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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 14:57:50 UTC

HMDB ID

HMDB0001192

Secondary Accession Numbers

HMDB01192

Metabolite Identification

Common Name

Diadenosine pentaphosphate

Description

Diadenosine pentaphosphate (AP5A) is a diadenosine polyphosphate. Diadenosine polyphosphates (APnAs, n = 3-6) are a family of endogenous vasoactive purine dinucleotides which have been isolated from thrombocytes. APnAs have been demonstrated to be involved in the control of vascular tone as well as the growth of vascular smooth muscle cells and hence, possibly, in atherogenesis. APnAs isolated substances are Ap3A, Ap4A, Ap5A, and Ap6A. APnAs are naturally occurring substances that facilitate tear secretion; they are released from the corneal epithelium, they stimulate tear production and therefore they may be considered as physiological modulators of tear secretion. The APnAs were discovered in the mid-sixties in the course of studies on aminoacyl-tRNA synthetases (aaRS). APnAs have emerged as intracellular and extracellular signalling molecules implicated in the maintenance and regulation of vital cellular functions and become considered as second messengers. Great variety of physiological and pathological effects in mammalian cells was found to be associated with alterations of APnAs. APnAs are polyphosphated nucleotidic substances which are found in the CNS and are known to be released in a calcium-dependent manner from storage vesicles in brain synaptosomes. AP5A is a specific adenylate kinase inhibitor in the hippocampus, decreasing the rate of decomposition of ADP and the formation of ATP; a pathway that influences the availability of purines in the central nervous system. AP5A in nanomolar concentrations is found to significantly stimulate the proliferation of vascular smooth muscle cells. AP5A is a P2X agonist. The activation of nucleotide ion tropic receptors increases intracellular calcium concentration, resulting in calcium/calmodulin-dependent protein kinase II (CaMKII) activation. AP5A is an avid inhibitor of eosinophil-derived neurotoxin (EDN). EDN is a catalytically proficient member of the pancreatic ribonuclease superfamily secreted along with other eosinophil granule proteins during innate host defense responses and various eosinophil-related inflammatory and allergic diseases. The ribonucleolytic activity of EDN is central to its antiviral and neurotoxic activities and possibly to other facets of its biological activity. AP5A have been identified in human platelets and shown to be important modulator of cardiovascular function. AP5A is stored in synaptic vesicles and released upon nerve terminal depolarization. At the extracellular level, AP5A can stimulate presynaptic dinucleotide receptors. Responses to AP5A have been described in isolated synaptic terminals (synaptosomes) from several brain areas in different animal species, including man. Dinucleotide receptors are ligand-operated ion channels that allow the influx of cations into the terminals. These cations reach a threshold for N- and P/Q-type voltage-dependent calcium channels, which become activated. The activation of the dinucleotide receptor together with the activation of these calcium channels triggers the release of neurotransmitters. The ability of Ap5A to promote glutamate, GABA or acetylcholine release has been described. (PMID: 11212966 , 12738682 , 11810214 , 9607303 , 8922753 , 10094777 , 16401072 , 16819989 , 17721817 , 17361116 , 14502438 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02231218592D          

 57 62  0  0  1  0            999 V2000
    3.4206  -18.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4206  -19.1347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1351  -19.5472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8495  -19.1347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8495  -18.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1351  -17.8972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6342  -19.3897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1191  -18.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6342  -18.0548    0.0000 N   0  0  2  0  0  0  0  0  0  0  0  0
    5.8891  -17.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6738  -17.0152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6738  -16.1902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8891  -15.9353    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4042  -16.6027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5792  -16.6027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6342  -15.1507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3412  -15.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0949  -16.0409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9070  -15.5152    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.5257  -16.0609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3077  -15.7980    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.9264  -16.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4709  -14.9893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0896  -15.5350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7083  -16.0808    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.3271  -16.6265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8716  -15.2721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4903  -15.8179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1090  -16.3636    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.2723  -15.5549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7278  -16.9093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8910  -16.1006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5097  -16.6463    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.6730  -15.8376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1285  -17.1921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2917  -16.3834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9092  -14.6902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6594  -15.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9652  -18.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5838  -18.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5060  -19.3678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2631  -19.6957    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.8088  -19.0770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.3891  -18.3667    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.4429  -20.5009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7169  -17.6097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6301  -19.1548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8972  -21.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3169  -21.8298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1221  -21.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1999  -20.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7945  -22.1281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5446  -21.7848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6225  -20.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9502  -20.4854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7166  -22.9494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1351  -20.3722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9  5  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 14 15  1  6  0  0  0
 13 16  1  6  0  0  0
 12 17  1  1  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  2  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  2  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  2  0  0  0  0
 19 18  1  0  0  0  0
 19 37  1  0  0  0  0
 19 38  2  0  0  0  0
 35 39  1  0  0  0  0
 39 40  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 40  1  0  0  0  0
 42 45  1  6  0  0  0
 44 46  1  1  0  0  0
 43 47  1  1  0  0  0
 45 48  1  0  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 51 45  1  0  0  0  0
 50 52  1  0  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 54 55  2  0  0  0  0
 55 51  1  0  0  0  0
 52 56  1  0  0  0  0
  3 57  1  0  0  0  0
M  END

HMDB0001192
     RDKit          3D
Diadenosine pentaphosphate
 86 91  0  0  0  0  0  0  0  0999 V2000
   12.0157    1.2054    2.6533 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9574    0.4166    2.1485 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9956   -0.0388    2.9671 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9832   -0.7921    2.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9485   -1.0830    1.1791 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8822   -0.6559    0.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9195    0.1144    0.7918 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6938    0.4017   -0.2556 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1813   -0.1571   -1.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0485   -0.8191   -1.0133 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1809   -1.5634   -1.9026 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9830   -1.7844   -1.2514 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2309   -0.6404   -1.5131 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7806   -0.8242   -1.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1348    0.3918   -1.4359 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5040    0.3511   -1.0607 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.0732   -1.0897   -0.9217 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5638    1.1047   -2.2546 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2683    1.1152    0.4261 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6611    1.6237    0.5576 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.3682    2.6409   -0.5211 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4919    2.3461    2.0817 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6057    0.3273    0.3651 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8583   -0.8801    1.4960 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.7046   -2.2443    0.8211 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4363   -0.8207    2.1288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2264   -0.8361    2.7717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6403   -0.0167    2.4216 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.5518    0.8182    1.1846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9864    1.0168    3.7356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9711   -1.0585    2.2651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4884   -1.0895    0.6555 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.1460   -2.4549    0.4460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1939   -0.9422   -0.4231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6425    0.0783    0.3591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4351   -0.2152   -0.7493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4612    0.8934   -0.9547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2414    0.9627    0.1871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2728    0.0585   -0.0581 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.3328    0.2597    0.9103 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3436    1.0451    1.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5307    0.9312    2.6153 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2968    0.0785    1.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5796   -0.3775    2.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3940    0.0282    3.2442 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0878   -1.2572    1.2778 N   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3672   -1.6809    0.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1178   -1.2245    0.0365 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5316   -0.3417    0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7231    0.5294   -1.4471 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.5374   -0.3867   -2.0657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3495    0.6254   -2.1267 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.1019   -0.6348   -2.6691 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3738   -0.5546   -3.0364 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9974    0.6702   -3.5268 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8810   -0.7998   -3.1692 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4813    0.4698   -3.1108 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9716    1.0519    2.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8379    1.9289    3.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1936   -1.1744    3.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6222   -0.0729   -2.3473 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6306   -2.5671   -2.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6673    0.2668   -1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7567   -0.9167   -0.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3266   -1.6709   -1.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0610    1.8908   -2.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4152    1.6216    2.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6761   -1.7154    2.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1016    1.4217    3.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2662   -0.0704   -0.8572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9389   -1.1800   -0.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8024   -0.3560   -1.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9223    1.8450   -1.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9130   -0.9758   -0.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5418    1.6797    2.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4582   -0.6060    4.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9368    0.9153    3.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8032   -2.3835   -0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1748    1.5146   -1.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0238   -1.1741   -2.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3362    1.4234   -2.8839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5183   -0.6143   -3.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7904   -1.4077   -3.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1780    0.5186   -4.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1312   -1.3416   -4.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8250    1.1991   -3.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  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
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 28 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 32 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 43 44  2  0
 44 45  1  0
 44 46  1  0
 46 47  2  0
 47 48  1  0
 48 49  2  0
 39 50  1  0
 50 51  1  0
 50 52  1  0
 52 53  1  0
 13 54  1  0
 54 55  1  0
 54 56  1  0
 56 57  1  0
  7  2  1  0
 56 11  1  0
 10  6  1  0
 52 37  1  0
 49 40  1  0
 49 43  1  0
  1 58  1  0
  1 59  1  0
  4 60  1  0
  9 61  1  0
 11 62  1  0
 13 63  1  1
 14 64  1  0
 14 65  1  0
 18 66  1  0
 22 67  1  0
 26 68  1  0
 30 69  1  0
 34 70  1  0
 36 71  1  0
 36 72  1  0
 37 73  1  0
 39 74  1  6
 41 75  1  0
 45 76  1  0
 45 77  1  0
 47 78  1  0
 50 79  1  1
 51 80  1  0
 52 81  1  6
 53 82  1  0
 54 83  1  6
 55 84  1  0
 56 85  1  6
 57 86  1  0
M  END


  Mrv0541 02231218592D          

 57 62  0  0  1  0            999 V2000
    3.4206  -18.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4206  -19.1347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1351  -19.5472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8495  -19.1347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8495  -18.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1351  -17.8972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6342  -19.3897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1191  -18.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6342  -18.0548    0.0000 N   0  0  2  0  0  0  0  0  0  0  0  0
    5.8891  -17.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6738  -17.0152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6738  -16.1902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8891  -15.9353    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4042  -16.6027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5792  -16.6027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6342  -15.1507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3412  -15.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0949  -16.0409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9070  -15.5152    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.5257  -16.0609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3077  -15.7980    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.9264  -16.3437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4709  -14.9893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0896  -15.5350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7083  -16.0808    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.3271  -16.6265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8716  -15.2721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4903  -15.8179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1090  -16.3636    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.2723  -15.5549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7278  -16.9093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8910  -16.1006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5097  -16.6463    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.6730  -15.8376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1285  -17.1921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2917  -16.3834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9092  -14.6902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6594  -15.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9652  -18.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5838  -18.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5060  -19.3678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2631  -19.6957    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.8088  -19.0770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.3891  -18.3667    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.4429  -20.5009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7169  -17.6097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6301  -19.1548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8972  -21.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3169  -21.8298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1221  -21.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1999  -20.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7945  -22.1281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5446  -21.7848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6225  -20.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9502  -20.4854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7166  -22.9494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1351  -20.3722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9  5  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 14 15  1  6  0  0  0
 13 16  1  6  0  0  0
 12 17  1  1  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  2  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  2  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  2  0  0  0  0
 19 18  1  0  0  0  0
 19 37  1  0  0  0  0
 19 38  2  0  0  0  0
 35 39  1  0  0  0  0
 39 40  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 40  1  0  0  0  0
 42 45  1  6  0  0  0
 44 46  1  1  0  0  0
 43 47  1  1  0  0  0
 45 48  1  0  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 51 45  1  0  0  0  0
 50 52  1  0  0  0  0
 52 53  2  0  0  0  0
 53 54  1  0  0  0  0
 54 55  2  0  0  0  0
 55 51  1  0  0  0  0
 52 56  1  0  0  0  0
  3 57  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001192

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC=NC2=C1N=CN2[C@@H]1OC(COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2OC([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H29N10O22P5/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(47-19)1-45-53(35,36)49-55(39,40)51-57(43,44)52-56(41,42)50-54(37,38)46-2-8-12(32)14(34)20(48-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H2,21,23,25)(H2,22,24,26)/t7-,8?,11-,12-,13-,14-,19?,20-/m1/s1

> <INCHI_KEY>
OIMACDRJUANHTJ-OEOQABFDSA-N

> <FORMULA>
C20H29N10O22P5

> <MOLECULAR_WEIGHT>
916.3669

> <EXACT_MASS>
916.014595222

> <JCHEM_ACCEPTOR_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
70.63550731340399

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.20

> <JCHEM_LOGP>
-11.21874807780513

> <ALOGPS_LOGS>
-2.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-5

> <JCHEM_PKA>
1.1831844719560047

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.41807027191676926

> <JCHEM_PKA_STRONGEST_BASIC>
5.295214619772764

> <JCHEM_POLAR_SURFACE_AREA>
480.49999999999994

> <JCHEM_REFRACTIVITY>
176.97669999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.92e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001192
     RDKit          3D
Diadenosine pentaphosphate
 86 91  0  0  0  0  0  0  0  0999 V2000
   12.0157    1.2054    2.6533 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9574    0.4166    2.1485 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9956   -0.0388    2.9671 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9832   -0.7921    2.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9485   -1.0830    1.1791 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8822   -0.6559    0.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9195    0.1144    0.7918 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6938    0.4017   -0.2556 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1813   -0.1571   -1.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0485   -0.8191   -1.0133 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1809   -1.5634   -1.9026 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9830   -1.7844   -1.2514 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2309   -0.6404   -1.5131 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7806   -0.8242   -1.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1348    0.3918   -1.4359 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5040    0.3511   -1.0607 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.0732   -1.0897   -0.9217 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5638    1.1047   -2.2546 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2683    1.1152    0.4261 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6611    1.6237    0.5576 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.3682    2.6409   -0.5211 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4919    2.3461    2.0817 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6057    0.3273    0.3651 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8583   -0.8801    1.4960 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.7046   -2.2443    0.8211 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4363   -0.8207    2.1288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2264   -0.8361    2.7717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6403   -0.0167    2.4216 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.5518    0.8182    1.1846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9864    1.0168    3.7356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9711   -1.0585    2.2651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4884   -1.0895    0.6555 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.1460   -2.4549    0.4460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1939   -0.9422   -0.4231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6425    0.0783    0.3591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4351   -0.2152   -0.7493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4612    0.8934   -0.9547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2414    0.9627    0.1871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2728    0.0585   -0.0581 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.3328    0.2597    0.9103 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3436    1.0451    1.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5307    0.9312    2.6153 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2968    0.0785    1.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5796   -0.3775    2.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3940    0.0282    3.2442 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0878   -1.2572    1.2778 N   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3672   -1.6809    0.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1178   -1.2245    0.0365 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5316   -0.3417    0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7231    0.5294   -1.4471 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.5374   -0.3867   -2.0657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3495    0.6254   -2.1267 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.1019   -0.6348   -2.6691 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3738   -0.5546   -3.0364 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9974    0.6702   -3.5268 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8810   -0.7998   -3.1692 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4813    0.4698   -3.1108 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9716    1.0519    2.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8379    1.9289    3.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1936   -1.1744    3.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6222   -0.0729   -2.3473 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6306   -2.5671   -2.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6673    0.2668   -1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7567   -0.9167   -0.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3266   -1.6709   -1.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0610    1.8908   -2.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4152    1.6216    2.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6761   -1.7154    2.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1016    1.4217    3.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2662   -0.0704   -0.8572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9389   -1.1800   -0.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8024   -0.3560   -1.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9223    1.8450   -1.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9130   -0.9758   -0.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5418    1.6797    2.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4582   -0.6060    4.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9368    0.9153    3.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8032   -2.3835   -0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1748    1.5146   -1.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0238   -1.1741   -2.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3362    1.4234   -2.8839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5183   -0.6143   -3.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7904   -1.4077   -3.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1780    0.5186   -4.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1312   -1.3416   -4.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8250    1.1991   -3.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  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
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 28 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 32 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 43 44  2  0
 44 45  1  0
 44 46  1  0
 46 47  2  0
 47 48  1  0
 48 49  2  0
 39 50  1  0
 50 51  1  0
 50 52  1  0
 52 53  1  0
 13 54  1  0
 54 55  1  0
 54 56  1  0
 56 57  1  0
  7  2  1  0
 56 11  1  0
 10  6  1  0
 52 37  1  0
 49 40  1  0
 49 43  1  0
  1 58  1  0
  1 59  1  0
  4 60  1  0
  9 61  1  0
 11 62  1  0
 13 63  1  1
 14 64  1  0
 14 65  1  0
 18 66  1  0
 22 67  1  0
 26 68  1  0
 30 69  1  0
 34 70  1  0
 36 71  1  0
 36 72  1  0
 37 73  1  0
 39 74  1  6
 41 75  1  0
 45 76  1  0
 45 77  1  0
 47 78  1  0
 50 79  1  1
 51 80  1  0
 52 81  1  6
 53 82  1  0
 54 83  1  6
 55 84  1  0
 56 85  1  6
 57 86  1  0
M  END

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  C   UNK     0       6.385 -34.178   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       6.385 -35.718   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       7.719 -36.488   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.052 -35.718   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.052 -34.178   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       7.719 -33.408   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      10.517 -36.194   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      11.422 -34.948   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      10.517 -33.702   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      10.993 -32.238   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.458 -31.762   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      12.458 -30.222   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.993 -29.746   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.088 -30.992   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.548 -30.992   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      10.517 -28.281   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      13.704 -29.317   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      15.110 -29.943   0.000  0.00  0.00           O+0
HETATM   19  P   UNK     0      16.626 -28.962   0.000  0.00  0.00           P+0
HETATM   20  O   UNK     0      17.781 -29.980   0.000  0.00  0.00           O+0
HETATM   21  P   UNK     0      19.241 -29.490   0.000  0.00  0.00           P+0
HETATM   22  O   UNK     0      20.396 -30.508   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      19.546 -27.980   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      20.701 -28.999   0.000  0.00  0.00           O+0
HETATM   25  P   UNK     0      21.855 -30.017   0.000  0.00  0.00           P+0
HETATM   26  O   UNK     0      23.011 -31.036   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      22.160 -28.508   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      23.315 -29.527   0.000  0.00  0.00           O+0
HETATM   29  P   UNK     0      24.470 -30.545   0.000  0.00  0.00           P+0
HETATM   30  O   UNK     0      24.775 -29.036   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      25.625 -31.564   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      25.930 -30.054   0.000  0.00  0.00           O+0
HETATM   33  P   UNK     0      27.085 -31.073   0.000  0.00  0.00           P+0
HETATM   34  O   UNK     0      27.390 -29.564   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      28.240 -32.092   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      28.545 -30.582   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      16.631 -27.422   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      18.031 -28.330   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      27.935 -33.601   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      29.090 -34.620   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      28.945 -36.153   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      30.358 -36.765   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      31.376 -35.610   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      30.593 -34.285   0.000  0.00  0.00           C+0
HETATM   45  N   UNK     0      30.693 -38.268   0.000  0.00  0.00           N+0
HETATM   46  O   UNK     0      31.205 -32.871   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      32.910 -35.756   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      29.675 -39.423   0.000  0.00  0.00           C+0
HETATM   49  N   UNK     0      30.458 -40.749   0.000  0.00  0.00           N+0
HETATM   50  C   UNK     0      31.961 -40.413   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      32.106 -38.880   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      33.216 -41.306   0.000  0.00  0.00           C+0
HETATM   53  N   UNK     0      34.617 -40.665   0.000  0.00  0.00           N+0
HETATM   54  C   UNK     0      34.762 -39.132   0.000  0.00  0.00           C+0
HETATM   55  N   UNK     0      33.507 -38.239   0.000  0.00  0.00           N+0
HETATM   56  N   UNK     0      33.071 -42.839   0.000  0.00  0.00           N+0
HETATM   57  N   UNK     0       7.719 -38.028   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   57                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5   10                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   10   15                                                  
CONECT   15   14                                                            
CONECT   16   13                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19                                                       
CONECT   19   20   18   37   38                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21   25                                                       
CONECT   23   21                                                            
CONECT   24   21                                                            
CONECT   25   22   26   27   28                                             
CONECT   26   25   29                                                       
CONECT   27   25                                                            
CONECT   28   25                                                            
CONECT   29   26   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29   33                                                       
CONECT   32   29                                                            
CONECT   33   31   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33   39                                                       
CONECT   36   33                                                            
CONECT   37   19                                                            
CONECT   38   19                                                            
CONECT   39   35   40                                                       
CONECT   40   39   41   44                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   45                                                  
CONECT   43   42   44   47                                                  
CONECT   44   43   40   46                                                  
CONECT   45   42   48   51                                                  
CONECT   46   44                                                            
CONECT   47   43                                                            
CONECT   48   45   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51   52                                                  
CONECT   51   50   45   55                                                  
CONECT   52   50   53   56                                                  
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   51                                                       
CONECT   56   52                                                            
CONECT   57    3                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  124    0
END

COMPND    HMDB0001192
HETATM    1  N1  UNL     1      12.016   1.205   2.653  1.00  0.00           N  
HETATM    2  C1  UNL     1      10.957   0.417   2.148  1.00  0.00           C  
HETATM    3  N2  UNL     1       9.996  -0.039   2.967  1.00  0.00           N  
HETATM    4  C2  UNL     1       8.983  -0.792   2.491  1.00  0.00           C  
HETATM    5  N3  UNL     1       8.948  -1.083   1.179  1.00  0.00           N  
HETATM    6  C3  UNL     1       9.882  -0.656   0.310  1.00  0.00           C  
HETATM    7  C4  UNL     1      10.920   0.114   0.792  1.00  0.00           C  
HETATM    8  N4  UNL     1      11.694   0.402  -0.256  1.00  0.00           N  
HETATM    9  C5  UNL     1      11.181  -0.157  -1.364  1.00  0.00           C  
HETATM   10  N5  UNL     1      10.049  -0.819  -1.013  1.00  0.00           N  
HETATM   11  C6  UNL     1       9.181  -1.563  -1.903  1.00  0.00           C  
HETATM   12  O1  UNL     1       7.983  -1.784  -1.251  1.00  0.00           O  
HETATM   13  C7  UNL     1       7.231  -0.640  -1.513  1.00  0.00           C  
HETATM   14  C8  UNL     1       5.781  -0.824  -1.124  1.00  0.00           C  
HETATM   15  O2  UNL     1       5.135   0.392  -1.436  1.00  0.00           O  
HETATM   16  P1  UNL     1       3.504   0.351  -1.061  1.00  0.00           P  
HETATM   17  O3  UNL     1       3.073  -1.090  -0.922  1.00  0.00           O  
HETATM   18  O4  UNL     1       2.564   1.105  -2.255  1.00  0.00           O  
HETATM   19  O5  UNL     1       3.268   1.115   0.426  1.00  0.00           O  
HETATM   20  P2  UNL     1       1.661   1.624   0.558  1.00  0.00           P  
HETATM   21  O6  UNL     1       1.368   2.641  -0.521  1.00  0.00           O  
HETATM   22  O7  UNL     1       1.492   2.346   2.082  1.00  0.00           O  
HETATM   23  O8  UNL     1       0.606   0.327   0.365  1.00  0.00           O  
HETATM   24  P3  UNL     1       0.858  -0.880   1.496  1.00  0.00           P  
HETATM   25  O9  UNL     1       0.705  -2.244   0.821  1.00  0.00           O  
HETATM   26  O10 UNL     1       2.436  -0.821   2.129  1.00  0.00           O  
HETATM   27  O11 UNL     1      -0.226  -0.836   2.772  1.00  0.00           O  
HETATM   28  P4  UNL     1      -1.640  -0.017   2.422  1.00  0.00           P  
HETATM   29  O12 UNL     1      -1.552   0.818   1.185  1.00  0.00           O  
HETATM   30  O13 UNL     1      -1.986   1.017   3.736  1.00  0.00           O  
HETATM   31  O14 UNL     1      -2.971  -1.058   2.265  1.00  0.00           O  
HETATM   32  P5  UNL     1      -3.488  -1.090   0.656  1.00  0.00           P  
HETATM   33  O15 UNL     1      -4.146  -2.455   0.446  1.00  0.00           O  
HETATM   34  O16 UNL     1      -2.194  -0.942  -0.423  1.00  0.00           O  
HETATM   35  O17 UNL     1      -4.642   0.078   0.359  1.00  0.00           O  
HETATM   36  C9  UNL     1      -5.435  -0.215  -0.749  1.00  0.00           C  
HETATM   37  C10 UNL     1      -6.461   0.893  -0.955  1.00  0.00           C  
HETATM   38  O18 UNL     1      -7.241   0.963   0.187  1.00  0.00           O  
HETATM   39  C11 UNL     1      -8.273   0.058  -0.058  1.00  0.00           C  
HETATM   40  N6  UNL     1      -9.333   0.260   0.910  1.00  0.00           N  
HETATM   41  C12 UNL     1      -9.344   1.045   1.997  1.00  0.00           C  
HETATM   42  N7  UNL     1     -10.531   0.931   2.615  1.00  0.00           N  
HETATM   43  C13 UNL     1     -11.297   0.079   1.944  1.00  0.00           C  
HETATM   44  C14 UNL     1     -12.580  -0.378   2.155  1.00  0.00           C  
HETATM   45  N8  UNL     1     -13.394   0.028   3.244  1.00  0.00           N  
HETATM   46  N9  UNL     1     -13.088  -1.257   1.278  1.00  0.00           N  
HETATM   47  C15 UNL     1     -12.367  -1.681   0.225  1.00  0.00           C  
HETATM   48  N10 UNL     1     -11.118  -1.224   0.036  1.00  0.00           N  
HETATM   49  C16 UNL     1     -10.532  -0.342   0.867  1.00  0.00           C  
HETATM   50  C17 UNL     1      -8.723   0.529  -1.447  1.00  0.00           C  
HETATM   51  O19 UNL     1      -9.537  -0.387  -2.066  1.00  0.00           O  
HETATM   52  C18 UNL     1      -7.349   0.625  -2.127  1.00  0.00           C  
HETATM   53  O20 UNL     1      -7.102  -0.635  -2.669  1.00  0.00           O  
HETATM   54  C19 UNL     1       7.374  -0.555  -3.036  1.00  0.00           C  
HETATM   55  O21 UNL     1       6.997   0.670  -3.527  1.00  0.00           O  
HETATM   56  C20 UNL     1       8.881  -0.800  -3.169  1.00  0.00           C  
HETATM   57  O22 UNL     1       9.481   0.470  -3.111  1.00  0.00           O  
HETATM   58  H1  UNL     1      12.972   1.052   2.303  1.00  0.00           H  
HETATM   59  H2  UNL     1      11.838   1.929   3.365  1.00  0.00           H  
HETATM   60  H3  UNL     1       8.194  -1.174   3.122  1.00  0.00           H  
HETATM   61  H4  UNL     1      11.622  -0.073  -2.347  1.00  0.00           H  
HETATM   62  H5  UNL     1       9.631  -2.567  -2.147  1.00  0.00           H  
HETATM   63  H6  UNL     1       7.667   0.267  -1.066  1.00  0.00           H  
HETATM   64  H7  UNL     1       5.757  -0.917  -0.022  1.00  0.00           H  
HETATM   65  H8  UNL     1       5.327  -1.671  -1.636  1.00  0.00           H  
HETATM   66  H9  UNL     1       3.061   1.891  -2.641  1.00  0.00           H  
HETATM   67  H10 UNL     1       1.415   1.622   2.762  1.00  0.00           H  
HETATM   68  H11 UNL     1       2.676  -1.715   2.420  1.00  0.00           H  
HETATM   69  H12 UNL     1      -1.102   1.422   3.986  1.00  0.00           H  
HETATM   70  H13 UNL     1      -2.266  -0.070  -0.857  1.00  0.00           H  
HETATM   71  H14 UNL     1      -5.939  -1.180  -0.545  1.00  0.00           H  
HETATM   72  H15 UNL     1      -4.802  -0.356  -1.654  1.00  0.00           H  
HETATM   73  H16 UNL     1      -5.922   1.845  -1.158  1.00  0.00           H  
HETATM   74  H17 UNL     1      -7.913  -0.976  -0.083  1.00  0.00           H  
HETATM   75  H18 UNL     1      -8.542   1.680   2.345  1.00  0.00           H  
HETATM   76  H19 UNL     1     -13.458  -0.606   4.069  1.00  0.00           H  
HETATM   77  H20 UNL     1     -13.937   0.915   3.287  1.00  0.00           H  
HETATM   78  H21 UNL     1     -12.803  -2.384  -0.456  1.00  0.00           H  
HETATM   79  H22 UNL     1      -9.175   1.515  -1.301  1.00  0.00           H  
HETATM   80  H23 UNL     1      -9.024  -1.174  -2.313  1.00  0.00           H  
HETATM   81  H24 UNL     1      -7.336   1.423  -2.884  1.00  0.00           H  
HETATM   82  H25 UNL     1      -6.518  -0.614  -3.447  1.00  0.00           H  
HETATM   83  H26 UNL     1       6.790  -1.408  -3.448  1.00  0.00           H  
HETATM   84  H27 UNL     1       6.178   0.519  -4.092  1.00  0.00           H  
HETATM   85  H28 UNL     1       9.131  -1.342  -4.085  1.00  0.00           H  
HETATM   86  H29 UNL     1       8.825   1.199  -3.236  1.00  0.00           H  
CONECT    1    2   58   59
CONECT    2    3    3    7
CONECT    3    4
CONECT    4    5    5   60
CONECT    5    6
CONECT    6    7    7   10
CONECT    7    8
CONECT    8    9    9
CONECT    9   10   61
CONECT   10   11
CONECT   11   12   56   62
CONECT   12   13
CONECT   13   14   54   63
CONECT   14   15   64   65
CONECT   15   16
CONECT   16   17   17   18   19
CONECT   18   66
CONECT   19   20
CONECT   20   21   21   22   23
CONECT   22   67
CONECT   23   24
CONECT   24   25   25   26   27
CONECT   26   68
CONECT   27   28
CONECT   28   29   29   30   31
CONECT   30   69
CONECT   31   32
CONECT   32   33   33   34   35
CONECT   34   70
CONECT   35   36
CONECT   36   37   71   72
CONECT   37   38   52   73
CONECT   38   39
CONECT   39   40   50   74
CONECT   40   41   49
CONECT   41   42   42   75
CONECT   42   43
CONECT   43   44   44   49
CONECT   44   45   46
CONECT   45   76   77
CONECT   46   47   47
CONECT   47   48   78
CONECT   48   49   49
CONECT   50   51   52   79
CONECT   51   80
CONECT   52   53   81
CONECT   53   82
CONECT   54   55   56   83
CONECT   55   84
CONECT   56   57   85
CONECT   57   86
END

HMDB0001192
     RDKit          3D
Diadenosine pentaphosphate
 86 91  0  0  0  0  0  0  0  0999 V2000
   12.0157    1.2054    2.6533 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9574    0.4166    2.1485 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9956   -0.0388    2.9671 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9832   -0.7921    2.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9485   -1.0830    1.1791 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8822   -0.6559    0.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9195    0.1144    0.7918 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6938    0.4017   -0.2556 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1813   -0.1571   -1.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0485   -0.8191   -1.0133 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1809   -1.5634   -1.9026 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9830   -1.7844   -1.2514 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2309   -0.6404   -1.5131 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7806   -0.8242   -1.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1348    0.3918   -1.4359 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5040    0.3511   -1.0607 P   0  0  0  0  0  5  0  0  0  0  0  0
    3.0732   -1.0897   -0.9217 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5638    1.1047   -2.2546 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2683    1.1152    0.4261 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6611    1.6237    0.5576 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.3682    2.6409   -0.5211 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4919    2.3461    2.0817 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6057    0.3273    0.3651 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8583   -0.8801    1.4960 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.7046   -2.2443    0.8211 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4363   -0.8207    2.1288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2264   -0.8361    2.7717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6403   -0.0167    2.4216 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.5518    0.8182    1.1846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9864    1.0168    3.7356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9711   -1.0585    2.2651 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4884   -1.0895    0.6555 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.1460   -2.4549    0.4460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1939   -0.9422   -0.4231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6425    0.0783    0.3591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4351   -0.2152   -0.7493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4612    0.8934   -0.9547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2414    0.9627    0.1871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2728    0.0585   -0.0581 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.3328    0.2597    0.9103 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3436    1.0451    1.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5307    0.9312    2.6153 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2968    0.0785    1.9440 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5796   -0.3775    2.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3940    0.0282    3.2442 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0878   -1.2572    1.2778 N   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3672   -1.6809    0.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1178   -1.2245    0.0365 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5316   -0.3417    0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7231    0.5294   -1.4471 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.5374   -0.3867   -2.0657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3495    0.6254   -2.1267 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.1019   -0.6348   -2.6691 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3738   -0.5546   -3.0364 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9974    0.6702   -3.5268 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8810   -0.7998   -3.1692 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4813    0.4698   -3.1108 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9716    1.0519    2.3028 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8379    1.9289    3.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1936   -1.1744    3.1215 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6222   -0.0729   -2.3473 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6306   -2.5671   -2.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6673    0.2668   -1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7567   -0.9167   -0.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3266   -1.6709   -1.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0610    1.8908   -2.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4152    1.6216    2.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6761   -1.7154    2.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1016    1.4217    3.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2662   -0.0704   -0.8572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9389   -1.1800   -0.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8024   -0.3560   -1.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9223    1.8450   -1.1585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9130   -0.9758   -0.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5418    1.6797    2.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4582   -0.6060    4.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.9368    0.9153    3.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8032   -2.3835   -0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1748    1.5146   -1.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0238   -1.1741   -2.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3362    1.4234   -2.8839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5183   -0.6143   -3.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7904   -1.4077   -3.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1780    0.5186   -4.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1312   -1.3416   -4.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8250    1.1991   -3.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  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
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 28 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 32 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 43 44  2  0
 44 45  1  0
 44 46  1  0
 46 47  2  0
 47 48  1  0
 48 49  2  0
 39 50  1  0
 50 51  1  0
 50 52  1  0
 52 53  1  0
 13 54  1  0
 54 55  1  0
 54 56  1  0
 56 57  1  0
  7  2  1  0
 56 11  1  0
 10  6  1  0
 52 37  1  0
 49 40  1  0
 49 43  1  0
  1 58  1  0
  1 59  1  0
  4 60  1  0
  9 61  1  0
 11 62  1  0
 13 63  1  1
 14 64  1  0
 14 65  1  0
 18 66  1  0
 22 67  1  0
 26 68  1  0
 30 69  1  0
 34 70  1  0
 36 71  1  0
 36 72  1  0
 37 73  1  0
 39 74  1  6
 41 75  1  0
 45 76  1  0
 45 77  1  0
 47 78  1  0
 50 79  1  1
 51 80  1  0
 52 81  1  6
 53 82  1  0
 54 83  1  6
 55 84  1  0
 56 85  1  6
 57 86  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Diadenosine pentaphosphoric acid	Generator
Bis(5'-adenosyl) pentaphosphate	HMDB
Bis(adenosine)-5'-pentaphosphate	HMDB
P1,P5-Bis(5'-adenosyl) pentaphosphate	HMDB
Ap5a	MeSH, HMDB
P(1),P(5)-Bis(5'-adenosyl)pentaphosphate	MeSH, HMDB
P(1),P(5)-Di(adenosine-5'-)pentaphosphate	MeSH, HMDB
({[({[(2R,3S,4R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)({[({[(3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinate	Generator, HMDB
Diadenosine pentaphosphate	MeSH

Chemical Formula

C₂₀H₂₉N₁₀O₂₂P₅

Average Molecular Weight

916.3669

Monoisotopic Molecular Weight

916.014595222

IUPAC Name

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

Traditional Name

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

CAS Registry Number

41708-91-2

SMILES

NC1=NC=NC2=C1N=CN2[C@@H]1OC(COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2OC([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C20H29N10O22P5/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(47-19)1-45-53(35,36)49-55(39,40)51-57(43,44)52-56(41,42)50-54(37,38)46-2-8-12(32)14(34)20(48-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H2,21,23,25)(H2,22,24,26)/t7-,8?,11-,12-,13-,14-,19?,20-/m1/s1

InChI Key

OIMACDRJUANHTJ-OEOQABFDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

(5'->5')-dinucleotides

Sub Class

Not Available

Direct Parent

(5'->5')-dinucleotides

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Intervention

Hemodialysis (HMDB: HMDB0001192)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 12738682)

Source

Endogenous

Endogenous (HMDB: HMDB0001192)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.92 g/L	ALOGPS
logP	-0.2	ALOGPS
logP	-11	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	0.42	ChemAxon
pKa (Strongest Basic)	5.3	ChemAxon
Physiological Charge	-5	ChemAxon
Hydrogen Acceptor Count	24	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	480.5 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	176.98 m³·mol⁻¹	ChemAxon
Polarizability	70.64 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	249.747	32859911
AllCCS	[M-H]-	250.173	32859911
DeepCCS	[M-2H]-	254.386	30932474
DeepCCS	[M+Na]+	228.162	30932474
AllCCS	[M+H]+	249.7	32859911
AllCCS	[M+H-H2O]+	250.2	32859911
AllCCS	[M+NH4]+	249.3	32859911
AllCCS	[M+Na]+	249.1	32859911
AllCCS	[M-H]-	250.2	32859911
AllCCS	[M+Na-2H]-	253.3	32859911
AllCCS	[M+HCOO]-	256.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.99 minutes	32390414
Predicted by Siyang on May 30, 2022	11.9362 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	9.6 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	679.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	992.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	243.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	28.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	177.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	84.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	409.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	388.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	977.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	681.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	199.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	785.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	212.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	327.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	759.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	503.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	747.2 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.24 +/- 0.09 uM	Adult (>18 years old)	Both	Hemodialysis	12738682	details

Associated Disorders and Diseases

Disease References

Hemodialysis
Jankowski J, Jankowski V, Laufer U, van der Giet M, Henning L, Tepel M, Zidek W, Schluter H: Identification and quantification of diadenosine polyphosphate concentrations in human plasma. Arterioscler Thromb Vasc Biol. 2003 Jul 1;23(7):1231-8. Epub 2003 May 8. [PubMed:12738682 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022479

KNApSAcK ID

Not Available

Chemspider ID

35013028

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477724

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Jankowski J, Potthoff W, van der Giet M, Tepel M, Zidek W, Schluter H: High-performance liquid chromatographic assay of the diadenosine polyphosphates in human platelets. Anal Biochem. 1999 Apr 10;269(1):72-8. [PubMed:10094777 ]
Hollah P, Hausberg M, Kosch M, Barenbrock M, Letzel M, Schlatter E, Rahn KH: A novel assay for determination of diadenosine polyphosphates in human platelets: studies in normotensive subjects and in patients with essential hypertension. J Hypertens. 2001 Feb;19(2):237-45. [PubMed:11212966 ]
Miras-Portugal MT, Pintor J, Gualix J: Ca2+ signalling in brain synaptosomes activated by dinucleotides. J Membr Biol. 2003 Jul 1;194(1):1-10. [PubMed:14502438 ]
Pintor J, Carracedo G, Alonso MC, Bautista A, Peral A: Presence of diadenosine polyphosphates in human tears. Pflugers Arch. 2002 Jan;443(3):432-6. Epub 2001 Aug 23. [PubMed:11810214 ]
Jankowski J, Jankowski V, Laufer U, van der Giet M, Henning L, Tepel M, Zidek W, Schluter H: Identification and quantification of diadenosine polyphosphate concentrations in human plasma. Arterioscler Thromb Vasc Biol. 2003 Jul 1;23(7):1231-8. Epub 2003 May 8. [PubMed:12738682 ]
Kisselev LL, Justesen J, Wolfson AD, Frolova LY: Diadenosine oligophosphates (Ap(n)A), a novel class of signalling molecules? FEBS Lett. 1998 May 8;427(2):157-63. [PubMed:9607303 ]
Pintor J, King BF, Miras-Portugal MT, Burnstock G: Selectivity and activity of adenine dinucleotides at recombinant P2X2 and P2Y1 purinoceptors. Br J Pharmacol. 1996 Nov;119(5):1006-12. [PubMed:8922753 ]
Baker MD, Holloway DE, Swaminathan GJ, Acharya KR: Crystal structures of eosinophil-derived neurotoxin (EDN) in complex with the inhibitors 5'-ATP, Ap3A, Ap4A, and Ap5A. Biochemistry. 2006 Jan 17;45(2):416-26. [PubMed:16401072 ]
Leon D, Hervas C, Miras-Portugal MT: P2Y1 and P2X7 receptors induce calcium/calmodulin-dependent protein kinase II phosphorylation in cerebellar granule neurons. Eur J Neurosci. 2006 Jun;23(11):2999-3013. [PubMed:16819989 ]
Sperlagh B, Vizi ES: Extracellular interconversion of nucleotides reveals an ecto-adenylate kinase activity in the rat hippocampus. Neurochem Res. 2007 Nov;32(11):1978-89. Epub 2007 Aug 25. [PubMed:17721817 ]
Jankowski V, Karadogan S, Vanholder R, Nofer JR, Herget-Rosenthal S, van der Giet M, Tolle M, Tran TN, Zidek W, Jankowski J: Paracrine stimulation of vascular smooth muscle proliferation by diadenosine polyphosphates released from proximal tubule epithelial cells. Kidney Int. 2007 May;71(10):994-1000. Epub 2007 Mar 14. [PubMed:17361116 ]

Showing metabocard for Diadenosine pentaphosphate (HMDB0001192)

MOL for HMDB0001192 (Diadenosine pentaphosphate)

3D MOL for HMDB0001192 (Diadenosine pentaphosphate)

3D SDF for HMDB0001192 (Diadenosine pentaphosphate)

3D-SDF for HMDB0001192 (Diadenosine pentaphosphate)

PDB for HMDB0001192 (Diadenosine pentaphosphate)

3D PDB for HMDB0001192 (Diadenosine pentaphosphate)

SMILES for HMDB0001192 (Diadenosine pentaphosphate)

INCHI for HMDB0001192 (Diadenosine pentaphosphate)

Structure for HMDB0001192 (Diadenosine pentaphosphate)

3D Structure for HMDB0001192 (Diadenosine pentaphosphate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices