NP-MRD: Showing NP-Card for (2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid (NP0285432)

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Record Information

Version

2.0

Created at

2022-09-09 13:36:05 UTC

Updated at

2022-09-09 13:36:05 UTC

NP-MRD ID

NP0285432

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid

Description

PA(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), also known as PA(18:0/22:6), Belongs to the class of organic compounds known as 1,2-diacylglycerol-3-phosphates. These are glycerol-3-phosphates in which the glycerol moiety is bonded to two aliphatic chains through ester linkages. Thus, PA(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is considered to be a glycerophosphate lipid molecule. PA(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, PA(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) participates in a number of enzymatic reactions. In particular, PA(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be biosynthesized from lpa(18:0/0:0) And docosahexaenoyl-CoA; which is mediated by the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase. In addition, PA(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) can be converted into DG(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0); Which is mediated by the enzyme phosphatidate phosphatase. (2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid is found in Trypanosoma brucei. In humans, PA(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is involved in the metabolic disorder called de novo triacylglycerol biosynthesis pathway.

Structure

MOL 3D MOL SDF PDB SMILES InChI

PA(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
  Mrv1652309161705552D          

 53 52  0  0  1  0            999 V2000
   -0.1691    0.3607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8792    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5896    0.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2414   -0.3494    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5796   -0.3494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5412    0.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2514    0.3607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0097    0.3436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620    0.6480    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.9002    0.0209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2620    1.3958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2996    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2996    1.5409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0137    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7278    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4420    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1561    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8702    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5843    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2984    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0125    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7266    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4407    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1549    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8690    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5831    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2972    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0114    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7255    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.4396    0.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235   -1.5406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0376   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7517   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4659   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2909   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0050   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7191   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5441   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2582   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9724   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7974   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5115   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2256   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0506   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7647   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4788   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3038   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0179   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.7320   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.5570   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.2712   -0.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.9853   -0.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  4  1  1  0  0  0
  2  3  1  0  0  0  0
  3 12  1  0  0  0  0
  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  9  7  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 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  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31  5  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  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
M  END

     RDKit          3D

125124  0  0  0  0  0  0  0  0999 V2000
   15.5350    0.5959   -1.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6288    1.7119   -0.7081 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0851    1.3868    0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8081    1.2734    0.8895 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7493    1.4582   -0.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8148    0.4027   -0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7972   -0.8084    0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6503   -1.4790    1.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2720   -2.0103    2.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1590   -1.9734    2.9382 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9403   -1.3038    2.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4789   -0.2776    3.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3683   -0.3035    4.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3168   -1.2912    3.9902 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4066   -2.5002    3.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6070   -2.7974    2.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5216   -1.9312    1.7431 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7324   -1.5430    0.3055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661   -1.8592   -0.5973 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5976   -2.5953   -0.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4452   -1.7695   -0.9642 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3329   -0.5096   -0.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0190   -0.2250    0.8001 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4127    0.4762   -0.5928 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1882    1.6961    0.0135 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2392    2.0323    0.3475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0124    2.0294   -0.8164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3039    0.9332   -1.5712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8875   -0.1798   -1.2244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1220    1.0210   -2.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3307   -0.3639   -3.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1186   -1.2782   -2.4744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5230   -0.7556   -2.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3220   -1.6533   -1.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7913   -1.8419    0.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6965   -0.5348    0.7859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0472    0.1437    0.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0568   -0.7163    1.5990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4005   -0.0686    1.7053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9711    0.2244    0.3386 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3687    0.8728    0.5150 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9013    1.1530   -0.8480 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2133    1.7548   -1.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.5077    1.1735   -0.7820 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.0026    0.5928    0.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.3415   -0.6762    0.8779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6158    2.7642   -1.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1836    2.5577   -2.1433 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1745    3.6619   -3.3737 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.0325    5.0934   -2.8749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8716    3.4710   -4.6875 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7542    3.5437   -3.9090 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4512    1.0024   -1.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.9815    0.0758   -2.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.8375   -0.0848   -0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3831    2.5579   -0.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9904    2.1004   -1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.7954    1.2146    1.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5130    1.0416    1.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1623    2.4318    0.1979 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1975    1.7892   -1.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0087    0.6871   -1.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9588   -1.4382   -0.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9877   -2.4843    0.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6983   -1.0404    1.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1023   -2.5838    2.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0877   -2.4805    3.9569 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2454   -1.9798    2.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2522   -0.6530    1.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1913    0.5603    3.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1943    0.5765    4.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3349   -0.7413    3.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0861   -1.6347    5.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1817   -3.2837    3.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7677   -3.7681    1.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5739   -2.4495    1.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4401   -0.9639    2.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292   -0.9865    0.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.2864   -2.6752   -1.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4135   -1.4061   -1.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7667   -2.2603   -0.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3950   -2.6031    0.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

PA(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))
  Mrv1652309161705552D          

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M  END
> <DATABASE_ID>
NP0285432

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C43H73O8P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-43(45)51-41(40-50-52(46,47)48)39-49-42(44)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,21-22,26,28,32,34,41H,3-4,6,8-10,12,14-16,18,20,23-25,27,29-31,33,35-40H2,1-2H3,(H2,46,47,48)/b7-5-,13-11-,19-17-,22-21-,28-26-,34-32-/t41-/m1/s1

> <INCHI_KEY>
SFHGEOGVGJYLEK-USQBYQOHSA-N

> <FORMULA>
C43H73O8P

> <MOLECULAR_WEIGHT>
749.023

> <EXACT_MASS>
748.504306309

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
125

> <JCHEM_AVERAGE_POLARIZABILITY>
88.7729406387524

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecanoyloxy)propoxy]phosphonic acid

> <ALOGPS_LOGP>
9.15

> <JCHEM_LOGP>
13.264547130666667

> <ALOGPS_LOGS>
-7.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.343234174269949

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3174056081542314

> <JCHEM_PKA_STRONGEST_BASIC>
-6.745836962379279

> <JCHEM_POLAR_SURFACE_AREA>
119.35999999999999

> <JCHEM_REFRACTIVITY>
222.0794

> <JCHEM_ROTATABLE_BOND_COUNT>
38

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.97e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PA(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-SEP-17         0                                  
HETATM    1  C   UNK     0      -0.316   0.673   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.641   1.436   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.967   0.673   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0       0.451  -0.652   0.000  0.00  0.00           H+0
HETATM    5  O   UNK     0      -1.082  -0.652   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.010   1.439   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.336   0.673   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       5.618   0.641   0.000  0.00  0.00           O+0
HETATM    9  P   UNK     0       4.222   1.210   0.000  0.00  0.00           P+0
HETATM   10  O   UNK     0       3.547   0.039   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.222   2.605   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.293   1.436   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.293   2.876   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -5.626   0.665   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.959   1.436   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.292   0.665   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.625   1.436   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -10.958   0.665   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -12.291   1.436   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -13.624   0.665   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -14.957   1.436   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -16.290   0.665   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -17.623   1.436   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -18.956   0.665   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -20.289   1.436   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -21.622   0.665   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -22.955   1.436   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -24.288   0.665   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -25.621   1.436   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -26.954   0.665   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.471  -1.436   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.471  -2.876   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -3.804  -0.665   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.137  -1.436   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -6.470  -0.665   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -8.010  -0.665   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -9.343  -1.436   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -10.676  -0.665   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0     -12.216  -0.665   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -13.549  -1.436   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -14.882  -0.665   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0     -16.422  -0.665   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -17.755  -1.436   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -19.088  -0.665   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -20.628  -0.665   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -21.961  -1.436   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -23.294  -0.665   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -24.834  -0.665   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -26.167  -1.436   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -27.500  -0.665   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0     -29.040  -0.665   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0     -30.373  -1.436   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0     -31.706  -0.665   0.000  0.00  0.00           C+0
CONECT    1    2    5    4    6                                             
CONECT    2    1    3                                                       
CONECT    3    2   12                                                       
CONECT    4    1                                                            
CONECT    5    1   31                                                       
CONECT    6    1    7                                                       
CONECT    7    6    9                                                       
CONECT    8    9                                                            
CONECT    9    8   10   11    7                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    3   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   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                                                            
CONECT   31    5   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   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                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  104    0
END

View in JSmol

Synonyms

Value	Source
(2R)-1-(Phosphonooxy)-3-(stearoyloxy)propan-2-yl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate	ChEBI
1-Octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-sn-glycero-3-phosphate	ChEBI
1-Octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphate	ChEBI
PA(18:0/22:6)	ChEBI
(2R)-1-(Phosphonooxy)-3-(stearoyloxy)propan-2-yl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid	Generator
1-Octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-sn-glycero-3-phosphoric acid	Generator
1-Octadecanoyl-2-(4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoyl)-sn-glycero-3-phosphoric acid	Generator
1-stearoyl-2-docosahexaenoyl-sn-glycero-3-phosphate	SMPDB, HMDB
1-stearoyl-2-docosahexaenoyl-sn-phosphatidic acid	SMPDB, HMDB
PA(18:0/22:6)	SMPDB, ChEBI
PA(18:0/22:6n3)	SMPDB, HMDB
PA(18:0/22:6w3)	SMPDB, HMDB
PA(40:6)	SMPDB, HMDB
Phosphatidic acid(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))	SMPDB, HMDB
Phosphatidic acid(18:0/22:6)	SMPDB, HMDB
Phosphatidic acid(18:0/22:6n3)	SMPDB, HMDB
Phosphatidic acid(18:0/22:6w3)	SMPDB, HMDB
Phosphatidic acid(40:6)	SMPDB, HMDB
Phosphatidate(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))	SMPDB, HMDB
Phosphatidate(18:0/22:6)	SMPDB, HMDB
Phosphatidate(18:0/22:6n3)	SMPDB, HMDB
Phosphatidate(18:0/22:6w3)	SMPDB, HMDB
Phosphatidate(40:6)	SMPDB, HMDB
PA(18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))	SMPDB

Chemical Formula

C₄₃H₇₃O₈P

Average Mass

749.0230 Da

Monoisotopic Mass

748.50431 Da

IUPAC Name

[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecanoyloxy)propoxy]phosphonic acid

Traditional Name

(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C43H73O8P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-43(45)51-41(40-50-52(46,47)48)39-49-42(44)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,21-22,26,28,32,34,41H,3-4,6,8-10,12,14-16,18,20,23-25,27,29-31,33,35-40H2,1-2H3,(H2,46,47,48)/b7-5-,13-11-,19-17-,22-21-,28-26-,34-32-/t41-/m1/s1

InChI Key

SFHGEOGVGJYLEK-USQBYQOHSA-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 1,2-diacylglycerol-3-phosphates. These are glycerol-3-phosphates in which the glycerol moiety is bonded to two aliphatic chains through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

1,2-diacylglycerol-3-phosphates

Alternative Parents

Substituents

1,2-diacylglycerol-3-phosphate
Fatty acid ester
Monoalkyl phosphate
Dicarboxylic acid or derivatives
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Carboxylic acid ester
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1,2-diacyl-sn-glycerol 3-phosphate (CHEBI:77258 )
Diacylglycerophosphates (LMGP10010039 )

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	9.15	ALOGPS
logP	13.26	ChemAxon
logS	-7	ALOGPS
pKa (Strongest Acidic)	1.32	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	38	ChemAxon
Refractivity	222.08 m³·mol⁻¹	ChemAxon
Polarizability	88.77 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

HMDB0114893

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24779562

PDB ID

Not Available

ChEBI ID

77258

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid (NP0285432)

MOL for NP0285432 ((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid)

3D MOL for NP0285432 ((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid)

3D SDF for NP0285432 ((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid)

3D-SDF for NP0285432 ((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid)

PDB for NP0285432 ((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid)

3D PDB for NP0285432 ((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid)

SMILES for NP0285432 ((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid)

INCHI for NP0285432 ((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid)

Structure for NP0285432 ((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid)

3D Structure for NP0285432 ((2r)-2-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid)