Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (21) Show 21 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:47:19 UTC

HMDB ID

HMDB0000050

Secondary Accession Numbers

HMDB0004401
HMDB0004402
HMDB0004421
HMDB00050
HMDB04401
HMDB04402
HMDB04421

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>
HMDB0000050

> <DATABASE_NAME>
hmdb

> <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 View NMR Assignments View Stereo Labels

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 Molecular Weight

267.2413

Monoisotopic Molecular Weight

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 )

Ontology

Physiological effect

Health effect

Septic shock (HMDB: HMDB0000050)

Disposition

Biological location

Cellular substructure

Organelle

Mitochondria

Mitochondria (HMDB: HMDB0000050)

Biofluid or Excreta

Cerebrospinal fluid (HMDB: HMDB0000050)

Excreta

Non-excretory biofluid

Cellular Cytoplasm (PMID: 15882454)
Blood (PMID: 6656991)
Cerebrospinal Fluid (CSF) (PMID: 6656991)
Saliva (PMID: 23857558)

Tissue substructure

All tissues (HMDB: HMDB0000050)
All tissues (HMDB: HMDB0000050)

Tissue

All Tissues (HMDB: HMDB0000050)

Organ

Placenta (HMDB: HMDB0000050)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000050)

Source

Endogenous

Endogenous (HMDB: HMDB0000050)

Plant

Animal

Animal (HMDB: HMDB0000050)

Exogenous

Food

Food (HMDB: HMDB0000050)

Animal origin

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Poultry

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

Caprae

Domestic goat (FooDB: FOOD00529)

Venison

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

Swine

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

Equine

Horse (FooDB: FOOD00378)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Cabbage

Onion-family vegetable

Allium (FooDB: FOOD00005)
Garden onion (FooDB: FOOD00006)
Leek (FooDB: FOOD00007)
Garden onion (var.) (FooDB: FOOD00226)
Shallot (FooDB: FOOD00243)
Wild leek (FooDB: FOOD00396)
Red onion (FooDB: FOOD00962)
Green onion (FooDB: FOOD00963)
Onion-family vegetables (FooDB: FOOD00855)

Root vegetable

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. baccatum) (FooDB: FOOD00231)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Chicory leaves (FooDB: FOOD00250)
Swiss chard (FooDB: FOOD00237)
Malabar spinach (FooDB: FOOD00404)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)
Rocket salad (FooDB: FOOD00244)
Green vegetables (FooDB: FOOD00872)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Horseradish tree (FooDB: FOOD00379)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Sacred lotus (FooDB: FOOD00402)
Okra (FooDB: FOOD00420)
Nopal (FooDB: FOOD00416)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)

Brassica

Brassicas (FooDB: FOOD00857)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)
Citrus (FooDB: FOOD00859)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Strawberry (FooDB: FOOD00083)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Sparkleberry (FooDB: FOOD00190)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Lingonberry (FooDB: FOOD00194)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Muscadine grape (FooDB: FOOD00203)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Alaska blueberry (FooDB: FOOD00380)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Wampee (FooDB: FOOD00980)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Cape gooseberry (FooDB: FOOD00988)
Lantern fruit (FooDB: FOOD00986)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Fruits (FooDB: FOOD00871)

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Japanese walnut (FooDB: FOOD00240)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Chinese chestnut (FooDB: FOOD00331)
Hazelnut (FooDB: FOOD00376)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)
Mixed nuts (FooDB: FOOD00771)
Nuts (FooDB: FOOD00869)

Cereal and cereal product

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)
Other bread (FooDB: FOOD00269)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)
Pulses (FooDB: FOOD00867)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Cantaloupe melon (FooDB: FOOD00984)
Acorn squash (FooDB: FOOD00972)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Dish

Other dish

Taco shell (FooDB: FOOD00991)
Tostada shell (FooDB: FOOD00992)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Synthetic

Personal care products

Personal care products (HMDB: HMDB0000050)

Process

Naturally occurring process

Biological process

Biochemical pathway

Azathioprine Action Pathway (HMDB: HMDB0000050)

Metabolic pathway

Purine Metabolism (HMDB: HMDB0000050)
Methionine Metabolism (PathBank: SMP0087342)
Selenoamino Acid Metabolism (PathBank: SMP0000029)
Betaine Metabolism (PathBank: SMP0000123)
Adenine and Adenosine Salvage I (PathBank: SMP0002081)
Adenine and Adenosine Salvage II (PathBank: SMP0002083)
Adenine and Adenosine Salvage III (PathBank: SMP0002084)
Purine Ribonucleosides Degradation (PathBank: SMP0002088)
Adenosine Nucleotides Degradation (PathBank: SMP0002103)
Methionine Metabolism and Salvage (PathBank: SMP0002310)
Cytokinins Degradation (PathBank: SMP0012058)

Disease pathway

Adenosine Deaminase Deficiency (HMDB: HMDB0000050)
Adenylosuccinate Lyase Deficiency (PathBank: SMP0000167)
Gout or Kelley-Seegmiller Syndrome (PathBank: SMP0000365)
Lesch-Nyhan Syndrome (LNS) (PathBank: SMP0000364)
Molybdenum Cofactor Deficiency (PathBank: SMP0000203)
Xanthine Dehydrogenase Deficiency (Xanthinuria) (PathBank: SMP0000220)
Purine Nucleoside Phosphorylase Deficiency (PathBank: SMP0000210)
AICA-Ribosiduria (PathBank: SMP0000168)
Cystathionine beta-Synthase Deficiency (PathBank: SMP0000177)
Hypermethioninemia (PathBank: SMP0000341)
S-Adenosylhomocysteine (SAH) Hydrolase Deficiency (PathBank: SMP0000214)
Glycine N-Methyltransferase Deficiency (PathBank: SMP0000222)
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD) (PathBank: SMP0000340)
Methionine Adenosyltransferase Deficiency (PathBank: SMP0000221)
Xanthinuria Type I (PathBank: SMP0000512)
Xanthinuria Type II (PathBank: SMP0000513)
Adenine Phosphoribosyltransferase Deficiency (APRT) (PathBank: SMP0000535)
Mitochondrial DNA Depletion Syndrome (PathBank: SMP0000536)
Myoadenylate Deaminase Deficiency (PathBank: SMP0000537)
Homocystinuria-Megaloblastic Anemia Due to Defect in Cobalamin Metabolism, cblG Complementation Type (PathBank: SMP0000570)
Mitochondrial DNA Depletion Syndrome (PathBank: SMP0120601)

Drug action pathway

Azathioprine Action Pathway (PathBank: SMP0000427)
Mercaptopurine Action Pathway (PathBank: SMP0000428)
Thioguanine Action Pathway (PathBank: SMP0000430)

Protein pathway

Role

Industrial application

Personal care product

Personal care product (HMDB: HMDB0000050)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Pharmaceutical industry

Analgesic (HMDB: HMDB0000050)
anti-arrhythmia drug (HMDB: HMDB0000050)

Biomarker

Adenylosuccinate lyase deficiency (MarkerDB: MDB00000024)
Sepsis (MarkerDB: MDB00000024)

immunomodulator (HMDB: HMDB0000050)
platelet aggregation factor inhibitor (HMDB: HMDB0000050)

Indirect biological role

Metabotoxin

Metabotoxin (HMDB: HMDB0000050)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	235.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	37 mg/mL	Human Metabolome Project
LogP	-1.05	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Astarita_neg	151.0	30932474
[M-H]-	Baker	162.133	30932474
[M-H]-	MetCCS_test_neg	155.2	30932474
[M+H]+	Astarita_pos	151.3	30932474
[M+H]+	Baker	156.967	30932474
[M+H]+	MetCCS_test_pos	155.71	30932474
[M-H]-	Not Available	158.2	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000145
[M+H]+	Not Available	156.5	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000145

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	160.038	31661259
DarkChem	[M-H]-	156.184	31661259
AllCCS	[M+H]+	160.422	32859911
AllCCS	[M-H]-	159.221	32859911
DeepCCS	[M+H]+	162.827	30932474
DeepCCS	[M-H]-	160.46	30932474
DeepCCS	[M-2H]-	194.339	30932474
DeepCCS	[M+Na]+	169.517	30932474
AllCCS	[M+H]+	160.4	32859911
AllCCS	[M+H-H2O]+	156.9	32859911
AllCCS	[M+NH4]+	163.7	32859911
AllCCS	[M+Na]+	164.6	32859911
AllCCS	[M-H]-	159.2	32859911
AllCCS	[M+Na-2H]-	158.7	32859911
AllCCS	[M+HCOO]-	158.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Adenosine	NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1	3472.6	Standard polar	33892256
Adenosine	NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1	1712.7	Standard non polar	33892256
Adenosine	NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1	2593.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Adenosine,1TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O	2670.2	Semi standard non polar	33892256
Adenosine,1TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H]1O	2671.0	Semi standard non polar	33892256
Adenosine,1TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC2=C(N)N=CN=C21	2660.9	Semi standard non polar	33892256
Adenosine,1TMS,isomer #4	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O	2711.3	Semi standard non polar	33892256
Adenosine,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O	2605.5	Semi standard non polar	33892256
Adenosine,2TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C	2600.5	Semi standard non polar	33892256
Adenosine,2TMS,isomer #3	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]1O	2648.9	Semi standard non polar	33892256
Adenosine,2TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H]1O[Si](C)(C)C	2607.3	Semi standard non polar	33892256
Adenosine,2TMS,isomer #5	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]1O	2651.8	Semi standard non polar	33892256
Adenosine,2TMS,isomer #6	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O[Si](C)(C)C	2640.9	Semi standard non polar	33892256
Adenosine,2TMS,isomer #7	C[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O)[Si](C)(C)C	2659.3	Semi standard non polar	33892256
Adenosine,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2569.9	Semi standard non polar	33892256
Adenosine,3TMS,isomer #2	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C	2621.9	Semi standard non polar	33892256
Adenosine,3TMS,isomer #3	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O	2617.5	Semi standard non polar	33892256
Adenosine,3TMS,isomer #4	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O	2631.0	Semi standard non polar	33892256
Adenosine,3TMS,isomer #5	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2621.6	Semi standard non polar	33892256
Adenosine,3TMS,isomer #6	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H]1O	2642.3	Semi standard non polar	33892256
Adenosine,3TMS,isomer #7	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21	2633.4	Semi standard non polar	33892256
Adenosine,4TMS,isomer #1	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2630.3	Semi standard non polar	33892256
Adenosine,4TMS,isomer #1	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2712.2	Standard non polar	33892256
Adenosine,4TMS,isomer #1	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3681.5	Standard polar	33892256
Adenosine,4TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O	2642.5	Semi standard non polar	33892256
Adenosine,4TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O	2784.1	Standard non polar	33892256
Adenosine,4TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O	3406.1	Standard polar	33892256
Adenosine,4TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C	2639.8	Semi standard non polar	33892256
Adenosine,4TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C	2771.1	Standard non polar	33892256
Adenosine,4TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C	3366.6	Standard polar	33892256
Adenosine,4TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H]1O[Si](C)(C)C	2643.5	Semi standard non polar	33892256
Adenosine,4TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H]1O[Si](C)(C)C	2795.9	Standard non polar	33892256
Adenosine,4TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H]1O[Si](C)(C)C	3336.5	Standard polar	33892256
Adenosine,5TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2689.3	Semi standard non polar	33892256
Adenosine,5TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2768.0	Standard non polar	33892256
Adenosine,5TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	3158.7	Standard polar	33892256
Adenosine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O	2926.5	Semi standard non polar	33892256
Adenosine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H]1O	2920.6	Semi standard non polar	33892256
Adenosine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC2=C(N)N=CN=C21	2911.6	Semi standard non polar	33892256
Adenosine,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O	2906.2	Semi standard non polar	33892256
Adenosine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3078.2	Semi standard non polar	33892256
Adenosine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3076.1	Semi standard non polar	33892256
Adenosine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O	3062.2	Semi standard non polar	33892256
Adenosine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H]1O[Si](C)(C)C(C)(C)C	3070.4	Semi standard non polar	33892256
Adenosine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3042.6	Semi standard non polar	33892256
Adenosine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3035.9	Semi standard non polar	33892256
Adenosine,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O)[Si](C)(C)C(C)(C)C	3062.0	Semi standard non polar	33892256
Adenosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3224.8	Semi standard non polar	33892256
Adenosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3226.4	Semi standard non polar	33892256
Adenosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3227.4	Semi standard non polar	33892256
Adenosine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O	3221.6	Semi standard non polar	33892256
Adenosine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3212.1	Semi standard non polar	33892256
Adenosine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@@H]1O	3230.8	Semi standard non polar	33892256
Adenosine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21	3215.2	Semi standard non polar	33892256
Adenosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3402.4	Semi standard non polar	33892256
Adenosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3520.5	Standard non polar	33892256
Adenosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3871.2	Standard polar	33892256
Adenosine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3369.8	Semi standard non polar	33892256
Adenosine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3596.8	Standard non polar	33892256
Adenosine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3644.5	Standard polar	33892256
Adenosine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3376.3	Semi standard non polar	33892256
Adenosine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3592.8	Standard non polar	33892256
Adenosine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3618.2	Standard polar	33892256
Adenosine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@@H]1O[Si](C)(C)C(C)(C)C	3363.7	Semi standard non polar	33892256
Adenosine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@@H]1O[Si](C)(C)C(C)(C)C	3595.8	Standard non polar	33892256
Adenosine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@@H]1O[Si](C)(C)C(C)(C)C	3594.8	Standard polar	33892256
Adenosine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3562.3	Semi standard non polar	33892256
Adenosine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3694.1	Standard non polar	33892256
Adenosine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3538.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Adenosine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-0f7w-1890000000-5c70a5423faa5e8eceaf	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Adenosine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-001v-0691000000-8f88854b7d5adec5c558	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Adenosine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-001s-0790000000-cc3bcd977e11efd4ea25	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Adenosine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)	splash10-00di-9460000000-3ae19bfaa5d2df72f9b1	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Adenosine GC-MS (3 TMS)	splash10-0gc0-0590000000-05874cecded3009c1f4d	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Adenosine GC-MS (4 TMS)	splash10-0fsv-1792000000-b37fd6826f28aaf9e825	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Adenosine GC-EI-TOF (Non-derivatized)	splash10-0f7w-1890000000-5c70a5423faa5e8eceaf	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Adenosine GC-EI-TOF (Non-derivatized)	splash10-001v-0691000000-8f88854b7d5adec5c558	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Adenosine GC-EI-TOF (Non-derivatized)	splash10-001s-0790000000-cc3bcd977e11efd4ea25	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Adenosine GC-EI-TOF (Non-derivatized)	splash10-00di-9460000000-3ae19bfaa5d2df72f9b1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Adenosine GC-MS (Non-derivatized)	splash10-0gc0-0590000000-05874cecded3009c1f4d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Adenosine GC-MS (Non-derivatized)	splash10-0fsv-1792000000-b37fd6826f28aaf9e825	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adenosine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4v-9560000000-986f3b1dfa5d898ed7a2	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adenosine GC-MS (3 TMS) - 70eV, Positive	splash10-01c4-6912500000-ae103f43432726c1ad22	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adenosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adenosine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adenosine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adenosine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adenosine GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adenosine GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adenosine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adenosine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adenosine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adenosine GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Adenosine GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-001i-0940000000-da71247788bf1ba222e2	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-001i-0920000000-f2e8ec028abdd674b5e3	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-001i-0910000000-815ed65588c07415cd65	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-001i-1910000000-2780e737da8848411c4f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-053r-1900000000-c6c1128990661334c15b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-001i-0910000000-35f90965f1f3c2b3236b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine LC-ESI-QFT , negative-QTOF	splash10-001i-0910000000-65268017a112bc263b5e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine LC-ESI-QFT , negative-QTOF	splash10-001i-0900000000-375c0e137f7068cf49af	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine LC-ESI-QFT , negative-QTOF	splash10-001i-0900000000-ad5db8e5cbaacc341347	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine LC-ESI-QFT , negative-QTOF	splash10-001i-0900000000-718be441310a581854a6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine LC-ESI-QFT , negative-QTOF	splash10-001i-0900000000-765c0fccf80d24951ef9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine LC-ESI-QFT , negative-QTOF	splash10-053r-2900000000-2f0ca594f7cc031e54e7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine LC-ESI-QQ , negative-QTOF	splash10-001i-0940000000-da71247788bf1ba222e2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine LC-ESI-QQ , negative-QTOF	splash10-001i-0920000000-f2e8ec028abdd674b5e3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine LC-ESI-QQ , negative-QTOF	splash10-001i-0910000000-815ed65588c07415cd65	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine LC-ESI-QQ , negative-QTOF	splash10-001i-1910000000-bbdd67de0fcb7c302c8f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine LC-ESI-QQ , negative-QTOF	splash10-053r-1900000000-2c12434eaabba59a0a6c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine LC-ESI-QTOF , negative-QTOF	splash10-001i-0910000000-35f90965f1f3c2b3236b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine Linear Ion Trap , negative-QTOF	splash10-001i-0980000000-56af5755b924f7c42369	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine Linear Ion Trap , negative-QTOF	splash10-001i-0980000000-25acc7da5b6ea2bee529	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine Linear Ion Trap , negative-QTOF	splash10-001i-3900000000-602d3adcf68051f2992d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine Linear Ion Trap , negative-QTOF	splash10-001i-4900000000-85777953862ffa85a828	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine Linear Ion Trap , negative-QTOF	splash10-014i-0090000000-8c7c25ea99344e167af5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine Linear Ion Trap , negative-QTOF	splash10-014i-0090000000-2de6609bcaad91b510b5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Adenosine 40V, Negative-QTOF	splash10-001i-1900000000-0f76e400a56cad0d0fca	2021-09-20	HMDB team, MONA	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 400 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Mitochondria
Lysosome

Biospecimen Locations

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

Tissue Locations

All Tissues
Placenta

Pathways

Name	SMPDB/PathBank	KEGG
Purine metabolism	Not Available
Selenocompound metabolism	Not Available
Adenosine Deaminase Deficiency		Not Available
Adenylosuccinate Lyase Deficiency		Not Available
Gout or Kelley-Seegmiller Syndrome		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.505 +/- 0.142 uM	Adult (>18 years old)	Both	Normal	7056808	details
Blood	Detected and Quantified	5.66 +/- 1.71 uM	Adult (>18 years old)	Both	Normal	7056808	details
Blood	Detected and Quantified	0.285 +/- 0.060 uM	Adult (>18 years old)	Both	Normal	6736187	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.2 (0.1-0.3) uM	Adult (>18 years old)	Both	Normal	6656991	details
Blood	Detected and Quantified	0.0425 +/- 0.0029 uM	Adult (>18 years old)	Both	Normal	17172976	details
Blood	Detected and Quantified	0.31 +/- 0.29 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Breast Milk	Detected and Quantified	2.96 +/- 5.88 uM	Adult (>18 years old)	Female	Normal	7702711	details
Cellular Cytoplasm	Detected and Quantified	1.20 (0.90-1.50) uM	Adult (>18 years old)	Both	Normal	15882454	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.01 +/- 0.002 uM	Adult (>18 years old)	Not Specified	Normal	15028034	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0 - 0.1 uM	Adult (>18 years old)	Both	Normal	6656991	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21330412	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Saliva	Detected and Quantified	0.38 +/- 0.28 uM	Adult (>18 years old)	Female	Normal	23857558	details
Saliva	Detected and Quantified	0.24 +/- 0.32 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected and Quantified	0.242 +/- 0.133 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.306 +/- 0.156 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Urine	Detected and Quantified	0.3.4 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	27504266	details
Urine	Detected and Quantified	0-3.8 umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	27504266	details
Urine	Detected and Quantified	0.17 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19309105	details
Urine	Detected and Quantified	<2 umol/mmol creatinine	Not Specified	Not Specified	Normal	21963049	details
Urine	Detected and Quantified	1.4 (0.9-2.3) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0-11 umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	9.3 +/- 8.044 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	4.7+/-7.0 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	12927681	details
Urine	Detected and Quantified	17.5+/-14.6 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	12927681	details
Urine	Detected and Quantified	0.2 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	30817767	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.50 (0.09-0.92) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15116424	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.126 +/- 0.018 uM	Adult (>18 years old)	Both	Septic shock	17172976	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Irritable bowel syndrome	21330412	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Unclassified IBD	27609529	details
Saliva	Detected and Quantified	0.40 +/- 0.20 uM	Adult (>18 years old)	Male	Alzheimer's disease	23857558	details
Saliva	Detected and Quantified	0.48 +/- 0.32 uM	Adult (>18 years old)	Male	Frontotemporal lobe dementia	23857558	details
Saliva	Detected and Quantified	0.30 +/- 0.08 uM	Adult (>18 years old)	Both	Lewy body disease	23857558	details
Urine	Detected and Quantified	6.3-7.2 umol/mmol creatinine	Infant (0-1 year old)	Both	Adenylosuccinase deficiency	27504266	details
Urine	Detected and Quantified	7.1 umol/mmol creatinine	Adult (>18 years old)	Male	Adenosine kinase deficiency	21963049	details
Urine	Detected and Quantified	9.9 umol/mmol creatinine	Adolescent (13-18 years old)	Female	Adenosine kinase deficiency	21963049	details
Urine	Detected and Quantified	3.329 +/- 1.977 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Septic shock
Kaufmann I, Hoelzl A, Schliephake F, Hummel T, Chouker A, Lysenko L, Peter K, Thiel M: Effects of adenosine on functions of polymorphonuclear leukocytes from patients with septic shock. Shock. 2007 Jan;27(1):25-31. [PubMed:17172976 ]
Irritable bowel syndrome
Ponnusamy K, Choi JN, Kim J, Lee SY, Lee CH: Microbial community and metabolomic comparison of irritable bowel syndrome faeces. J Med Microbiol. 2011 Jun;60(Pt 6):817-27. doi: 10.1099/jmm.0.028126-0. Epub 2011 Feb 17. [PubMed:21330412 ]
Crohn's disease
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Ulcerative colitis
Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
Colorectal cancer
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Alzheimer's disease
Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Frontotemporal dementia
Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Lewy body disease
Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Adenosine kinase deficiency
Bjursell MK, Blom HJ, Cayuela JA, Engvall ML, Lesko N, Balasubramaniam S, Brandberg G, Halldin M, Falkenberg M, Jakobs C, Smith D, Struys E, von Dobeln U, Gustafsson CM, Lundeberg J, Wedell A: Adenosine kinase deficiency disrupts the methionine cycle and causes hypermethioninemia, encephalopathy, and abnormal liver function. Am J Hum Genet. 2011 Oct 7;89(4):507-15. doi: 10.1016/j.ajhg.2011.09.004. Epub 2011 Sep 28. [PubMed:21963049 ]
Adenylosuccinate lyase deficiency
Donti TR, Cappuccio G, Hubert L, Neira J, Atwal PS, Miller MJ, Cardon AL, Sutton VR, Porter BE, Baumer FM, Wangler MF, Sun Q, Emrick LT, Elsea SH: Diagnosis of adenylosuccinate lyase deficiency by metabolomic profiling in plasma reveals a phenotypic spectrum. Mol Genet Metab Rep. 2016 Jul 27;8:61-6. doi: 10.1016/j.ymgmr.2016.07.007. eCollection 2016 Sep. [PubMed:27504266 ]

Associated OMIM IDs

266600 (Crohn's disease)
114500 (Colorectal cancer)
104300 (Alzheimer's disease)
600274 (Frontotemporal dementia)
610247 (Eosinophilic esophagitis)
614300 (Adenosine kinase deficiency)
103050 (Adenylosuccinate lyase deficiency)

External Links

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

VMH ID

ADN

MarkerDB ID

MDB00000024

Good Scents ID

Not Available

References

Synthesis Reference

Liao, Ben-ren; Yuan, Zhen-wen. Synthesis of adenosine from inosine. Huaxue Shiji (2006), 28(10), 633-634.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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. [PubMed:6656991 ]
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. [PubMed:15116424 ]
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. [PubMed:15882454 ]
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 ]
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. [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. [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 ]
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. [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 ]

Only showing the first 10 proteins. There are 21 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 5'-nucleotidase

General function:: Involved in hydrolase activity
Specific function:: Hydrolyzes extracellular nucleotides into membrane permeable nucleosides.
Gene Name:: NT5E
Uniprot ID:: P21589
Molecular weight:: 57948.125

Reactions

Adenosine monophosphate + Water → Adenosine + Phosphate	details

Enzyme Details

2. Cytosolic 5'-nucleotidase 1B

General function:: Involved in nucleotide binding
Specific function:: Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides. Helps to regulate adenosine levels (By similarity).
Gene Name:: NT5C1B
Uniprot ID:: Q96P26
Molecular weight:: 68803.055

Reactions

Adenosine monophosphate + Water → Adenosine + Phosphate	details

Enzyme Details

3. Cytosolic 5'-nucleotidase 1A

General function:: Involved in nucleotide binding
Specific function:: Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides and has a broad substrate specificity. Helps to regulate adenosine levels in heart during ischemia and hypoxia.
Gene Name:: NT5C1A
Uniprot ID:: Q9BXI3
Molecular weight:: 41020.145

Reactions

Adenosine monophosphate + Water → Adenosine + Phosphate	details

Enzyme Details

4. 5'(3')-deoxyribonucleotidase, cytosolic type

General function:: Involved in metal ion binding
Specific function:: Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides, with a preference for dUMP and dTMP, intermediate activity towards dGMP, and low activity towards dCMP and dAMP.
Gene Name:: NT5C
Uniprot ID:: Q8TCD5
Molecular weight:: Not Available

Reactions

Adenosine monophosphate + Water → Adenosine + Phosphate	details

Enzyme Details

5. Deoxycytidine kinase

General function:: Involved in ATP binding
Specific function:: Required for the phosphorylation of the deoxyribonucleosides deoxycytidine (dC), deoxyguanosine (dG) and deoxyadenosine (dA). Has broad substrate specificity, and does not display selectivity based on the chirality of the substrate. It is also an essential enzyme for the phosphorylation of numerous nucleoside analogs widely employed as antiviral and chemotherapeutic agents.
Gene Name:: DCK
Uniprot ID:: P27707
Molecular weight:: 30518.315

Reactions

Adenosine triphosphate + Adenosine → ADP + Adenosine monophosphate	details

Enzyme Details

6. 5'(3')-deoxyribonucleotidase, mitochondrial

General function:: Involved in phosphatase activity
Specific function:: Dephosphorylates specifically the 5' and 2'(3')-phosphates of uracil and thymine deoxyribonucleotides, and so protects mitochondrial DNA replication from excess dTTP. Has only marginal activity towards dIMP and dGMP.
Gene Name:: NT5M
Uniprot ID:: Q9NPB1
Molecular weight:: Not Available

Reactions

Adenosine monophosphate + Water → Adenosine + Phosphate	details

Enzyme Details

7. Adenosine kinase

General function:: Involved in adenosine kinase activity
Specific function:: ATP dependent phosphorylation of adenosine and other related nucleoside analogs to monophosphate derivatives. Serves as a potential regulator of concentrations of extracellular adenosine and intracellular adenine nucleotides.
Gene Name:: ADK
Uniprot ID:: P55263
Molecular weight:: 38702.93

Reactions

Adenosine triphosphate + Adenosine → ADP + Adenosine monophosphate	details

References

Boison D: Adenosine kinase, epilepsy and stroke: mechanisms and therapies. Trends Pharmacol Sci. 2006 Dec;27(12):652-8. Epub 2006 Oct 23. [PubMed:17056128 ]

Enzyme Details

8. Putative adenosylhomocysteinase 3

General function:: Involved in adenosylhomocysteinase activity
Specific function:: Not Available
Gene Name:: AHCYL2
Uniprot ID:: Q96HN2
Molecular weight:: 66592.445

Reactions

S-Adenosylhomocysteine + Water → Homocysteine + Adenosine	details
Se-Adenosylselenohomocysteine + Water → Adenosine + Selenohomocysteine	details

Enzyme Details

9. Adenosylhomocysteinase

General function:: Involved in adenosylhomocysteinase activity
Specific function:: Adenosylhomocysteine is a competitive inhibitor of S-adenosyl-L-methionine-dependent methyl transferase reactions; therefore adenosylhomocysteinase may play a key role in the control of methylations via regulation of the intracellular concentration of adenosylhomocysteine.
Gene Name:: AHCY
Uniprot ID:: P23526
Molecular weight:: 47715.715

Reactions

S-Adenosylhomocysteine + Water → Homocysteine + Adenosine	details
Se-Adenosylselenohomocysteine + Water → Adenosine + Selenohomocysteine	details

Enzyme Details

10. Putative adenosylhomocysteinase 2

General function:: Involved in adenosylhomocysteinase activity
Specific function:: Not Available
Gene Name:: AHCYL1
Uniprot ID:: O43865
Molecular weight:: 53753.0

Reactions

S-Adenosylhomocysteine + Water → Homocysteine + Adenosine	details
Se-Adenosylselenohomocysteine + Water → Adenosine + Selenohomocysteine	details

Only showing the first 10 proteins. There are 21 proteins in total.

Show all enzymes and transporters

Showing metabocard for Adenosine (HMDB0000050)

MOL for HMDB0000050 (Adenosine)

3D MOL for HMDB0000050 (Adenosine)

3D SDF for HMDB0000050 (Adenosine)

3D-SDF for HMDB0000050 (Adenosine)

PDB for HMDB0000050 (Adenosine)

3D PDB for HMDB0000050 (Adenosine)

SMILES for HMDB0000050 (Adenosine)

INCHI for HMDB0000050 (Adenosine)

Structure for HMDB0000050 (Adenosine)

3D Structure for HMDB0000050 (Adenosine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

References

Reactions

Reactions

Reactions