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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 14:57:50 UTC

HMDB ID

HMDB0000905

Secondary Accession Numbers

HMDB00905

Metabolite Identification

Common Name

Deoxyadenosine monophosphate

Description

Deoxyadenosine monophosphate (dAMP), also known as deoxyadenylic acid or deoxyadenylate in its conjugate acid and conjugate base forms, respectively, is a derivative of the common nucleic acid AMP, or adenosine monophosphate, in which the -OH (hydroxyl) group on the 2' carbon on the nucleotide's pentose has been reduced to just a hydrogen atom (hence the "deoxy-" part of the name). Additionally, the monophosphate of the name indicates that two of the phosphoryl groups of GTP have been removed, most likely by hydrolysis. It is a monomer used in DNA.

Structure

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

HMDB0000905
     RDKit          3D
Deoxyadenosine monophosphate
 36 38  0  0  0  0  0  0  0  0999 V2000
    5.7812   -1.3255    0.4663 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3757   -1.5358    0.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8070   -2.7210    0.2219 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4425   -2.8420    0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6202   -1.8068    0.2287 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1351   -0.5922    0.4949 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4984   -0.4476    0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7784    0.8215    0.8964 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6155    1.4837    0.9298 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6096    0.6161    0.6728 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2835    1.0663    0.4576 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2114    1.9262   -0.8515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3315    1.9956   -0.9600 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7527    3.1344   -0.2715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6840    0.7557   -0.2233 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8269    0.0155   -0.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8884   -1.1943   -0.1754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4227   -1.3662    0.4556 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.5365   -1.7437   -0.3619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2280   -2.4880    1.7741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7675    0.1673    1.2422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5366    0.0196   -0.0433 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1754   -0.4369    0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4294   -2.0322    0.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0908   -3.8424   -0.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5529    2.5475    1.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2105    1.6508    1.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6690    2.8800   -0.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5529    1.2714   -1.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6871    2.0207   -1.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6799    2.9431    0.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0622    1.0471    0.8181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5270   -0.0991   -1.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7400    0.5486   -0.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5440   -3.1431    1.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2032    0.7055    0.5648 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
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 18 21  1  0
 15 22  1  0
  7  2  1  0
 22 11  1  0
 10  6  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  9 26  1  0
 11 27  1  1
 12 28  1  0
 12 29  1  0
 13 30  1  6
 14 31  1  0
 15 32  1  1
 16 33  1  0
 16 34  1  0
 20 35  1  0
 21 36  1  0
M  END


  Mrv1652309042000142D          

 22 24  0  0  1  0            999 V2000
    0.9617    0.4182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5960   -0.0209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1917    0.1708    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2475    1.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3312    0.5192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6761   -0.8677    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4844    0.6761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0628   -0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1082    1.2440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0805    0.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4672   -1.2196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1429    0.2055    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8851   -0.5750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1780   -0.6970    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7390    0.6795    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9305    0.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1534   -1.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5507   -0.0976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3836   -0.0976    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3871   -0.9339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2164   -0.0976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3871    0.7353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  1  1  1  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6 11  2  0  0  0  0
  7 12  1  0  0  0  0
  8 13  1  0  0  0  0
 10 14  2  0  0  0  0
 10 15  1  0  0  0  0
 12 16  1  1  0  0  0
 13 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  2  0  0  0  0
  5  9  1  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000905

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C10H14N5O6P/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(21-7)2-20-22(17,18)19/h3-7,16H,1-2H2,(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1

> <INCHI_KEY>
KHWCHTKSEGGWEX-RRKCRQDMSA-N

> <FORMULA>
C10H14N5O6P

> <MOLECULAR_WEIGHT>
331.2218

> <EXACT_MASS>
331.068169717

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
28.980183076216395

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.44

> <JCHEM_LOGP>
-3.847898303907523

> <ALOGPS_LOGS>
-2.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.2598694502185745

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.231362812852561

> <JCHEM_PKA_STRONGEST_BASIC>
3.9396602503688625

> <JCHEM_POLAR_SURFACE_AREA>
165.83999999999997

> <JCHEM_REFRACTIVITY>
72.5578

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
DAMP

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000905
     RDKit          3D
Deoxyadenosine monophosphate
 36 38  0  0  0  0  0  0  0  0999 V2000
    5.7812   -1.3255    0.4663 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3757   -1.5358    0.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8070   -2.7210    0.2219 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4425   -2.8420    0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6202   -1.8068    0.2287 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1351   -0.5922    0.4949 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4984   -0.4476    0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7784    0.8215    0.8964 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6155    1.4837    0.9298 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6096    0.6161    0.6728 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2835    1.0663    0.4576 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2114    1.9262   -0.8515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3315    1.9956   -0.9600 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7527    3.1344   -0.2715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6840    0.7557   -0.2233 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8269    0.0155   -0.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8884   -1.1943   -0.1754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4227   -1.3662    0.4556 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.5365   -1.7437   -0.3619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2280   -2.4880    1.7741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7675    0.1673    1.2422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5366    0.0196   -0.0433 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1754   -0.4369    0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4294   -2.0322    0.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0908   -3.8424   -0.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5529    2.5475    1.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2105    1.6508    1.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6690    2.8800   -0.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5529    1.2714   -1.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6871    2.0207   -1.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6799    2.9431    0.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0622    1.0471    0.8181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5270   -0.0991   -1.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7400    0.5486   -0.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5440   -3.1431    1.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2032    0.7055    0.5648 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
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 18 21  1  0
 15 22  1  0
  7  2  1  0
 22 11  1  0
 10  6  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  9 26  1  0
 11 27  1  1
 12 28  1  0
 12 29  1  0
 13 30  1  6
 14 31  1  0
 15 32  1  1
 16 33  1  0
 16 34  1  0
 20 35  1  0
 21 36  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  N   UNK     0       1.795   0.781   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.979  -0.039   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.358   0.319   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.329   2.335   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.352   0.969   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       3.129  -1.620   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0      -0.904   1.262   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.117  -1.073   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       3.935   2.322   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.750   0.351   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.605  -2.277   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.133   0.384   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.652  -1.073   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       5.932  -1.301   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       6.979   1.268   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -3.604   0.859   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.153  -2.543   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -4.761  -0.182   0.000  0.00  0.00           O+0
HETATM   19  P   UNK     0      -6.316  -0.182   0.000  0.00  0.00           P+0
HETATM   20  O   UNK     0      -6.323  -1.743   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -7.871  -0.182   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -6.323   1.373   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10    9                                                  
CONECT    6    2   11                                                       
CONECT    7    3   12                                                       
CONECT    8    3   13                                                       
CONECT    9    4    5                                                       
CONECT   10    5   14   15                                                  
CONECT   11    6   14                                                       
CONECT   12    7   16   13                                                  
CONECT   13    8   17   12                                                  
CONECT   14   10   11                                                       
CONECT   15   10                                                            
CONECT   16   12   18                                                       
CONECT   17   13                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0000905
HETATM    1  N1  UNL     1       5.781  -1.326   0.466  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.376  -1.536   0.481  1.00  0.00           C  
HETATM    3  N2  UNL     1       3.807  -2.721   0.222  1.00  0.00           N  
HETATM    4  C2  UNL     1       2.442  -2.842   0.102  1.00  0.00           C  
HETATM    5  N3  UNL     1       1.620  -1.807   0.229  1.00  0.00           N  
HETATM    6  C3  UNL     1       2.135  -0.592   0.495  1.00  0.00           C  
HETATM    7  C4  UNL     1       3.498  -0.448   0.627  1.00  0.00           C  
HETATM    8  N4  UNL     1       3.778   0.821   0.896  1.00  0.00           N  
HETATM    9  C5  UNL     1       2.615   1.484   0.930  1.00  0.00           C  
HETATM   10  N5  UNL     1       1.610   0.616   0.673  1.00  0.00           N  
HETATM   11  C6  UNL     1       0.284   1.066   0.458  1.00  0.00           C  
HETATM   12  C7  UNL     1       0.211   1.926  -0.852  1.00  0.00           C  
HETATM   13  C8  UNL     1      -1.332   1.996  -0.960  1.00  0.00           C  
HETATM   14  O1  UNL     1      -1.753   3.134  -0.271  1.00  0.00           O  
HETATM   15  C9  UNL     1      -1.684   0.756  -0.223  1.00  0.00           C  
HETATM   16  C10 UNL     1      -2.827   0.015  -0.904  1.00  0.00           C  
HETATM   17  O2  UNL     1      -2.888  -1.194  -0.175  1.00  0.00           O  
HETATM   18  P1  UNL     1      -4.423  -1.366   0.456  1.00  0.00           P  
HETATM   19  O3  UNL     1      -5.537  -1.744  -0.362  1.00  0.00           O  
HETATM   20  O4  UNL     1      -4.228  -2.488   1.774  1.00  0.00           O  
HETATM   21  O5  UNL     1      -4.768   0.167   1.242  1.00  0.00           O  
HETATM   22  O6  UNL     1      -0.537   0.020  -0.043  1.00  0.00           O  
HETATM   23  H1  UNL     1       6.175  -0.437   0.817  1.00  0.00           H  
HETATM   24  H2  UNL     1       6.429  -2.032   0.081  1.00  0.00           H  
HETATM   25  H3  UNL     1       2.091  -3.842  -0.083  1.00  0.00           H  
HETATM   26  H4  UNL     1       2.553   2.547   1.155  1.00  0.00           H  
HETATM   27  H5  UNL     1      -0.211   1.651   1.209  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.669   2.880  -0.755  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.553   1.271  -1.693  1.00  0.00           H  
HETATM   30  H8  UNL     1      -1.687   2.021  -1.996  1.00  0.00           H  
HETATM   31  H9  UNL     1      -1.680   2.943   0.692  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.062   1.047   0.818  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.527  -0.099  -1.958  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.740   0.549  -0.815  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.544  -3.143   1.405  1.00  0.00           H  
HETATM   36  H14 UNL     1      -5.203   0.705   0.565  1.00  0.00           H  
CONECT    1    2   23   24
CONECT    2    3    3    7
CONECT    3    4
CONECT    4    5    5   25
CONECT    5    6
CONECT    6    7    7   10
CONECT    7    8
CONECT    8    9    9
CONECT    9   10   26
CONECT   10   11
CONECT   11   12   22   27
CONECT   12   13   28   29
CONECT   13   14   15   30
CONECT   14   31
CONECT   15   16   22   32
CONECT   16   17   33   34
CONECT   17   18
CONECT   18   19   19   20   21
CONECT   20   35
CONECT   21   36
END

HMDB0000905
     RDKit          3D
Deoxyadenosine monophosphate
 36 38  0  0  0  0  0  0  0  0999 V2000
    5.7812   -1.3255    0.4663 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3757   -1.5358    0.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8070   -2.7210    0.2219 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4425   -2.8420    0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6202   -1.8068    0.2287 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1351   -0.5922    0.4949 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4984   -0.4476    0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7784    0.8215    0.8964 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6155    1.4837    0.9298 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6096    0.6161    0.6728 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2835    1.0663    0.4576 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2114    1.9262   -0.8515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3315    1.9956   -0.9600 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7527    3.1344   -0.2715 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6840    0.7557   -0.2233 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8269    0.0155   -0.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8884   -1.1943   -0.1754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4227   -1.3662    0.4556 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.5365   -1.7437   -0.3619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2280   -2.4880    1.7741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7675    0.1673    1.2422 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5366    0.0196   -0.0433 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1754   -0.4369    0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4294   -2.0322    0.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0908   -3.8424   -0.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5529    2.5475    1.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2105    1.6508    1.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6690    2.8800   -0.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5529    1.2714   -1.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6871    2.0207   -1.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6799    2.9431    0.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0622    1.0471    0.8181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5270   -0.0991   -1.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7400    0.5486   -0.8149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5440   -3.1431    1.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2032    0.7055    0.5648 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
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 18 21  1  0
 15 22  1  0
  7  2  1  0
 22 11  1  0
 10  6  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  9 26  1  0
 11 27  1  1
 12 28  1  0
 12 29  1  0
 13 30  1  6
 14 31  1  0
 15 32  1  1
 16 33  1  0
 16 34  1  0
 20 35  1  0
 21 36  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2'-dAMP	ChEBI
2'-Deoxy-5'-adenosine monophosphate	ChEBI
2'-Deoxy-AMP	ChEBI
2'-Deoxyadenosine 5'-(dihydrogen phosphate)	ChEBI
2'-Deoxyadenosine 5'-phosphate	ChEBI
2'-Deoxyadenosine monophosphate	ChEBI
2'-DEOXYADENOSINE-5'-monophosphATE	ChEBI
2'-Deoxyadenylic acid	ChEBI
dAMP	ChEBI
Deoxy-5'-adenylic acid	ChEBI
Deoxy-AMP	ChEBI
Deoxyadenosine 5'-monophosphate	ChEBI
Deoxyadenosine 5'-phosphate	ChEBI
Deoxyadenylic acid	ChEBI
2'-Deoxyadenosine 5'-monophosphate	Kegg
2'-Deoxy-5'-adenosine monophosphoric acid	Generator
2'-Deoxyadenosine 5'-(dihydrogen phosphoric acid)	Generator
2'-Deoxyadenosine 5'-phosphoric acid	Generator
2'-Deoxyadenosine monophosphoric acid	Generator
2'-DEOXYADENOSINE-5'-monophosphoric acid	Generator
2'-Deoxyadenylate	Generator
Deoxy-5'-adenylate	Generator
Deoxyadenosine 5'-monophosphoric acid	Generator
Deoxyadenosine 5'-phosphoric acid	Generator
Deoxyadenylate	Generator
2'-Deoxyadenosine 5'-monophosphoric acid	Generator
Deoxyadenosine monophosphoric acid	Generator
2'-Deoxy-5'-adenylate	HMDB
2'-Deoxy-5'-adenylic acid	HMDB
2'-Deoxy-adenosine 5'-phosphorate	HMDB
2'-Deoxy-adenosine 5'-phosphoric acid	HMDB
2'-Deoxyadenosine-5'-phosphate	HMDB
Deoxyadenosine-phosphate	HMDB
PdA	HMDB
2'-Deoxy-5'-adenosine monophosphate, ammonium salt	HMDB
2'-Deoxy-5'-adenosine monophosphate, disodium salt	HMDB
2'Deoxy-5'-AMP	HMDB
dAMP CPD	HMDB

Chemical Formula

C₁₀H₁₄N₅O₆P

Average Molecular Weight

331.2218

Monoisotopic Molecular Weight

331.068169717

IUPAC Name

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

Traditional Name

DAMP

CAS Registry Number

653-63-4

SMILES

NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1

InChI Identifier

InChI=1S/C10H14N5O6P/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(21-7)2-20-22(17,18)19/h3-7,16H,1-2H2,(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1

InChI Key

KHWCHTKSEGGWEX-RRKCRQDMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside monophosphates. These are purine nucleotides with monophosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine deoxyribonucleotides

Direct Parent

Purine 2'-deoxyribonucleoside monophosphates

Alternative Parents

Substituents

Purine 2'-deoxyribonucleoside monophosphate
6-aminopurine
Imidazopyrimidine
Purine
Aminopyrimidine
Monoalkyl phosphate
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Pyrimidine
Imidolactam
Alkyl phosphate
Azole
Imidazole
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Azacycle
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

purine 2'-deoxyribonucleoside 5'-monophosphate (CHEBI:17713 )
2'-deoxyadenosine 5'-phosphate (CHEBI:17713 )
Deoxyribonucleotides (C00360 )

Ontology

Not Available

Liver (HMDB: HMDB0000905)
Spleen (HMDB: HMDB0000905)

Excreta

Biofluid or Excreta

Feces (PMID: 27543620)

Cellular substructure

Organelle

Lysosome (HMDB: HMDB0000905)
Mitochondrion (HMDB: HMDB0000905)

Cytoplasm (HMDB: HMDB0000905)

Source

Endogenous

Endogenous (HMDB: HMDB0000905)

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Vegetable

Cabbage

Onion-family vegetable

Root vegetable

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)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
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)

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. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
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)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
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)

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)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
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)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
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)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)

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)

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)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)

Cereal and cereal product

Cereal

Cereal product

Pasta (FooDB: FOOD00273)
Bulgur (FooDB: FOOD00741)
Semolina (FooDB: FOOD00745)
Flour (FooDB: FOOD00799)

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

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

Bean

Green lentil (FooDB: FOOD00970)

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)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

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

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Soy sauce (FooDB: FOOD00694)
Miso (FooDB: FOOD00695)
Tofu (FooDB: FOOD00696)
Soy milk (FooDB: FOOD00736)
Soy cream (FooDB: FOOD00784)

Dish

Other dish

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

Tea

Herbal tea

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

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Thioguanine Action Pathway (HMDB: HMDB0000905)
Azathioprine Action Pathway (PathBank: SMP0000427)
Mercaptopurine Action Pathway (PathBank: SMP0000428)
Thioguanine Action Pathway (PathBank: SMP0000430)

Disease pathway

Gout or Kelley-Seegmiller Syndrome (PathBank: SMP0120709)
Xanthine Dehydrogenase Deficiency (Xanthinuria) (PathBank: SMP0120717)
Mitochondrial DNA Depletion Syndrome (PathBank: SMP0120820)
Adenylosuccinate Lyase Deficiency (PathBank: SMP0120670)
AICA-Ribosiduria (PathBank: SMP0120673)
Purine Nucleoside Phosphorylase Deficiency (PathBank: SMP0120756)
Adenine Phosphoribosyltransferase Deficiency (APRT) (PathBank: SMP0120819)
Myoadenylate Deaminase Deficiency (PathBank: SMP0120821)
Adenosine Deaminase Deficiency (PathBank: SMP0120448)
Lesch-Nyhan Syndrome (LNS) (PathBank: SMP0120508)
Molybdenum Cofactor Deficiency (PathBank: SMP0120752)
Xanthinuria Type II (PathBank: SMP0120797)
Xanthinuria Type I (PathBank: SMP0120577)
Mitochondrial DNA Depletion Syndrome (PathBank: SMP0000536)

Metabolic pathway

Purine Metabolism (PathBank: SMP0063668)
Purine Metabolism (HMDB: HMDB0000905)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	148 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	168.1	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000157
[M+H]+	Not Available	168.6	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000157

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.71 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-3.8	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.23	ChemAxon
pKa (Strongest Basic)	3.94	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	165.84 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	72.56 m³·mol⁻¹	ChemAxon
Polarizability	28.98 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]+	172.164	31661259
DarkChem	[M-H]-	168.107	31661259
AllCCS	[M+H]+	172.011	32859911
AllCCS	[M-H]-	168.282	32859911
DeepCCS	[M+H]+	161.378	30932474
DeepCCS	[M-H]-	158.982	30932474
DeepCCS	[M-2H]-	192.562	30932474
DeepCCS	[M+Na]+	167.596	30932474
AllCCS	[M+H]+	172.0	32859911
AllCCS	[M+H-H2O]+	169.0	32859911
AllCCS	[M+NH4]+	174.8	32859911
AllCCS	[M+Na]+	175.6	32859911
AllCCS	[M-H]-	168.3	32859911
AllCCS	[M+Na-2H]-	167.9	32859911
AllCCS	[M+HCOO]-	167.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.37 minutes	32390414
Predicted by Siyang on May 30, 2022	9.224 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	8.72 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	378.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	877.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	220.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	53.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	151.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	55.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	329.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	278.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	776.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	571.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	58.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	584.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	153.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	156.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	602.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	359.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	302.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Deoxyadenosine monophosphate	NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1	3777.1	Standard polar	33892256
Deoxyadenosine monophosphate	NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1	2353.0	Standard non polar	33892256
Deoxyadenosine monophosphate	NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1	3168.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Deoxyadenosine monophosphate,1TMS,isomer #1	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N)N=CN=C32)O[C@@H]1COP(=O)(O)O	2958.3	Semi standard non polar	33892256
Deoxyadenosine monophosphate,1TMS,isomer #2	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)C[C@@H]1O	3057.6	Semi standard non polar	33892256
Deoxyadenosine monophosphate,1TMS,isomer #3	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1	3028.5	Semi standard non polar	33892256
Deoxyadenosine monophosphate,2TMS,isomer #1	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N)N=CN=C32)O[C@@H]1COP(=O)(O)O[Si](C)(C)C	2979.6	Semi standard non polar	33892256
Deoxyadenosine monophosphate,2TMS,isomer #1	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N)N=CN=C32)O[C@@H]1COP(=O)(O)O[Si](C)(C)C	2990.1	Standard non polar	33892256
Deoxyadenosine monophosphate,2TMS,isomer #1	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N)N=CN=C32)O[C@@H]1COP(=O)(O)O[Si](C)(C)C	4930.6	Standard polar	33892256
Deoxyadenosine monophosphate,2TMS,isomer #2	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O)O1	2945.4	Semi standard non polar	33892256
Deoxyadenosine monophosphate,2TMS,isomer #2	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O)O1	3060.5	Standard non polar	33892256
Deoxyadenosine monophosphate,2TMS,isomer #2	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O)O1	5268.8	Standard polar	33892256
Deoxyadenosine monophosphate,2TMS,isomer #3	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)C[C@@H]1O)O[Si](C)(C)C	2989.1	Semi standard non polar	33892256
Deoxyadenosine monophosphate,2TMS,isomer #3	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)C[C@@H]1O)O[Si](C)(C)C	3017.1	Standard non polar	33892256
Deoxyadenosine monophosphate,2TMS,isomer #3	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)C[C@@H]1O)O[Si](C)(C)C	4724.1	Standard polar	33892256
Deoxyadenosine monophosphate,2TMS,isomer #4	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O1	3029.5	Semi standard non polar	33892256
Deoxyadenosine monophosphate,2TMS,isomer #4	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O1	3088.0	Standard non polar	33892256
Deoxyadenosine monophosphate,2TMS,isomer #4	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C)O1	4807.2	Standard polar	33892256
Deoxyadenosine monophosphate,2TMS,isomer #5	C[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1)[Si](C)(C)C	2987.1	Semi standard non polar	33892256
Deoxyadenosine monophosphate,2TMS,isomer #5	C[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1)[Si](C)(C)C	3174.9	Standard non polar	33892256
Deoxyadenosine monophosphate,2TMS,isomer #5	C[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1)[Si](C)(C)C	5087.0	Standard polar	33892256
Deoxyadenosine monophosphate,3TMS,isomer #1	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N)N=CN=C32)O[C@@H]1COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2953.0	Semi standard non polar	33892256
Deoxyadenosine monophosphate,3TMS,isomer #1	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N)N=CN=C32)O[C@@H]1COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3009.8	Standard non polar	33892256
Deoxyadenosine monophosphate,3TMS,isomer #1	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N)N=CN=C32)O[C@@H]1COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	4534.4	Standard polar	33892256
Deoxyadenosine monophosphate,3TMS,isomer #2	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C)O1	2977.2	Semi standard non polar	33892256
Deoxyadenosine monophosphate,3TMS,isomer #2	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C)O1	3081.0	Standard non polar	33892256
Deoxyadenosine monophosphate,3TMS,isomer #2	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C)O1	4551.9	Standard polar	33892256
Deoxyadenosine monophosphate,3TMS,isomer #3	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)O[C@@H]1COP(=O)(O)O	2906.0	Semi standard non polar	33892256
Deoxyadenosine monophosphate,3TMS,isomer #3	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)O[C@@H]1COP(=O)(O)O	3193.6	Standard non polar	33892256
Deoxyadenosine monophosphate,3TMS,isomer #3	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)O[C@@H]1COP(=O)(O)O	4671.1	Standard polar	33892256
Deoxyadenosine monophosphate,3TMS,isomer #4	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O1	3006.3	Semi standard non polar	33892256
Deoxyadenosine monophosphate,3TMS,isomer #4	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O1	3116.4	Standard non polar	33892256
Deoxyadenosine monophosphate,3TMS,isomer #4	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O1	4290.3	Standard polar	33892256
Deoxyadenosine monophosphate,3TMS,isomer #5	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)C[C@@H]1O	2987.0	Semi standard non polar	33892256
Deoxyadenosine monophosphate,3TMS,isomer #5	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)C[C@@H]1O	3154.8	Standard non polar	33892256
Deoxyadenosine monophosphate,3TMS,isomer #5	C[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)C[C@@H]1O	4304.9	Standard polar	33892256
Deoxyadenosine monophosphate,4TMS,isomer #1	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O1	3003.0	Semi standard non polar	33892256
Deoxyadenosine monophosphate,4TMS,isomer #1	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O1	3077.2	Standard non polar	33892256
Deoxyadenosine monophosphate,4TMS,isomer #1	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O1	4064.6	Standard polar	33892256
Deoxyadenosine monophosphate,4TMS,isomer #2	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)O[C@@H]1COP(=O)(O)O[Si](C)(C)C	2979.8	Semi standard non polar	33892256
Deoxyadenosine monophosphate,4TMS,isomer #2	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)O[C@@H]1COP(=O)(O)O[Si](C)(C)C	3145.8	Standard non polar	33892256
Deoxyadenosine monophosphate,4TMS,isomer #2	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)O[C@@H]1COP(=O)(O)O[Si](C)(C)C	4036.6	Standard polar	33892256
Deoxyadenosine monophosphate,4TMS,isomer #3	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)C[C@@H]1O)O[Si](C)(C)C	3010.3	Semi standard non polar	33892256
Deoxyadenosine monophosphate,4TMS,isomer #3	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)C[C@@H]1O)O[Si](C)(C)C	3171.5	Standard non polar	33892256
Deoxyadenosine monophosphate,4TMS,isomer #3	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)C[C@@H]1O)O[Si](C)(C)C	3811.1	Standard polar	33892256
Deoxyadenosine monophosphate,5TMS,isomer #1	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)O[C@@H]1COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3034.3	Semi standard non polar	33892256
Deoxyadenosine monophosphate,5TMS,isomer #1	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)O[C@@H]1COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3110.7	Standard non polar	33892256
Deoxyadenosine monophosphate,5TMS,isomer #1	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)O[C@@H]1COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	3613.7	Standard polar	33892256
Deoxyadenosine monophosphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N)N=CN=C32)O[C@@H]1COP(=O)(O)O	3233.3	Semi standard non polar	33892256
Deoxyadenosine monophosphate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)C[C@@H]1O	3284.0	Semi standard non polar	33892256
Deoxyadenosine monophosphate,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1	3222.6	Semi standard non polar	33892256
Deoxyadenosine monophosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N)N=CN=C32)O[C@@H]1COP(=O)(O)O[Si](C)(C)C(C)(C)C	3441.4	Semi standard non polar	33892256
Deoxyadenosine monophosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N)N=CN=C32)O[C@@H]1COP(=O)(O)O[Si](C)(C)C(C)(C)C	3445.6	Standard non polar	33892256
Deoxyadenosine monophosphate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N)N=CN=C32)O[C@@H]1COP(=O)(O)O[Si](C)(C)C(C)(C)C	4944.1	Standard polar	33892256
Deoxyadenosine monophosphate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O)O1	3366.9	Semi standard non polar	33892256
Deoxyadenosine monophosphate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O)O1	3536.1	Standard non polar	33892256
Deoxyadenosine monophosphate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O)O1	5144.2	Standard polar	33892256
Deoxyadenosine monophosphate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)C[C@@H]1O)O[Si](C)(C)C(C)(C)C	3427.4	Semi standard non polar	33892256
Deoxyadenosine monophosphate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)C[C@@H]1O)O[Si](C)(C)C(C)(C)C	3444.4	Standard non polar	33892256
Deoxyadenosine monophosphate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)C[C@@H]1O)O[Si](C)(C)C(C)(C)C	4779.1	Standard polar	33892256
Deoxyadenosine monophosphate,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O1	3429.7	Semi standard non polar	33892256
Deoxyadenosine monophosphate,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O1	3531.0	Standard non polar	33892256
Deoxyadenosine monophosphate,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O1	4832.2	Standard polar	33892256
Deoxyadenosine monophosphate,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1)[Si](C)(C)C(C)(C)C	3390.5	Semi standard non polar	33892256
Deoxyadenosine monophosphate,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1)[Si](C)(C)C(C)(C)C	3623.6	Standard non polar	33892256
Deoxyadenosine monophosphate,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(=O)(O)O)O1)[Si](C)(C)C(C)(C)C	4920.7	Standard polar	33892256
Deoxyadenosine monophosphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N)N=CN=C32)O[C@@H]1COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3574.5	Semi standard non polar	33892256
Deoxyadenosine monophosphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N)N=CN=C32)O[C@@H]1COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3591.8	Standard non polar	33892256
Deoxyadenosine monophosphate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N)N=CN=C32)O[C@@H]1COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	4609.2	Standard polar	33892256
Deoxyadenosine monophosphate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O1	3575.1	Semi standard non polar	33892256
Deoxyadenosine monophosphate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O1	3726.6	Standard non polar	33892256
Deoxyadenosine monophosphate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O1	4604.5	Standard polar	33892256
Deoxyadenosine monophosphate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)O[C@@H]1COP(=O)(O)O	3536.2	Semi standard non polar	33892256
Deoxyadenosine monophosphate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)O[C@@H]1COP(=O)(O)O	3825.4	Standard non polar	33892256
Deoxyadenosine monophosphate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)O[C@@H]1COP(=O)(O)O	4597.8	Standard polar	33892256
Deoxyadenosine monophosphate,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1	3594.6	Semi standard non polar	33892256
Deoxyadenosine monophosphate,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1	3721.2	Standard non polar	33892256
Deoxyadenosine monophosphate,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1	4437.1	Standard polar	33892256
Deoxyadenosine monophosphate,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OP(=O)(O)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[C@@H]1O	3578.2	Semi standard non polar	33892256
Deoxyadenosine monophosphate,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OP(=O)(O)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[C@@H]1O	3788.5	Standard non polar	33892256
Deoxyadenosine monophosphate,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OP(=O)(O)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[C@@H]1O	4365.5	Standard polar	33892256
Deoxyadenosine monophosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1	3739.9	Semi standard non polar	33892256
Deoxyadenosine monophosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1	3834.2	Standard non polar	33892256
Deoxyadenosine monophosphate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1	4279.1	Standard polar	33892256
Deoxyadenosine monophosphate,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)O[C@@H]1COP(=O)(O)O[Si](C)(C)C(C)(C)C	3722.0	Semi standard non polar	33892256
Deoxyadenosine monophosphate,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)O[C@@H]1COP(=O)(O)O[Si](C)(C)C(C)(C)C	3929.5	Standard non polar	33892256
Deoxyadenosine monophosphate,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)O[C@@H]1COP(=O)(O)O[Si](C)(C)C(C)(C)C	4131.4	Standard polar	33892256
Deoxyadenosine monophosphate,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(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[C@@H]1O)O[Si](C)(C)C(C)(C)C	3729.4	Semi standard non polar	33892256
Deoxyadenosine monophosphate,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(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[C@@H]1O)O[Si](C)(C)C(C)(C)C	3924.7	Standard non polar	33892256
Deoxyadenosine monophosphate,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(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[C@@H]1O)O[Si](C)(C)C(C)(C)C	4022.6	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Lysosome

Biospecimen Locations

Feces

Tissue Locations

Liver
Spleen

Pathways

Name	SMPDB/PathBank	KEGG
Purine metabolism	Not Available
Adenosine Deaminase Deficiency		Not Available
Adenylosuccinate Lyase Deficiency		Not Available
Gout or Kelley-Seegmiller Syndrome		Not Available
Lesch-Nyhan Syndrome (LNS)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022311

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Deoxyadenosine_monophosphate

METLIN ID

3461

PubChem Compound

12599

PDB ID

Not Available

ChEBI ID

17713

Food Biomarker Ontology

Not Available

VMH ID

DAMP

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Scarano, E. Incorporation of adenine-C14 into deoxyadenylic acid. Bollettino - Societa Italiana di Biologia Sperimentale (1958), 34 1620-1.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Hohenester E, Hutchinson WL, Pepys MB, Wood SP: Crystal structure of a decameric complex of human serum amyloid P component with bound dAMP. J Mol Biol. 1997 Jun 20;269(4):570-8. [PubMed:9217261 ]
Avkin S, Adar S, Blander G, Livneh Z: Quantitative measurement of translesion replication in human cells: evidence for bypass of abasic sites by a replicative DNA polymerase. Proc Natl Acad Sci U S A. 2002 Mar 19;99(6):3764-9. Epub 2002 Mar 12. [PubMed:11891323 ]
Duarte V, Muller JG, Burrows CJ: Insertion of dGMP and dAMP during in vitro DNA synthesis opposite an oxidized form of 7,8-dihydro-8-oxoguanine. Nucleic Acids Res. 1999 Jan 15;27(2):496-502. [PubMed:9862971 ]
Chen XR, Li GM, Wang JR, Chen JJ: [Portal hemodynamics in patients with different syndromes of cirrhosis]. Zhong Xi Yi Jie He Xue Bao. 2004 May;2(3):178-81. [PubMed:15339437 ]
Zhong H, Zang KT: Therapeutic approaches for chronic gastralgia based on differentiation of symptoms and signs. Di Yi Jun Yi Da Xue Xue Bao. 2002 Jul;22(7):639-40. [PubMed:12376299 ]
Hashimoto K, Tominaga Y, Nakabeppu Y, Moriya M: Futile short-patch DNA base excision repair of adenine:8-oxoguanine mispair. Nucleic Acids Res. 2004 Nov 5;32(19):5928-34. Print 2004. [PubMed:15531653 ]
Zhang Q, Zhang WT, Wei JJ, Wang XB, Liu P: [Combined use of factor analysis and cluster analysis in classification of traditional Chinese medical syndromes in patients with posthepatitic cirrhosis]. Zhong Xi Yi Jie He Xue Bao. 2005 Jan;3(1):14-8. [PubMed:15644152 ]
Levine RL, Yang IY, Hossain M, Pandya GA, Grollman AP, Moriya M: Mutagenesis induced by a single 1,N6-ethenodeoxyadenosine adduct in human cells. Cancer Res. 2000 Aug 1;60(15):4098-104. [PubMed:10945616 ]
Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]

Only showing the first 10 proteins. There are 12 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

Deoxyadenosine monophosphate + Water → Deoxyadenosine + 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

Deoxyadenosine monophosphate + Water → Deoxyadenosine + 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

Deoxyadenosine monophosphate + Water → Deoxyadenosine + 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

Deoxyadenosine monophosphate + Water → Deoxyadenosine + Phosphate	details

Enzyme Details

5. 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

Deoxyadenosine monophosphate + Water → Deoxyadenosine + Phosphate	details

Enzyme Details

6. Adenylate kinase isoenzyme 1

General function:: Involved in ATP binding
Specific function:: Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. Small ubiquitous enzyme involved in energy metabolism and nucleotide synthesis that is essential for maintenance and cell growth.
Gene Name:: AK1
Uniprot ID:: P00568
Molecular weight:: 21634.725

Reactions

Adenosine triphosphate + Deoxyadenosine monophosphate → ADP + dADP	details

Enzyme Details

7. Adenylate kinase isoenzyme 4, mitochondrial

General function:: Involved in ATP binding
Specific function:: Catalyzes the reversible transfer of the terminal phosphate group between ATP and AMP. May also be active with GTP (By similarity).
Gene Name:: AK4
Uniprot ID:: P27144
Molecular weight:: 25267.83

Reactions

Adenosine triphosphate + Deoxyadenosine monophosphate → ADP + dADP	details

Enzyme Details

8. Adenylate kinase 7

General function:: Involved in ATP binding
Specific function:: Adenylate kinase involved in maintaining ciliary structure and function (By similarity). Has highest activity toward AMP, and weaker activity toward dAMP, CMP and dCMP.
Gene Name:: AK7
Uniprot ID:: Q96M32
Molecular weight:: 82657.68

Reactions

Adenosine triphosphate + Deoxyadenosine monophosphate → ADP + dADP	details

Enzyme Details

9. Adenylate kinase isoenzyme 5

General function:: Involved in ATP binding
Specific function:: Active on AMP and dAMP with ATP as a donor. When GTP is used as phosphate donor, the enzyme phosphorylates AMP, CMP, and to a small extent dCMP.
Gene Name:: AK5
Uniprot ID:: Q9Y6K8
Molecular weight:: 60313.985

Reactions

Adenosine triphosphate + Deoxyadenosine monophosphate → ADP + dADP	details

Enzyme Details

10. Cytosolic 5'-nucleotidase 3

General function:: Involved in magnesium ion binding
Specific function:: Can act both as nucleotidase and as phosphotransferase.
Gene Name:: NT5C3
Uniprot ID:: Q9H0P0
Molecular weight:: 33914.91

Reactions

Deoxyadenosine monophosphate + Water → Deoxyadenosine + Phosphate	details

Only showing the first 10 proteins. There are 12 proteins in total.

Show all enzymes and transporters

Showing metabocard for Deoxyadenosine monophosphate (HMDB0000905)

MOL for HMDB0000905 (Deoxyadenosine monophosphate)

3D MOL for HMDB0000905 (Deoxyadenosine monophosphate)

3D SDF for HMDB0000905 (Deoxyadenosine monophosphate)

3D-SDF for HMDB0000905 (Deoxyadenosine monophosphate)

PDB for HMDB0000905 (Deoxyadenosine monophosphate)

3D PDB for HMDB0000905 (Deoxyadenosine monophosphate)

SMILES for HMDB0000905 (Deoxyadenosine monophosphate)

INCHI for HMDB0000905 (Deoxyadenosine monophosphate)

Structure for HMDB0000905 (Deoxyadenosine monophosphate)

3D Structure for HMDB0000905 (Deoxyadenosine monophosphate)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

Reactions

Reactions

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