NP-MRD: Showing NP-Card for (2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-n-(2-{[2-(tetracosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)butanimidic acid (NP0283293)

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Record Information

Version

2.0

Created at

2022-09-09 10:29:46 UTC

Updated at

2022-09-09 10:29:46 UTC

NP-MRD ID

NP0283293

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-n-(2-{[2-(tetracosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)butanimidic acid

Description

Lignocericyl coenzyme A, also known as lignoceroyl-CoA or C24:0-CoA, belongs to the class of organic compounds known as very long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a very long aliphatic chain of 22 carbon atoms or more. Thus, lignocericyl coenzyme A is considered to be a fatty ester lipid molecule. (2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-n-(2-{[2-(tetracosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)butanimidic acid is found in Apis cerana. (2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-n-(2-{[2-(tetracosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)butanimidic acid was first documented in 2006 (PMID: 17139608). Lignocericyl coenzyme A is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05091314122D          

 73 75  0  0  0  0            999 V2000
    2.8806   29.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2831   30.4758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6331   30.4758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5950   29.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3095   29.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0240   29.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7385   29.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4529   29.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1674   29.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8819   29.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5963   29.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3108   29.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0253   29.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7398   29.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4542   29.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1687   29.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8832   29.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5976   29.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3121   29.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0266   29.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7410   29.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4555   29.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1700   29.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8845   29.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5989   29.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6002   29.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3147   29.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4568   29.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7423   29.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6015   35.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4581   31.3008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7728   37.1936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1323   37.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3160   35.4258    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.8858   29.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3134   29.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4380   38.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6217   35.7033    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   30.0697   35.0902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.4581   29.6508    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   32.1916   38.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3517   37.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7436   29.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2092   36.4178    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.4581   30.4758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2779   39.3195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1713   29.6508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.0292   29.6508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8591   38.0141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.0192   36.8581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6843   38.4990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5448   37.1715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8858   28.4133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3134   30.4758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4422   35.6171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1726   29.2383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7436   28.4133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0761   34.3443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1801   33.1181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0150   33.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2996   33.0613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4746   34.4903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9976   32.5383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3476   32.5383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6015   34.1883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1726   31.7133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4022   36.2463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.2412   34.2833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1726   33.3633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6281   33.7312    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   27.8871   33.7758    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   27.1726   32.5383    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.0279   29.2383    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
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 11 10  1  0  0  0  0
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 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
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 27 26  1  0  0  0  0
 29 28  1  0  0  0  0
 34 30  1  1  0  0  0
 35 26  1  0  0  0  0
 36 25  1  0  0  0  0
 39 34  1  0  0  0  0
 39 38  1  0  0  0  0
 41 37  2  0  0  0  0
 42 37  1  0  0  0  0
 43 40  1  0  0  0  0
 44 38  1  0  0  0  0
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 45  3  1  0  0  0  0
 45 31  1  0  0  0  0
 45 40  1  0  0  0  0
 46 41  1  0  0  0  0
 47 28  1  4  0  0  0
 47 35  2  0  0  0  0
 48 27  1  4  0  0  0
 48 43  2  0  0  0  0
 49 32  2  0  0  0  0
 49 41  1  0  0  0  0
 50 32  1  0  0  0  0
 50 42  2  0  0  0  0
 51 33  2  0  0  0  0
 51 37  1  0  0  0  0
 52 33  1  0  0  0  0
 52 42  1  0  0  0  0
 44 52  1  1  0  0  0
 53 35  1  0  0  0  0
 54 36  2  0  0  0  0
 38 55  1  6  0  0  0
 40 56  1  1  0  0  0
 57 43  1  0  0  0  0
 65 30  1  0  0  0  0
 66 31  1  0  0  0  0
 67 34  1  0  0  0  0
 67 44  1  0  0  0  0
 39 68  1  6  0  0  0
 70 58  1  0  0  0  0
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 71 61  1  0  0  0  0
 71 62  2  0  0  0  0
 71 65  1  0  0  0  0
 71 69  1  0  0  0  0
 72 63  1  0  0  0  0
 72 64  2  0  0  0  0
 72 66  1  0  0  0  0
 72 69  1  0  0  0  0
 73 29  1  0  0  0  0
 73 36  1  0  0  0  0
M  END

     RDKit          3D

155157  0  0  0  0  0  0  0  0999 V2000
    3.5419    3.7086    4.5714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8410    2.3399    3.9574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0398    1.2826    4.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3174   -0.0702    4.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9549   -0.0701    2.6166 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2201   -1.4492    2.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213   -1.3121    0.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0252   -2.5764   -0.2453 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6480   -2.3515   -1.7020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1864   -1.9493   -1.8064 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8467   -1.6571   -3.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5371   -1.1996   -3.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6963   -2.0627   -3.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9897   -2.7829   -2.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0809   -2.0345   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4276   -3.0198    0.4071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3883   -2.3276    1.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7822   -3.2354    2.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0202   -4.4843    2.9909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5258   -4.3821    3.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0591   -5.8313    3.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3867   -6.0400    3.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2498   -5.4685    2.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6653   -5.7900    2.6893 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9354   -6.4366    3.7113 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9676   -5.2555    1.5863 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.4656   -6.1206    2.0347 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6638   -5.8694    1.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2176   -4.6314    1.1441 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2410   -3.5017    0.7616 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3060   -2.6488    1.2005 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2932   -2.7700   -0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9972   -1.4270    0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4258    0.3461   -1.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8635    2.3948   -1.9758 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7206    4.6867   -2.8879 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1660    2.6953   -1.8308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2598    3.1325   -2.6134 P   0  0  1  0  0  5  0  0  0  0  0  0
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   -2.5790    3.1104   -1.5624 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.8677    5.7858   -3.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.9590    5.8358   -2.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3116    6.0468   -2.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1081    6.8369   -3.1013 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9102    5.4548   -1.1897 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2142    4.6831   -0.3167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8922    4.4981   -0.4926 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2186    5.0551   -1.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5008    3.0287   -1.9771 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.5087    2.1210   -1.9916 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3898    2.6658   -0.9666 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9107    2.4907    0.2900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5864    1.0744    1.0701 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.3426    1.2516    1.9154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8282    0.6889    2.1866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2968   -0.2313    0.0383 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6873    3.7238    5.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 05091314122D          

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 39 34  1  0  0  0  0
 39 38  1  0  0  0  0
 41 37  2  0  0  0  0
 42 37  1  0  0  0  0
 43 40  1  0  0  0  0
 44 38  1  0  0  0  0
 45  2  1  0  0  0  0
 45  3  1  0  0  0  0
 45 31  1  0  0  0  0
 45 40  1  0  0  0  0
 46 41  1  0  0  0  0
 47 28  1  4  0  0  0
 47 35  2  0  0  0  0
 48 27  1  4  0  0  0
 48 43  2  0  0  0  0
 49 32  2  0  0  0  0
 49 41  1  0  0  0  0
 50 32  1  0  0  0  0
 50 42  2  0  0  0  0
 51 33  2  0  0  0  0
 51 37  1  0  0  0  0
 52 33  1  0  0  0  0
 52 42  1  0  0  0  0
 44 52  1  1  0  0  0
 53 35  1  0  0  0  0
 54 36  2  0  0  0  0
 38 55  1  6  0  0  0
 40 56  1  1  0  0  0
 57 43  1  0  0  0  0
 65 30  1  0  0  0  0
 66 31  1  0  0  0  0
 67 34  1  0  0  0  0
 67 44  1  0  0  0  0
 39 68  1  6  0  0  0
 70 58  1  0  0  0  0
 70 59  1  0  0  0  0
 70 60  2  0  0  0  0
 70 68  1  0  0  0  0
 71 61  1  0  0  0  0
 71 62  2  0  0  0  0
 71 65  1  0  0  0  0
 71 69  1  0  0  0  0
 72 63  1  0  0  0  0
 72 64  2  0  0  0  0
 72 66  1  0  0  0  0
 72 69  1  0  0  0  0
 73 29  1  0  0  0  0
 73 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0283293

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCCCCCCCCC(=O)SCCN=C(O)CCN=C(O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12

> <INCHI_IDENTIFIER>
InChI=1S/C45H82N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-36(54)73-29-28-47-35(53)26-27-48-43(57)40(56)45(2,3)31-66-72(63,64)69-71(61,62)65-30-34-39(68-70(58,59)60)38(55)44(67-34)52-33-51-37-41(46)49-32-50-42(37)52/h32-34,38-40,44,55-56H,4-31H2,1-3H3,(H,47,53)(H,48,57)(H,61,62)(H,63,64)(H2,46,49,50)(H2,58,59,60)/t34-,38-,39-,40+,44-/m1/s1

> <INCHI_KEY>
MOYMQYZWIUKGGY-JBKAVQFISA-N

> <FORMULA>
C45H82N7O17P3S

> <MOLECULAR_WEIGHT>
1118.156

> <EXACT_MASS>
1117.470074459

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
119.55780071041336

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-(2-{[2-(tetracosanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidic acid

> <ALOGPS_LOGP>
4.63

> <JCHEM_LOGP>
3.4644299751811256

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
1.9025255967499666

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8206482635950914

> <JCHEM_PKA_STRONGEST_BASIC>
4.936698900482182

> <JCHEM_POLAR_SURFACE_AREA>
370.61000000000007

> <JCHEM_REFRACTIVITY>
274.4993000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
42

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-N-(2-{[2-(tetracosanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-MAY-13         0                                  
HETATM    1  C   UNK     0       5.377  54.578   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      50.928  56.888   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      47.848  56.888   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.711  55.348   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.044  54.578   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.378  55.348   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.712  54.578   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.045  55.348   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.379  54.578   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.713  55.348   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.046  54.578   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.380  55.348   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.714  54.578   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.048  55.348   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.381  54.578   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.715  55.348   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.049  54.578   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      25.382  55.348   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.716  54.578   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.050  55.348   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      29.383  54.578   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      30.717  55.348   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      32.051  54.578   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      33.384  55.348   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      34.718  54.578   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      44.054  55.348   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      45.387  54.578   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      40.053  54.578   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      38.719  55.348   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      53.389  65.358   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      49.388  58.428   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      61.176  69.428   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      56.247  70.720   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      54.723  66.128   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      42.720  54.578   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      36.052  55.348   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      58.684  71.239   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      57.161  66.646   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      56.130  65.502   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      49.388  55.348   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      60.091  71.865   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      58.523  69.707   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      48.055  54.578   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      56.391  67.980   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      49.388  56.888   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0      60.252  73.396   0.000  0.00  0.00           N+0
HETATM   47  N   UNK     0      41.386  55.348   0.000  0.00  0.00           N+0
HETATM   48  N   UNK     0      46.721  55.348   0.000  0.00  0.00           N+0
HETATM   49  N   UNK     0      61.337  70.960   0.000  0.00  0.00           N+0
HETATM   50  N   UNK     0      59.769  68.802   0.000  0.00  0.00           N+0
HETATM   51  N   UNK     0      57.277  71.865   0.000  0.00  0.00           N+0
HETATM   52  N   UNK     0      57.017  69.387   0.000  0.00  0.00           N+0
HETATM   53  O   UNK     0      42.720  53.038   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      36.052  56.888   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      58.692  66.485   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      50.722  54.578   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      48.055  53.038   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      54.275  64.109   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      56.336  61.820   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      54.161  61.935   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      52.826  61.714   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      51.286  64.382   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      52.262  60.738   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      49.182  60.738   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      53.389  63.818   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0      50.722  59.198   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0      54.884  67.660   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0      56.450  63.995   0.000  0.00  0.00           O+0
HETATM   69  O   UNK     0      50.722  62.278   0.000  0.00  0.00           O+0
HETATM   70  P   UNK     0      55.306  62.965   0.000  0.00  0.00           P+0
HETATM   71  P   UNK     0      52.056  63.048   0.000  0.00  0.00           P+0
HETATM   72  P   UNK     0      50.722  60.738   0.000  0.00  0.00           P+0
HETATM   73  S   UNK     0      37.385  54.578   0.000  0.00  0.00           S+0
CONECT    1    4                                                            
CONECT    2   45                                                            
CONECT    3   45                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   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   36                                                       
CONECT   26   27   35                                                       
CONECT   27   26   48                                                       
CONECT   28   29   47                                                       
CONECT   29   28   73                                                       
CONECT   30   34   65                                                       
CONECT   31   45   66                                                       
CONECT   32   49   50                                                       
CONECT   33   51   52                                                       
CONECT   34   30   39   67                                                  
CONECT   35   26   47   53                                                  
CONECT   36   25   54   73                                                  
CONECT   37   41   42   51                                                  
CONECT   38   39   44   55                                                  
CONECT   39   34   38   68                                                  
CONECT   40   43   45   56                                                  
CONECT   41   37   46   49                                                  
CONECT   42   37   50   52                                                  
CONECT   43   40   48   57                                                  
CONECT   44   38   52   67                                                  
CONECT   45    2    3   31   40                                             
CONECT   46   41                                                            
CONECT   47   28   35                                                       
CONECT   48   27   43                                                       
CONECT   49   32   41                                                       
CONECT   50   32   42                                                       
CONECT   51   33   37                                                       
CONECT   52   33   42   44                                                  
CONECT   53   35                                                            
CONECT   54   36                                                            
CONECT   55   38                                                            
CONECT   56   40                                                            
CONECT   57   43                                                            
CONECT   58   70                                                            
CONECT   59   70                                                            
CONECT   60   70                                                            
CONECT   61   71                                                            
CONECT   62   71                                                            
CONECT   63   72                                                            
CONECT   64   72                                                            
CONECT   65   30   71                                                       
CONECT   66   31   72                                                       
CONECT   67   34   44                                                       
CONECT   68   39   70                                                       
CONECT   69   71   72                                                       
CONECT   70   58   59   60   68                                             
CONECT   71   61   62   65   69                                             
CONECT   72   63   64   66   69                                             
CONECT   73   29   36                                                       
MASTER        0    0    0    0    0    0    0    0   73    0  150    0
END

View in JSmol

Synonyms

Value	Source
C24:0-CoA	ChEBI
C24:0-coenzyme A	ChEBI
Lignoceroyl-CoA	ChEBI
Lignoceroyl-coenzyme A	ChEBI
Tetracosanoyl-coenzyme A	ChEBI

Chemical Formula

C₄₅H₈₂N₇O₁₇P₃S

Average Mass

1118.1560 Da

Monoisotopic Mass

1117.47007 Da

IUPAC Name

(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-(2-{[2-(tetracosanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidic acid

Traditional Name

(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-N-(2-{[2-(tetracosanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)butanimidic acid

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCCCCCCCC(=O)SCCN=C(O)CCN=C(O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12

InChI Identifier

InChI=1S/C45H82N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-36(54)73-29-28-47-35(53)26-27-48-43(57)40(56)45(2,3)31-66-72(63,64)69-71(61,62)65-30-34-39(68-70(58,59)60)38(55)44(67-34)52-33-51-37-41(46)49-32-50-42(37)52/h32-34,38-40,44,55-56H,4-31H2,1-3H3,(H,47,53)(H,48,57)(H,61,62)(H,63,64)(H2,46,49,50)(H2,58,59,60)/t34-,38-,39-,40+,44-/m1/s1

InChI Key

MOYMQYZWIUKGGY-JBKAVQFISA-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
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as very long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a very long aliphatic chain of 22 carbon atoms or more.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Very long-chain fatty acyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Ribonucleoside 3'-phosphate
Pentose phosphate
Pentose-5-phosphate
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Imidolactam
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Monosaccharide
Pyrimidine
Alkyl phosphate
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Azole
Heteroaromatic compound
Carbothioic s-ester
Secondary alcohol
Thiocarboxylic acid ester
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Sulfenyl compound
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Organosulfur compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Primary amine
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

very long-chain fatty acyl-CoA (CHEBI:52974 )

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	4.63	ALOGPS
logP	3.46	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.94	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	370.61 Å²	ChemAxon
Rotatable Bond Count	42	ChemAxon
Refractivity	274.5 m³·mol⁻¹	ChemAxon
Polarizability	119.56 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0060239

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

C16529

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3082227

PDB ID

Not Available

ChEBI ID

52974

Good Scents ID

Not Available

References

General References

Alconada TM, Juarez MP: Acyl-CoA oxidase activity from Beauveria bassiana, an entomopathogenic fungus. J Basic Microbiol. 2006;46(6):435-43. doi: 10.1002/jobm.200610136. [PubMed:17139608 ]
LOTUS database [Link]

Showing NP-Card for (2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-n-(2-{[2-(tetracosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)butanimidic acid (NP0283293)

MOL for NP0283293 ((2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-n-(2-{[2-(tetracosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)butanimidic acid)

3D MOL for NP0283293 ((2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-n-(2-{[2-(tetracosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)butanimidic acid)

3D SDF for NP0283293 ((2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-n-(2-{[2-(tetracosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)butanimidic acid)

3D-SDF for NP0283293 ((2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-n-(2-{[2-(tetracosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)butanimidic acid)

PDB for NP0283293 ((2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-n-(2-{[2-(tetracosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)butanimidic acid)

3D PDB for NP0283293 ((2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-n-(2-{[2-(tetracosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)butanimidic acid)

SMILES for NP0283293 ((2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-n-(2-{[2-(tetracosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)butanimidic acid)

INCHI for NP0283293 ((2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-n-(2-{[2-(tetracosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)butanimidic acid)

Structure for NP0283293 ((2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-n-(2-{[2-(tetracosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)butanimidic acid)

3D Structure for NP0283293 ((2r)-4-[({[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-3,3-dimethyl-n-(2-{[2-(tetracosanoylsulfanyl)ethyl]-c-hydroxycarbonimidoyl}ethyl)butanimidic acid)