP0172987

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C42H78NO8P/c1-6-8-10-12-14-16-18-20-21-23-24-26-28-30-32-34-41(44)48-38-40(39-50-52(46,47)49-37-36-43(3,4)5)51-42(45)35-33-31-29-27-25-22-19-17-15-13-11-9-7-2/h14,16-17,19-21,40H,6-13,15,18,22-39H2,1-5H3/b16-14-,19-17-,21-20-/t40-/m1/s1

> <INCHI_KEY>
PPCVNZFMCABQCL-KXESGEQTSA-N

> <FORMULA>
C42H78NO8P

> <MOLECULAR_WEIGHT>
756.0444

> <EXACT_MASS>
755.546504989

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
90.26323805698321

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
5.40

> <JCHEM_LOGP>
7.91716873919492

> <ALOGPS_LOGS>
-7.44

> <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>
228.41690000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
39

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.96e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lecithin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      37.940 -19.241   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      36.624 -20.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      35.308 -19.241   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      39.257 -20.001   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      33.991 -20.001   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      36.624 -21.521   0.000  0.00  0.00           O+0
HETATM    7  P   UNK     0      40.573 -19.241   0.000  0.00  0.00           P+0
HETATM    8  O   UNK     0      41.333 -20.557   0.000  0.00  0.00           O-1
HETATM    9  O   UNK     0      39.813 -17.925   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      41.889 -18.481   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      43.206 -19.241   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      44.522 -18.481   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      45.838 -19.241   0.000  0.00  0.00           N+1
HETATM   14  C   UNK     0      45.078 -20.557   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      47.057 -17.650   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      47.155 -20.001   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.985 -20.001   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.319 -19.231   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.652 -20.001   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.986 -19.231   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.320 -20.001   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.653 -19.231   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.987 -19.231   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.321 -20.001   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.654 -19.231   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      21.988 -19.231   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      23.322 -20.001   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      24.655 -19.231   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      25.989 -20.001   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      27.323 -19.231   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      28.657 -20.001   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      29.990 -19.231   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      31.324 -20.001   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      32.658 -19.231   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      32.658 -17.691   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      15.285 -22.291   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      16.619 -21.521   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      17.952 -22.291   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      19.286 -21.521   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      20.620 -22.291   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      21.953 -21.521   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      23.287 -22.291   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      24.621 -22.291   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      25.955 -21.521   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      27.288 -22.291   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      28.622 -21.521   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      29.956 -22.291   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      31.289 -21.521   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      32.623 -22.291   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      33.957 -21.521   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      35.290 -22.291   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      35.290 -23.831   0.000  0.00  0.00           O+0
HETATM   53  H   UNK     0      38.280 -21.029   0.000  0.00  0.00           H+0
CONECT    1    2    4                                                       
CONECT    2    1    3    6   53                                             
CONECT    3    2    5                                                       
CONECT    4    1    7                                                       
CONECT    5    3   34                                                       
CONECT    6    2   51                                                       
CONECT    7    4    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
CONECT   17   18                                                            
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35    5                                                  
CONECT   35   34                                                            
CONECT   36   37                                                            
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50    6   52                                                  
CONECT   52   51                                                            
CONECT   53    2                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  104    0
END

View in JSmol

Synonyms

Value	Source
Phosphatidylcholine(18:2/16:1)	HMDB
Lecithin	HMDB
PC(18:2/16:1)	HMDB
GPCho(18:2/16:1)	HMDB
Phosphatidylcholine(34:3)	HMDB
GPCho(34:3)	HMDB
1-Linoleoyl-2-palmitoleoyl-sn-glycero-3-phosphocholine	HMDB
1-(9Z,12Z-Octadecadienoyl)-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholine	HMDB
PC(34:3)	HMDB
PC(18:2(9Z,12Z)/16:1(9Z))	Lipid Annotator

Chemical Formula

C₄₂H₇₈NO₈P

Average Mass

756.0444 Da

Monoisotopic Mass

755.54650 Da

IUPAC Name

(2-{[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C42H78NO8P/c1-6-8-10-12-14-16-18-20-21-23-24-26-28-30-32-34-41(44)48-38-40(39-50-52(46,47)49-37-36-43(3,4)5)51-42(45)35-33-31-29-27-25-22-19-17-15-13-11-9-7-2/h14,16-17,19-21,40H,6-13,15,18,22-39H2,1-5H3/b16-14-,19-17-,21-20-/t40-/m1/s1

InChI Key

PPCVNZFMCABQCL-KXESGEQTSA-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
Aphis gossypii	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

Diacylglycerophosphocholines (LMGP01011620 )

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	5.4	ALOGPS
logP	7.92	ChemAxon
logS	-7.4	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	39	ChemAxon
Refractivity	228.42 m³·mol⁻¹	ChemAxon
Polarizability	90.26 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

HMDB0008134

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB025324

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

52922719

PDB ID

Not Available

ChEBI ID

89601

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2-{[(2r)-2-[(9z)-hexadec-9-enoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium (NP0172987)

MOL for NP0172987 ((2-{[(2r)-2-[(9z)-hexadec-9-enoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium)

3D MOL for NP0172987 ((2-{[(2r)-2-[(9z)-hexadec-9-enoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium)

3D SDF for NP0172987 ((2-{[(2r)-2-[(9z)-hexadec-9-enoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium)

3D-SDF for NP0172987 ((2-{[(2r)-2-[(9z)-hexadec-9-enoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium)

PDB for NP0172987 ((2-{[(2r)-2-[(9z)-hexadec-9-enoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium)

3D PDB for NP0172987 ((2-{[(2r)-2-[(9z)-hexadec-9-enoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium)

SMILES for NP0172987 ((2-{[(2r)-2-[(9z)-hexadec-9-enoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium)

INCHI for NP0172987 ((2-{[(2r)-2-[(9z)-hexadec-9-enoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium)

Structure for NP0172987 ((2-{[(2r)-2-[(9z)-hexadec-9-enoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium)

3D Structure for NP0172987 ((2-{[(2r)-2-[(9z)-hexadec-9-enoyloxy]-3-[(9z,12z)-octadeca-9,12-dienoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium)