NP-MRD: Showing NP-Card for Adenosine (NP0000860)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2022-01-11 18:46:50 UTC

NP-MRD ID

NP0000860

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Adenosine

Description

Adenosine is a nucleoside that is composed of adenine and D-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. For instance, adenosine plays an important role in energy transfer as adenosine triphosphate (ATP) and adenosine diphosphate (ADP). It also plays a role in signal transduction as cyclic adenosine monophosphate (cAMP). Adenosine itself is both a neurotransmitter and potent vasodilator. When administered intravenously adenosine causes transient heart block in the AV node. Due to the effects of adenosine on AV node-dependent supraventricular tachycardia, adenosine is considered a class V antiarrhythmic agent. Overdoses of adenosine intake (as a drug) can lead to several side effects including chest pain, feeling faint, shortness of breath, and tingling of the senses. Serious side effects include a worsening dysrhythmia and low blood pressure. When present in sufficiently high levels, adenosine can act as an immunotoxin and a metabotoxin. An immunotoxin disrupts, limits the function, or destroys immune cells. A metabotoxin is an endogenous metabolite that causes adverse health effects at chronically high levels. Chronically high levels of adenosine are associated with adenosine deaminase deficiency. Adenosine is a precursor to deoxyadenosine, which is a precursor to dATP. A buildup of dATP in cells inhibits ribonucleotide reductase and prevents DNA synthesis, so cells are unable to divide. Since developing T cells and B cells are some of the most mitotically active cells, they are unable to divide and propagate to respond to immune challenges. High levels of deoxyadenosine also lead to an increase in S-adenosylhomocysteine, which is toxic to immature lymphocytes.

Structure

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

HMDB0000050
     RDKit          3D
Adenosine
 32 34  0  0  0  0  0  0  0  0999 V2000
    5.3560    0.3128    0.2063 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1979   -0.4958    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3401   -1.7909    0.6423 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2304   -2.5542    0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0079   -2.0397    0.4245 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8386   -0.7524    0.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9637    0.0535   -0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5258    1.2626   -0.3911 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1791    1.1955   -0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7440   -0.0293   -0.2644 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6040   -0.5758   -0.2832 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3933   -0.0438   -1.2657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6176    0.2509   -0.7116 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4501    1.1799   -1.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6605    1.3766   -0.8312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126    0.8535    0.6194 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2507    1.0003    1.4943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274   -0.2420    1.0531 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9814   -1.3277    1.4539 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8874    0.3605   -0.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6972    0.8698    1.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2755   -3.6011    0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5698    2.0279   -0.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5505   -1.6837   -0.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1695   -0.6774   -0.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9724    2.1567   -1.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7257    0.6659   -2.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8363    0.5739   -0.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6051    1.7626    0.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4194    1.9875    1.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5180    0.1167    1.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6189   -2.1933    1.1867 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
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  7  2  1  0
 18 11  1  0
 10  6  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  9 23  1  0
 11 24  1  6
 13 25  1  1
 14 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  6
 17 30  1  0
 18 31  1  1
 19 32  1  0
M  END

640
  Mrv1652309032023502D          

 19 21  0  0  1  0            999 V2000
    4.9010    0.6808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8071    1.0969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8647    2.5471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3238    1.6527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -0.3570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -1.6848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.1959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.6710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6321    1.0955    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1159    0.4272    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1182    1.7621    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9025    1.5058    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5707    1.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3411   -1.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  1 13  1  0  0  0  0
 10  2  1  6  0  0  0
 12  3  1  6  0  0  0
  4 14  1  0  0  0  0
 11  5  1  1  0  0  0
  5 15  1  0  0  0  0
  5 16  1  0  0  0  0
  6 16  2  0  0  0  0
  6 17  1  0  0  0  0
  7 15  2  0  0  0  0
  7 19  1  0  0  0  0
  8 18  1  0  0  0  0
  8 19  2  0  0  0  0
  9 18  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000860

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1

> <INCHI_KEY>
OIRDTQYFTABQOQ-KQYNXXCUSA-N

> <FORMULA>
C10H13N5O4

> <MOLECULAR_WEIGHT>
267.2413

> <EXACT_MASS>
267.096753929

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.28306076008305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

> <ALOGPS_LOGP>
-1.21

> <JCHEM_LOGP>
-2.0909638716666668

> <ALOGPS_LOGS>
-1.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.891216626641981

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.45400327595609

> <JCHEM_PKA_STRONGEST_BASIC>
3.921276940416587

> <JCHEM_POLAR_SURFACE_AREA>
139.54

> <JCHEM_REFRACTIVITY>
63.1956

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
adenosine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000050
     RDKit          3D
Adenosine
 32 34  0  0  0  0  0  0  0  0999 V2000
    5.3560    0.3128    0.2063 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1979   -0.4958    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3401   -1.7909    0.6423 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2304   -2.5542    0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0079   -2.0397    0.4245 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8386   -0.7524    0.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9637    0.0535   -0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5258    1.2626   -0.3911 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1791    1.1955   -0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7440   -0.0293   -0.2644 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6040   -0.5758   -0.2832 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3933   -0.0438   -1.2657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6176    0.2509   -0.7116 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4501    1.1799   -1.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6605    1.3766   -0.8312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126    0.8535    0.6194 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2507    1.0003    1.4943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274   -0.2420    1.0531 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9814   -1.3277    1.4539 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8874    0.3605   -0.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6972    0.8698    1.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2755   -3.6011    0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5698    2.0279   -0.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5505   -1.6837   -0.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1695   -0.6774   -0.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9724    2.1567   -1.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7257    0.6659   -2.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8363    0.5739   -0.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6051    1.7626    0.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4194    1.9875    1.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5180    0.1167    1.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6189   -2.1933    1.1867 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
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  7  2  1  0
 18 11  1  0
 10  6  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  9 23  1  0
 11 24  1  6
 13 25  1  1
 14 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  6
 17 30  1  0
 18 31  1  1
 19 32  1  0
M  END

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 640                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  O   UNK     0       9.149   1.271   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.240   2.048   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.214   4.755   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.804   3.085   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       7.205  -0.666   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       7.205  -3.145   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       4.414  -0.366   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       3.080  -2.676   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       4.414  -4.986   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       6.780   2.045   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.683   0.797   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.687   3.289   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.151   2.811   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.399   3.714   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.747  -1.136   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.103  -1.906   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.747  -2.676   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.414  -3.446   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.080  -1.136   0.000  0.00  0.00           C+0
CONECT    1   11   13                                                       
CONECT    2   10                                                            
CONECT    3   12                                                            
CONECT    4   14                                                            
CONECT    5   11   15   16                                                  
CONECT    6   16   17                                                       
CONECT    7   15   19                                                       
CONECT    8   18   19                                                       
CONECT    9   18                                                            
CONECT   10    2   11   12                                                  
CONECT   11    1    5   10                                                  
CONECT   12    3   10   13                                                  
CONECT   13    1   12   14                                                  
CONECT   14    4   13                                                       
CONECT   15    5    7   17                                                  
CONECT   16    5    6                                                       
CONECT   17    6   15   18                                                  
CONECT   18    8    9   17                                                  
CONECT   19    7    8                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0000050
HETATM    1  N1  UNL     1       5.356   0.313   0.206  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.198  -0.496   0.280  1.00  0.00           C  
HETATM    3  N2  UNL     1       4.340  -1.791   0.642  1.00  0.00           N  
HETATM    4  C2  UNL     1       3.230  -2.554   0.710  1.00  0.00           C  
HETATM    5  N3  UNL     1       2.008  -2.040   0.424  1.00  0.00           N  
HETATM    6  C3  UNL     1       1.839  -0.752   0.061  1.00  0.00           C  
HETATM    7  C4  UNL     1       2.964   0.053  -0.016  1.00  0.00           C  
HETATM    8  N4  UNL     1       2.526   1.263  -0.391  1.00  0.00           N  
HETATM    9  C5  UNL     1       1.179   1.195  -0.537  1.00  0.00           C  
HETATM   10  N5  UNL     1       0.744  -0.029  -0.264  1.00  0.00           N  
HETATM   11  C6  UNL     1      -0.604  -0.576  -0.283  1.00  0.00           C  
HETATM   12  O1  UNL     1      -1.393  -0.044  -1.266  1.00  0.00           O  
HETATM   13  C7  UNL     1      -2.618   0.251  -0.712  1.00  0.00           C  
HETATM   14  C8  UNL     1      -3.450   1.180  -1.535  1.00  0.00           C  
HETATM   15  O2  UNL     1      -4.660   1.377  -0.831  1.00  0.00           O  
HETATM   16  C9  UNL     1      -2.213   0.854   0.619  1.00  0.00           C  
HETATM   17  O3  UNL     1      -3.251   1.000   1.494  1.00  0.00           O  
HETATM   18  C10 UNL     1      -1.227  -0.242   1.053  1.00  0.00           C  
HETATM   19  O4  UNL     1      -1.981  -1.328   1.454  1.00  0.00           O  
HETATM   20  H1  UNL     1       5.887   0.360  -0.675  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.697   0.870   1.019  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.275  -3.601   0.994  1.00  0.00           H  
HETATM   23  H4  UNL     1       0.570   2.028  -0.833  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.550  -1.684  -0.447  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.169  -0.677  -0.551  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.972   2.157  -1.727  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.726   0.666  -2.464  1.00  0.00           H  
HETATM   28  H9  UNL     1      -4.836   0.574  -0.270  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.605   1.763   0.470  1.00  0.00           H  
HETATM   30  H11 UNL     1      -3.419   1.987   1.593  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.518   0.117   1.793  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.619  -2.193   1.187  1.00  0.00           H  
CONECT    1    2   20   21
CONECT    2    3    3    7
CONECT    3    4
CONECT    4    5    5   22
CONECT    5    6
CONECT    6    7    7   10
CONECT    7    8
CONECT    8    9    9
CONECT    9   10   23
CONECT   10   11
CONECT   11   12   18   24
CONECT   12   13
CONECT   13   14   16   25
CONECT   14   15   26   27
CONECT   15   28
CONECT   16   17   18   29
CONECT   17   30
CONECT   18   19   31
CONECT   19   32
END

HMDB0000050
     RDKit          3D
Adenosine
 32 34  0  0  0  0  0  0  0  0999 V2000
    5.3560    0.3128    0.2063 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1979   -0.4958    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3401   -1.7909    0.6423 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2304   -2.5542    0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0079   -2.0397    0.4245 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8386   -0.7524    0.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9637    0.0535   -0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5258    1.2626   -0.3911 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1791    1.1955   -0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7440   -0.0293   -0.2644 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6040   -0.5758   -0.2832 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3933   -0.0438   -1.2657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6176    0.2509   -0.7116 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4501    1.1799   -1.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6605    1.3766   -0.8312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126    0.8535    0.6194 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2507    1.0003    1.4943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274   -0.2420    1.0531 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9814   -1.3277    1.4539 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8874    0.3605   -0.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6972    0.8698    1.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2755   -3.6011    0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5698    2.0279   -0.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5505   -1.6837   -0.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1695   -0.6774   -0.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9724    2.1567   -1.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7257    0.6659   -2.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8363    0.5739   -0.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6051    1.7626    0.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4194    1.9875    1.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5180    0.1167    1.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6189   -2.1933    1.1867 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
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  7  2  1  0
 18 11  1  0
 10  6  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  9 23  1  0
 11 24  1  6
 13 25  1  1
 14 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  6
 17 30  1  0
 18 31  1  1
 19 32  1  0
M  END

View in JSmol

Synonyms

Value	Source
(2R,3R,4S,5R)-2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol	ChEBI
6-Amino-9-beta-D-ribofuranosyl-9H-purine	ChEBI
9-beta-D-Ribofuranosidoadenine	ChEBI
9-beta-D-Ribofuranosyl-9H-purin-6-amine	ChEBI
Ade-rib	ChEBI
Adenine deoxyribonucleoside	ChEBI
Adenocard	ChEBI
Adenocor	ChEBI
Adenoscan	ChEBI
Adenosin	ChEBI
Adenyldeoxyriboside	ChEBI
Ado	ChEBI
beta-D-Adenosine	ChEBI
Deoxyadenosine	ChEBI
Desoxyadenosine	ChEBI
6-Amino-9-b-D-ribofuranosyl-9H-purine	Generator
6-Amino-9-β-D-ribofuranosyl-9H-purine	Generator
9-b-D-Ribofuranosidoadenine	Generator
9-Β-D-ribofuranosidoadenine	Generator
9-b-D-Ribofuranosyl-9H-purin-6-amine	Generator
9-Β-D-ribofuranosyl-9H-purin-6-amine	Generator
b-D-Adenosine	Generator
Β-D-adenosine	Generator
1-(6-Amino-9H-purin-9-yl)-1-deoxy-beta-D-ribofuranose	HMDB
1-(6-Amino-9H-purin-9-yl)-1-deoxy-beta-delta-ribofuranose	HMDB
6-Amino-9beta-D-ribofuranosyl-9H-purine	HMDB
6-Amino-9beta-delta-ribofuranosyl-9H-purine	HMDB
9-beta-D-Arabinofuranosyladenine	HMDB
9-beta-D-Ribofuranosyladenine	HMDB
9-beta-delta-Arabinofuranosyladenine	HMDB
9-beta-delta-Ribofuranosidoadenine	HMDB
9-beta-delta-Ribofuranosyl-9H-purin-6-amine	HMDB
9-beta-delta-Ribofuranosyladenine	HMDB
9beta-D-Ribofuranosyl-9H-purin-6-amine	HMDB
9beta-D-Ribofuranosyladenine	HMDB
9beta-delta-Ribofuranosyl-9H-purin-6-amine	HMDB
9beta-delta-Ribofuranosyladenine	HMDB
Adenine nucleoside	HMDB
Adenine riboside	HMDB
Adenine-9beta-D-ribofuranoside	HMDB
Adenine-9beta-delta-ribofuranoside	HMDB
beta-Adenosine	HMDB
beta-delta-Adenosine	HMDB
Boniton	HMDB
Myocol	HMDB
Nucleocardyl	HMDB
Sandesin	HMDB

Chemical Formula

C₁₀H₁₃N₅O₄

Average Mass

267.2413 Da

Monoisotopic Mass

267.09675 Da

IUPAC Name

(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

Traditional Name

adenosine

CAS Registry Number

58-61-7

SMILES

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

InChI Identifier

InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7-,10-/m1/s1

InChI Key

OIRDTQYFTABQOQ-KQYNXXCUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, simulated)	Ahselim			2022-01-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 400 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, simulated)	varshavi.d26@gmail.com	Not Available	Not Available	2021-08-08	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Abelmoschus esculentus	FooDB	FooDB
Acanthopanax giraldii	KNApSAcK Database	22123792
Acanthus ebracteatus	KNApSAcK Database	22123792
Acanthus ilicifolius	KNApSAcK Database	22123792
Actinidia chinensis	FooDB	FooDB
Adiantum lunulatum	KNApSAcK Database	22123792
Agaricus bisporus	FooDB	FooDB
Agave	FooDB	FooDB
Alangium platanifolium	LOTUS Database	35616633
Allium ampeloprasum	FooDB	FooDB
Allium ascalonicum	FooDB	FooDB
Allium cepa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium cepa L.	FooDB	FooDB
Allium chinense	LOTUS Database	35616633
Allium fistulosum	FooDB	FooDB
Allium sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Allium schoenoprasum	FooDB	FooDB
Allium tuberosum	FooDB	FooDB
Allium tuberosum Rottl.ex Spreng.	KNApSAcK Database	22123792
Aloysia triphylla	FooDB	FooDB
Alternaria alternata	LOTUS Database	35616633
Amaranthus	FooDB	FooDB
Amelanchier alnifolia	FooDB	FooDB
Anacardium occidentale	FooDB	FooDB
Ananas comosus	FooDB	FooDB
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anethum graveolens	FooDB	FooDB
Angelica acutiloba	LOTUS Database	35616633
Angelica archangelica	LOTUS Database	35616633
Angelica dahurica	LOTUS Database	35616633
Angelica keiskei	FooDB	FooDB
Annona cherimola	FooDB	FooDB
Annona muricata	FooDB	FooDB
Annona reticulata	FooDB	FooDB
Annona squamosa	FooDB	FooDB
Anser anser	FooDB	FooDB
Anthriscus cerefolium	FooDB	FooDB
Apium graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Apium graveolens var. dulce	FooDB	FooDB
Apium graveolens var. rapaceum	FooDB	FooDB
Apium graveolens var. secalinum	FooDB	FooDB
Aplysia kurodai	LOTUS Database	35616633
Arabidopsis thaliana	KNApSAcK Database	22123792
Arachis hypogaea	FooDB	FooDB
Arctium lappa	FooDB	FooDB
Argemone mexicana	LOTUS Database	35616633
Armoracia rusticana	FooDB	FooDB
Artemisia dracunculus	FooDB	FooDB
Artemisia vulgaris	FooDB	FooDB
Artocarpus altilis	FooDB	FooDB
Artocarpus heterophyllus	FooDB	FooDB
Asparagus officinalis	KNApSAcK Database	22123792
Asterias forbesi	LOTUS Database	35616633
Atractylodes lancea	KNApSAcK Database	22123792
Attalea speciosa	FooDB	FooDB
Auricularia auricula-judae	FooDB	FooDB
Auricularia polytricha	FooDB	FooDB
Avena sativa L.	FooDB	FooDB
Averrhoa carambola	FooDB	FooDB
Azadirachta indica	LOTUS Database	35616633
Basella alba	FooDB	FooDB
Benincasa hispida	FooDB	FooDB
Bertholletia excelsa	FooDB	FooDB
Beta vulgaris	FooDB	FooDB
Beta vulgaris ssp. cicla	FooDB	FooDB
Bison bison	FooDB	FooDB
Borago officinalis	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Brachystemma calycinum	LOTUS Database	35616633
Brassica alboglabra	FooDB	FooDB
Brassica juncea	FooDB	FooDB
Brassica napus	FooDB	FooDB
Brassica napus var. napus	FooDB	FooDB
Brassica oleracea	FooDB	FooDB
Brassica oleracea var. botrytis	FooDB	FooDB
Brassica oleracea var. capitata	FooDB	FooDB
Brassica oleracea var. gemmifera	FooDB	FooDB
Brassica oleracea var. gongylodes	FooDB	FooDB
Brassica oleracea var. italica	FooDB	FooDB
Brassica oleracea var. sabauda	FooDB	FooDB
Brassica oleracea var. viridis	FooDB	FooDB
Brassica rapa	FooDB	FooDB
Brassica rapa ssp. chinensis	FooDB	FooDB
Brassica rapa var. pekinensis	FooDB	FooDB
Brassica rapa var. rapa	FooDB	FooDB
Brassica ruvo	FooDB	FooDB
Brosimum alicastrum	FooDB	FooDB
Broussonetia papyrifera	LOTUS Database	35616633
Bubalus bubalis	FooDB	FooDB
Byrsonima crassifolia	FooDB	FooDB
Cajanus cajan	FooDB	FooDB
Canarium ovatum	FooDB	FooDB
Cannabis sativa	CannabisDB	Not Available
Cantharellus cibarius	FooDB	FooDB
Capparis flavicans	KNApSAcK Database	22123792
Capparis spinosa	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Capsicum annuum	FooDB	FooDB
Capsicum annuum L.	FooDB	FooDB
Capsicum annuum var. annuum	FooDB	FooDB
Capsicum chinense	FooDB	FooDB
Capsicum pubescens	FooDB	FooDB
Carica papaya L.	FooDB	FooDB
Carissa macrocarpa	FooDB	FooDB
Carthamus tinctorius	FooDB	FooDB
Carum carvi	FooDB	FooDB
Carya	FooDB	FooDB
Carya illinoinensis	FooDB	FooDB
Cassytha filiformis	KNApSAcK Database	22123792
Castanea	FooDB	FooDB
Castanea crenata	FooDB	FooDB
Castanea mollissima	FooDB	FooDB
Castanea sativa	FooDB	FooDB
Castilleja densiflora	LOTUS Database	35616633
Ceratonia siliqua	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Chamaemelum nobile	FooDB	FooDB
Chamerion angustifolium	FooDB	FooDB
Chenopodium album	FooDB	FooDB
Chenopodium quinoa	FooDB	FooDB
Chlamydomonas reinhardtii	LOTUS Database	35616633
Chrysanthemum coronarium	FooDB	FooDB
Cicer arietinum	FooDB	FooDB
Cichorium endivia	FooDB	FooDB
Cichorium intybus	FooDB	FooDB
Cinnamomum	FooDB	FooDB
Cinnamomum aromaticum	FooDB	FooDB
Cinnamomum verum	FooDB	FooDB
Cirsium	FooDB	FooDB
Citrullus lanatus	FooDB	FooDB
Citrus ×limon (L.) Burm. f. (pro sp.)	FooDB	FooDB
Citrus aurantiifolia	FooDB	FooDB
Citrus latifolia	FooDB	FooDB
Citrus limon	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus maxima	FooDB	FooDB
Citrus paradisi	FooDB	FooDB
Citrus reticulata	FooDB	FooDB
Citrus unshiu	KNApSAcK Database	22123792
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	FooDB
Cliona celata	LOTUS Database	35616633
Clitoria ternatea	LOTUS Database	35616633
Cnidium officinale	LOTUS Database	35616633
Cocos nucifera	FooDB	FooDB
Codonopsis pilosula	LOTUS Database	35616633
Codonopsis pilosula subsp. tangshen	Plant	KNApSAcK
Codonopsis tangshen OLIV.	KNApSAcK Database	22123792
Coffea arabica	KNApSAcK Database	22123792
Coffea arabica L.	Plant	KNApSAcK
Coffea canephora	KNApSAcK Database	22123792
Coix lacryma-jobi	LOTUS Database	35616633
Colocasia esculenta	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Corchorus olitorius	FooDB	FooDB
Coriandrum sativum	LOTUS Database	35616633
Coriandrum sativum L.	FooDB	FooDB
Corylus	FooDB	FooDB
Corylus avellana	FooDB	FooDB
Crateva religiosa	FooDB	FooDB
Crocus sativus	KNApSAcK Database	22123792
Cucumis melo	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cucumis metuliferus	FooDB	FooDB
Cucumis sativus	LOTUS Database	35616633
Cucumis sativus L.	KNApSAcK Database	22123792
Cucurbita	FooDB	FooDB
Cucurbita maxima	FooDB	FooDB
Cucurbita moschata	FooDB	FooDB
Cuminum cyminum	FooDB	FooDB
Curcuma longa	FooDB	FooDB
Cydonia oblonga	FooDB	FooDB
Cymbopogon citratus	FooDB	FooDB
Cynara cardunculus	FooDB	FooDB
Cynara scolymus	FooDB	FooDB
Cynomorium songaricum	LOTUS Database	35616633
Daphnia magna	LOTUS Database	35616633
Daphnia pulex	LOTUS Database	35616633
Datura metel	Plant	KNApSAcK
Daucus carota	FooDB	FooDB
Daucus carota ssp. sativus	FooDB	FooDB
Dimocarpus longan	FooDB	FooDB
Dioscorea	FooDB	FooDB
Dioscorea opposita	KNApSAcK Database	22123792
Dioscorea oppositifolia	LOTUS Database	35616633
Dioscorea pentaphylla	FooDB	FooDB
Dioscorea polystachya	LOTUS Database	35616633
Diospyros	FooDB	FooDB
Diospyros kaki	FooDB	FooDB
Diospyros virginiana	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Durio zibethinus	FooDB	FooDB
Dysphania ambrosioides	FooDB	FooDB
Elaeis	FooDB	FooDB
Eleocharis dulcis	FooDB	FooDB
Elettaria cardamomum	FooDB	FooDB
Eleutherococcus giraldii	LOTUS Database	35616633
Empetrum nigrum	FooDB	FooDB
Equus caballus	FooDB	FooDB
Eragrostis tef	FooDB	FooDB
Eriobotrya japonica	FooDB	FooDB
Eruca vesicaria subsp. Sativa	FooDB	FooDB
Eugenia javanica	FooDB	FooDB
Eugenia uniflora	FooDB	FooDB
Eunicella cavolini	LOTUS Database	35616633
Euodia fargesii	LOTUS Database	35616633
Eurycoma longifolia	LOTUS Database	35616633
Eutrema japonicum	FooDB	FooDB
Fagopyrum esculentum	FooDB	FooDB
Fagopyrum tataricum	FooDB	FooDB
Fagus	FooDB	FooDB
Feijoa sellowiana	FooDB	FooDB
Ficus carica	FooDB	FooDB
Flammulina velutipes	FooDB	FooDB
Foeniculum vulgare	FooDB	FooDB
Fragaria x ananassa	FooDB	FooDB
Fritillaria cirrhosa	KNApSAcK Database	22123792
Fritillaria yuminensis	LOTUS Database	35616633
Gallus gallus	FooDB	FooDB
Ganoderma japonicum	LOTUS Database	35616633
Garcinia mangostana	FooDB	FooDB
Gastrodia elata	KNApSAcK Database	22123792
Gaylussacia baccata	FooDB	FooDB
Ginkgo biloba	FooDB	FooDB
Glehnia littoralis	LOTUS Database	35616633
Glycine max	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Gnaphalium polycaulon	LOTUS Database	35616633
Gossypium	FooDB	FooDB
Grifola frondosa	FooDB	FooDB
Hedysarum alpinum	FooDB	FooDB
Helianthus annuus L.	FooDB	FooDB
Helianthus tuberosus	FooDB	FooDB
Helichrysum arenarium	LOTUS Database	35616633
Hemerocallis fulva	LOTUS Database	35616633
Hibiscus sabbariffa	FooDB	FooDB
Hippophae rhamnoides	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Hordeum vulgare	FooDB	FooDB
Houttuynia cordata	KNApSAcK Database	22123792
Hyacinthoides non-scripta	LOTUS Database	35616633
Hydrangea macrophylla	LOTUS Database	35616633
Hyssopus officinalis L.	FooDB	FooDB
Ilex cornuta	LOTUS Database	35616633
Illicium verum	FooDB	FooDB
Ipomoea aquatica	FooDB	FooDB
Ipomoea batatas	FooDB	FooDB
Isatis tinctoria	LOTUS Database	35616633
Juglans	FooDB	FooDB
Juglans ailanthifolia	FooDB	FooDB
Juglans cinerea	FooDB	FooDB
Juglans nigra L.	FooDB	FooDB
Juglans regia	FooDB	FooDB
Junceella juncea	-	KNApSAcK
Kaempferia parviflora	LOTUS Database	35616633
Lablab purpureus	FooDB	FooDB
Lactarius subplinthogalus	LOTUS Database	35616633
Lactuca sativa	FooDB	FooDB
Lagenaria siceraria	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Lathyrus sativus	FooDB	FooDB
Laurus nobilis L.	FooDB	FooDB
Lens culinaris	FooDB	FooDB
Lentinus edodes	FooDB	FooDB
Lepidium sativum	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Levisticum officinale	FooDB	FooDB
Ligusticum sinense	LOTUS Database	35616633
Lilium mackliniae	LOTUS Database	35616633
Lilium pumilum	LOTUS Database	35616633
Linum usitatissimum	FooDB	FooDB
Litchi chinensis	FooDB	FooDB
Litoria verreauxii	LOTUS Database	35616633
Lotus corniculatus	LOTUS Database	35616633
Luffa aegyptiaca	FooDB	FooDB
Lupinus	FooDB	FooDB
Lupinus albus	KNApSAcK Database	22123792
Macadamia	FooDB	FooDB
Macadamia tetraphylla	FooDB	FooDB
Malpighia emarginata	FooDB	FooDB
Malus	FooDB	FooDB
Malus pumila	FooDB	FooDB
Mammea americana	FooDB	FooDB
Mangifera indica	FooDB	FooDB
Manihot esculenta	FooDB	FooDB
Manilkara zapota	FooDB	FooDB
Maranta arundinacea	FooDB	FooDB
Marchantia polymorpha	LOTUS Database	35616633
Matricaria recutita	FooDB	FooDB
Matteuccia struthiopteris	FooDB	FooDB
Maytenus hookeri	LOTUS Database	35616633
Medicago sativa	Plant	KNApSAcK
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Melicope semecarpifolia	LOTUS Database	35616633
Melissa officinalis L.	FooDB	FooDB
Mentha	FooDB	FooDB
Mentha aquatica	FooDB	FooDB
Mentha arvensis	FooDB	FooDB
Mentha spicata	FooDB	FooDB
Mentha x piperita	FooDB	FooDB
Mespilus germanica	FooDB	FooDB
Metroxylon sagu	FooDB	FooDB
Mikania laevigata	LOTUS Database	35616633
Mollugo oppositifolia	LOTUS Database	35616633
Momordica charantia	FooDB	FooDB
Morchellaceae	FooDB	FooDB
Morella rubra	FooDB	FooDB
Moringa oleifera	FooDB	FooDB
Morus	FooDB	FooDB
Morus alba	LOTUS Database	35616633
Morus nigra	FooDB	FooDB
Musa acuminata	FooDB	FooDB
Musa x paradisiaca	FooDB	FooDB
Mycoplasmopsis bovis	LOTUS Database	35616633
Myrica	FooDB	FooDB
Myristica fragrans	FooDB	FooDB
Nelumbo	FooDB	FooDB
Nelumbo nucifera	FooDB	FooDB
Nephelium lappaceum	FooDB	FooDB
Neptunea antiqua	LOTUS Database	35616633
Nigrospora oryzae	LOTUS Database	35616633
Notechis scutatus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Nuphar lutea	FooDB	FooDB
Ocimum basilicum	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oenothera biennis	FooDB	FooDB
Olea europaea	FooDB	FooDB
Oligomeris linifolia	LOTUS Database	35616633
Ophiocordyceps sinensis	LOTUS Database	35616633
Opuntia	FooDB	FooDB
Opuntia cochenillifera	FooDB	FooDB
Opuntia macrorhiza	FooDB	FooDB
Origanum majorana	FooDB	FooDB
Origanum onites	FooDB	FooDB
Origanum vulgare	FooDB	FooDB
Origanum X majoricum	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Oryza rufipogon	FooDB	FooDB
Oryza sativa	FooDB	FooDB
Ovis aries	FooDB	FooDB
Oxytropis myriophylla	KNApSAcK Database	22123792
Oxytropis racemosa	LOTUS Database	35616633
Pachliopta aristolochiae	LOTUS Database	35616633
Pachyrhizus erosus	FooDB	FooDB
Paeonia obovata	LOTUS Database	35616633
Paeonia suffruticosa	LOTUS Database	35616633
Panax ginseng	FooDB	FooDB
Panax Japonicus	LOTUS Database	35616633
Pangium edule	FooDB	FooDB
Panicum miliaceum	FooDB	FooDB
Paralepista flaccida	LOTUS Database	35616633
Passiflora edulis	FooDB	FooDB
Pastinaca sativa	FooDB	FooDB
Pediomelum esculentum	FooDB	FooDB
Perideridia oregana	FooDB	FooDB
Persea americana	FooDB	FooDB
Petasites japonicus	FooDB	FooDB
Petroselinum crispum	FooDB	FooDB
Phaseolus coccineus	FooDB	FooDB
Phaseolus lunatus	FooDB	FooDB
Phaseolus vulgaris	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Phlebodium decumanum	LOTUS Database	35616633
Phoebe formosana	LOTUS Database	35616633
Phoenix dactylifera	FooDB	FooDB
Photinia melanocarpa	FooDB	FooDB
Phyllostachys edulis	FooDB	FooDB
Physalis	FooDB	FooDB
Physalis philadelphica var. immaculata	FooDB	FooDB
Phytolacca americana	FooDB	FooDB
Pimenta dioica	FooDB	FooDB
Pimpinella anisum	FooDB	FooDB
Pinus	FooDB	FooDB
Pinus edulis	FooDB	FooDB
Piper nigrum L.	FooDB	FooDB
Pistacia vera	FooDB	FooDB
Pisum sativum	FooDB	FooDB
Pleurotus ostreatus	FooDB	FooDB
Polygonatum sibiricum	LOTUS Database	35616633
Polygonum alpinum	FooDB	FooDB
Populus alba	LOTUS Database	35616633
Portulaca oleracea	FooDB	FooDB
Pouteria sapota	FooDB	FooDB
Prunus armeniaca	FooDB	FooDB
Prunus avium	FooDB	FooDB
Prunus avium L.	FooDB	FooDB
Prunus cerasus	FooDB	FooDB
Prunus domestica	FooDB	FooDB
Prunus dulcis	FooDB	FooDB
Prunus persica	FooDB	FooDB
Prunus persica var. nucipersica	FooDB	FooDB
Prunus persica var. persica	FooDB	FooDB
Prunus tomentosa	FooDB	FooDB
Prunus virginiana	FooDB	FooDB
Pseudomyrmex triplarinus	LOTUS Database	35616633
Psidium cattleianum	FooDB	FooDB
Psidium guajava	FooDB	FooDB
Psophocarpus tetragonolobus	FooDB	FooDB
Punica granatum	FooDB	FooDB
Pyrus communis	FooDB	FooDB
Pyrus pyrifolia	FooDB	FooDB
Quercus	FooDB	FooDB
Raphanus sativus	FooDB	FooDB
Raphanus sativus var. longipinnatus	FooDB	FooDB
Raphanus sativus var. sativus	FooDB	FooDB
Rheum rhabarbarum	FooDB	FooDB
Ribes aureum	FooDB	FooDB
Ribes glandulosum	FooDB	FooDB
Ribes nigrum	FooDB	FooDB
Ribes rubrum	FooDB	FooDB
Ribes uva-crispa	FooDB	FooDB
Rosa	FooDB	FooDB
Rubus arcticus	FooDB	FooDB
Rubus chamaemorus	FooDB	FooDB
Rubus idaeus	FooDB	FooDB
Rubus occidentalis	FooDB	FooDB
Rubus spectabilis	FooDB	FooDB
Rumex	FooDB	FooDB
Rumex acetosa	FooDB	FooDB
Rumex articus	FooDB	FooDB
Sagittaria latifolia	FooDB	FooDB
Salix pulchra	FooDB	FooDB
Salmonella enterica	LOTUS Database	35616633
Salvia elegans	FooDB	FooDB
Salvia hispanica	FooDB	FooDB
Salvia officinalis	FooDB	FooDB
Salvia rosmarinus	FooDB	FooDB
Sambucus nigra	FooDB	FooDB
Sambucus nigra L.	FooDB	FooDB
Saposhnikovia divaricata	LOTUS Database	35616633
Satureja hortensis L.	FooDB	FooDB
Satureja montana	FooDB	FooDB
Sauropus androgynus	LOTUS Database	35616633
Scaphium affine	LOTUS Database	35616633
Scleropyrum pentandrum	LOTUS Database	35616633
Scorzonera hispanica	FooDB	FooDB
Secale cereale	FooDB	FooDB
Sechium edule	FooDB	FooDB
Senna tora	LOTUS Database	35616633
Sesamum indicum	FooDB	FooDB
Sesbania bispinosa	FooDB	FooDB
Sinapis alba	FooDB	FooDB
Sisymbrium	FooDB	FooDB
Smilax bracteata	LOTUS Database	35616633
Solanum incanum	LOTUS Database	35616633
Solanum lycopersicum	FooDB	FooDB
Solanum lycopersicum var. cerasiforme	FooDB	FooDB
Solanum lycopersicum var. lycopersicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Solanum melongena	FooDB	FooDB
Solanum quitoense	FooDB	FooDB
Solanum tuberosum	FooDB	FooDB
Sorbus aucuparia	FooDB	FooDB
Sorghum bicolor	FooDB	FooDB
Spinacia oleracea	FooDB	FooDB
Streptomyces herbaceus	LOTUS Database	35616633
Streptomyces piomogenus	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Strychnos lucida	KNApSAcK Database	22123792
Subergorgia suberosa	-	KNApSAcK
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Synechococcus elongatus	LOTUS Database	35616633
Syzygium aromaticum	FooDB	FooDB
Syzygium cumini	FooDB	FooDB
Syzygium jambos	FooDB	FooDB
Tamarindus indica	FooDB	FooDB
Taraxacum officinale	FooDB	FooDB
Tethya aurantium	LOTUS Database	35616633
Tetragonia tetragonioides	FooDB	FooDB
Thelesperma	FooDB	FooDB
Thymus pulegioides	FooDB	FooDB
Thymus vulgaris	FooDB	FooDB
Tilia cordata	FooDB	FooDB
Tilia L.	FooDB	FooDB
Tinospora crispa	Plant	KNApSAcK
Torilis japonica	LOTUS Database	35616633
Trachyspermum ammi	LOTUS Database	35616633
Tragopogon porrifolius	FooDB	FooDB
Trigonella foenum-graecum	FooDB	FooDB
Triticum	FooDB	FooDB
Triticum aestivum	KNApSAcK Database	22123792
Triticum durum	FooDB	FooDB
Triticum spelta	FooDB	FooDB
Triticum turanicum	FooDB	FooDB
Trypanosoma brucei	LOTUS Database	35616633
Tuber indicum	LOTUS Database	35616633
Typha angustifolia	FooDB	FooDB
Ulva pertusa	LOTUS Database	35616633
Vaccinium	FooDB	FooDB
Vaccinium angustifolium	FooDB	FooDB
Vaccinium angustifolium X Vaccinium corymbosum	FooDB	FooDB
Vaccinium arboreum	FooDB	FooDB
Vaccinium corymbosum	FooDB	FooDB
Vaccinium deliciosum	FooDB	FooDB
Vaccinium elliottii	FooDB	FooDB
Vaccinium macrocarpon	FooDB	FooDB
Vaccinium myrtilloides	FooDB	FooDB
Vaccinium myrtillus	FooDB	FooDB
Vaccinium ovalifolium	FooDB	FooDB
Vaccinium ovatum	FooDB	FooDB
Vaccinium oxycoccos	FooDB	FooDB
Vaccinium parvifolium	FooDB	FooDB
Vaccinium reticulatum	FooDB	FooDB
Vaccinium stamineum	FooDB	FooDB
Vaccinium uliginosum	FooDB	FooDB
Vaccinium vitis-idaea	FooDB	FooDB
Valerianella locusta	FooDB	FooDB
Vanilla	FooDB	FooDB
Verbena officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Viburnum edule	FooDB	FooDB
Vicia faba	FooDB	FooDB
Vigna aconitifolia	FooDB	FooDB
Vigna angularis	FooDB	FooDB
Vigna mungo	FooDB	FooDB
Vigna radiata	FooDB	FooDB
Vigna umbellata	FooDB	FooDB
Vigna unguiculata	FooDB	FooDB
Vigna unguiculata ssp. cylindrica	FooDB	FooDB
Vigna unguiculata ssp. unguiculata	FooDB	FooDB
Vigna unguiculata var. sesquipedalis	FooDB	FooDB
Vitis	FooDB	FooDB
Vitis aestivalis	FooDB	FooDB
Vitis labrusca	FooDB	FooDB
Vitis rotundifolia	FooDB	FooDB
Vitis vinifera L.	FooDB	FooDB
Xanthosoma sagittifolium	FooDB	FooDB
Zea mays	LOTUS Database	35616633
Zea mays L.	KNApSAcK Database	22123792
Zingiber officinale	FooDB	FooDB
Zizania	FooDB	FooDB
Zizania aquatica	FooDB	FooDB
Ziziphus zizyphus	FooDB	FooDB

Species Where Detected

Species Name	Source	Reference
Homo sapiens (Urine)	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Not Available

Direct Parent

Purine nucleosides

Alternative Parents

Substituents

Purine nucleoside
Glycosyl compound
N-glycosyl compound
6-aminopurine
Pentose monosaccharide
Imidazopyrimidine
Purine
Aminopyrimidine
Monosaccharide
N-substituted imidazole
Pyrimidine
Imidolactam
Tetrahydrofuran
Azole
Imidazole
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Azacycle
Oxacycle
Organic oxygen compound
Organic nitrogen compound
Alcohol
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Amine
Primary alcohol
Primary amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

adenosines (CHEBI:16335 )
Ribonucleosides (C00212 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	235.5 °C	Not Available
Boiling Point	676.27 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	37 mg/mL	Wishart, D. S., Tzur, D., Knox, C., Eisner, R., Guo, A. C., Young, N., ... & Querengesser, L. (2007). HMDB: the human metabolome database. Nucleic acids research, 35(suppl_1), D521-D526.
LogP	-1.05	Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

Predicted Properties

Property	Value	Source
Water Solubility	14 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-2.1	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	12.45	ChemAxon
pKa (Strongest Basic)	3.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	139.54 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	63.2 m³·mol⁻¹	ChemAxon
Polarizability	25.28 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000050

DrugBank ID

DB00640

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

60961

PDB ID

Not Available

ChEBI ID

16335

Good Scents ID

rw1136651

References

General References

Skalhegg BS, Funderud A, Henanger HH, Hafte TT, Larsen AC, Kvissel AK, Eikvar S, Orstavik S: Protein kinase A (PKA)--a potential target for therapeutic intervention of dysfunctional immune cells. Curr Drug Targets. 2005 Sep;6(6):655-64. [PubMed:16178799 ]
Maytin M, Colucci WS: Cardioprotection: a new paradigm in the management of acute heart failure syndromes. Am J Cardiol. 2005 Sep 19;96(6A):26G-31G. [PubMed:16181820 ]
Dodge-Kafka KL, Soughayer J, Pare GC, Carlisle Michel JJ, Langeberg LK, Kapiloff MS, Scott JD: The protein kinase A anchoring protein mAKAP coordinates two integrated cAMP effector pathways. Nature. 2005 Sep 22;437(7058):574-8. [PubMed:16177794 ]
Gheorghiade M, Teerlink JR, Mebazaa A: Pharmacology of new agents for acute heart failure syndromes. Am J Cardiol. 2005 Sep 19;96(6A):68G-73G. [PubMed:16181825 ]
Jansen RW, Kruijt JK, van Berkel TJ, Meijer DK: Coupling of the antiviral drug ara-AMP to lactosaminated albumin leads to specific uptake in rat and human hepatocytes. Hepatology. 1993 Jul;18(1):146-52. [PubMed:7686877 ]
Yamamoto T, Moriwaki Y, Takahashi S, Fujita T, Tsutsumi Z, Yamakita J, Shimizu K, Shiota M, Ohta S, Higashino K: Determination of adenosine and deoxyadenosine in urine by high-performance liquid chromatography with column switching. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):55-61. [PubMed:9869364 ]
Koeris M, Funke L, Shrestha J, Rich A, Maas S: Modulation of ADAR1 editing activity by Z-RNA in vitro. Nucleic Acids Res. 2005 Sep 21;33(16):5362-70. Print 2005. [PubMed:16177183 ]
Vidotto C, Fousert D, Akkermann M, Griesmacher A, Muller MM: Purine and pyrimidine metabolites in children's urine. Clin Chim Acta. 2003 Sep;335(1-2):27-32. [PubMed:12927681 ]
Sonousi A, Mahran HA, Ibrahim IM, Ibrahim MN, Elfiky AA, Elshemey WM: Novel adenosine derivatives against SARS-CoV-2 RNA-dependent RNA polymerase: an in silico perspective. Pharmacol Rep. 2021 Dec;73(6):1754-1764. doi: 10.1007/s43440-021-00300-9. Epub 2021 Jun 24. [PubMed:34165771 ]

Showing NP-Card for Adenosine (NP0000860)

MOL for NP0000860 (Adenosine)

3D MOL for NP0000860 (Adenosine)

3D SDF for NP0000860 (Adenosine)

3D-SDF for NP0000860 (Adenosine)

PDB for NP0000860 (Adenosine)

3D PDB for NP0000860 (Adenosine)

SMILES for NP0000860 (Adenosine)

INCHI for NP0000860 (Adenosine)

Structure for NP0000860 (Adenosine)

3D Structure for NP0000860 (Adenosine)