NP-MRD: Showing NP-Card for {[(2r,3r,4s,5s)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid (NP0203316)

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Record Information

Version

2.0

Created at

2022-09-04 22:44:39 UTC

Updated at

2022-09-04 22:44:39 UTC

NP-MRD ID

NP0203316

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{[(2r,3r,4s,5s)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid

Description

{[(2R,3R,4S,5S)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. {[(2r,3r,4s,5s)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid is found in Arabidopsis thaliana. Based on a literature review very few articles have been published on {[(2R,3R,4S,5S)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052200442D          

 38 41  0  0  1  0            999 V2000
    3.2789    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0098   -1.7070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -2.3744    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7798   -3.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5868   -3.3306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -4.1152    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.0571   -4.3701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6264   -3.8603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0967   -4.8998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9037   -5.0714    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.7321   -5.8783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0752   -4.2644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7106   -5.2429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9656   -6.0275    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7725   -6.1990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0275   -6.9837    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8345   -7.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0894   -7.9398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4754   -7.5967    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7304   -8.3814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6685   -7.4252    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1164   -8.0383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4135   -6.6406    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6066   -6.4691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7403   -2.1195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0728   -2.6044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7403   -1.2945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0728   -0.8096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  2  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 24 23  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 24 33  1  0  0  0  0
 33 34  1  1  0  0  0
 13 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 11 37  1  0  0  0  0
 37 38  1  6  0  0  0
M  END

     RDKit          3D

 63 66  0  0  0  0  0  0  0  0999 V2000
   10.1409    0.4273   -0.0624 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9121    0.0020    0.4787 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8536   -0.4545    1.7605 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7012   -0.8645    2.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5524   -0.8488    1.6159 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5402   -0.4050    0.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7198    0.0136   -0.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4423    0.3999   -1.4844 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1252    0.2143   -1.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5553   -0.2804   -0.5752 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1815   -0.6313   -0.3284 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5595    0.3826    0.3369 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7361    1.0664   -0.5065 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3273    1.0190    0.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9752   -0.3278    0.1554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5628   -0.5627    0.7805 P   0  0  1  0  0  5  0  0  0  0  0  0
   -0.9130   -2.0338    0.5647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6131   -0.2602    2.4380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6691    0.3431   -0.0858 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1808    1.2379    2.5189 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.6454    0.6847   -0.6989 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9952    2.0491   -0.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1956    2.4897    0.8312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9675   -0.4114    0.3240 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.3292   -0.5902    0.4722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3008   -1.6757   -0.2350 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7909   -2.8152    0.3541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8138   -1.4792   -0.0275 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1029   -2.3910   -0.7925 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7173    0.4083   -1.8384 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4311    0.1105   -2.2946 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4328   -0.8983   -1.6078 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5554   -1.9471   -1.4623 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9410   -0.2196   -0.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2385    1.3860   -0.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7401   -1.2134    3.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5776    0.4242   -2.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1913   -1.5904    0.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0937    2.1272   -0.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3419    1.4931    1.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6618    1.5801   -0.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2198    0.1161    2.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8854    0.8566    3.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4934   -0.0733   -0.8933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3500    0.4749   -1.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0446    1.9923    0.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9747    2.7503   -1.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5285    2.2156    1.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4393   -0.1655    1.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5341   -0.4938    1.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.6800   -3.5579   -0.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6250   -1.6190    1.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1934    1.0152   -2.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7575   -2.5103   -0.6714 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
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 14 15  1  0
 16 15  1  6
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 16 17  2  0
 16 19  1  0
 20 19  1  6
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 20 21  2  0
 20 23  1  0
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 25 26  1  0
 26 27  1  0
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 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
 13 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 10  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
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 37 11  1  0
 33 24  1  0
  1 39  1  0
  1 40  1  0
  9 42  1  0
 11 43  1  1
 13 44  1  6
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 18 47  1  0
 22 48  1  0
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 33 58  1  1
 34 59  1  0
 35 60  1  6
 36 61  1  0
 37 62  1  6
 38 63  1  0
  4 41  1  0
M  END


  Mrv1652309052200442D          

 38 41  0  0  1  0            999 V2000
    3.2789    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0098   -1.7070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -2.3744    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7798   -3.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5868   -3.3306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -4.1152    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.0571   -4.3701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6264   -3.8603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0967   -4.8998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9037   -5.0714    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.7321   -5.8783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0752   -4.2644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7106   -5.2429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9656   -6.0275    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7725   -6.1990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0275   -6.9837    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8345   -7.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0894   -7.9398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1164   -8.0383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6066   -6.4691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7403   -2.1195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0728   -2.6044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7403   -1.2945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0728   -0.8096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  2  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
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 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
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 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 24 23  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 24 33  1  0  0  0  0
 33 34  1  1  0  0  0
 13 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 11 37  1  0  0  0  0
 37 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0203316

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=C2N=CN([C@H]3O[C@H](COP(O)(=O)OP(O)(=O)O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@H](O)[C@@H]3O)C2=NC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C16H25N5O15P2/c17-13-7-14(19-3-18-13)21(4-20-7)15-11(26)9(24)6(33-15)2-32-37(28,29)36-38(30,31)35-16-12(27)10(25)8(23)5(1-22)34-16/h3-6,8-12,15-16,22-27H,1-2H2,(H,28,29)(H,30,31)(H2,17,18,19)/t5-,6-,8-,9+,10+,11+,12-,15+,16+/m1/s1

> <INCHI_KEY>
WFPZSXYXPSUOPY-UVQQJNGXSA-N

> <FORMULA>
C16H25N5O15P2

> <MOLECULAR_WEIGHT>
589.344

> <EXACT_MASS>
589.082239121

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
48.60473973935633

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3R,4S,5S)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid

> <JCHEM_LOGP>
-6.7725679530330645

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.107282857130621

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7298676687415737

> <JCHEM_PKA_STRONGEST_BASIC>
3.99312463028185

> <JCHEM_POLAR_SURFACE_AREA>
311.75

> <JCHEM_REFRACTIVITY>
117.08580000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3R,4S,5S)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([hydroxy([(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphoryl]oxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  N   UNK     0       6.121   3.850   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       7.454   1.540   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       6.121  -0.770   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       3.322   2.016   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.322  -0.476   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.752  -3.186   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.846  -4.432   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.322  -5.897   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.829  -6.217   0.000  0.00  0.00           O+0
HETATM   16  P   UNK     0       5.305  -7.682   0.000  0.00  0.00           P+0
HETATM   17  O   UNK     0       3.840  -8.158   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.769  -7.206   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.780  -9.146   0.000  0.00  0.00           O+0
HETATM   20  P   UNK     0       7.287  -9.467   0.000  0.00  0.00           P+0
HETATM   21  O   UNK     0       6.967 -10.973   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.607  -7.960   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.793  -9.787   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.269 -11.251   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.775 -11.572   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      11.251 -13.036   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.758 -13.356   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      13.234 -14.821   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      10.221 -14.181   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.697 -15.645   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.714 -13.860   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.684 -15.005   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.239 -12.396   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       6.732 -12.076   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.382  -3.956   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.136  -4.862   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       1.382  -2.416   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       0.136  -1.511   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10   12   37                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   35                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   24                                                       
CONECT   24   23   25   33                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   24   34                                                  
CONECT   34   33                                                            
CONECT   35   13   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   11   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
{[(2R,3R,4S,5S)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl]oxy})phosphinate	Generator

Chemical Formula

C₁₆H₂₅N₅O₁₅P₂

Average Mass

589.3440 Da

Monoisotopic Mass

589.08224 Da

IUPAC Name

{[(2R,3R,4S,5S)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid

Traditional Name

[(2R,3R,4S,5S)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([hydroxy([(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphoryl]oxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

NC1=C2N=CN([C@H]3O[C@H](COP(O)(=O)OP(O)(=O)O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@H](O)[C@@H]3O)C2=NC=N1

InChI Identifier

InChI=1S/C16H25N5O15P2/c17-13-7-14(19-3-18-13)21(4-20-7)15-11(26)9(24)6(33-15)2-32-37(28,29)36-38(30,31)35-16-12(27)10(25)8(23)5(1-22)34-16/h3-6,8-12,15-16,22-27H,1-2H2,(H,28,29)(H,30,31)(H2,17,18,19)/t5-,6-,8-,9+,10+,11+,12-,15+,16+/m1/s1

InChI Key

WFPZSXYXPSUOPY-UVQQJNGXSA-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
Arabidopsis thaliana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine nucleotide sugars

Direct Parent

Purine nucleotide sugars

Alternative Parents

Substituents

Purine nucleotide sugar
Purine ribonucleoside diphosphate
Purine ribonucleoside monophosphate
Pentose-5-phosphate
Pentose phosphate
N-glycosyl compound
Glycosyl compound
Organic pyrophosphate
Monosaccharide phosphate
6-aminopurine
Purine
Imidazopyrimidine
Monoalkyl phosphate
Aminopyrimidine
Imidolactam
Alkyl phosphate
Pyrimidine
Phosphoric acid ester
Oxane
Organic phosphoric acid derivative
N-substituted imidazole
Monosaccharide
Heteroaromatic compound
Tetrahydrofuran
Imidazole
Azole
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	-6.8	ChemAxon
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	3.99	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	311.75 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	117.09 m³·mol⁻¹	ChemAxon
Polarizability	48.6 Å³	ChemAxon
Number of Rings	4	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

Not Available

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

162979523

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {[(2r,3r,4s,5s)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid (NP0203316)

MOL for NP0203316 ({[(2r,3r,4s,5s)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

3D MOL for NP0203316 ({[(2r,3r,4s,5s)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

3D SDF for NP0203316 ({[(2r,3r,4s,5s)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

3D-SDF for NP0203316 ({[(2r,3r,4s,5s)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

PDB for NP0203316 ({[(2r,3r,4s,5s)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

3D PDB for NP0203316 ({[(2r,3r,4s,5s)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

SMILES for NP0203316 ({[(2r,3r,4s,5s)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

INCHI for NP0203316 ({[(2r,3r,4s,5s)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

Structure for NP0203316 ({[(2r,3r,4s,5s)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

3D Structure for NP0203316 ({[(2r,3r,4s,5s)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)