NP-MRD: Showing NP-Card for Adenosine tetraphosphate (NP0086763)

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Record Information

Version

2.0

Created at

2022-05-11 16:30:18 UTC

Updated at

2022-05-11 16:30:18 UTC

NP-MRD ID

NP0086763

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Adenosine tetraphosphate

Description

Adenosine tetraphosphate, also known as AP4 or ATPP, 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 tetraphosphate is a strong basic compound (based on its pKa). Adenosine tetraphosphate exists in all living organisms, ranging from bacteria to humans. Adenosine tetraphosphate is found in Kitasatospora aureofaciens. Adenosine tetraphosphate was first documented in 1985 (PMID: 3852686). A purine ribonucleoside 5'-tetraphosphate having adenine as the nucleobase (PMID: 11810214) (PMID: 7849106) (PMID: 11752128).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231219052D          

 35 37  0  0  1  0            999 V2000
    3.7428    0.9802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9520    1.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2585   -0.2762    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2046    1.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9368    2.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2405    0.7834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5734    0.1855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0806   -1.1051    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7127    2.3010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2102    2.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5101    1.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9301   -0.3255    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2102   -1.0899    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6407   -1.9491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4987    2.0134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1950    3.3720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1354   -0.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6954   -1.8506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5450   -0.6737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2801   -0.6737    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1014   -0.6737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2801    0.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2801   -1.4987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9264   -0.6737    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7476   -0.6737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9264    0.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9264   -1.4987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5726   -0.6737    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3938   -0.6737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5726    0.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5726   -1.4987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2189   -0.6737    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0402   -0.6737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2189    0.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2189   -1.4987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  1  1  1  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  6  0  0  0
 10 15  2  0  0  0  0
 10 16  1  0  0  0  0
 12 17  1  1  0  0  0
 13 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  2  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  2  0  0  0  0
 25 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
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  2  0  0  0  0
  5  9  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
M  END

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
   -7.3646    2.6834   -2.5033 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2439    2.5239   -1.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5327    3.5857   -1.2816 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4706    3.4449   -0.4796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1044    2.2333   -0.0392 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7836    1.1031   -0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8764    1.2773   -1.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3637    0.0261   -1.3917 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6090   -0.8528   -0.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6252   -0.1896   -0.0812 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5963   -0.7231    0.7516 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3064   -0.4521    0.2386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5272   -1.1294    1.1979 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0680   -1.1276    0.8112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6239   -1.8118    1.8046 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2671   -1.9019    1.5275 P   0  0  1  0  0  5  0  0  0  0  0  0
    2.9874   -2.0247    2.8706 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6969   -3.2705    0.6323 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7906   -0.4853    0.8101 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4519   -0.5846    0.4467 P   0  0  1  0  0  5  0  0  0  0  0  0
    4.9743   -1.9547    0.8599 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6226   -0.4266   -1.2223 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2279    0.6457    1.2934 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8728    1.7685    0.2074 P   0  0  1  0  0  5  0  0  0  0  0  0
    4.8439    2.8800    0.0081 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2620    2.4687    0.8823 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1798    1.0872   -1.2935 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7455    1.4244   -1.8364 P   0  0  2  0  0  5  0  0  0  0  0  0
    7.7276    2.5551   -2.8635 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3600    0.0467   -2.6084 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7670    1.8392   -0.5542 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1333   -2.4947    1.2368 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0936   -2.9276    2.5811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5827   -2.2151    0.8187 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4080   -2.7236    1.8011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5618    3.6126   -2.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0382    1.9257   -2.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8854    4.3050   -0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8129   -1.9211   -0.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5872   -0.3123    1.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6777   -0.5790    2.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1148   -1.4875   -0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2724   -0.0691    0.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7294   -3.0877   -0.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7922   -0.1799   -1.6770 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0604    3.2964    1.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8635   -0.7441   -2.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2061    2.7236   -0.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6579   -3.2276    0.5811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8138   -2.4075    3.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7424   -2.6759   -0.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9732   -3.4694    1.5043 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
 16 15  1  1
 16 18  1  0
 16 17  2  0
 16 19  1  0
 20 19  1  6
 20 22  1  0
 20 21  2  0
 20 23  1  0
 24 23  1  1
 24 26  1  0
 24 25  2  0
 24 27  1  0
 28 27  1  1
 28 30  1  0
 28 31  1  0
 28 29  2  0
 13 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
  7  2  1  0
 34 11  1  0
 10  6  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  9 39  1  0
 11 40  1  1
 13 41  1  1
 14 42  1  0
 14 43  1  0
 18 44  1  0
 22 45  1  0
 26 46  1  0
 30 47  1  0
 31 48  1  0
 32 49  1  6
 33 50  1  0
 34 51  1  6
 35 52  1  0
M  END


  Mrv0541 02231219052D          

 35 37  0  0  1  0            999 V2000
    3.7428    0.9802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9520    1.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2585   -0.2762    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2046    1.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9368    2.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2405    0.7834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5734    0.1855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0806   -1.1051    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7127    2.3010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2102    2.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5101    1.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9301   -0.3255    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2102   -1.0899    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6407   -1.9491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4987    2.0134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1950    3.3720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1354   -0.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6954   -1.8506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5450   -0.6737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2801   -0.6737    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1014   -0.6737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2801    0.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2801   -1.4987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9264   -0.6737    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7476   -0.6737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9264    0.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9264   -1.4987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5726   -0.6737    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3938   -0.6737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5726    0.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5726   -1.4987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2189   -0.6737    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0402   -0.6737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2189    0.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2189   -1.4987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  1  1  1  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
  8 14  1  6  0  0  0
 10 15  2  0  0  0  0
 10 16  1  0  0  0  0
 12 17  1  1  0  0  0
 13 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  2  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  2  0  0  0  0
 25 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
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  2  0  0  0  0
  5  9  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086763

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H17N5O16P4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(28-10)1-27-33(21,22)30-35(25,26)31-34(23,24)29-32(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H,25,26)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1

> <INCHI_KEY>
WWMWAMFHUSTZTA-KQYNXXCUSA-N

> <FORMULA>
C10H17N5O16P4

> <MOLECULAR_WEIGHT>
587.1609

> <EXACT_MASS>
586.962075569

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
42.12276945721869

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <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}phosphonic acid

> <ALOGPS_LOGP>
-0.16

> <JCHEM_LOGP>
-7.170684213539284

> <ALOGPS_LOGS>
-2.09

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.642557176214848

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.5940258109428269

> <JCHEM_PKA_STRONGEST_BASIC>
4.996477528553174

> <JCHEM_POLAR_SURFACE_AREA>
325.65999999999997

> <JCHEM_REFRACTIVITY>
106.68719999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.76e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
adenosine tetraphosphic acid

> <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       6.987   1.830   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       5.510   2.268   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.083  -0.516   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.849   3.094   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.482   3.801   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       4.182   1.462   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       4.804   0.346   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.750  -2.063   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       6.930   4.295   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       4.126   4.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.819   2.197   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.603  -0.608   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.126  -2.034   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.796  -3.638   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       2.798   3.758   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       4.097   6.294   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       2.119  -0.191   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.165  -3.454   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.017  -1.258   0.000  0.00  0.00           O+0
HETATM   20  P   UNK     0      -0.523  -1.258   0.000  0.00  0.00           P+0
HETATM   21  O   UNK     0      -2.056  -1.258   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.523   0.276   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.523  -2.798   0.000  0.00  0.00           O+0
HETATM   24  P   UNK     0      -3.596  -1.258   0.000  0.00  0.00           P+0
HETATM   25  O   UNK     0      -5.129  -1.258   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -3.596   0.276   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -3.596  -2.798   0.000  0.00  0.00           O+0
HETATM   28  P   UNK     0      -6.669  -1.258   0.000  0.00  0.00           P+0
HETATM   29  O   UNK     0      -8.202  -1.258   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -6.669   0.276   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -6.669  -2.798   0.000  0.00  0.00           O+0
HETATM   32  P   UNK     0      -9.742  -1.258   0.000  0.00  0.00           P+0
HETATM   33  O   UNK     0     -11.275  -1.258   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -9.742   0.276   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -9.742  -2.798   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10    9                                                  
CONECT    6    2   11                                                       
CONECT    7    3   12                                                       
CONECT    8    3   13   14                                                  
CONECT    9    4    5                                                       
CONECT   10    5   15   16                                                  
CONECT   11    6   15                                                       
CONECT   12    7   17   13                                                  
CONECT   13    8   18   12                                                  
CONECT   14    8                                                            
CONECT   15   10   11                                                       
CONECT   16   10                                                            
CONECT   17   12   19                                                       
CONECT   18   13                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20   24                                                       
CONECT   22   20                                                            
CONECT   23   20                                                            
CONECT   24   21   25   26   27                                             
CONECT   25   24   28                                                       
CONECT   26   24                                                            
CONECT   27   24                                                            
CONECT   28   25   29   30   31                                             
CONECT   29   28   32                                                       
CONECT   30   28                                                            
CONECT   31   28                                                            
CONECT   32   29   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
Adenosine 5'-tetraphosphate	ChEBI
Adenosine 5'-tetraphosphoric acid	Generator
Adenosine tetraphosphoric acid	Generator
Ap4	HMDB
ATPP	HMDB
P4A	HMDB

Chemical Formula

C₁₀H₁₇N₅O₁₆P₄

Average Mass

587.1609 Da

Monoisotopic Mass

586.96208 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}phosphonic acid

Traditional Name

adenosine tetraphosphic acid

CAS Registry Number

Not Available

SMILES

NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C10H17N5O16P4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(28-10)1-27-33(21,22)30-35(25,26)31-34(23,24)29-32(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H,25,26)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1

InChI Key

WWMWAMFHUSTZTA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Kitasatospora aureofaciens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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:18334 )
purine ribonucleoside 5'-tetraphosphate (CHEBI:18334 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.16	ALOGPS
logP	-7.2	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	0.59	ChemAxon
pKa (Strongest Basic)	5	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	325.66 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	106.69 m³·mol⁻¹	ChemAxon
Polarizability	42.12 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0001364

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022579

KNApSAcK ID

Not Available

Chemspider ID

13390

KEGG Compound ID

C03483

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Adenosine 5'-tetraphosphate

METLIN ID

6191

PubChem Compound

14003

PDB ID

Not Available

ChEBI ID

18334

Good Scents ID

Not Available

References

General References

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. doi: 10.1007/s004240100696. Epub 2001 Aug 23. [PubMed:11810214 ]
Luthje J, Baringer J, Ogilvie A: Effects of diadenosine triphosphate (Ap3A) and diadenosine tetraphosphate (Ap4A) on platelet aggregation in unfractionated human blood. Blut. 1985 Dec;51(6):405-13. doi: 10.1007/BF00320727. [PubMed:3852686 ]
Sillero MA, Del Valle M, Zaera E, Michelena P, Garcia AG, Sillero A: Diadenosine 5',5"-P1,P4-tetraphosphate (Ap4A), ATP and catecholamine content in bovine adrenal medulla, chromaffin granules and chromaffin cells. Biochimie. 1994;76(5):404-9. doi: 10.1016/0300-9084(94)90116-3. [PubMed:7849106 ]
Pintor J, Peral A, Hoyle CH, Redick C, Douglass J, Sims I, Yerxa B: Effects of diadenosine polyphosphates on tear secretion in New Zealand white rabbits. J Pharmacol Exp Ther. 2002 Jan;300(1):291-7. doi: 10.1124/jpet.300.1.291. [PubMed:11752128 ]

Showing NP-Card for Adenosine tetraphosphate (NP0086763)

MOL for NP0086763 (Adenosine tetraphosphate)

3D MOL for NP0086763 (Adenosine tetraphosphate)

3D SDF for NP0086763 (Adenosine tetraphosphate)

3D-SDF for NP0086763 (Adenosine tetraphosphate)

PDB for NP0086763 (Adenosine tetraphosphate)

3D PDB for NP0086763 (Adenosine tetraphosphate)

SMILES for NP0086763 (Adenosine tetraphosphate)

INCHI for NP0086763 (Adenosine tetraphosphate)

Structure for NP0086763 (Adenosine tetraphosphate)

3D Structure for NP0086763 (Adenosine tetraphosphate)