You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (269) Show 269 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

HMDB0000045

Secondary Accession Numbers

HMDB00045

Metabolite Identification

Common Name

Adenosine monophosphate

Description

Adenosine monophosphate, also known as 5'-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. AMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase adenine. AMP can be produced during ATP synthesis by the enzyme adenylate kinase. AMP has recently been approved as a 'Bitter Blocker' additive to foodstuffs. When AMP is added to bitter foods or foods with a bitter aftertaste it makes them seem 'sweeter'. This potentially makes lower calorie food products more palatable.

Structure

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

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
   -5.8427   -1.7205   -0.1184 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9364   -0.6182   -0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3270    0.6326    0.2098 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4675    1.6681    0.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1793    1.4188   -0.0328 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7081    0.1906   -0.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6055   -0.8505   -0.3620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8997   -1.9677   -0.6874 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6182   -1.5969   -0.8498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4704   -0.2790   -0.6408 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3113    0.5413   -0.7010 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8501   -0.1497   -0.9778 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9091    0.6653   -0.6832 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0293   -0.0715    0.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4689   -1.1052   -0.8064 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7064   -1.9364   -0.0354 P   0  0  1  0  0  5  0  0  0  0  0  0
    4.5517   -3.4053   -0.3733 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1845   -1.3323   -0.5991 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5361   -1.7047    1.6350 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4136    1.7335    0.2779 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1523    2.8864   -0.4470 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0467    1.1485    0.6582 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8347    2.1158    1.0552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7767   -1.6612   -0.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5507   -2.6244    0.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7894    2.6841    0.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8118   -2.2981   -1.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3803    1.3766   -1.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2825    1.1138   -1.6258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9101    0.5861    0.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7210   -0.4235    1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6872   -2.0844   -1.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0340   -0.9085    1.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0541    1.8730    1.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3087    2.7475   -1.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2438    0.3571    1.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5804    2.9989    0.7422 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 16 15  1  6
 16 17  2  0
 16 18  1  0
 16 19  1  0
 13 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
  7  2  1  0
 22 11  1  0
 10  6  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  9 27  1  0
 11 28  1  6
 13 29  1  6
 14 30  1  0
 14 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  1
 21 35  1  0
 22 36  1  1
 23 37  1  0
M  END

131
  Mrv1652309032023502D          

 23 25  0  0  1  0            999 V2000
    6.9922    2.1365    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    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
    7.4759    1.4682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6604    2.6202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5084    2.8048    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  2  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
    4.1159    0.4272    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  5  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1  8  2  0  0  0  0
  2 16  1  0  0  0  0
  2 17  1  0  0  0  0
 14  3  1  6  0  0  0
 15  4  1  6  0  0  0
  5 18  1  0  0  0  0
 16  9  1  1  0  0  0
  9 19  1  0  0  0  0
  9 20  1  0  0  0  0
 10 20  2  0  0  0  0
 10 21  1  0  0  0  0
 11 19  2  0  0  0  0
 11 23  1  0  0  0  0
 12 22  1  0  0  0  0
 12 23  2  0  0  0  0
 13 22  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000045

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1

> <INCHI_KEY>
UDMBCSSLTHHNCD-KQYNXXCUSA-N

> <FORMULA>
C10H14N5O7P

> <MOLECULAR_WEIGHT>
347.2212

> <EXACT_MASS>
347.063084339

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
29.957102512672282

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-3.13

> <JCHEM_LOGP>
-4.740681198452267

> <ALOGPS_LOGS>
-2.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.252553227745937

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.224067419365932

> <JCHEM_PKA_STRONGEST_BASIC>
3.920119321056712

> <JCHEM_POLAR_SURFACE_AREA>
186.07000000000002

> <JCHEM_REFRACTIVITY>
74.06850000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.31e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
adenylate

> <JCHEM_VEBER_RULE>
0

$$$$

https://cactus.nci.nih.gov/chemical/structure/NC1=C2N=CN(%5BC@@H%5D3O%5BC@H%5...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:36})
 37 39  0  0  0  0  0  0  0  0999 V2000
   -5.8167    2.4258   -0.6351 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1398    1.3551   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7571    1.1986   -0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8035    1.8956   -0.9359 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6545    1.3013   -0.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8005    0.1830   -0.0275 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7379   -0.7496    0.3565 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9095   -1.1249    1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5516   -0.1046    0.2726 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5098   -1.1808    0.1750 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6836   -1.6240    1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8245   -0.6713   -0.4188 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354    0.2446    0.4923 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8370    0.9776    0.1912 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.6669    1.9629   -1.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2846    1.8303    1.4814 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8698   -0.0382   -0.1116 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8526   -2.2099   -0.7713 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1896   -2.0557   -1.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1457   -3.5416   -0.3441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6620   -1.9212   -0.6476 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0741   -1.6234   -1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3506   -3.0670   -0.1427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1251    0.0913    0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8512   -0.7607    1.0343 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1449   -0.5736    1.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7816    0.4538    0.6587 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3364    3.0792   -1.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7721    2.5207   -0.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7229    1.6434   -1.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4952   -1.5129   -0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6247   -0.1653   -1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0044    2.6555   -0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1228    2.2998    1.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7574   -4.2285   -0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2826   -3.8479   -0.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7058   -1.2851    1.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  2  3  2  0  0  0  0
  2 27  1  0  0  0  0
  3  4  1  0  0  0  0
  3 24  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5 30  1  0  0  0  0
  6  7  1  0  0  0  0
  6 24  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  7 21  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 10 18  1  0  0  0  0
 12 13  1  0  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  2  0  0  0  0
 15 33  1  0  0  0  0
 16 34  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 20 35  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 36  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 37  1  0  0  0  0
M  END
$$$$

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 131                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  P   UNK     0      13.052   3.988   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0       9.149   1.271   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.240   2.048   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.214   4.755   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      11.804   3.085   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      13.955   2.741   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      14.299   4.891   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      12.149   5.236   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       7.205  -0.666   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       7.205  -3.145   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       4.414  -0.366   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       3.080  -2.676   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       4.414  -4.986   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       6.780   2.045   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.687   3.289   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.683   0.797   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.151   2.811   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.399   3.714   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.747  -1.136   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.103  -1.906   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.747  -2.676   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.414  -3.446   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.080  -1.136   0.000  0.00  0.00           C+0
CONECT    1    5    6    7    8                                             
CONECT    2   16   17                                                       
CONECT    3   14                                                            
CONECT    4   15                                                            
CONECT    5    1   18                                                       
CONECT    6    1                                                            
CONECT    7    1                                                            
CONECT    8    1                                                            
CONECT    9   16   19   20                                                  
CONECT   10   20   21                                                       
CONECT   11   19   23                                                       
CONECT   12   22   23                                                       
CONECT   13   22                                                            
CONECT   14    3   15   16                                                  
CONECT   15    4   14   17                                                  
CONECT   16    2    9   14                                                  
CONECT   17    2   15   18                                                  
CONECT   18    5   17                                                       
CONECT   19    9   11   21                                                  
CONECT   20    9   10                                                       
CONECT   21   10   19   22                                                  
CONECT   22   12   13   21                                                  
CONECT   23   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    https://cactus.nci.nih.gov/chemical/structure/NC1=C2N=CN(%5BC@@H%5D3O%5BC@H%5... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  N   UNL     1      -5.817   2.426  -0.635  1.00  0.00           N  
HETATM    2  C   UNL     1      -5.140   1.355  -0.078  1.00  0.00           C  
HETATM    3  C   UNL     1      -3.757   1.199  -0.273  1.00  0.00           C  
HETATM    4  N   UNL     1      -2.804   1.896  -0.936  1.00  0.00           N  
HETATM    5  C   UNL     1      -1.655   1.301  -0.793  1.00  0.00           C  
HETATM    6  N   UNL     1      -1.800   0.183  -0.028  1.00  0.00           N  
HETATM    7  C   UNL     1      -0.738  -0.750   0.356  1.00  0.00           C  
HETATM    8  H   UNL     1      -0.909  -1.125   1.365  1.00  0.00           H  
HETATM    9  O   UNL     1       0.552  -0.105   0.273  1.00  0.00           O  
HETATM   10  C   UNL     1       1.510  -1.181   0.175  1.00  0.00           C  
HETATM   11  H   UNL     1       1.684  -1.624   1.156  1.00  0.00           H  
HETATM   12  C   UNL     1       2.825  -0.671  -0.419  1.00  0.00           C  
HETATM   13  O   UNL     1       3.435   0.245   0.492  1.00  0.00           O  
HETATM   14  P   UNL     1       4.837   0.978   0.191  1.00  0.00           P  
HETATM   15  O   UNL     1       4.667   1.963  -1.071  1.00  0.00           O  
HETATM   16  O   UNL     1       5.285   1.830   1.481  1.00  0.00           O  
HETATM   17  O   UNL     1       5.870  -0.038  -0.112  1.00  0.00           O  
HETATM   18  C   UNL     1       0.853  -2.210  -0.771  1.00  0.00           C  
HETATM   19  H   UNL     1       1.190  -2.056  -1.796  1.00  0.00           H  
HETATM   20  O   UNL     1       1.146  -3.542  -0.344  1.00  0.00           O  
HETATM   21  C   UNL     1      -0.662  -1.921  -0.648  1.00  0.00           C  
HETATM   22  H   UNL     1      -1.074  -1.623  -1.612  1.00  0.00           H  
HETATM   23  O   UNL     1      -1.351  -3.067  -0.143  1.00  0.00           O  
HETATM   24  C   UNL     1      -3.125   0.091   0.318  1.00  0.00           C  
HETATM   25  N   UNL     1      -3.851  -0.761   1.034  1.00  0.00           N  
HETATM   26  C   UNL     1      -5.145  -0.574   1.190  1.00  0.00           C  
HETATM   27  N   UNL     1      -5.782   0.454   0.659  1.00  0.00           N  
HETATM   28  H   UNL     1      -5.336   3.079  -1.167  1.00  0.00           H  
HETATM   29  H   UNL     1      -6.772   2.521  -0.497  1.00  0.00           H  
HETATM   30  H   UNL     1      -0.723   1.643  -1.219  1.00  0.00           H  
HETATM   31  H   UNL     1       3.495  -1.513  -0.592  1.00  0.00           H  
HETATM   32  H   UNL     1       2.625  -0.165  -1.363  1.00  0.00           H  
HETATM   33  H   UNL     1       4.004   2.655  -0.943  1.00  0.00           H  
HETATM   34  H   UNL     1       6.123   2.300   1.371  1.00  0.00           H  
HETATM   35  H   UNL     1       0.757  -4.229  -0.903  1.00  0.00           H  
HETATM   36  H   UNL     1      -1.283  -3.848  -0.709  1.00  0.00           H  
HETATM   37  H   UNL     1      -5.706  -1.285   1.778  1.00  0.00           H  
CONECT    1    2   28   29                                            
CONECT    2    1    3    3   27                                       
CONECT    3    2    2    4   24                                       
CONECT    4    3    5    5                                            
CONECT    5    4    4    6   30                                       
CONECT    6    5    7   24                                            
CONECT    7    6    8    9   21                                       
CONECT    8    7                                                      
CONECT    9    7   10                                                 
CONECT   10    9   11   12   18                                       
CONECT   11   10                                                      
CONECT   12   10   13   31   32                                       
CONECT   13   12   14                                                 
CONECT   14   13   15   16   17                                       
CONECT   14   17                                                      
CONECT   15   14   33                                                 
CONECT   16   14   34                                                 
CONECT   17   14   14                                                 
CONECT   18   10   19   20   21                                       
CONECT   19   18                                                      
CONECT   20   18   35                                                 
CONECT   21   18   22    7   23                                       
CONECT   22   21                                                      
CONECT   23   21   36                                                 
CONECT   24    6    3   25   25                                       
CONECT   25   24   24   26                                            
CONECT   26   25   27   27   37                                       
CONECT   27   26   26    2                                            
CONECT   28    1                                                      
CONECT   29    1                                                      
CONECT   30    5                                                      
CONECT   31   12                                                      
CONECT   32   12                                                      
CONECT   33   15                                                      
CONECT   34   16                                                      
CONECT   35   20                                                      
CONECT   36   23                                                      
CONECT   37   26                                                      
MASTER        0    0    0    0    0    0    0    0   37    0   37    0
END

https://cactus.nci.nih.gov/chemical/structure/NC1=C2N=CN(%5BC@@H%5D3O%5BC@H%5...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:36})
 37 39  0  0  0  0  0  0  0  0999 V2000
   -5.8167    2.4258   -0.6351 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1398    1.3551   -0.0778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7571    1.1986   -0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8035    1.8956   -0.9359 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6545    1.3013   -0.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8005    0.1830   -0.0275 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7379   -0.7496    0.3565 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9095   -1.1249    1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5516   -0.1046    0.2726 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5098   -1.1808    0.1750 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6836   -1.6240    1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8245   -0.6713   -0.4188 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354    0.2446    0.4923 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8370    0.9776    0.1912 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.6669    1.9629   -1.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2846    1.8303    1.4814 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8698   -0.0382   -0.1116 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8526   -2.2099   -0.7713 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1896   -2.0557   -1.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1457   -3.5416   -0.3441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6620   -1.9212   -0.6476 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0741   -1.6234   -1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3506   -3.0670   -0.1427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1251    0.0913    0.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8512   -0.7607    1.0343 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1449   -0.5736    1.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7816    0.4538    0.6587 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3364    3.0792   -1.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7721    2.5207   -0.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7229    1.6434   -1.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4952   -1.5129   -0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6247   -0.1653   -1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0044    2.6555   -0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1228    2.2998    1.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7574   -4.2285   -0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2826   -3.8479   -0.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7058   -1.2851    1.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  2  3  2  0  0  0  0
  2 27  1  0  0  0  0
  3  4  1  0  0  0  0
  3 24  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5 30  1  0  0  0  0
  6  7  1  0  0  0  0
  6 24  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  7 21  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 10 18  1  0  0  0  0
 12 13  1  0  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  2  0  0  0  0
 15 33  1  0  0  0  0
 16 34  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 20 35  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 36  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 37  1  0  0  0  0
M  END
$$$$

View in JSmol View Stereo Labels

Synonyms

Value	Source
5'-Adenosine monophosphate	ChEBI
5'-Adenylic acid	ChEBI
5'-AMP	ChEBI
5'-O-Phosphonoadenosine	ChEBI
Adenosine 5'-(dihydrogen phosphate)	ChEBI
Adenosine 5'-phosphate	ChEBI
Adenosine phosphate	ChEBI
Adenosine-5'-monophosphoric acid	ChEBI
Adenosine-5'p	ChEBI
Adenosini phosphas	ChEBI
Adenylate	ChEBI
Adenylic acid	ChEBI
Ado5'p	ChEBI
AMP	ChEBI
Fosfato de adenosina	ChEBI
pA	ChEBI
PAdo	ChEBI
Phosphate d'adenosine	ChEBI
Adenosine 5'-monophosphate	Kegg
Adenyl	Kegg
5'-Adenosine monophosphoric acid	Generator
5'-Adenylate	Generator
Adenosine 5'-(dihydrogen phosphoric acid)	Generator
Adenosine 5'-phosphoric acid	Generator
Adenosine phosphoric acid	Generator
Adenosine-5'-monophosphate	Generator
Phosphoric acid d'adenosine	Generator
Adenosine 5'-monophosphoric acid	Generator
Adenosine monophosphoric acid	Generator
Adenosine 5'-phosphorate	HMDB
Adenosine-5'-monophosphorate	HMDB
Adenosine-5-monophosphorate	HMDB
Adenosine-5-monophosphoric acid	HMDB
Adenosine-monophosphate	HMDB
Adenosine-phosphate	HMDB
Adenovite	HMDB
Cardiomone	HMDB
Lycedan	HMDB
Muscle adenylate	HMDB
Muscle adenylic acid	HMDB
My-b-den	HMDB
My-beta-den	HMDB
Phosaden	HMDB
Phosphaden	HMDB
Phosphentaside	HMDB
5'-Phosphate, adenosine	HMDB
Acid, 2'-adenylic	HMDB
2'-Adenylic acid	HMDB
Adenosine 3' phosphate	HMDB
Disodium, adenosine phosphate	HMDB
Phosphate dipotassium, adenosine	HMDB
Adenosine 2'-phosphate	HMDB
Adenosine 5' phosphate	HMDB
Adenosine phosphate dipotassium	HMDB
Dipotassium, adenosine phosphate	HMDB
2' Adenylic acid	HMDB
5' Adenylic acid	HMDB
Acid, 5'-adenylic	HMDB
Adenosine 3'-phosphate	HMDB
monoPhosphate, 2'-adenosine	HMDB
Phosphate disodium, adenosine	HMDB
2' Adenosine monophosphate	HMDB
2'-AMP	HMDB
2'-Adenosine monophosphate	HMDB
Adenosine 2' phosphate	HMDB
Adenosine phosphate disodium	HMDB

Chemical Formula

C₁₀H₁₄N₅O₇P

Average Molecular Weight

347.2212

Monoisotopic Molecular Weight

347.063084339

IUPAC Name

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

Traditional Name

adenylate

CAS Registry Number

61-19-8

SMILES

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

InChI Identifier

InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1

InChI Key

UDMBCSSLTHHNCD-KQYNXXCUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

Purine ribonucleoside monophosphates

Alternative Parents

Substituents

Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Aminopyrimidine
Monoalkyl phosphate
Alkyl phosphate
Monosaccharide
Pyrimidine
Imidolactam
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Tetrahydrofuran
Azole
Imidazole
Heteroaromatic compound
Secondary alcohol
1,2-diol
Organoheterocyclic compound
Oxacycle
Azacycle
Organonitrogen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Alcohol
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

adenosine 5'-phosphate (CHEBI:16027 )
purine ribonucleoside 5'-monophosphate (CHEBI:16027 )
Ribonucleotides (C00020 )

Ontology

Endogenous

Biological location:

Tissue and substructures:

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Biochemical process:

Fatty acid metabolism

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	195 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	10 mg/mL at 20 °C	BEILSTEIN
LogP	Not Available	Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.31 g/L	ALOGPS
logP	-3.1	ALOGPS
logP	-4.7	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	3.92	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	186.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	74.07 m³·mol⁻¹	ChemAxon
Polarizability	29.96 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 Spectral Properties

Collision Cross Sections

Name	Adduct	Type	Data Source	Value	Reference
DeepCCS	[M+H]+	Experimental	Astarita_pos	167.0	30932474
AllCCS	[M-H]-	Experimental	Not Available	173.1	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000144
AllCCS	[M+H]+	Experimental	Not Available	172.0	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000144
DarkChem	[M+H]+	Predicted	Not Available	176.415	31661259
DarkChem	[M-H]-	Predicted	Not Available	169.936	31661259
AllCCS	[M+H]+	Predicted	Not Available	175.112	32859911
AllCCS	[M-H]-	Predicted	Not Available	170.275	32859911

Retention Indices

Underivatized

Not Available

Derivatized

Derivative	Value	Reference
Adenosine monophosphate,1TMS,#1	3077.793	https://arxiv.org/abs/1905.12712
Adenosine monophosphate,1TMS,#2	3063.6353	https://arxiv.org/abs/1905.12712
Adenosine monophosphate,1TMS,#3	3168.5747	https://arxiv.org/abs/1905.12712
Adenosine monophosphate,1TMS,#4	3150.3025	https://arxiv.org/abs/1905.12712
Adenosine monophosphate,2TMS,#1	2971.2905	https://arxiv.org/abs/1905.12712
Adenosine monophosphate,2TMS,#2	3073.799	https://arxiv.org/abs/1905.12712
Adenosine monophosphate,2TMS,#3	3026.5361	https://arxiv.org/abs/1905.12712
Adenosine monophosphate,2TMS,#4	3062.331	https://arxiv.org/abs/1905.12712
Adenosine monophosphate,2TMS,#5	3012.8374	https://arxiv.org/abs/1905.12712
Adenosine monophosphate,2TMS,#6	3105.9402	https://arxiv.org/abs/1905.12712
Adenosine monophosphate,2TMS,#7	3131.4758	https://arxiv.org/abs/1905.12712
Adenosine monophosphate,2TMS,#8	3089.0671	https://arxiv.org/abs/1905.12712
Adenosine monophosphate,1TBDMS,#1	3350.3337	https://arxiv.org/abs/1905.12712
Adenosine monophosphate,1TBDMS,#2	3331.6167	https://arxiv.org/abs/1905.12712
Adenosine monophosphate,1TBDMS,#3	3399.6584	https://arxiv.org/abs/1905.12712
Adenosine monophosphate,1TBDMS,#4	3346.7031	https://arxiv.org/abs/1905.12712
Adenosine monophosphate,2TBDMS,#1	3470.6577	https://arxiv.org/abs/1905.12712
Adenosine monophosphate,2TBDMS,#2	3527.5088	https://arxiv.org/abs/1905.12712
Adenosine monophosphate,2TBDMS,#3	3444.6606	https://arxiv.org/abs/1905.12712
Adenosine monophosphate,2TBDMS,#4	3510.4646	https://arxiv.org/abs/1905.12712
Adenosine monophosphate,2TBDMS,#5	3431.6926	https://arxiv.org/abs/1905.12712
Adenosine monophosphate,2TBDMS,#6	3533.615	https://arxiv.org/abs/1905.12712
Adenosine monophosphate,2TBDMS,#7	3531.2244	https://arxiv.org/abs/1905.12712
Adenosine monophosphate,2TBDMS,#8	3489.9814	https://arxiv.org/abs/1905.12712

Spectra

GC-MS

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (5 TMS)	splash10-014i-0974000000-7ce25c09f93913b81e9b	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-014i-0975000000-8175538459abaf92d36f	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-0974000000-7ce25c09f93913b81e9b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-0975000000-8175538459abaf92d36f	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002b-9713000000-019182f931e395f479cd	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0gl0-4942400000-fb8ced86745a4de1b047	2017-10-06	View Spectrum

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-052b-0209001000-f6c3cf706bb3b839d180	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-053s-0395300000-e2a342872025e6e960ae	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-2b9fb262817de641a5cd	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-053r-0007920000-ee7bab39079e225a1b07	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0109000000-52331e416cbdd8218b97	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-014i-3900000000-ddc799b6e2bb5d5ac9a6	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-68d6660e0cfbfb8f02ad	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-0900000000-27f73c3a0a9566986a0e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03dm-0007009001-639c5cafae90b10dfc5f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0290000000-e0b5612abd24736e70da	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0039210000-3e5b716531d739ca25d9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-0009000000-9232b7438abb1f6256b6	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0007-2109007000-3e1cf347bd9e054b9368	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0006-0002009000-b840e6edcca65562937b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-03di-0190000000-948ec97ae442eda212cb	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-0009000000-bd1c10704f289141803a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0002-0109000000-433eab5bd833cd92f290	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-000b-0709000000-fa268a51905a453bc6f5	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-002b-9104000000-bc358c1d8c03290fc49d	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0913000000-52bfdec6ec6f2f9422f4	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-9bf867ba72f77732e0ce	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900000000-fab6495d31eac8de123c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0032-6709000000-fd9ea223f556b17d2d3a	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0059-8900000000-3937203187746280b10a	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9200000000-5947ff2a364087cb0e38	2016-09-12	View Spectrum

NMR

Spectrum Type	Description	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	View Spectrum
2D NMR	[¹H, ¹H] 2D NMR Spectrum (predicted)	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, H₂O, predicted)	2012-12-04	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Mitochondria
Nucleus
Lysosome
Endoplasmic reticulum
Golgi apparatus
Peroxisome

Biospecimen Locations

Blood
Cellular Cytoplasm
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

All Tissues
Placenta

Pathways

Name	SMPDB/Pathwhiz	KEGG
Transcription/Translation	SMP00019	Not Available
Purine Metabolism
Urea Cycle
Histidine Metabolism
Ethanol Degradation		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	5.1+/- 1.3 uM	Adult (>18 years old)	Female	Normal	13654353	details
Blood	Detected and Quantified	51.0 (10.0-92.0) uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	14.0 +/- 3.0 uM	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	6.2 +/- 3.1 uM	Adult (>18 years old)	Male	Normal	13654353	details
Cellular Cytoplasm	Detected and Quantified	80.0 (71.0-89.0) uM	Children (1-13 years old)	Both	Normal	15882454	details
Cellular Cytoplasm	Detected and Quantified	23 uM	Children (1-13 years old)	Both	Normal	1781403	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	< 0.2 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	29808030	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Saliva	Detected and Quantified	0.793 +/- 0.705 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	3.70 +/- 3.32 uM	Adult (>18 years old)	Female	Normal	23857558	details
Saliva	Detected and Quantified	0.912 +/- 0.994 uM	Adult (>18 years old)	Both	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	1.04 +/- 1.08 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	1.19 +/- 2.66 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	1.51 +/- 1.44 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	1.60 +/- 1.12 uM	Adult (>18 years old)	Both	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.124 +/- 0.284 uM	Adult (>18 years old)	Male	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.30 +/- 0.14 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected and Quantified	0.99 +/- 0.16 uM	Adult (>18 years old)	Both	Normal	11310987	details
Saliva	Detected and Quantified	1.24 +/- 0.33 uM	Adult (>18 years old)	Both	Normal	11310987	details
Saliva	Detected and Quantified	1.10 +/- 0.29 uM	Adult (>18 years old)	Both	Normal	11310987	details
Saliva	Detected and Quantified	0.321 +/- 0.506 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22932811	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Metastatic melanoma	28923537	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 but not Quantified	Not Quantified	Adult (>18 years old)	Male	Attachment loss	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Missing teeth	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Periodontal Probing Depth	31026179	details
Saliva	Detected and Quantified	1.39 +/- 1.25 uM	Adult (>18 years old)	Male	Alzheimer's disease	23857558	details
Saliva	Detected and Quantified	3.72 +/- 4.53 uM	Adult (>18 years old)	Male	Frontotemporal lobe dementia	23857558	details
Saliva	Detected and Quantified	4.12 +/- 6.43 uM	Adult (>18 years old)	Both	Lewy body disease	23857558	details

Associated Disorders and Diseases

Disease References

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 ]
Metastatic melanoma
Frankel AE, Coughlin LA, Kim J, Froehlich TW, Xie Y, Frenkel EP, Koh AY: Metagenomic Shotgun Sequencing and Unbiased Metabolomic Profiling Identify Specific Human Gut Microbiota and Metabolites Associated with Immune Checkpoint Therapy Efficacy in Melanoma Patients. Neoplasia. 2017 Oct;19(10):848-855. doi: 10.1016/j.neo.2017.08.004. Epub 2017 Sep 15. [PubMed:28923537 ]
Colorectal cancer
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 ]
Attachment loss
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Missing teeth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]

Associated OMIM IDs

266600 (Crohn's disease)
114500 (Colorectal cancer)
104300 (Alzheimer's disease)
600274 (Frontotemporal dementia)

External Links

DrugBank ID

DB00131

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

PDB ID

Not Available

ChEBI ID

16027

Food Biomarker Ontology

Not Available

VMH ID

AMP

MarkerDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 ]
BISHOP C, RANKINE DM, TALBOTT JH: The nucleotides in normal human blood. J Biol Chem. 1959 May;234(5):1233-7. [PubMed:13654353 ]
Lin CY, Ishida M: Elevation of cAMP levels in cerebrospinal fluid of patients with neonatal meningitis. Pediatrics. 1983 Jun;71(6):932-4. [PubMed:6304612 ]
Pagani R, Tabucchi A, Carlucci F, Leoncini R, Consolmagno E, Molinelli M, Valerio P: Some aspects of purine nucleotide metabolism in human lymphocytes before and after infection with HIV-1 virus: nucleotide content. Adv Exp Med Biol. 1991;309B:43-6. [PubMed:1781403 ]
Drezner MK, Neelon FA, Curtis HB, Lebovitz HE: Renal cyclic adenosine monophosphate: an accurate index of parathyroid function. Metabolism. 1976 Oct;25(10):1103-12. [PubMed:184364 ]
Aschenbach WG, Sakamoto K, Goodyear LJ: 5' adenosine monophosphate-activated protein kinase, metabolism and exercise. Sports Med. 2004;34(2):91-103. [PubMed:14965188 ]
Subramanian GM, Cronin PW, Poley G, Weinstein A, Stoughton SM, Zhong J, Ou Y, Zmuda JF, Osborn BL, Freimuth WW: A phase 1 study of PAmAb, a fully human monoclonal antibody against Bacillus anthracis protective antigen, in healthy volunteers. Clin Infect Dis. 2005 Jul 1;41(1):12-20. Epub 2005 May 24. [PubMed:15937757 ]
Aurbach GD: Genetic disorders involving parathyroid hormone and calcitonin. Birth Defects Orig Artic Ser. 1971 May;7(6):48-54. [PubMed:4155962 ]
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 ]
Post RM, Cramer H, Goodwin FK: Cyclic AMP in cerebrospinal fluid of manic and depressive patients. Psychol Med. 1977 Nov;7(4):599-605. [PubMed:201957 ]
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 269 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. Acetyl-coenzyme A synthetase, cytoplasmic

General function:: Involved in acetate-CoA ligase activity
Specific function:: Activates acetate so that it can be used for lipid synthesis or for energy generation.
Gene Name:: ACSS2
Uniprot ID:: Q9NR19
Molecular weight:: 78579.11

Reactions

Adenosine triphosphate + Acetic acid + Coenzyme A → Adenosine monophosphate + Pyrophosphate + Acetyl-CoA	details
Acetyl adenylate + Coenzyme A → Adenosine monophosphate + Acetyl-CoA	details
Propinol adenylate + Coenzyme A → Adenosine monophosphate + Propionyl-CoA	details

Enzyme Details

8. Acetyl-coenzyme A synthetase 2-like, mitochondrial

General function:: Involved in acetate-CoA ligase activity
Specific function:: Important for maintaining normal body temperature during fasting and for energy homeostasis. Essential for energy expenditure under ketogenic conditions (By similarity). Converts acetate to acetyl-CoA so that it can be used for oxidation through the tricarboxylic cycle to produce ATP and CO(2).
Gene Name:: ACSS1
Uniprot ID:: Q9NUB1
Molecular weight:: 74625.88

Reactions

Adenosine triphosphate + Acetic acid + Coenzyme A → Adenosine monophosphate + Pyrophosphate + Acetyl-CoA	details
Acetyl adenylate + Coenzyme A → Adenosine monophosphate + Acetyl-CoA	details
Propinol adenylate + Coenzyme A → Adenosine monophosphate + Propionyl-CoA	details

Enzyme Details

9. Ectonucleoside triphosphate diphosphohydrolase 1

General function:: Involved in hydrolase activity
Specific function:: In the nervous system, could hydrolyze ATP and other nucleotides to regulate purinergic neurotransmission. Could also be implicated in the prevention of platelet aggregation by hydrolyzing platelet-activating ADP to AMP. Hydrolyzes ATP and ADP equally well.
Gene Name:: ENTPD1
Uniprot ID:: P49961
Molecular weight:: 58706.0

Reactions

Adenosine triphosphate + Water → Adenosine monophosphate + Phosphate	details
ADP + Water → Adenosine monophosphate + Phosphate	details

Enzyme Details

10. Soluble calcium-activated nucleotidase 1

General function:: Involved in calcium ion binding
Specific function:: Calcium-dependent nucleotidase with a preference for UDP. The order of activity with different substrates is UDP > GDP > UTP > GTP. Has very low activity towards ADP and even lower activity towards ATP. Does not hydrolyze AMP and GMP. Involved in proteoglycan synthesis.
Gene Name:: CANT1
Uniprot ID:: Q8WVQ1
Molecular weight:: 44839.24

Only showing the first 10 proteins. There are 269 proteins in total.

Show all enzymes and transporters

Showing metabocard for Adenosine monophosphate (HMDB0000045)

MOL for HMDB0000045 (Adenosine monophosphate)

3D MOL for HMDB0000045 (Adenosine monophosphate)

3D SDF for HMDB0000045 (Adenosine monophosphate)

3D-SDF for HMDB0000045 (Adenosine monophosphate)

PDB for HMDB0000045 (Adenosine monophosphate)

3D PDB for HMDB0000045 (Adenosine monophosphate)

SMILES for HMDB0000045 (Adenosine monophosphate)

INCHI for HMDB0000045 (Adenosine monophosphate)

Structure for HMDB0000045 (Adenosine monophosphate)

3D Structure for HMDB0000045 (Adenosine monophosphate)

Collision Cross Sections

Retention Indices

Underivatized

Derivatized

GC-MS

LC-MS/MS

NMR

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions