NP-MRD: Showing NP-Card for [hydroxy([hydroxy([(2r,3s,4r,5r)-4-hydroxy-3-{[hydroxy(phosphonooxy)phosphoryl]oxy}-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphoryl]oxyphosphonic acid (NP0290985)

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Record Information

Version

2.0

Created at

2022-09-09 21:54:26 UTC

Updated at

2022-09-09 21:54:26 UTC

NP-MRD ID

NP0290985

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[hydroxy([hydroxy([(2r,3s,4r,5r)-4-hydroxy-3-{[hydroxy(phosphonooxy)phosphoryl]oxy}-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphoryl]oxyphosphonic acid

Description

Guanosine 3'-diphosphate 5'-triphosphate, also known as guanosine 5'-triphosphate,3'-diphosphate or guanosine pentaphosphate, belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety. Guanosine 3'-diphosphate 5'-triphosphate is an extremely strong acidic compound (based on its pKa). Guanosine 3'-diphosphate 5'-triphosphate exists in all living organisms, ranging from bacteria to humans. [hydroxy([hydroxy([(2r,3s,4r,5r)-4-hydroxy-3-{[hydroxy(phosphonooxy)phosphoryl]oxy}-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphoryl]oxyphosphonic acid is found in Streptomyces griseus. These are purine ribobucleotides with triphosphate group linked to the ribose moiety.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 08131209302D          

 44 46  0  0  0  0            999 V2000
   -1.8505   -3.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831   -3.2299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0865   -2.8174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3984   -3.4849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9115   -2.8174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0773   -5.7579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0377   -6.2876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5476   -4.7183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7813   -4.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5988   -3.4955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6289   -4.8304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7565   -3.1968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7867   -4.5317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4704   -4.6126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8350   -3.6341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3572   -3.2599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0283   -4.7673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6042   -3.3793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831   -2.4049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -4.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4919   -5.2480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4464   -3.6780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9391   -4.3492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2927   -5.5029    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1138   -4.1630    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2716   -3.8642    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.6635   -4.4410    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6927   -4.0136    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7831   -3.9515    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4610   -3.5525    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7471   -4.2326    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4164   -2.0209    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  1  0  0  0
  6  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 11 10  2  0  0  0  0
 12  2  2  0  0  0  0
 12  4  1  0  0  0  0
 13  7  1  0  0  0  0
 13 10  1  0  0  0  0
 14  8  2  0  0  0  0
 14 10  1  0  0  0  0
 15  2  1  0  0  0  0
 15  7  1  0  0  0  0
  9 15  1  1  0  0  0
  5 16  1  6  0  0  0
 17  8  1  0  0  0  0
 30  1  1  0  0  0  0
 31  3  1  0  0  0  0
 31  9  1  0  0  0  0
  6 32  1  6  0  0  0
 36 18  1  0  0  0  0
 36 19  1  0  0  0  0
 36 20  2  0  0  0  0
 36 33  1  0  0  0  0
 37 21  1  0  0  0  0
 37 22  1  0  0  0  0
 37 23  2  0  0  0  0
 37 34  1  0  0  0  0
 38 24  1  0  0  0  0
 38 25  2  0  0  0  0
 38 30  1  0  0  0  0
 38 35  1  0  0  0  0
 39 26  1  0  0  0  0
 39 27  2  0  0  0  0
 39 32  1  0  0  0  0
 39 33  1  0  0  0  0
 40 28  1  0  0  0  0
 40 29  2  0  0  0  0
 40 34  1  0  0  0  0
 40 35  1  0  0  0  0
  3 41  1  6  0  0  0
  5 42  1  1  0  0  0
  6 43  1  1  0  0  0
  9 44  1  6  0  0  0
M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
   -2.4257   -5.9272    0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2419   -4.9014    0.5691 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9694   -4.1905   -0.2274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9398   -4.7461   -0.9882 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7004   -4.0201   -1.8174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6961   -4.5357   -2.6090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4493   -2.6570   -1.8652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0274   -1.6933   -2.5780 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4153   -0.5564   -2.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4426   -0.7592   -1.3410 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6181    0.2415   -0.8005 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2728   -0.0462   -0.7310 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7040    0.9178    0.0607 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2909    0.3735    1.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3497   -0.2809    0.4299 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4264   -0.8659    1.5937 P   0  0  2  0  0  5  0  0  0  0  0  0
    1.7213   -1.5512    2.7309 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3175    0.4232    2.2555 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499   -1.9767    0.8357 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7913   -1.1590    0.2117 P   0  0  1  0  0  5  0  0  0  0  0  0
    4.3798    0.1111   -0.5179 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7561   -0.6658    1.5230 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7293   -2.1601   -0.7568 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3404   -1.6520   -0.6658 P   0  0  0  0  0  5  0  0  0  0  0  0
    7.3566   -0.1620   -0.8746 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9018   -1.9990    0.9009 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3041   -2.4622   -1.7948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8185    1.5896    0.8432 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1059    2.7588    0.1627 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9923    4.1396    1.0874 P   0  0  1  0  0  5  0  0  0  0  0  0
   -3.3683    4.6198    1.5581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9883    3.8334    2.4170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3143    5.4413    0.2456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0395    4.9767   -0.7309 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.5884    4.2545   -1.9336 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7155    6.4000   -1.2934 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0807    4.0010    0.0711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9042    0.5429    0.6767 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1634    1.0196    0.8786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4597   -2.0777   -1.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7388   -2.8479   -0.2894 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5266   -4.0152   -2.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6952    0.4100   -2.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7282    1.2064   -1.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1539    1.6333   -0.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7349    1.2084    1.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1848   -0.3096    1.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7499    0.8320    2.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8394   -1.4579    2.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7179   -2.9643    1.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0795   -2.1108   -2.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5559    1.7533    1.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0602    3.9981    2.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5597    6.1984   -1.7589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7277    3.6896   -0.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6248   -0.3129    1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4116    0.9093    1.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9949   -2.4188    0.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 14 15  1  0
 16 15  1  6
 16 18  1  0
 16 17  2  0
 16 19  1  0
 20 19  1  1
 20 22  1  0
 20 21  2  0
 20 23  1  0
 23 24  1  0
 24 26  1  0
 24 27  1  0
 24 25  2  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7 40  2  0
 40 41  1  0
 41  3  1  0
  3  2  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
 11 38  1  0
 38 39  1  0
 38 28  1  0
 28 29  1  0
 30 29  1  6
 30 32  1  0
 30 31  2  0
 30 33  1  0
 33 34  1  0
 34 36  1  0
 34 37  1  0
 34 35  2  0
 28 13  1  0
 40 10  1  0
  5  7  1  0
 13 45  1  6
 14 46  1  0
 14 47  1  0
 18 48  1  0
 22 49  1  0
 26 50  1  0
 27 51  1  0
 11 44  1  6
  9 43  1  0
 41 58  1  0
  2  1  1  0
  6 42  1  0
 38 56  1  1
 39 57  1  0
 28 52  1  1
 32 53  1  0
 36 54  1  0
 37 55  1  0
M  END


  Mrv0541 08131209302D          

 44 46  0  0  0  0            999 V2000
   -1.8505   -3.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831   -3.2299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0865   -2.8174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3984   -3.4849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9115   -2.8174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1831   -2.4049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -4.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.4464   -3.6780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9391   -4.3492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2927   -5.5029    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1138   -4.1630    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2716   -3.8642    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.6635   -4.4410    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6927   -4.0136    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7831   -3.9515    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4610   -3.5525    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7471   -4.2326    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4164   -2.0209    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  1  0  0  0
  6  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 11 10  2  0  0  0  0
 12  2  2  0  0  0  0
 12  4  1  0  0  0  0
 13  7  1  0  0  0  0
 13 10  1  0  0  0  0
 14  8  2  0  0  0  0
 14 10  1  0  0  0  0
 15  2  1  0  0  0  0
 15  7  1  0  0  0  0
  9 15  1  1  0  0  0
  5 16  1  6  0  0  0
 17  8  1  0  0  0  0
 30  1  1  0  0  0  0
 31  3  1  0  0  0  0
 31  9  1  0  0  0  0
  6 32  1  6  0  0  0
 36 18  1  0  0  0  0
 36 19  1  0  0  0  0
 36 20  2  0  0  0  0
 36 33  1  0  0  0  0
 37 21  1  0  0  0  0
 37 22  1  0  0  0  0
 37 23  2  0  0  0  0
 37 34  1  0  0  0  0
 38 24  1  0  0  0  0
 38 25  2  0  0  0  0
 38 30  1  0  0  0  0
 38 35  1  0  0  0  0
 39 26  1  0  0  0  0
 39 27  2  0  0  0  0
 39 32  1  0  0  0  0
 39 33  1  0  0  0  0
 40 28  1  0  0  0  0
 40 29  2  0  0  0  0
 40 34  1  0  0  0  0
 40 35  1  0  0  0  0
  3 41  1  6  0  0  0
  5 42  1  1  0  0  0
  6 43  1  1  0  0  0
  9 44  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0290985

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3O)[C@]([H])(O)[C@]1([H])OP(O)(=O)OP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H18N5O20P5/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6(32-39(26,27)33-36(18,19)20)3(31-9)1-30-38(24,25)35-40(28,29)34-37(21,22)23/h2-3,5-6,9,16H,1H2,(H,24,25)(H,26,27)(H,28,29)(H2,18,19,20)(H2,21,22,23)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1

> <INCHI_KEY>
KCPMACXZAITQAX-UUOKFMHZSA-N

> <FORMULA>
C10H18N5O20P5

> <MOLECULAR_WEIGHT>
683.1402

> <EXACT_MASS>
682.923320601

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
49.14601871156242

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[hydroxy({[(2R,3S,4R,5R)-4-hydroxy-2-({[hydroxy({[hydroxy(phosphonooxy)phosphoryl]oxy})phosphoryl]oxy}methyl)-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-3-yl]oxy})phosphoryl]oxy}phosphonic acid

> <ALOGPS_LOGP>
0.16

> <JCHEM_LOGP>
-3.522397434666666

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-6

> <JCHEM_PKA>
1.720987897556638

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8389009730210342

> <JCHEM_POLAR_SURFACE_AREA>
388.8600000000001

> <JCHEM_REFRACTIVITY>
129.56669999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.68e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{hydroxy[(2R,3S,4R,5R)-4-hydroxy-5-(6-hydroxy-2-imino-3H-purin-9-yl)-2-[({hydroxy[hydroxy(phosphonooxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphoryl}oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-AUG-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-AUG-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   36  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   37  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   38  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   39  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   40  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   41  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    3   30                                                       
CONECT    2   12   15                                                       
CONECT    3    1    6   31   41                                             
CONECT    4    7    8   12                                                  
CONECT    5    6    9   16   42                                             
CONECT    6    3    5   32   43                                             
CONECT    7    4   13   15                                                  
CONECT    8    4   14   17                                                  
CONECT    9    5   15   31   44                                             
CONECT   10   11   13   14                                                  
CONECT   11   10                                                            
CONECT   12    2    4                                                       
CONECT   13    7   10                                                       
CONECT   14    8   10                                                       
CONECT   15    2    7    9                                                  
CONECT   16    5                                                            
CONECT   17    8                                                            
CONECT   18   36                                                            
CONECT   19   36                                                            
CONECT   20   36                                                            
CONECT   21   37                                                            
CONECT   22   37                                                            
CONECT   23   37                                                            
CONECT   24   38                                                            
CONECT   25   38                                                            
CONECT   26   39                                                            
CONECT   27   39                                                            
CONECT   28   40                                                            
CONECT   29   40                                                            
CONECT   30    1   38                                                       
CONECT   31    3    9                                                       
CONECT   32    6   39                                                       
CONECT   33   36   39                                                       
CONECT   34   37   40                                                       
CONECT   35   38   40                                                       
CONECT   36   18   19   20   33                                             
CONECT   37   21   22   23   34                                             
CONECT   38   24   25   30   35                                             
CONECT   39   26   27   32   33                                             
CONECT   40   28   29   34   35                                             
CONECT   41    3                                                            
CONECT   42    5                                                            
CONECT   43    6                                                            
CONECT   44    9                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   92    0
END

View in JSmol

Synonyms

Value	Source
Guanosine 5'-triphosphate,3'-diphosphate	ChEBI
Guanosine pentaphosphate	ChEBI
Guanosine 5'-triphosphoric acid,3'-diphosphoric acid	Generator
Guanosine pentaphosphoric acid	Generator
Guanosine 3'-diphosphoric acid 5'-triphosphoric acid	Generator
3'-Diphosphate 5'-triphosphate, guanosine	HMDB
Pentaphosphate, guanosine	HMDB
Guanosine 3' diphosphate 5' triphosphate	HMDB
5'-Triphosphate, guanosine 3'-diphosphate	HMDB

Chemical Formula

C₁₀H₁₈N₅O₂₀P₅

Average Mass

683.1402 Da

Monoisotopic Mass

682.92332 Da

IUPAC Name

{[hydroxy({[(2R,3S,4R,5R)-4-hydroxy-2-({[hydroxy({[hydroxy(phosphonooxy)phosphoryl]oxy})phosphoryl]oxy}methyl)-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-3-yl]oxy})phosphoryl]oxy}phosphonic acid

Traditional Name

{hydroxy[(2R,3S,4R,5R)-4-hydroxy-5-(6-hydroxy-2-imino-3H-purin-9-yl)-2-[({hydroxy[hydroxy(phosphonooxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphoryl}oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H][C@]1(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3O)[C@]([H])(O)[C@]1([H])OP(O)(=O)OP(O)(O)=O

InChI Identifier

InChI=1S/C10H18N5O20P5/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6(32-39(26,27)33-36(18,19)20)3(31-9)1-30-38(24,25)35-40(28,29)34-37(21,22)23/h2-3,5-6,9,16H,1H2,(H,24,25)(H,26,27)(H,28,29)(H2,18,19,20)(H2,21,22,23)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1

InChI Key

KCPMACXZAITQAX-UUOKFMHZSA-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
Streptomyces griseus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

Purine ribonucleoside triphosphates

Alternative Parents

Substituents

Purine ribonucleoside triphosphate
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Ribonucleoside 3'-phosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-oxopurine
Hypoxanthine
Monosaccharide phosphate
Organic pyrophosphate
Imidazopyrimidine
Purine
Aminopyrimidine
Monoalkyl phosphate
Pyrimidone
Alkyl phosphate
Pyrimidine
Phosphoric acid ester
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Tetrahydrofuran
Vinylogous amide
Azole
Imidazole
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Azacycle
Oxacycle
Hydrocarbon derivative
Amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Primary amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

guanosine 5'-phosphate (CHEBI:16690 )
guanosine bisphosphate (CHEBI:16690 )

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	0.16	ALOGPS
logP	-3.5	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	0.84	ChemAxon
Physiological Charge	-6	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	388.86 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	129.57 m³·mol⁻¹	ChemAxon
Polarizability	49.15 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

HMDB0060480

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

34987

KEGG Compound ID

C04494

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

38166

PDB ID

Not Available

ChEBI ID

16690

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [hydroxy([hydroxy([(2r,3s,4r,5r)-4-hydroxy-3-{[hydroxy(phosphonooxy)phosphoryl]oxy}-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphoryl]oxyphosphonic acid (NP0290985)

MOL for NP0290985 ([hydroxy([hydroxy([(2r,3s,4r,5r)-4-hydroxy-3-{[hydroxy(phosphonooxy)phosphoryl]oxy}-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphoryl]oxyphosphonic acid)

3D MOL for NP0290985 ([hydroxy([hydroxy([(2r,3s,4r,5r)-4-hydroxy-3-{[hydroxy(phosphonooxy)phosphoryl]oxy}-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphoryl]oxyphosphonic acid)

3D SDF for NP0290985 ([hydroxy([hydroxy([(2r,3s,4r,5r)-4-hydroxy-3-{[hydroxy(phosphonooxy)phosphoryl]oxy}-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphoryl]oxyphosphonic acid)

3D-SDF for NP0290985 ([hydroxy([hydroxy([(2r,3s,4r,5r)-4-hydroxy-3-{[hydroxy(phosphonooxy)phosphoryl]oxy}-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphoryl]oxyphosphonic acid)

PDB for NP0290985 ([hydroxy([hydroxy([(2r,3s,4r,5r)-4-hydroxy-3-{[hydroxy(phosphonooxy)phosphoryl]oxy}-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphoryl]oxyphosphonic acid)

3D PDB for NP0290985 ([hydroxy([hydroxy([(2r,3s,4r,5r)-4-hydroxy-3-{[hydroxy(phosphonooxy)phosphoryl]oxy}-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphoryl]oxyphosphonic acid)

SMILES for NP0290985 ([hydroxy([hydroxy([(2r,3s,4r,5r)-4-hydroxy-3-{[hydroxy(phosphonooxy)phosphoryl]oxy}-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphoryl]oxyphosphonic acid)

INCHI for NP0290985 ([hydroxy([hydroxy([(2r,3s,4r,5r)-4-hydroxy-3-{[hydroxy(phosphonooxy)phosphoryl]oxy}-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphoryl]oxyphosphonic acid)

Structure for NP0290985 ([hydroxy([hydroxy([(2r,3s,4r,5r)-4-hydroxy-3-{[hydroxy(phosphonooxy)phosphoryl]oxy}-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphoryl]oxyphosphonic acid)

3D Structure for NP0290985 ([hydroxy([hydroxy([(2r,3s,4r,5r)-4-hydroxy-3-{[hydroxy(phosphonooxy)phosphoryl]oxy}-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphoryl]oxyphosphonic acid)