NP-MRD: Showing NP-Card for adenosine-5'-pentaphosphate (NP0223486)

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Record Information

Version

2.0

Created at

2022-09-06 01:35:53 UTC

Updated at

2022-09-06 01:35:53 UTC

NP-MRD ID

NP0223486

Secondary Accession Numbers

None

Natural Product Identification

Common Name

adenosine-5'-pentaphosphate

Description

Adenosine 5'-pentaphosphate, also known as pppppa, belongs to the class of organic compounds known as purine ribonucleoside polyphosphates. These are purine ribobucleotides with polyphosphate (with 4 or more phosphate) group linked to the ribose moiety. Adenosine 5'-pentaphosphate is a strong basic compound (based on its pKa). Adenosine 5'-pentaphosphate exists in all living organisms, ranging from bacteria to humans. adenosine-5'-pentaphosphate is found in Kitasatospora aureofaciens. A nucleoside pentaphosphate that is adenosine in which a hexahydrogen pentaphosphate is attached at the 5' position.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231216252D          

 39 41  0  0  1  0            999 V2000
   -8.0591    2.3987    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3054    2.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6380    2.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5518    3.3686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7448    3.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3323    2.8256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5118    2.7394    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9598    3.3525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2061    3.0169    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4916    3.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7772    3.0169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0627    3.4294    0.0000 P   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6502    2.7150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4752    4.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3482    3.8419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3663    3.4294    0.0000 P   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0462    2.7150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7788    4.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0807    3.0169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7952    3.4294    0.0000 P   0  0  1  0  0  0  0  0  0  0  0  0
    2.2077    2.7150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3827    4.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5097    3.8419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2241    3.4294    0.0000 P   0  0  1  0  0  0  0  0  0  0  0  0
    2.8116    2.7150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6366    4.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9386    3.0169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6531    3.4294    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.3676    3.8419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0656    2.7150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2406    4.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2923    2.1964    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6792    1.6444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0993    2.0249    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4349    1.2712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8843    2.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7981    1.3920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4655    0.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2192    1.2427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  6  0  0  0
 12 14  2  0  0  0  0
 12 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  1  0  0  0
 16 18  2  0  0  0  0
 16 19  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  6  0  0  0
 20 22  2  0  0  0  0
 20 23  1  0  0  0  0
 24 23  1  1  0  0  0
 24 25  1  6  0  0  0
 24 26  2  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  2  0  0  0  0
  9 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
  7 34  1  0  0  0  0
 34 35  1  1  0  0  0
  6 36  1  0  0  0  0
  3 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
  2 39  1  0  0  0  0
M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
   -7.6809    1.9149    2.3671 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7448    1.7173    1.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2672    2.7257    0.5688 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3728    2.5226   -0.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9273    1.2771   -0.6593 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3814    0.2567    0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2967    0.4299    1.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5295   -0.7745    1.6220 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7796   -1.6641    0.9516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0622   -1.0468   -0.0051 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1535   -1.6902   -0.9107 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8830   -1.7799   -0.3851 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9728   -1.6044   -1.4024 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6297   -1.1296   -0.8901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1392   -2.0886   -0.0080 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3649   -1.5764    0.5776 P   0  0  2  0  0  5  0  0  0  0  0  0
    2.3825   -1.6367   -0.5646 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9273   -2.6005    1.7840 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2100    0.0156    1.0843 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4000    1.0127    0.4205 P   0  0  1  0  0  5  0  0  0  0  0  0
    1.8683    1.7655   -0.7970 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8012    2.1766    1.5837 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7619    0.1691   -0.0490 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6779   -0.4056    1.2239 P   0  0  2  0  0  5  0  0  0  0  0  0
    5.0555   -1.8704    1.0264 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7879   -0.2722    2.6432 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1205    0.4493    1.4323 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2842    1.6974    0.3212 P   0  0  2  0  0  5  0  0  0  0  0  0
    5.7552    2.9622    0.9595 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3919    1.4191   -1.0864 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9270    1.9582   -0.0437 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7804    0.4994   -0.0383 P   0  0  0  0  0  5  0  0  0  0  0  0
    8.5521   -0.2054    1.2799 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2949   -0.4521   -1.3438 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4136    0.8131   -0.1925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6282   -0.5646   -2.2878 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1117   -0.5920   -3.5806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0724   -1.0608   -2.2593 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1621   -2.0272   -3.2834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4568    2.5431    3.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5898    1.4301    2.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0206    3.3831   -1.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7526   -2.7424    1.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5142   -2.7432   -1.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8200   -2.5132   -2.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0289   -0.9902   -1.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7980   -0.1509   -0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5706   -3.5263    1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0078    2.5314    2.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8899    0.6642    2.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9676    2.2641   -1.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9951    0.1070   -2.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9491    0.2096    0.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5265    0.4226   -1.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6097    0.2608   -3.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7972   -0.2735   -2.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4861   -1.6168   -4.1353 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
 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
 24 23  1  6
 24 26  1  0
 24 25  2  0
 24 27  1  0
 28 27  1  1
 28 30  1  0
 28 29  2  0
 28 31  1  0
 31 32  1  0
 32 34  1  0
 32 35  1  0
 32 33  2  0
 13 36  1  0
 36 37  1  0
 36 38  1  0
 38 39  1  0
 10  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  6  7  1  0
 38 11  1  0
  1 40  1  0
  1 41  1  0
  9 43  1  0
 11 44  1  6
 13 45  1  6
 14 46  1  0
 14 47  1  0
 18 48  1  0
 22 49  1  0
 26 50  1  0
 30 51  1  0
 34 52  1  0
 35 53  1  0
 36 54  1  1
 37 55  1  0
 38 56  1  6
 39 57  1  0
  4 42  1  0
M  END


  Mrv0541 02231216252D          

 39 41  0  0  1  0            999 V2000
   -8.0591    2.3987    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3054    2.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6380    2.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5518    3.3686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7448    3.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3323    2.8256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5118    2.7394    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9598    3.3525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2061    3.0169    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4916    3.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7772    3.0169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0627    3.4294    0.0000 P   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6502    2.7150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4752    4.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3482    3.8419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3663    3.4294    0.0000 P   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0462    2.7150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7788    4.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0807    3.0169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7952    3.4294    0.0000 P   0  0  1  0  0  0  0  0  0  0  0  0
    2.2077    2.7150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3827    4.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5097    3.8419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2241    3.4294    0.0000 P   0  0  1  0  0  0  0  0  0  0  0  0
    2.8116    2.7150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6366    4.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9386    3.0169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6531    3.4294    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.3676    3.8419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0656    2.7150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2406    4.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2923    2.1964    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6792    1.6444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0993    2.0249    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4349    1.2712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8843    2.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7981    1.3920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4655    0.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2192    1.2427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  6  0  0  0
 12 14  2  0  0  0  0
 12 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  1  0  0  0
 16 18  2  0  0  0  0
 16 19  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  6  0  0  0
 20 22  2  0  0  0  0
 20 23  1  0  0  0  0
 24 23  1  1  0  0  0
 24 25  1  6  0  0  0
 24 26  2  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  2  0  0  0  0
  9 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
  7 34  1  0  0  0  0
 34 35  1  1  0  0  0
  6 36  1  0  0  0  0
  3 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
  2 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0223486

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H18N5O19P5/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(30-10)1-29-36(21,22)32-38(25,26)34-39(27,28)33-37(23,24)31-35(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H,25,26)(H,27,28)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1

> <INCHI_KEY>
WYJWVZZCMBUPSP-KQYNXXCUSA-N

> <FORMULA>
C10H18N5O19P5

> <MOLECULAR_WEIGHT>
667.1408

> <EXACT_MASS>
666.928405979

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
47.61047511582346

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.44

> <JCHEM_LOGP>
-8.19848031989204

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-5

> <JCHEM_PKA>
1.1737481125150913

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.4165114763639113

> <JCHEM_PKA_STRONGEST_BASIC>
4.997281373508824

> <JCHEM_POLAR_SURFACE_AREA>
372.18999999999994

> <JCHEM_REFRACTIVITY>
117.56009999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.58e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
adenosine-5'-pentaphosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0     -15.044   4.478   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0     -13.637   3.851   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -12.391   4.756   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0     -12.230   6.288   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0     -10.724   6.608   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -9.954   5.274   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -8.422   5.114   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -7.392   6.258   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -5.985   5.632   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.651   6.402   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.317   5.632   0.000  0.00  0.00           O+0
HETATM   12  P   UNK     0      -1.984   6.402   0.000  0.00  0.00           P+0
HETATM   13  O   UNK     0      -1.214   5.068   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.754   7.735   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -0.650   7.172   0.000  0.00  0.00           O+0
HETATM   16  P   UNK     0       0.684   6.402   0.000  0.00  0.00           P+0
HETATM   17  O   UNK     0      -0.086   5.068   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.454   7.735   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.017   5.632   0.000  0.00  0.00           O+0
HETATM   20  P   UNK     0       3.351   6.402   0.000  0.00  0.00           P+0
HETATM   21  O   UNK     0       4.121   5.068   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.581   7.735   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.685   7.172   0.000  0.00  0.00           O+0
HETATM   24  P   UNK     0       6.018   6.402   0.000  0.00  0.00           P+0
HETATM   25  O   UNK     0       5.248   5.068   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.788   7.735   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       7.352   5.632   0.000  0.00  0.00           O+0
HETATM   28  P   UNK     0       8.686   6.402   0.000  0.00  0.00           P+0
HETATM   29  O   UNK     0      10.020   7.172   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       9.456   5.068   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       7.916   7.735   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -6.146   4.100   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -5.001   3.070   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -7.652   3.780   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -8.278   2.373   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0     -10.984   4.130   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0     -10.823   2.598   0.000  0.00  0.00           N+0
HETATM   38  C   UNK     0     -12.069   1.693   0.000  0.00  0.00           C+0
HETATM   39  N   UNK     0     -13.476   2.320   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   39                                                  
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   36                                                  
CONECT    7    6    8   34                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   32                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   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   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28                                                            
CONECT   32    9   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    7   35                                                  
CONECT   35   34                                                            
CONECT   36    6    3   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38    2                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

View in JSmol

Synonyms

Value	Source
5'-O-[(S)-Hydroxy{[(R)-hydroxy{[(R)-hydroxy{[(S)-hydroxy(phosphonooxy)phosphoryl]oxy}phosphoryl]oxy}phosphoryl]oxy}phosphoryl]adenosine	ChEBI
5'-O-[Hydroxy({hydroxy[(hydroxy{[hydroxy(phosphonooxy)phosphoryl]oxy}phosphoryl)oxy]phosphoryl}oxy)phosphoryl]adenosine	ChEBI
ADENOSINE-5'-pentaphosphATE	ChEBI
Pppppa	ChEBI
ADENOSINE-5'-pentaphosphoric acid	Generator
Adenosine 5'-pentaphosphoric acid	Generator
Adenosine 5'-(hexahydrogen pentaphosphoric acid)	HMDB
Adenosine 5'-pentaphosphate	ChEBI

Chemical Formula

C₁₀H₁₈N₅O₁₉P₅

Average Mass

667.1408 Da

Monoisotopic Mass

666.92841 Da

IUPAC Name

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

Traditional Name

adenosine-5'-pentaphosphate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H18N5O19P5/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(30-10)1-29-36(21,22)32-38(25,26)34-39(27,28)33-37(23,24)31-35(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H,25,26)(H,27,28)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1

InChI Key

WYJWVZZCMBUPSP-KQYNXXCUSA-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
Kitasatospora aureofaciens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine ribonucleoside polyphosphates. These are purine ribobucleotides with polyphosphate (with 4 or more phosphate) 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 polyphosphates

Alternative Parents

Substituents

Purine ribonucleoside polyphosphate
Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Aminopyrimidine
Monoalkyl phosphate
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Imidolactam
Alkyl phosphate
Pyrimidine
Azole
Tetrahydrofuran
Imidazole
Heteroaromatic compound
Secondary alcohol
1,2-diol
Organoheterocyclic compound
Azacycle
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Amine
Primary amine
Organic oxygen compound
Alcohol
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

adenosine 5'-phosphate (CHEBI:40096 )
nucleoside pentaphosphate (CHEBI:40096 )

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	0.44	ALOGPS
logP	-8.2	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	0.42	ChemAxon
pKa (Strongest Basic)	5	ChemAxon
Physiological Charge	-5	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	372.19 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	117.56 m³·mol⁻¹	ChemAxon
Polarizability	47.61 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