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enzymes (9) Show 9 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:48:16 UTC

HMDB ID

HMDB0000085

Secondary Accession Numbers

HMDB00085

Metabolite Identification

Common Name

Deoxyguanosine

Description

Deoxyguanosine, also known as dG, belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2‚Äô. Deoxyguanosine is a nucleoside consisting of the base guanine and the sugar deoxyribose. Deoxyguanosine is one of the four deoxyribonucleosides that make up DNA. Deoxyguanosine exists in all living species, ranging from bacteria to plants to humans. Deoxyguanosine participates in a number of enzymatic reactions. In particular, deoxyguanosine can be biosynthesized from 2'-deoxyguanosine 5'-monophosphate through the enzyme known as cytosolic purine 5'-nucleotidase. In addition, deoxyguanosine can be converted into 2'-deoxyguanosine 5'-monophosphate (dGMP); which is mediated by the enzyme deoxyguanosine kinase. Deoxyguanosine is involved in the rare, inherited metabolic disorder called the purine nucleoside phosphorylase deficiency (PNP deficiency). In particular PNP deficiency is characterized by elevated levels of dGTP (deoxyguanosine triphosphate). PNP accounts for approximately 4% of patients with severe combined immunodeficiency (PMID: 1931007 ). PNP-deficient patients suffer from recurrent infections, usually beginning in the first year of life. Two thirds of patients have evidence of neurologic disorders with spasticity, developmental delay and mental retardation. Deoxyguanosine can be converted to 8-hydroxy-deoxyguanosine (8-OHdG) due to hydroxyl radical attack at the C8 of guanine. 8-hydroxy-deoxyguanosine is a sensitive marker of the DNA damage This damage, if left unrepaired, has been proposed to contribute to mutagenicity and cancer promotion.

Structure

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

HMDB0000085
     RDKit          3D
Deoxyguanosine
 32 34  0  0  0  0  0  0  0  0999 V2000
    4.3718   -2.0550    0.1038 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7318   -0.7937   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3868   -0.7145    0.0077 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7010    0.4263   -0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4404    1.5703   -0.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5235    2.5474   -0.5946 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2803    2.0653   -0.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3967    0.7565   -0.1151 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6539   -0.1493    0.1722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5848    0.3511    1.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6364   -0.7341    1.1595 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0805   -1.9032    1.6717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6945   -0.8801   -0.3473 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9512   -0.1232   -0.7989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9057    1.1988   -0.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5584   -0.3210   -0.8687 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136    1.4809   -0.5843 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4676    2.5032   -0.8591 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4464    0.3027   -0.3966 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3796   -2.4398    1.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8209   -2.5899   -0.6701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6341    2.6754   -0.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3128   -1.1507    0.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0865    0.3505    2.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0154    1.3033    0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5908   -0.4657    1.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7634   -2.5168    0.9448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7903   -1.9306   -0.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8531   -0.5891   -0.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0151   -0.2003   -1.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1274    1.7723   -1.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4938    0.2529   -0.4835 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  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
  5 17  1  0
 17 18  2  0
 17 19  1  0
 19  2  1  0
  8  4  1  0
 16  9  1  0
  1 20  1  0
  1 21  1  0
  7 22  1  0
  9 23  1  1
 10 24  1  0
 10 25  1  0
 11 26  1  1
 12 27  1  0
 13 28  1  1
 14 29  1  0
 14 30  1  0
 15 31  1  0
 19 32  1  0
M  END


  Mrv1652309032023512D          

 19 21  0  0  0  0            999 V2000
    4.9452    0.3673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2308   -0.0451    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9452   -1.2827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6597   -0.8702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6597   -0.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4443    0.2096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9293   -0.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4443   -1.1252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6993   -1.9100    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2143   -2.5773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6992   -3.2449    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4442   -4.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9963   -4.6426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4838   -2.9899    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1513   -3.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4839   -2.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2307   -0.8702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5162   -1.2827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9452    1.1923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 19  1  2  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  2 17  1  0  0  0  0
 17  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
  9 16  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000085

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C10H13N5O4/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6/h3-6,16-17H,1-2H2,(H3,11,13,14,18)/t4-,5+,6+/m0/s1

> <INCHI_KEY>
YKBGVTZYEHREMT-KVQBGUIXSA-N

> <FORMULA>
C10H13N5O4

> <MOLECULAR_WEIGHT>
267.2413

> <EXACT_MASS>
267.096753929

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.238180518018385

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one

> <ALOGPS_LOGP>
-1.75

> <JCHEM_LOGP>
-1.8055801330000003

> <ALOGPS_LOGS>
-1.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.886841415564113

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.158527534112794

> <JCHEM_PKA_STRONGEST_BASIC>
0.4648935108305678

> <JCHEM_POLAR_SURFACE_AREA>
134.98999999999998

> <JCHEM_REFRACTIVITY>
63.110399999999984

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-deoxyguanosine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000085
     RDKit          3D
Deoxyguanosine
 32 34  0  0  0  0  0  0  0  0999 V2000
    4.3718   -2.0550    0.1038 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7318   -0.7937   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3868   -0.7145    0.0077 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7010    0.4263   -0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4404    1.5703   -0.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5235    2.5474   -0.5946 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2803    2.0653   -0.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3967    0.7565   -0.1151 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6539   -0.1493    0.1722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5848    0.3511    1.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6364   -0.7341    1.1595 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0805   -1.9032    1.6717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6945   -0.8801   -0.3473 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9512   -0.1232   -0.7989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9057    1.1988   -0.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5584   -0.3210   -0.8687 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136    1.4809   -0.5843 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4676    2.5032   -0.8591 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4464    0.3027   -0.3966 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3796   -2.4398    1.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8209   -2.5899   -0.6701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6341    2.6754   -0.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3128   -1.1507    0.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0865    0.3505    2.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0154    1.3033    0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5908   -0.4657    1.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7634   -2.5168    0.9448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7903   -1.9306   -0.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8531   -0.5891   -0.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0151   -0.2003   -1.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1274    1.7723   -1.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4938    0.2529   -0.4835 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  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
  5 17  1  0
 17 18  2  0
 17 19  1  0
 19  2  1  0
  8  4  1  0
 16  9  1  0
  1 20  1  0
  1 21  1  0
  7 22  1  0
  9 23  1  1
 10 24  1  0
 10 25  1  0
 11 26  1  1
 12 27  1  0
 13 28  1  1
 14 29  1  0
 14 30  1  0
 15 31  1  0
 19 32  1  0
M  END

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  C   UNK     0       9.231   0.686   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       7.897  -0.084   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       9.231  -2.394   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      10.565  -1.624   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.565  -0.084   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      12.029   0.391   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      12.935  -0.855   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      12.029  -2.100   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      12.505  -3.565   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.600  -4.811   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.505  -6.057   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.029  -7.522   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      13.060  -8.666   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      13.970  -5.581   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      15.216  -6.486   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      13.970  -4.041   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.897  -1.624   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       6.564  -2.394   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       9.231   2.226   0.000  0.00  0.00           O+0
CONECT    1   19    2    5                                                  
CONECT    2    1   17                                                       
CONECT    3   17    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    1    4    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    4    7    9                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16    9   14                                                       
CONECT   17    2    3   18                                                  
CONECT   18   17                                                            
CONECT   19    1                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0000085
HETATM    1  N1  UNL     1       4.372  -2.055   0.104  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.732  -0.794  -0.101  1.00  0.00           C  
HETATM    3  N2  UNL     1       2.387  -0.714   0.008  1.00  0.00           N  
HETATM    4  C2  UNL     1       1.701   0.426  -0.167  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.440   1.570  -0.475  1.00  0.00           C  
HETATM    6  N3  UNL     1       1.523   2.547  -0.595  1.00  0.00           N  
HETATM    7  C4  UNL     1       0.280   2.065  -0.378  1.00  0.00           C  
HETATM    8  N4  UNL     1       0.397   0.757  -0.115  1.00  0.00           N  
HETATM    9  C5  UNL     1      -0.654  -0.149   0.172  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.585   0.351   1.278  1.00  0.00           C  
HETATM   11  C7  UNL     1      -2.636  -0.734   1.160  1.00  0.00           C  
HETATM   12  O1  UNL     1      -2.081  -1.903   1.672  1.00  0.00           O  
HETATM   13  C8  UNL     1      -2.694  -0.880  -0.347  1.00  0.00           C  
HETATM   14  C9  UNL     1      -3.951  -0.123  -0.799  1.00  0.00           C  
HETATM   15  O2  UNL     1      -3.906   1.199  -0.389  1.00  0.00           O  
HETATM   16  O3  UNL     1      -1.558  -0.321  -0.869  1.00  0.00           O  
HETATM   17  C10 UNL     1       3.814   1.481  -0.584  1.00  0.00           C  
HETATM   18  O4  UNL     1       4.468   2.503  -0.859  1.00  0.00           O  
HETATM   19  N5  UNL     1       4.446   0.303  -0.397  1.00  0.00           N  
HETATM   20  H1  UNL     1       4.380  -2.440   1.073  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.821  -2.590  -0.670  1.00  0.00           H  
HETATM   22  H3  UNL     1      -0.634   2.675  -0.421  1.00  0.00           H  
HETATM   23  H4  UNL     1      -0.313  -1.151   0.504  1.00  0.00           H  
HETATM   24  H5  UNL     1      -1.087   0.350   2.259  1.00  0.00           H  
HETATM   25  H6  UNL     1      -2.015   1.303   0.981  1.00  0.00           H  
HETATM   26  H7  UNL     1      -3.591  -0.466   1.608  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.763  -2.517   0.945  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.790  -1.931  -0.661  1.00  0.00           H  
HETATM   29  H10 UNL     1      -4.853  -0.589  -0.371  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.015  -0.200  -1.904  1.00  0.00           H  
HETATM   31  H12 UNL     1      -4.127   1.772  -1.178  1.00  0.00           H  
HETATM   32  H13 UNL     1       5.494   0.253  -0.484  1.00  0.00           H  
CONECT    1    2   20   21
CONECT    2    3    3   19
CONECT    3    4
CONECT    4    5    5    8
CONECT    5    6   17
CONECT    6    7    7
CONECT    7    8   22
CONECT    8    9
CONECT    9   10   16   23
CONECT   10   11   24   25
CONECT   11   12   13   26
CONECT   12   27
CONECT   13   14   16   28
CONECT   14   15   29   30
CONECT   15   31
CONECT   17   18   18   19
CONECT   19   32
END

HMDB0000085
     RDKit          3D
Deoxyguanosine
 32 34  0  0  0  0  0  0  0  0999 V2000
    4.3718   -2.0550    0.1038 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7318   -0.7937   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3868   -0.7145    0.0077 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7010    0.4263   -0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4404    1.5703   -0.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5235    2.5474   -0.5946 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2803    2.0653   -0.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3967    0.7565   -0.1151 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6539   -0.1493    0.1722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5848    0.3511    1.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6364   -0.7341    1.1595 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0805   -1.9032    1.6717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6945   -0.8801   -0.3473 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9512   -0.1232   -0.7989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9057    1.1988   -0.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5584   -0.3210   -0.8687 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8136    1.4809   -0.5843 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4676    2.5032   -0.8591 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4464    0.3027   -0.3966 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3796   -2.4398    1.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8209   -2.5899   -0.6701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6341    2.6754   -0.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3128   -1.1507    0.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0865    0.3505    2.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0154    1.3033    0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5908   -0.4657    1.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7634   -2.5168    0.9448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7903   -1.9306   -0.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8531   -0.5891   -0.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0151   -0.2003   -1.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1274    1.7723   -1.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4938    0.2529   -0.4835 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  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
  5 17  1  0
 17 18  2  0
 17 19  1  0
 19  2  1  0
  8  4  1  0
 16  9  1  0
  1 20  1  0
  1 21  1  0
  7 22  1  0
  9 23  1  1
 10 24  1  0
 10 25  1  0
 11 26  1  1
 12 27  1  0
 13 28  1  1
 14 29  1  0
 14 30  1  0
 15 31  1  0
 19 32  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Amino-9-(2-deoxy-9-beta-D-ribofuranosyl)-9H-purin-6-ol	ChEBI
9-(2-Deoxy-beta-D-erythro-pentofuranosyl)-guanine	ChEBI
dG	ChEBI
Guanine deoxy nucleoside	ChEBI
2'-Deoxyguanosine	Kegg
2-Amino-9-(2-deoxy-9-b-D-ribofuranosyl)-9H-purin-6-ol	Generator
2-Amino-9-(2-deoxy-9-β-D-ribofuranosyl)-9H-purin-6-ol	Generator
9-(2-Deoxy-b-D-erythro-pentofuranosyl)-guanine	Generator
9-(2-Deoxy-β-D-erythro-pentofuranosyl)-guanine	Generator
2'-Deoxy-guanosine	HMDB
2-Deoxyguanosine	HMDB
9-(2-Deoxy-b-D-erythro-pentofuranosyl)guanine	HMDB
9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)-guanine	HMDB
9-(2-Deoxy-beta-delta-erythro-pentofuranosyl)guanine	HMDB
Desoxyguanosine	HMDB
Guanine deoxyriboside	HMDB
Deoxyguanosine	ChEBI

Chemical Formula

C₁₀H₁₃N₅O₄

Average Molecular Weight

267.2413

Monoisotopic Molecular Weight

267.096753929

IUPAC Name

2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one

Traditional Name

2-deoxyguanosine

CAS Registry Number

961-07-9

SMILES

NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1

InChI Identifier

InChI=1S/C10H13N5O4/c11-10-13-8-7(9(18)14-10)12-3-15(8)6-1-4(17)5(2-16)19-6/h3-6,16-17H,1-2H2,(H3,11,13,14,18)/t4-,5+,6+/m0/s1

InChI Key

YKBGVTZYEHREMT-KVQBGUIXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Purine 2'-deoxyribonucleosides

Direct Parent

Purine 2'-deoxyribonucleosides

Alternative Parents

Substituents

Purine 2'-deoxyribonucleoside
6-oxopurine
Hypoxanthine
Purinone
Imidazopyrimidine
Purine
Aminopyrimidine
Pyrimidone
N-substituted imidazole
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
Tetrahydrofuran
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Amine
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

purine 2'-deoxyribonucleoside (CHEBI:17172 )
Deoxyribonucleosides (C00330 )

Ontology

Physiological effect

Adverse health effect

Genetic disorder

Inborn errors of metabolism

Disposition

Biological location

Excreta

Cellular substructure

Macromolecular complex

Ingestion

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Purine metabolism

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	300 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-1.30	BALZARINI,JM ET AL. (1989)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	156.765	30932474
[M-H]-	Not Available	158.4	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000098

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.5 g/L	ALOGPS
logP	10^(-1.8) g/L	ALOGPS
logP	10^(-1.8) g/L	ChemAxon
logS	10^(-1.4) g/L	ALOGPS
pKa (Strongest Acidic)	10.16	ChemAxon
pKa (Strongest Basic)	0.46	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	134.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	63.11 m³·mol⁻¹	ChemAxon
Polarizability	25.24 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]+	158.455	31661259
DarkChem	[M-H]-	157.464	31661259
AllCCS	[M+H]+	159.356	32859911
AllCCS	[M-H]-	159.135	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Deoxyguanosine	NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1	3520.5	Standard polar	33892256
Deoxyguanosine	NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1	2057.6	Standard non polar	33892256
Deoxyguanosine	NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1	3000.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Deoxyguanosine,1TMS,isomer #1	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=C(N)[NH]C3=O)O[C@@H]1CO	2679.8	Semi standard non polar	33892256
Deoxyguanosine,1TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N)[NH]C3=O)C[C@@H]1O	2650.4	Semi standard non polar	33892256
Deoxyguanosine,1TMS,isomer #3	C[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)[NH]1	2711.6	Semi standard non polar	33892256
Deoxyguanosine,1TMS,isomer #4	C[Si](C)(C)N1C(N)=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C1=O	2758.4	Semi standard non polar	33892256
Deoxyguanosine,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N)[NH]C3=O)C[C@@H]1O[Si](C)(C)C	2607.6	Semi standard non polar	33892256
Deoxyguanosine,2TMS,isomer #2	C[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O[Si](C)(C)C)[C@@H](CO)O2)C(=O)[NH]1	2623.6	Semi standard non polar	33892256
Deoxyguanosine,2TMS,isomer #3	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=C(N)N([Si](C)(C)C)C3=O)O[C@@H]1CO	2694.8	Semi standard non polar	33892256
Deoxyguanosine,2TMS,isomer #4	C[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO[Si](C)(C)C)O2)C(=O)[NH]1	2603.1	Semi standard non polar	33892256
Deoxyguanosine,2TMS,isomer #5	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N)N([Si](C)(C)C)C3=O)C[C@@H]1O	2672.3	Semi standard non polar	33892256
Deoxyguanosine,2TMS,isomer #6	C[Si](C)(C)N(C1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)[NH]1)[Si](C)(C)C	2616.8	Semi standard non polar	33892256
Deoxyguanosine,2TMS,isomer #7	C[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1[Si](C)(C)C	2705.4	Semi standard non polar	33892256
Deoxyguanosine,3TMS,isomer #1	C[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O2)C(=O)[NH]1	2593.2	Semi standard non polar	33892256
Deoxyguanosine,3TMS,isomer #1	C[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O2)C(=O)[NH]1	2884.6	Standard non polar	33892256
Deoxyguanosine,3TMS,isomer #1	C[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O2)C(=O)[NH]1	3957.9	Standard polar	33892256
Deoxyguanosine,3TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N)N([Si](C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C	2641.8	Semi standard non polar	33892256
Deoxyguanosine,3TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N)N([Si](C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C	2812.3	Standard non polar	33892256
Deoxyguanosine,3TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N)N([Si](C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C	4091.3	Standard polar	33892256
Deoxyguanosine,3TMS,isomer #3	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C3=O)O[C@@H]1CO	2623.8	Semi standard non polar	33892256
Deoxyguanosine,3TMS,isomer #3	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C3=O)O[C@@H]1CO	2954.3	Standard non polar	33892256
Deoxyguanosine,3TMS,isomer #3	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C3=O)O[C@@H]1CO	3801.6	Standard polar	33892256
Deoxyguanosine,3TMS,isomer #4	C[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O[Si](C)(C)C)[C@@H](CO)O2)C(=O)N1[Si](C)(C)C	2691.5	Semi standard non polar	33892256
Deoxyguanosine,3TMS,isomer #4	C[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O[Si](C)(C)C)[C@@H](CO)O2)C(=O)N1[Si](C)(C)C	2875.7	Standard non polar	33892256
Deoxyguanosine,3TMS,isomer #4	C[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O[Si](C)(C)C)[C@@H](CO)O2)C(=O)N1[Si](C)(C)C	3857.8	Standard polar	33892256
Deoxyguanosine,3TMS,isomer #5	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C3=O)C[C@@H]1O	2612.4	Semi standard non polar	33892256
Deoxyguanosine,3TMS,isomer #5	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C3=O)C[C@@H]1O	2981.4	Standard non polar	33892256
Deoxyguanosine,3TMS,isomer #5	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C3=O)C[C@@H]1O	3821.4	Standard polar	33892256
Deoxyguanosine,3TMS,isomer #6	C[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO[Si](C)(C)C)O2)C(=O)N1[Si](C)(C)C	2672.1	Semi standard non polar	33892256
Deoxyguanosine,3TMS,isomer #6	C[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO[Si](C)(C)C)O2)C(=O)N1[Si](C)(C)C	2907.4	Standard non polar	33892256
Deoxyguanosine,3TMS,isomer #6	C[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO[Si](C)(C)C)O2)C(=O)N1[Si](C)(C)C	3879.8	Standard polar	33892256
Deoxyguanosine,3TMS,isomer #7	C[Si](C)(C)N(C1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1[Si](C)(C)C)[Si](C)(C)C	2735.5	Semi standard non polar	33892256
Deoxyguanosine,3TMS,isomer #7	C[Si](C)(C)N(C1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1[Si](C)(C)C)[Si](C)(C)C	2990.0	Standard non polar	33892256
Deoxyguanosine,3TMS,isomer #7	C[Si](C)(C)N(C1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1[Si](C)(C)C)[Si](C)(C)C	3798.9	Standard polar	33892256
Deoxyguanosine,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C3=O)C[C@@H]1O[Si](C)(C)C	2650.0	Semi standard non polar	33892256
Deoxyguanosine,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C3=O)C[C@@H]1O[Si](C)(C)C	2974.3	Standard non polar	33892256
Deoxyguanosine,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)[NH]C3=O)C[C@@H]1O[Si](C)(C)C	3513.9	Standard polar	33892256
Deoxyguanosine,4TMS,isomer #2	C[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O2)C(=O)N1[Si](C)(C)C	2687.7	Semi standard non polar	33892256
Deoxyguanosine,4TMS,isomer #2	C[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O2)C(=O)N1[Si](C)(C)C	2897.3	Standard non polar	33892256
Deoxyguanosine,4TMS,isomer #2	C[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O2)C(=O)N1[Si](C)(C)C	3566.5	Standard polar	33892256
Deoxyguanosine,4TMS,isomer #3	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C3=O)O[C@@H]1CO	2758.6	Semi standard non polar	33892256
Deoxyguanosine,4TMS,isomer #3	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C3=O)O[C@@H]1CO	3013.1	Standard non polar	33892256
Deoxyguanosine,4TMS,isomer #3	C[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C3=O)O[C@@H]1CO	3447.9	Standard polar	33892256
Deoxyguanosine,4TMS,isomer #4	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C3=O)C[C@@H]1O	2726.3	Semi standard non polar	33892256
Deoxyguanosine,4TMS,isomer #4	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C3=O)C[C@@H]1O	3035.0	Standard non polar	33892256
Deoxyguanosine,4TMS,isomer #4	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C3=O)C[C@@H]1O	3478.6	Standard polar	33892256
Deoxyguanosine,5TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C	2773.2	Semi standard non polar	33892256
Deoxyguanosine,5TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C	3022.9	Standard non polar	33892256
Deoxyguanosine,5TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C	3225.9	Standard polar	33892256
Deoxyguanosine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=C(N)[NH]C3=O)O[C@@H]1CO	2900.9	Semi standard non polar	33892256
Deoxyguanosine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N)[NH]C3=O)C[C@@H]1O	2890.1	Semi standard non polar	33892256
Deoxyguanosine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)[NH]1	2914.9	Semi standard non polar	33892256
Deoxyguanosine,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C(N)=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C1=O	2930.5	Semi standard non polar	33892256
Deoxyguanosine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N)[NH]C3=O)C[C@@H]1O[Si](C)(C)C(C)(C)C	3032.3	Semi standard non polar	33892256
Deoxyguanosine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O2)C(=O)[NH]1	3036.8	Semi standard non polar	33892256
Deoxyguanosine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=C(N)N([Si](C)(C)C(C)(C)C)C3=O)O[C@@H]1CO	3108.3	Semi standard non polar	33892256
Deoxyguanosine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]1	3050.8	Semi standard non polar	33892256
Deoxyguanosine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N)N([Si](C)(C)C(C)(C)C)C3=O)C[C@@H]1O	3106.4	Semi standard non polar	33892256
Deoxyguanosine,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)N(C1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)[NH]1)[Si](C)(C)C(C)(C)C	3040.4	Semi standard non polar	33892256
Deoxyguanosine,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1[Si](C)(C)C(C)(C)C	3126.8	Semi standard non polar	33892256
Deoxyguanosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]1	3233.3	Semi standard non polar	33892256
Deoxyguanosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]1	3562.2	Standard non polar	33892256
Deoxyguanosine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)[NH]1	3957.0	Standard polar	33892256
Deoxyguanosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N)N([Si](C)(C)C(C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C(C)(C)C	3303.9	Semi standard non polar	33892256
Deoxyguanosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N)N([Si](C)(C)C(C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C(C)(C)C	3512.3	Standard non polar	33892256
Deoxyguanosine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N)N([Si](C)(C)C(C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C(C)(C)C	4056.3	Standard polar	33892256
Deoxyguanosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C3=O)O[C@@H]1CO	3205.1	Semi standard non polar	33892256
Deoxyguanosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C3=O)O[C@@H]1CO	3638.6	Standard non polar	33892256
Deoxyguanosine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C3=O)O[C@@H]1CO	3795.9	Standard polar	33892256
Deoxyguanosine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O2)C(=O)N1[Si](C)(C)C(C)(C)C	3302.1	Semi standard non polar	33892256
Deoxyguanosine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O2)C(=O)N1[Si](C)(C)C(C)(C)C	3578.4	Standard non polar	33892256
Deoxyguanosine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O2)C(=O)N1[Si](C)(C)C(C)(C)C	3827.4	Standard polar	33892256
Deoxyguanosine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C3=O)C[C@@H]1O	3205.3	Semi standard non polar	33892256
Deoxyguanosine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C3=O)C[C@@H]1O	3650.1	Standard non polar	33892256
Deoxyguanosine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C3=O)C[C@@H]1O	3834.0	Standard polar	33892256
Deoxyguanosine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)N1[Si](C)(C)C(C)(C)C	3311.9	Semi standard non polar	33892256
Deoxyguanosine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)N1[Si](C)(C)C(C)(C)C	3592.0	Standard non polar	33892256
Deoxyguanosine,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)N1[Si](C)(C)C(C)(C)C	3866.6	Standard polar	33892256
Deoxyguanosine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3305.9	Semi standard non polar	33892256
Deoxyguanosine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3677.1	Standard non polar	33892256
Deoxyguanosine,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C1=NC2=C(N=CN2[C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3769.5	Standard polar	33892256
Deoxyguanosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C3=O)C[C@@H]1O[Si](C)(C)C(C)(C)C	3403.9	Semi standard non polar	33892256
Deoxyguanosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C3=O)C[C@@H]1O[Si](C)(C)C(C)(C)C	3824.7	Standard non polar	33892256
Deoxyguanosine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[NH]C3=O)C[C@@H]1O[Si](C)(C)C(C)(C)C	3689.3	Standard polar	33892256
Deoxyguanosine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)N1[Si](C)(C)C(C)(C)C	3494.0	Semi standard non polar	33892256
Deoxyguanosine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)N1[Si](C)(C)C(C)(C)C	3774.9	Standard non polar	33892256
Deoxyguanosine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC2=C(N=CN2[C@H]2C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO[Si](C)(C)C(C)(C)C)O2)C(=O)N1[Si](C)(C)C(C)(C)C	3724.7	Standard polar	33892256
Deoxyguanosine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C3=O)O[C@@H]1CO	3492.8	Semi standard non polar	33892256
Deoxyguanosine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C3=O)O[C@@H]1CO	3852.1	Standard non polar	33892256
Deoxyguanosine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1C[C@H](N2C=NC3=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C3=O)O[C@@H]1CO	3627.1	Standard polar	33892256
Deoxyguanosine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C3=O)C[C@@H]1O	3495.2	Semi standard non polar	33892256
Deoxyguanosine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C3=O)C[C@@H]1O	3876.9	Standard non polar	33892256
Deoxyguanosine,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C3=O)C[C@@H]1O	3666.4	Standard polar	33892256
Deoxyguanosine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C(C)(C)C	3671.0	Semi standard non polar	33892256
Deoxyguanosine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C(C)(C)C	3968.8	Standard non polar	33892256
Deoxyguanosine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H](N2C=NC3=C2N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C3=O)C[C@@H]1O[Si](C)(C)C(C)(C)C	3553.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Deoxyguanosine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-001j-0891000000-3d776d25cb03b01b9339	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Deoxyguanosine GC-MS (4 TMS)	splash10-0f8a-2960000000-dfb317b7b1eb025d909e	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Deoxyguanosine GC-MS (5 TMS)	splash10-0udi-2913000000-1b2f5de9c93a151947ec	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Deoxyguanosine GC-EI-TOF (Non-derivatized)	splash10-001j-0891000000-3d776d25cb03b01b9339	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Deoxyguanosine GC-MS (Non-derivatized)	splash10-0f8a-2960000000-dfb317b7b1eb025d909e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Deoxyguanosine GC-MS (Non-derivatized)	splash10-0udi-2913000000-1b2f5de9c93a151947ec	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyguanosine GC-MS (Non-derivatized) - 70eV, Positive	splash10-052p-9580000000-831d1b4a56d55342e5d9	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyguanosine GC-MS (2 TMS) - 70eV, Positive	splash10-0006-8009000000-43fe5e369133cc5b35c0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyguanosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyguanosine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyguanosine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyguanosine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyguanosine GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyguanosine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyguanosine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyguanosine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyguanosine GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyguanosine GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyguanosine GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyguanosine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyguanosine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyguanosine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyguanosine GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyguanosine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deoxyguanosine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxyguanosine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0udi-0900000000-1ff2faf768c32875ae94	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxyguanosine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0udi-0900000000-6ecd3556539c87465829	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxyguanosine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0f89-2900000000-3c7a46a8b1ebc3478b0e	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxyguanosine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-014i-0090000000-d7b5f1fd49de4c188c2b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxyguanosine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-066r-1290000000-f1789943f3a3aa93bf11	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxyguanosine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-0pb9-1960000000-cae86b9369b467a619ac	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxyguanosine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-0a4i-2930000000-59733590e9e1f1f9e3ab	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxyguanosine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-0a59-3900000000-63f2d871818a0f9ea2c4	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxyguanosine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-0udi-0490000000-a0d35f9580527e157997	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxyguanosine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-0udi-0940000000-501ccdb19ac1399ea47d	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxyguanosine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-0pb9-2900000000-3c8141b790d1e751030c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxyguanosine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-0k96-6900000000-218b8cf773fa785dd6fc	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxyguanosine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-0006-9700000000-16fac3cb96899ba7c58c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxyguanosine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-0udi-0900000000-c020044f3d53ad944e38	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxyguanosine LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive-QTOF	splash10-0udi-0900000000-09d1a1821d4e622a1f9a	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxyguanosine LC-ESI-QQ , negative-QTOF	splash10-014i-0090000000-d7b5f1fd49de4c188c2b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxyguanosine LC-ESI-QQ , negative-QTOF	splash10-066r-1290000000-cf5beb73c1ce61ceb87b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxyguanosine LC-ESI-QQ , negative-QTOF	splash10-0pb9-1960000000-cae86b9369b467a619ac	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Deoxyguanosine LC-ESI-QQ , negative-QTOF	splash10-0a4i-2930000000-08d635c63c26f8baa811	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyguanosine 10V, Positive-QTOF	splash10-0udi-0920000000-d7d80ec246617036e55e	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyguanosine 20V, Positive-QTOF	splash10-0udi-0900000000-c5bd180b555397bc1ae5	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyguanosine 40V, Positive-QTOF	splash10-0udi-0900000000-c54d0a1dec8712b2b8f7	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyguanosine 10V, Negative-QTOF	splash10-014i-0290000000-393ce4bbd1a38882e581	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyguanosine 20V, Negative-QTOF	splash10-0udi-0910000000-7bc10bc144a1a343b08f	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deoxyguanosine 40V, Negative-QTOF	splash10-0pbc-4900000000-c3082fcc9288ad93f897	2016-09-12	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Mitochondria
Nucleus
Lysosome

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

All Tissues

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
Blood	Detected and Quantified	0 uM	Children (1 - 13 years old)	Both	Normal	Physician's Guide...	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	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
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Urine	Detected and Quantified	1.00 (0.00-2.00) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16613999	details
Urine	Detected and Quantified	0-5 umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	<1.0 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	10102915	details
Urine	Detected and Quantified	<0.1 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	30817767	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	11.0 (2.0-20.0) uM	Adult (>18 years old)	Both	Purine nucleoside phosphorylase (PNP) deficiency	16131572	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected and Quantified	177.0-322.0 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Purine nucleoside phosphorylase (PNP) deficiency	10102915	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] 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 ]
Purine nucleoside phosphorylase deficiency
Wevers RA, Engelke UF, Moolenaar SH, Brautigam C, de Jong JG, Duran R, de Abreu RA, van Gennip AH: 1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism. Clin Chem. 1999 Apr;45(4):539-48. [PubMed:10102915 ] Gandhi V, Kilpatrick JM, Plunkett W, Ayres M, Harman L, Du M, Bantia S, Davisson J, Wierda WG, Faderl S, Kantarjian H, Thomas D: A proof-of-principle pharmacokinetic, pharmacodynamic, and clinical study with purine nucleoside phosphorylase inhibitor immucillin-H (BCX-1777, forodesine). Blood. 2005 Dec 15;106(13):4253-60. Epub 2005 Aug 30. [PubMed:16131572 ]

Associated OMIM IDs

114500 (Colorectal cancer)
164050 (Purine nucleoside phosphorylase deficiency )

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012064

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17172

Food Biomarker Ontology

Not Available

VMH ID

DGSN

MarkerDB ID

MDB00000044

Good Scents ID

Not Available

References

Synthesis Reference

Noguchi, Toshitada; Hamamoto, Tomoki; Okuyama, Kiyoshi; Shibuya, Susumu. Process for producing 2'-deoxyguanosine. PCT Int. Appl. (2003), 31 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Gao K, Henning SM, Niu Y, Youssefian AA, Seeram NP, Xu A, Heber D: The citrus flavonoid naringenin stimulates DNA repair in prostate cancer cells. J Nutr Biochem. 2006 Feb;17(2):89-95. Epub 2005 Jun 20. [PubMed:16111881 ]
Podmore K, Farmer PB, Herbert KE, Jones GD, Martin EA: 32P-postlabelling approaches for the detection of 8-oxo-2'-deoxyguanosine-3'-monophosphate in DNA. Mutat Res. 1997 Aug 1;378(1-2):139-49. [PubMed:9288892 ]
Shibata T, Iio K, Kawai Y, Shibata N, Kawaguchi M, Toi S, Kobayashi M, Kobayashi M, Yamamoto K, Uchida K: Identification of a lipid peroxidation product as a potential trigger of the p53 pathway. J Biol Chem. 2006 Jan 13;281(2):1196-204. Epub 2005 Oct 26. [PubMed:16251187 ]
Gackowski D, Ciecierski M, Jawien A, Olinski R: Background level of 8-oxo-2'-deoxyguanosine in lymphocyte DNA does not correlate with the concentration of antioxidant vitamins in blood plasma. Acta Biochim Pol. 2001;48(2):535-9. [PubMed:11732622 ]
Takamura-Enya T, Watanabe M, Totsuka Y, Kanazawa T, Matsushima-Hibiya Y, Koyama K, Sugimura T, Wakabayashi K: Mono(ADP-ribosyl)ation of 2'-deoxyguanosine residue in DNA by an apoptosis-inducing protein, pierisin-1, from cabbage butterfly. Proc Natl Acad Sci U S A. 2001 Oct 23;98(22):12414-9. Epub 2001 Oct 9. [PubMed:11592983 ]
Palozza P, Serini S, Di Nicuolo F, Boninsegna A, Torsello A, Maggiano N, Ranelletti FO, Wolf FI, Calviello G, Cittadini A: beta-Carotene exacerbates DNA oxidative damage and modifies p53-related pathways of cell proliferation and apoptosis in cultured cells exposed to tobacco smoke condensate. Carcinogenesis. 2004 Aug;25(8):1315-25. Epub 2004 Apr 8. [PubMed:15073048 ]
Zaidi SN, Laidlaw I, Howell A, Potten CS, Cooper DP, O'Connor PJ: Normal human breast xenografts activate N-nitrosodimethylamine: identification of potential target cells for an environmental nitrosamine. Br J Cancer. 1992 Jul;66(1):79-83. [PubMed:1637681 ]
Gackowski D, Banaszkiewicz Z, Rozalski R, Jawien A, Olinski R: Persistent oxidative stress in colorectal carcinoma patients. Int J Cancer. 2002 Oct 1;101(4):395-7. [PubMed:12209966 ]
Araki S, Hayashi M, Tamagawa K, Saito M, Kato S, Komori T, Sakakihara Y, Mizutani T, Oda M: Neuropathological analysis in spinal muscular atrophy type II. Acta Neuropathol. 2003 Nov;106(5):441-8. Epub 2003 Jul 25. [PubMed:12898156 ]
Kato I, Ren J, Heilbrun LK, Djuric Z: Intra- and inter-individual variability in measurements of biomarkers for oxidative damage in vivo: Nutrition and Breast Health Study. Biomarkers. 2006 Mar-Apr;11(2):143-52. [PubMed:16766390 ]
Izzedine H, Launay-Vacher V, Aymard G, Legrand M, Deray G: Pharmacokinetics of abacavir in HIV-1-infected patients with impaired renal function. Nephron. 2001 Sep;89(1):62-7. [PubMed:11528234 ]
Wevers RA, Engelke UF, Moolenaar SH, Brautigam C, de Jong JG, Duran R, de Abreu RA, van Gennip AH: 1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism. Clin Chem. 1999 Apr;45(4):539-48. [PubMed:10102915 ]
Bowen P, Chen L, Stacewicz-Sapuntzakis M, Duncan C, Sharifi R, Ghosh L, Kim HS, Christov-Tzelkov K, van Breemen R: Tomato sauce supplementation and prostate cancer: lycopene accumulation and modulation of biomarkers of carcinogenesis. Exp Biol Med (Maywood). 2002 Nov;227(10):886-93. [PubMed:12424330 ]
Staal GE, Stoop JW, Zegers BJ, Siegenbeek van Heukelom LH, van der Vlist MJ, Wadman SK, Martin DW: Erythrocyte metabolism in purine nucleoside phosphorylase deficiency after enzyme replacement therapy by infusion of erythrocytes. J Clin Invest. 1980 Jan;65(1):103-8. [PubMed:6765955 ]
Blair IA: Lipid hydroperoxide-mediated DNA damage. Exp Gerontol. 2001 Sep;36(9):1473-81. [PubMed:11525870 ]
Schramm VL: Development of transition state analogues of purine nucleoside phosphorylase as anti-T-cell agents. Biochim Biophys Acta. 2002 Jul 18;1587(2-3):107-17. [PubMed:12084452 ]
Schilderman PA, Rhijnsburger E, Zwingmann I, Kleinjans JC: Induction of oxidative DNA damages and enhancement of cell proliferation in human lymphocytes in vitro by butylated hydroxyanisole. Carcinogenesis. 1995 Mar;16(3):507-12. [PubMed:7697806 ]
Kaneko T, Tahara S: Formation of 8-oxo-2'-deoxyguanosine in the DNA of human diploid fibroblasts by treatment with linoleic acid hydroperoxide and ferric ion. Lipids. 2000 Sep;35(9):961-5. [PubMed:11026616 ]
Hou SM, Nori P, Fang JL, Vaca CE: Methylglyoxal induces hprt mutation and DNA adducts in human T-lymphocytes in vitro. Environ Mol Mutagen. 1995;26(4):286-91. [PubMed:8575417 ]
Bialkowski K, Kowara R, Windorbska W, Olinski R: 8-Oxo-2'-deoxyguanosine level in lymphocytes DNA of cancer patients undergoing radiotherapy. Cancer Lett. 1996 Jan 19;99(1):93-7. [PubMed:8564935 ]
Markert ML: Purine nucleoside phosphorylase deficiency. Immunodefic Rev. 1991;3(1):45-81. [PubMed:1931007 ]

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

2'-Deoxyguanosine 5'-monophosphate + Water → Deoxyguanosine + 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

2'-Deoxyguanosine 5'-monophosphate + Water → Deoxyguanosine + 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

2'-Deoxyguanosine 5'-monophosphate + Water → Deoxyguanosine + 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

2'-Deoxyguanosine 5'-monophosphate + Water → Deoxyguanosine + 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

2'-Deoxyguanosine 5'-monophosphate + Water → Deoxyguanosine + Phosphate	details

Enzyme Details

6. Deoxyguanosine kinase, mitochondrial

General function:: Involved in ATP binding
Specific function:: Required for the phosphorylation of several deoxyribonucleosides and certain nucleoside analogs widely employed as antiviral and chemotherapeutic agents.
Gene Name:: DGUOK
Uniprot ID:: Q16854
Molecular weight:: 32055.53

Reactions

Adenosine triphosphate + Deoxyguanosine → ADP + 2'-Deoxyguanosine 5'-monophosphate	details

Enzyme Details

7. 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

2'-Deoxyguanosine 5'-monophosphate + Water → Deoxyguanosine + Phosphate	details

Enzyme Details

8. Cytosolic purine 5'-nucleotidase

General function:: Involved in 5'-nucleotidase activity
Specific function:: May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-monophosphate (IMP) and other purine nucleotides.
Gene Name:: NT5C2
Uniprot ID:: P49902
Molecular weight:: 64969.2

Reactions

2'-Deoxyguanosine 5'-monophosphate + Water → Deoxyguanosine + Phosphate	details

Enzyme Details

9. Purine nucleoside phosphorylase

General function:: Involved in purine-nucleoside phosphorylase activity
Specific function:: The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
Gene Name:: PNP
Uniprot ID:: P00491
Molecular weight:: 32117.69

Reactions

Deoxyguanosine + Phosphate → Guanine + Deoxyribose 1-phosphate	details

Showing metabocard for Deoxyguanosine (HMDB0000085)

MOL for HMDB0000085 (Deoxyguanosine)

3D MOL for HMDB0000085 (Deoxyguanosine)

3D SDF for HMDB0000085 (Deoxyguanosine)

3D-SDF for HMDB0000085 (Deoxyguanosine)

PDB for HMDB0000085 (Deoxyguanosine)

3D PDB for HMDB0000085 (Deoxyguanosine)

SMILES for HMDB0000085 (Deoxyguanosine)

INCHI for HMDB0000085 (Deoxyguanosine)

Structure for HMDB0000085 (Deoxyguanosine)

3D Structure for HMDB0000085 (Deoxyguanosine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

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