NP-MRD: Showing NP-Card for (2-{[(2r)-2-[(5z,8z,11z)-icosa-5,8,11-trienoyloxy]-3-[(9z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium (NP0223598)

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Record Information

Version

2.0

Created at

2022-09-06 01:44:22 UTC

Updated at

2022-09-06 01:44:22 UTC

NP-MRD ID

NP0223598

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2-{[(2r)-2-[(5z,8z,11z)-icosa-5,8,11-trienoyloxy]-3-[(9z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

Description

PC(18:1(9Z)/20:3(5Z,8Z,11Z)), also known as gpcho(18:1/20:3) Or phosphatidylcholine(18:1/20:3), 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(18:1(9Z)/20:3(5Z,8Z,11Z)) is considered to be a glycerophosphocholine lipid molecule. A phosphatidylcholine 38:4 In which the acyl groups specified at positions 1 and 2 are (9Z)-octadecenoyl and (5Z,8Z,11Z)-eicosatrienoyl respectively. PC(18:1(9Z)/20:3(5Z,8Z,11Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. PC(18:1(9Z)/20:3(5Z,8Z,11Z)) exists in all eukaryotes, ranging from yeast to humans. Within humans, PC(18:1(9Z)/20:3(5Z,8Z,11Z)) participates in a number of enzymatic reactions. In particular, S-adenosylhomocysteine and PC(18:1(9Z)/20:3(5Z,8Z,11Z)) can be biosynthesized from S-adenosylmethionine and pe-nme2(18:1(9Z)/20:3(5Z,8Z,11Z)); which is catalyzed by the enzyme phosphatidylethanolamine N-methyltransferase. In addition, cytidine monophosphate and PC(18:1(9Z)/20:3(5Z,8Z,11Z)) can be biosynthesized from CDP-choline and DG(18:1(9Z)/20:3(5Z,8Z,11Z)/0:0); Which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. (2-{[(2r)-2-[(5z,8z,11z)-icosa-5,8,11-trienoyloxy]-3-[(9z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium is found in Trypanosoma brucei. In humans, PC(18:1(9Z)/20:3(5Z,8Z,11Z)) is involved in phosphatidylcholine biosynthesis.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231222042D          

 57 56  0  0  1  0            999 V2000
   18.4198   -8.7756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7146   -9.1827    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.0094   -8.7756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1250   -9.1827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3043   -9.1827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7146   -9.9970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8301   -8.7756    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.2373   -9.4808    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   19.4230   -8.0704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5353   -8.3684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2405   -8.7756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9457   -8.3684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6509   -8.7756    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   22.2437   -9.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3035   -7.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3560   -9.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4437   -8.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1582   -9.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8726   -8.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5871   -9.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3016   -8.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0161   -9.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7306   -8.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4450   -9.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1595   -8.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8740   -8.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5884   -9.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3029   -8.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0174   -9.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7319   -8.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4464   -9.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1608   -8.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8753   -9.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5898   -8.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5898   -7.9452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4251  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1396   -9.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8540  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5686   -9.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2830  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9975   -9.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7120  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4264   -9.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1409  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8554  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5698   -9.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2843  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9988  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7133   -9.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4278  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1422  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8567   -9.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5712  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2856   -9.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0001  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0001  -11.2345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5430   -9.7920    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  1  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  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  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
 55  6  1  0  0  0  0
 55 56  2  0  0  0  0
  2 57  1  1  0  0  0
M  CHG  2   8  -1  13   1
M  END

     RDKit          3D

140139  0  0  0  0  0  0  0  0999 V2000
   -2.1203   -5.2386    2.5630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2472   -6.1360    2.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5194   -5.9297    0.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9553   -4.5176    0.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2189   -4.2279    1.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6964   -2.8095    0.6968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0129   -2.5405    1.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0594   -2.5092    2.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3925   -1.3539    3.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3826   -1.2814    4.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6766   -2.4128    4.7526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2647   -2.6237    4.5806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4063   -1.9031    3.9550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5950   -0.6379    3.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1049   -0.9263    1.8183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1132   -0.2698    1.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3639    0.8124    1.9208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4904    2.1131    1.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0575    1.9287   -0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938    3.1814   -1.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3353    3.3047   -2.2276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7127    4.2896   -0.5016 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8746    5.4869   -1.1914 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4126    6.6788   -0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9380    6.6201   -0.0822 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0181    6.4911   -0.9036 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7940    6.3868   -2.1484 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3943    6.4766   -0.3712 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7760    5.1598    0.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7534    3.9992   -0.7357 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6692    4.1341   -1.9330 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5995    2.9280   -2.7768 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9237    1.6073   -2.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2819    1.2893   -1.7259 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7768    2.0392   -0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0906    1.4409    0.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0001    0.0252    0.8474 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0687   -0.1266    2.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8683   -1.5291    2.4902 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2670   -2.4368    1.4538 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0876   -3.8466    1.9729 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4738   -4.7074    0.8994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1280   -4.2033    0.4618 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1028   -4.1366    1.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4069    5.6496   -1.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9197    4.5895   -2.0823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5874    4.7537   -2.2798 P   0  0  2  0  0  5  0  0  0  0  0  0
   -4.9171    6.0704   -2.9824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2919    4.7842   -0.7248 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.2075    3.4413   -3.1443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8460    3.8835   -4.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4174    2.7335   -5.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4354    1.7862   -5.5183 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.0954    2.3634   -5.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7877    1.3678   -6.8660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4369    0.6316   -4.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1635   -5.6391    2.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2967   -4.2009    2.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0012   -5.2902    3.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1572   -5.9725    2.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9022   -7.1870    2.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3379   -6.6393    0.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6345   -6.2313   -0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1679   -3.7872    0.5129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1727   -4.4678   -0.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1000   -4.2597    2.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0046   -4.9122    0.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9512   -2.0635    1.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8375   -2.7830   -0.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7757   -3.2419    0.8986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3548   -1.5342    0.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1582   -2.4171    3.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7672   -3.4947    3.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8059   -0.3539    3.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0816   -0.2696    4.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2196   -3.3734    4.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8445   -2.4726    5.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8458   -3.5539    5.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3487   -2.2638    3.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9570    0.1007    3.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5991   -0.2359    3.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5916   -1.7001    1.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8532   -0.5880    0.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7342    0.5083    1.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6562    1.0068    2.9289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0853    2.9125    1.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5689    2.3315    1.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0989    1.5444   -0.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5415    1.1453   -0.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4123    5.4757   -2.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5443    7.6316   -1.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5264    7.2300    0.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1 59  1  0
M  CHG  2  49  -1  53   1
M  END


  Mrv0541 02231222042D          

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 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55  6  1  0  0  0  0
 55 56  2  0  0  0  0
  2 57  1  1  0  0  0
M  CHG  2   8  -1  13   1
M  END
> <DATABASE_ID>
NP0223598

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C46H84NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h20-22,24-25,27,31,33,44H,6-19,23,26,28-30,32,34-43H2,1-5H3/b22-20-,24-21-,27-25-,33-31-/t44-/m1/s1

> <INCHI_KEY>
APIPSPZJMLSCBO-NRTPYZNRSA-N

> <FORMULA>
C46H84NO8P

> <MOLECULAR_WEIGHT>
810.1348

> <EXACT_MASS>
809.593455181

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
98.77619170041483

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-{[(2R)-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

> <ALOGPS_LOGP>
6.04

> <JCHEM_LOGP>
9.333521742528253

> <ALOGPS_LOGS>
-7.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8550572064466984

> <JCHEM_PKA_STRONGEST_BASIC>
-6.744217246680202

> <JCHEM_POLAR_SURFACE_AREA>
111.19

> <JCHEM_REFRACTIVITY>
247.93750000000009

> <JCHEM_ROTATABLE_BOND_COUNT>
42

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.84e-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      34.384 -16.381   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      33.067 -17.141   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.751 -16.381   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      35.700 -17.141   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      30.435 -17.141   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      33.067 -18.661   0.000  0.00  0.00           O+0
HETATM    7  P   UNK     0      37.016 -16.381   0.000  0.00  0.00           P+0
HETATM    8  O   UNK     0      37.776 -17.697   0.000  0.00  0.00           O-1
HETATM    9  O   UNK     0      36.256 -15.065   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      38.333 -15.621   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      39.649 -16.381   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      40.965 -15.621   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      42.282 -16.381   0.000  0.00  0.00           N+1
HETATM   14  C   UNK     0      41.522 -17.697   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      43.500 -14.790   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      43.598 -17.141   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.428 -16.371   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.762 -17.141   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.096 -16.371   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.429 -17.141   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.763 -16.371   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.097 -17.141   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.430 -16.371   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.764 -17.141   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.098 -16.371   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.431 -16.371   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      19.765 -17.141   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      21.099 -16.371   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      22.432 -17.141   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      23.766 -16.371   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      25.100 -17.141   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      26.433 -16.371   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      27.767 -17.141   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      29.101 -16.371   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      29.101 -14.831   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       6.394 -19.431   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.727 -18.661   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.061 -19.431   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      10.395 -18.661   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      11.728 -19.431   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      13.062 -18.661   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      14.396 -19.431   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      15.729 -18.661   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      17.063 -19.431   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      18.397 -19.431   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      19.730 -18.661   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      21.064 -19.431   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      22.398 -19.431   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      23.731 -18.661   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      25.065 -19.431   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      26.399 -19.431   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      27.733 -18.661   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      29.066 -19.431   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      30.400 -18.661   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      31.734 -19.431   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      31.734 -20.971   0.000  0.00  0.00           O+0
HETATM   57  H   UNK     0      34.614 -18.278   0.000  0.00  0.00           H+0
CONECT    1    2    4                                                       
CONECT    2    1    3    6   57                                             
CONECT    3    2    5                                                       
CONECT    4    1    7                                                       
CONECT    5    3   34                                                       
CONECT    6    2   55                                                       
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   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54    6   56                                                  
CONECT   56   55                                                            
CONECT   57    2                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  112    0
END

View in JSmol

Synonyms

Value	Source
1-Oleoyl-2-meadoyl-sn-glycero-3-phosphocholine	ChEBI
GPCho(18:1/20:3)	ChEBI
GPCho(18:1n9/20:3n9)	ChEBI
GPCho(18:1W9/20:3W9)	ChEBI
PC(18:1n9/20:3n9)	ChEBI
Phosphatidylcholine(18:1n9/20:3n9)	ChEBI
Phosphatidylcholine(18:1/20:3)	HMDB
PC(38:4)	HMDB
GPCho(38:4)	HMDB
Phosphatidylcholine(38:4)	HMDB
PC(18:1/20:3)	HMDB
Lecithin	HMDB
1-(9Z-Octadecenoyl)-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycero-3-phosphocholine	HMDB
PC(18:1(9Z)/20:3(5Z,8Z,11Z))	Lipid Annotator

Chemical Formula

C₄₆H₈₄NO₈P

Average Mass

810.1348 Da

Monoisotopic Mass

809.59346 Da

IUPAC Name

(2-{[(2R)-2-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C46H84NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h20-22,24-25,27,31,33,44H,6-19,23,26,28-30,32,34-43H2,1-5H3/b22-20-,24-21-,27-25-,33-31-/t44-/m1/s1

InChI Key

APIPSPZJMLSCBO-NRTPYZNRSA-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 38:4 (CHEBI:86178 )
Diacylglycerophosphocholines (LMGP01010904 )

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	6.04	ALOGPS
logP	9.33	ChemAxon
logS	-7.5	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	247.94 m³·mol⁻¹	ChemAxon
Polarizability	98.78 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

HMDB0008112

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB025302

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

24778947

PDB ID

Not Available

ChEBI ID

86178

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2-{[(2r)-2-[(5z,8z,11z)-icosa-5,8,11-trienoyloxy]-3-[(9z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium (NP0223598)

MOL for NP0223598 ((2-{[(2r)-2-[(5z,8z,11z)-icosa-5,8,11-trienoyloxy]-3-[(9z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium)

3D MOL for NP0223598 ((2-{[(2r)-2-[(5z,8z,11z)-icosa-5,8,11-trienoyloxy]-3-[(9z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium)

3D SDF for NP0223598 ((2-{[(2r)-2-[(5z,8z,11z)-icosa-5,8,11-trienoyloxy]-3-[(9z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium)

3D-SDF for NP0223598 ((2-{[(2r)-2-[(5z,8z,11z)-icosa-5,8,11-trienoyloxy]-3-[(9z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium)

PDB for NP0223598 ((2-{[(2r)-2-[(5z,8z,11z)-icosa-5,8,11-trienoyloxy]-3-[(9z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium)

3D PDB for NP0223598 ((2-{[(2r)-2-[(5z,8z,11z)-icosa-5,8,11-trienoyloxy]-3-[(9z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium)

SMILES for NP0223598 ((2-{[(2r)-2-[(5z,8z,11z)-icosa-5,8,11-trienoyloxy]-3-[(9z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium)

INCHI for NP0223598 ((2-{[(2r)-2-[(5z,8z,11z)-icosa-5,8,11-trienoyloxy]-3-[(9z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium)

Structure for NP0223598 ((2-{[(2r)-2-[(5z,8z,11z)-icosa-5,8,11-trienoyloxy]-3-[(9z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium)

3D Structure for NP0223598 ((2-{[(2r)-2-[(5z,8z,11z)-icosa-5,8,11-trienoyloxy]-3-[(9z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium)