MiMeDB: Showing metabocard for Adenosine (MMDBc0000015)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:24:50 UTC

Update Date

2024-10-09 23:13:38 UTC

Metabolite ID

MMDBc0000015

Metabolite 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>
MMDBc0000015

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₀H₁₃N₅O₄

Average Mass

267.2413

Monoisotopic Mass

267.096753929

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

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Lysosome
Mitochondria

Biospecimen Locations

All Tissues
Blood
Breast Milk
Cellular Cytoplasm
Cerebrospinal Fluid (CSF)
Feces
Placenta
Saliva
Urine

Tissue Locations

All Tissues
Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191677	5'-nucleotidase	Unknown	P21589	Homo sapiens
MMDBp0191680	Cytosolic 5'-nucleotidase 1B	Unknown	Q96P26	Homo sapiens
MMDBp0191681	Cytosolic 5'-nucleotidase 1A	Unknown	Q9BXI3	Homo sapiens
MMDBp0191682	5'(3')-deoxyribonucleotidase, cytosolic type	Unknown	Q8TCD5	Homo sapiens
MMDBp0191683	Deoxycytidine kinase	Enzyme	P27707	Homo sapiens
MMDBp0191684	5'(3')-deoxyribonucleotidase, mitochondrial	Unknown	Q9NPB1	Homo sapiens
MMDBp0192281	Adenosine kinase	Unknown	P55263	Homo sapiens
MMDBp0192301	Putative adenosylhomocysteinase 3	Unknown	Q96HN2	Homo sapiens
MMDBp0192302	Adenosylhomocysteinase	Unknown	P23526	Homo sapiens
MMDBp0192303	Putative adenosylhomocysteinase 2	Unknown	O43865	Homo sapiens
MMDBp0192304	Adenosine deaminase	Enzyme	P00813	Homo sapiens
MMDBp0193184	Adenosine receptor A1	Enzyme	P30542	Homo sapiens
MMDBp0193186	Adenosine receptor A2a	Enzyme	P29274	Homo sapiens
MMDBp0193188	Adenosine receptor A3	Enzyme	P33765	Homo sapiens
MMDBp0193189	Adenosine receptor A2b	Enzyme	P29275	Homo sapiens
MMDBp0193860	Cytosolic 5'-nucleotidase 3	Enzyme	Q9H0P0	Homo sapiens
MMDBp0193884	Adenosine 3'-phospho 5'-phosphosulfate transporter 1	Enzyme	Q8TB61	Homo sapiens
MMDBp0193932	Cytosolic purine 5'-nucleotidase	Unknown	P49902	Homo sapiens
MMDBp0193933	Purine nucleoside phosphorylase	Enzyme	P00491	Homo sapiens
MMDBp0196349	Adenosine 3'-phospho 5'-phosphosulfate transporter 2	Unknown	Q9H1N7	Homo sapiens
MMDBp0196704	Adenosine deaminase CECR1	Unknown	Q9NZK5

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0019299	Adenine	Adenosine	Purine nucleoside phosphorylase DeoD-type	Phosphorylation	PathBank	31602464
MMDBr0019301	Adenosine	Inosine	Adenosine deaminase	Hydrolytic deamination	PathBank	31602464
MMDBr0019305	Adenosine	Adenine	Riboflavin synthase	Synthesis	PathBank	31602464
MMDBr0019315	Adenosine	Adenine	Purine nucleoside phosphorylase DeoD-type	Phosphorylation	PathBank	31602464
MMDBr0019348	Adenosine monophosphate	Adenosine	Alkaline phosphatase	Dephosphorylation	PathBank	31602464
MMDBr0019448	S-Adenosylhomocysteine	Adenosine	Adenosylhomocysteinase	Reversible hydrolysis	PathBank	31602464
MMDBr0026013	Adenosine 3'-phosphate	Adenosine	5'/3'-nucleotidase SurE	Hydrolysis of nucleotide	RHEA	34755880
MMDBr0026022	Adenosine monophosphate	Adenosine	5'-nucleotidase SurE	Hydrolysis of nucleotide; Dephosphorylation	RHEA	34755880
MMDBr0026023	Cytidine monophosphate	Adenosine	5'-nucleotidase SurE	Hydrolysis of nucleotide; Dephosphorylation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Adenylosuccinate lyase deficiency	Increased	Association	Human Urine	HMDB	27504266
Alzheimer's disease		Association	Human Saliva	HMDB	23857558
Frontotemporal dementia		Association	Human Saliva	HMDB	23857558
Septic shock		Association	Human Blood	HMDB	17172976
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota	Apicomplexa	1		Microbial culture
Bacteria/Eubacteria	Firmicutes	495	Human ; Human stool; Human feces; Human sputum; Human subgingival plaque; Human saliva; Human pleural fluid plaque; Pig ; Human urine; Human mucosa; Human supragingival plaque; Cattle	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	526	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Rat ; Sheep ; River trout ; Cattle	Metabolic reconstruction
Bacteria	Actinobacteria	20	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	160	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	2	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	241	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human supragingival plaque; Human subgingival plaque; Human gastric fluid; Human urine	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	35	Human ; Human stool; Human feces; Human sputum; Human subgingival plaque; Human saliva; Human pleural fluid plaque; Pig ; Human urine; Human mucosa; Human supragingival plaque; Cattle	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Proteobacteria	17	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Rat ; Sheep ; River trout ; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	6	Human feces; Human	Metabolic reconstruction
Archaea	Thaumarchaeota	2		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	23	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	8		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	2	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	3	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	2		Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Basidiomycota	1	Human feces
Eukaryota/Fungi	Ascomycota	5	Human feces; Human saliva	Unknown
Archaea/Archaea	Euryarchaeota	26		Metabolic reconstruction
Archaea/Archaea	Crenarchaeota	4		Metabolic reconstruction
Bacteria/Eubacteria	Aquificae	1
Bacteria/Eubacteria	Chlorobi	8
Bacteria/Eubacteria	Cyanobacteria	17
Archaea	Euryarchaeota	1
Bacteria/Eubacteria	Acidobacteria	1
Bacteria	nah	2
Bacteria/Eubacteria	Thermotogae	1
Bacteria/Eubacteria	Deinococcus-thermus	1

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference
Drugs	U.S. Environmental Protection Agency	CompTox
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Urine	Detected and Quantified	7.1				umol/mmol creatinine	Adult (>18 years old)	Male	Adenosine kinase deficiency	HMDB	21963049
Human Urine	Detected and Quantified	9.9				umol/mmol creatinine	Adolescent (13-18 years old)	Female	Adenosine kinase deficiency	HMDB	21963049
Human Urine	Detected and Quantified			6.3	7.2	umol/mmol creatinine	Infant (0-1 year old)	Both	Adenylosuccinase deficiency	HMDB	27504266
Human Saliva	Detected and Quantified	0.40	0.20			uM	Adult (>18 years old)	Male	Alzheimer's disease	HMDB	23857558
Human Saliva	Detected and Quantified	0.48	0.32			uM	Adult (>18 years old)	Male	Frontotemporal lobe dementia	HMDB	23857558
Human Saliva	Detected and Quantified	0.30	0.08			uM	Adult (>18 years old)	Both	Lewy body disease	HMDB	23857558
Human Blood	Detected and Quantified	0.126	0.018			uM	Adult (>18 years old)	Both	Septic shock	HMDB	17172976
Human Urine	Detected and Quantified	0.17				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19309105
Human Urine	Detected and Quantified	0.2				umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	30817767
Human Urine	Detected and Quantified	<2				umol/mmol creatinine	Not Specified	Not Specified	Normal	HMDB	21963049
Human Cerebrospinal fluid (csf)	Detected and Quantified			0	0.1	uM	Adult (>18 years old)	Both	Normal	HMDB	6656991
Human Urine	Detected and Quantified			0	3.8	umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	HMDB	27504266
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.01	0.002			uM	Adult (>18 years old)	Not Specified	Normal	HMDB	15028034
Human Blood	Detected and Quantified	0.0425	0.0029			uM	Adult (>18 years old)	Both	Normal	HMDB	17172976
Human Blood	Detected and Quantified	0.2		0.1	0.3	uM	Adult (>18 years old)	Both	Normal	HMDB	6656991
Human Blood	Detected and Quantified	0.285	0.060			uM	Adult (>18 years old)	Both	Normal	HMDB	6736187
Human Urine	Detected and Quantified	0.3.4				umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	27504266
Human Saliva	Detected and Quantified	0.38	0.28			uM	Adult (>18 years old)	Female	Normal	HMDB	23857558
Human Urine	Detected and Quantified	0.50		0.09	0.92	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	15116424
Human Blood	Detected and Quantified	0.505	0.142			uM	Adult (>18 years old)	Both	Normal	HMDB	7056808
Human Cellular cytoplasm	Detected and Quantified	1.20		0.90	1.50	uM	Adult (>18 years old)	Both	Normal	HMDB	15882454
Human Urine	Detected and Quantified	1.4		0.9	2.3	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified	17.5	14.6			umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	12927681
Human Breast milk	Detected and Quantified	2.96	5.88			uM	Adult (>18 years old)	Female	Normal	HMDB	7702711
Human Urine	Detected and Quantified	4.7	7.0			umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	12927681
Human Blood	Detected and Quantified	5.66	1.71			uM	Adult (>18 years old)	Both	Normal	HMDB	7056808
Human Urine	Detected and Quantified	3.329	1.977			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	9.3	8.044			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified			0	11	umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Blood	Detected and Quantified	0.31	0.29			uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Saliva	Detected and Quantified	0.242	0.133			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.306	0.156			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	0.24	0.32			uM	Adult (>18 years old)	Both	Normal	HMDB	https://doi.org/10.1007/s11306-015-0840-5
Human All tissues	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21330412
Human Feces	Detected but not Quantified						Infant (0-1 year old)	Both	Normal	HMDB	22411374
Human Feces	Detected but not Quantified						Children (6 - 18 years old)	Not Specified	Normal	HMDB	27609529
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000050

DrugBank ID

DB00640

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

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. doi: 10.2174/1389450054863644. [PubMed:16178799 ]
Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18. doi: 10.1186/1742-4682-2-18. [PubMed:15882454 ]
Lee SH, Jung BH, Kim SY, Chung BC: A rapid and sensitive method for quantitation of nucleosides in human urine using liquid chromatography/mass spectrometry with direct urine injection. Rapid Commun Mass Spectrom. 2004;18(9):973-7. doi: 10.1002/rcm.1400. [PubMed:15116424 ]
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. doi: 10.1016/j.amjcard.2005.07.018. [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. doi: 10.1038/nature03966. [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. doi: 10.1016/j.amjcard.2005.07.023. [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 ]
Ballantyne PJ: Social context and outcomes for the ageing breast cancer patient: considerations for clinical practitioners. J Clin Nurs. 2004 Mar;13(3a):11-21. doi: 10.1111/j.1365-2702.2004.00921.x. [PubMed:15028034 ]
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. doi: 10.1016/s0378-4347(98)00402-2. [PubMed:9869364 ]
Eells JT, Spector R: Purine and pyrimidine base and nucleoside concentrations in human cerebrospinal fluid and plasma. Neurochem Res. 1983 Nov;8(11):1451-7. doi: 10.1007/BF00965000. [PubMed:6656991 ]
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. doi: 10.1093/nar/gki849. 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. doi: 10.1016/s0009-8981(03)00291-2. [PubMed:12927681 ]
Dunne VG, Bhattachayya S, Besser M, Rae C, Griffin JL: Metabolites from cerebrospinal fluid in aneurysmal subarachnoid haemorrhage correlate with vasospasm and clinical outcome: a pattern-recognition 1H NMR study. NMR Biomed. 2005 Feb;18(1):24-33. doi: 10.1002/nbm.918. [PubMed:15455468 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Adenosine (MMDBc0000015)

MOL for #<Metabolite:0x00007f91e0050630>

3D MOL for #<Metabolite:0x00007f91e0050630>

3D SDF for #<Metabolite:0x00007f91e0050630>

3D-SDF for #<Metabolite:0x00007f91e0050630>

PDB for #<Metabolite:0x00007f91e0050630>

3D PDB for #<Metabolite:0x00007f91e0050630>

SMILES for #<Metabolite:0x00007f91e0050630>

INCHI for #<Metabolite:0x00007f91e0050630>

Structure for #<Metabolite:0x00007f91e0050630>

3D Structure for #<Metabolite:0x00007f91e0050630>