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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-24 14:16:08 UTC

Update Date

2021-09-14 14:58:58 UTC

HMDB ID

HMDB0004824

Secondary Accession Numbers

HMDB04824

Metabolite Identification

Common Name

N2,N2-Dimethylguanosine

Description

N2,N2-Dimethylguanosine, also known as M22G, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. N2,N2-Dimethylguanosine has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make N2,N2-dimethylguanosine a potential biomarker for the consumption of these foods. N2,N2-Dimethylguanosine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on N2,N2-Dimethylguanosine.

Structure

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

HMDB0004824
     RDKit          3D
N2,N2-Dimethylguanosine
 39 41  0  0  0  0  0  0  0  0999 V2000
    4.0650    1.7911    0.7143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5450    0.4573    0.7738 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7255   -0.3275    1.9573 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8603   -0.0673   -0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5169   -0.5704   -1.4054 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9158   -1.0871   -2.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5288   -1.5536   -3.4696 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5402   -1.1050   -2.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6430   -1.5449   -3.4007 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5784   -1.3095   -2.8879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4572   -0.7197   -1.6558 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5523   -0.3588   -0.8648 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4399    0.7780   -0.0724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7978    0.8567    0.3306 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0825    1.9567    1.2852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3659    1.8268    2.4450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9518   -0.5054    0.9975 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2525   -0.9831    0.8911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0346   -1.3728    0.1449 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7987   -2.3293   -0.5392 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8478   -0.5916   -1.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5180   -0.0904   -0.3704 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5902    2.0859    1.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3217    2.5301    0.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8751    1.7707   -0.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7912   -0.8234    2.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1559    0.3128    2.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4585   -1.1382    1.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5159   -1.5471   -3.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4489   -0.1414   -1.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3622    0.9223   -0.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1739    1.8842    1.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9649    2.9432    0.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8860    2.2577    3.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6114   -0.3910    2.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9308   -0.3152    1.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2472   -1.8677    0.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4512   -1.9277   -1.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0047    0.2944    0.4453 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 11 21  1  0
 21 22  1  0
 22  4  1  0
 21  8  2  0
 19 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
 10 29  1  0
 12 30  1  6
 14 31  1  6
 15 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  1
 18 36  1  0
 19 37  1  1
 20 38  1  0
 22 39  1  0
M  END


  Mrv0541 02231219592D          

 22 24  0  0  1  0            999 V2000
   20.1109  -16.0745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2607  -19.0391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2638  -17.2442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3253  -18.1383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0577  -21.9047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6287  -19.4297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5527  -19.5908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0577  -19.4297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3432  -20.6672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5527  -20.9186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5578  -16.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6287  -18.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9142  -19.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8091  -18.8066    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.8114  -17.4717    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.5941  -18.5530    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.5955  -17.7280    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.3432  -19.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7721  -19.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0577  -21.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7721  -20.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0342  -20.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
 16  2  1  1  0  0  0
 17  3  1  1  0  0  0
  4 14  1  0  0  0  0
  4 15  1  0  0  0  0
  5 20  2  0  0  0  0
  6 12  1  0  0  0  0
  6 13  1  0  0  0  0
  6 18  1  0  0  0  0
 14  7  1  6  0  0  0
  7 19  1  0  0  0  0
  7 22  1  0  0  0  0
  8 18  1  0  0  0  0
  8 19  1  0  0  0  0
  9 18  2  0  0  0  0
  9 20  1  0  0  0  0
 10 21  1  0  0  0  0
 10 22  2  0  0  0  0
 15 11  1  6  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 17  1  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004824

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)C1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C12H17N5O5/c1-16(2)12-14-9-6(10(21)15-12)13-4-17(9)11-8(20)7(19)5(3-18)22-11/h4-5,7-8,11,18-20H,3H2,1-2H3,(H,14,15,21)/t5-,7-,8-,11-/m1/s1

> <INCHI_KEY>
RSPURTUNRHNVGF-IOSLPCCCSA-N

> <FORMULA>
C12H17N5O5

> <MOLECULAR_WEIGHT>
311.2939

> <EXACT_MASS>
311.122968679

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
30.377810879202222

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(dimethylamino)-6,9-dihydro-3H-purin-6-one

> <ALOGPS_LOGP>
-1.23

> <JCHEM_LOGP>
-1.6490219306666662

> <ALOGPS_LOGS>
-1.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.456219704439615

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.854097619550111

> <JCHEM_PKA_STRONGEST_BASIC>
2.591445763314515

> <JCHEM_POLAR_SURFACE_AREA>
132.44

> <JCHEM_REFRACTIVITY>
74.25699999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(dimethylamino)-3H-purin-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004824
     RDKit          3D
N2,N2-Dimethylguanosine
 39 41  0  0  0  0  0  0  0  0999 V2000
    4.0650    1.7911    0.7143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5450    0.4573    0.7738 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7255   -0.3275    1.9573 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8603   -0.0673   -0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5169   -0.5704   -1.4054 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9158   -1.0871   -2.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5288   -1.5536   -3.4696 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5402   -1.1050   -2.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6430   -1.5449   -3.4007 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5784   -1.3095   -2.8879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4572   -0.7197   -1.6558 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5523   -0.3588   -0.8648 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4399    0.7780   -0.0724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7978    0.8567    0.3306 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0825    1.9567    1.2852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3659    1.8268    2.4450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9518   -0.5054    0.9975 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2525   -0.9831    0.8911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0346   -1.3728    0.1449 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7987   -2.3293   -0.5392 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8478   -0.5916   -1.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5180   -0.0904   -0.3704 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5902    2.0859    1.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3217    2.5301    0.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8751    1.7707   -0.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7912   -0.8234    2.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1559    0.3128    2.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4585   -1.1382    1.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5159   -1.5471   -3.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4489   -0.1414   -1.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3622    0.9223   -0.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1739    1.8842    1.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9649    2.9432    0.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8860    2.2577    3.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6114   -0.3910    2.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9308   -0.3152    1.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2472   -1.8677    0.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4512   -1.9277   -1.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0047    0.2944    0.4453 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 11 21  1  0
 21 22  1  0
 22  4  1  0
 21  8  2  0
 19 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
 10 29  1  0
 12 30  1  6
 14 31  1  6
 15 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  1
 18 36  1  0
 19 37  1  1
 20 38  1  0
 22 39  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      37.540 -30.006   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      39.687 -35.540   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      39.692 -32.189   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      36.074 -33.858   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      33.708 -40.889   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      31.040 -36.269   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      36.498 -36.569   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      33.708 -36.269   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      32.374 -38.579   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      36.498 -39.048   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      36.508 -31.148   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.040 -34.729   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      29.707 -37.039   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      36.977 -35.106   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      36.981 -32.614   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      38.442 -34.632   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      38.445 -33.092   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      32.374 -37.039   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      35.041 -37.039   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      33.708 -39.349   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      35.041 -38.579   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      37.397 -37.809   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   16                                                            
CONECT    3   17                                                            
CONECT    4   14   15                                                       
CONECT    5   20                                                            
CONECT    6   12   13   18                                                  
CONECT    7   14   19   22                                                  
CONECT    8   18   19                                                       
CONECT    9   18   20                                                       
CONECT   10   21   22                                                       
CONECT   11    1   15                                                       
CONECT   12    6                                                            
CONECT   13    6                                                            
CONECT   14    4    7   16                                                  
CONECT   15    4   11   17                                                  
CONECT   16    2   14   17                                                  
CONECT   17    3   15   16                                                  
CONECT   18    6    8    9                                                  
CONECT   19    7    8   21                                                  
CONECT   20    5    9   21                                                  
CONECT   21   10   19   20                                                  
CONECT   22    7   10                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0004824
HETATM    1  C1  UNL     1       4.065   1.791   0.714  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.545   0.457   0.774  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.726  -0.327   1.957  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.860  -0.067  -0.340  1.00  0.00           C  
HETATM    5  N2  UNL     1       3.517  -0.570  -1.405  1.00  0.00           N  
HETATM    6  C4  UNL     1       2.916  -1.087  -2.480  1.00  0.00           C  
HETATM    7  O1  UNL     1       3.529  -1.554  -3.470  1.00  0.00           O  
HETATM    8  C5  UNL     1       1.540  -1.105  -2.496  1.00  0.00           C  
HETATM    9  N3  UNL     1       0.643  -1.545  -3.401  1.00  0.00           N  
HETATM   10  C6  UNL     1      -0.578  -1.309  -2.888  1.00  0.00           C  
HETATM   11  N4  UNL     1      -0.457  -0.720  -1.656  1.00  0.00           N  
HETATM   12  C7  UNL     1      -1.552  -0.359  -0.865  1.00  0.00           C  
HETATM   13  O2  UNL     1      -1.440   0.778  -0.072  1.00  0.00           O  
HETATM   14  C8  UNL     1      -2.798   0.857   0.331  1.00  0.00           C  
HETATM   15  C9  UNL     1      -3.083   1.957   1.285  1.00  0.00           C  
HETATM   16  O3  UNL     1      -2.366   1.827   2.445  1.00  0.00           O  
HETATM   17  C10 UNL     1      -2.952  -0.505   0.997  1.00  0.00           C  
HETATM   18  O4  UNL     1      -4.253  -0.983   0.891  1.00  0.00           O  
HETATM   19  C11 UNL     1      -2.035  -1.373   0.145  1.00  0.00           C  
HETATM   20  O5  UNL     1      -2.799  -2.329  -0.539  1.00  0.00           O  
HETATM   21  C12 UNL     1       0.848  -0.592  -1.411  1.00  0.00           C  
HETATM   22  N5  UNL     1       1.518  -0.090  -0.370  1.00  0.00           N  
HETATM   23  H1  UNL     1       4.590   2.086   1.647  1.00  0.00           H  
HETATM   24  H2  UNL     1       3.322   2.530   0.368  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.875   1.771  -0.076  1.00  0.00           H  
HETATM   26  H4  UNL     1       2.791  -0.823   2.295  1.00  0.00           H  
HETATM   27  H5  UNL     1       4.156   0.313   2.781  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.458  -1.138   1.711  1.00  0.00           H  
HETATM   29  H7  UNL     1      -1.516  -1.547  -3.365  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.449  -0.141  -1.530  1.00  0.00           H  
HETATM   31  H9  UNL     1      -3.362   0.922  -0.619  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.174   1.884   1.538  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.965   2.943   0.791  1.00  0.00           H  
HETATM   34  H12 UNL     1      -2.886   2.258   3.199  1.00  0.00           H  
HETATM   35  H13 UNL     1      -2.611  -0.391   2.030  1.00  0.00           H  
HETATM   36  H14 UNL     1      -4.931  -0.315   1.073  1.00  0.00           H  
HETATM   37  H15 UNL     1      -1.247  -1.868   0.714  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.451  -1.928  -1.147  1.00  0.00           H  
HETATM   39  H17 UNL     1       1.005   0.294   0.445  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4
CONECT    3   26   27   28
CONECT    4    5    5   22
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9   21   21
CONECT    9   10   10
CONECT   10   11   29
CONECT   11   12   21
CONECT   12   13   19   30
CONECT   13   14
CONECT   14   15   17   31
CONECT   15   16   32   33
CONECT   16   34
CONECT   17   18   19   35
CONECT   18   36
CONECT   19   20   37
CONECT   20   38
CONECT   21   22
CONECT   22   39
END

HMDB0004824
     RDKit          3D
N2,N2-Dimethylguanosine
 39 41  0  0  0  0  0  0  0  0999 V2000
    4.0650    1.7911    0.7143 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5450    0.4573    0.7738 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7255   -0.3275    1.9573 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8603   -0.0673   -0.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5169   -0.5704   -1.4054 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9158   -1.0871   -2.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5288   -1.5536   -3.4696 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5402   -1.1050   -2.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6430   -1.5449   -3.4007 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5784   -1.3095   -2.8879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4572   -0.7197   -1.6558 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5523   -0.3588   -0.8648 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4399    0.7780   -0.0724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7978    0.8567    0.3306 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0825    1.9567    1.2852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3659    1.8268    2.4450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9518   -0.5054    0.9975 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2525   -0.9831    0.8911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0346   -1.3728    0.1449 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7987   -2.3293   -0.5392 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8478   -0.5916   -1.4112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5180   -0.0904   -0.3704 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5902    2.0859    1.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3217    2.5301    0.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8751    1.7707   -0.0759 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7912   -0.8234    2.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1559    0.3128    2.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4585   -1.1382    1.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5159   -1.5471   -3.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4489   -0.1414   -1.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3622    0.9223   -0.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1739    1.8842    1.5381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9649    2.9432    0.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8860    2.2577    3.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6114   -0.3910    2.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9308   -0.3152    1.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2472   -1.8677    0.7137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4512   -1.9277   -1.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0047    0.2944    0.4453 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 11 21  1  0
 21 22  1  0
 22  4  1  0
 21  8  2  0
 19 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
 10 29  1  0
 12 30  1  6
 14 31  1  6
 15 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  1
 18 36  1  0
 19 37  1  1
 20 38  1  0
 22 39  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,2-Dimethylguanosine	ChEBI
2-(Dimethylamino)-9-(beta-D-ribofuranosyl)-1,9-dihydro-6H-purin-6-one	ChEBI
2-Dimethylamino-6-oxypurine riboside	ChEBI
m22g	ChEBI
N2-Dimethylguanosine	ChEBI
2-(Dimethylamino)-9-(b-D-ribofuranosyl)-1,9-dihydro-6H-purin-6-one	Generator
2-(Dimethylamino)-9-(β-D-ribofuranosyl)-1,9-dihydro-6H-purin-6-one	Generator
N,N- Dimethylguanosine	HMDB
N,N-Dimethyl-guanosine	HMDB
m(2)2g	MeSH, HMDB
m2(2)g	MeSH, HMDB
N(2),N(2)-Dimethylguanosine	MeSH, HMDB
m(2)(2)g	MeSH, HMDB
N2,N2-Dimethylguanosine	MeSH

Chemical Formula

C₁₂H₁₇N₅O₅

Average Molecular Weight

311.2939

Monoisotopic Molecular Weight

311.122968679

IUPAC Name

9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(dimethylamino)-6,9-dihydro-3H-purin-6-one

Traditional Name

9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-(dimethylamino)-3H-purin-6-one

CAS Registry Number

2140-67-2

SMILES

CN(C)C1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C12H17N5O5/c1-16(2)12-14-9-6(10(21)15-12)13-4-17(9)11-8(20)7(19)5(3-18)22-11/h4-5,7-8,11,18-20H,3H2,1-2H3,(H,14,15,21)/t5-,7-,8-,11-/m1/s1

InChI Key

RSPURTUNRHNVGF-IOSLPCCCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Not Available

Direct Parent

Purine nucleosides

Alternative Parents

Substituents

Purine nucleoside
Glycosyl compound
N-glycosyl compound
Hypoxanthine
Pentose monosaccharide
Imidazopyrimidine
Purine
Dialkylarylamine
Aminopyrimidine
Hydroxypyrimidine
Monosaccharide
N-substituted imidazole
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Azacycle
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methylguanosine (CHEBI:19289 )

Ontology

Physiological effect

Health effect

Renal system and urinary system

Renal disorder

Uremia (HMDB: HMDB0004824)
Kidney disease (HMDB: HMDB0004824)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 9607216)

Organ

Placenta (HMDB: HMDB0004824)

Excreta

Biofluid or Excreta

Urine (PMID: 15116424)

Source

Endogenous

Endogenous (HMDB: HMDB0004824)

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)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Kidney disease (MarkerDB: MDB00000454)
Chronic kidney disease (MarkerDB: MDB00000454)
Uremia (MarkerDB: MDB00000454)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	235 - 236 °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]-	MetCCS_train_neg	169.162	30932474
[M+H]+	MetCCS_train_pos	170.574	30932474
[M-H]-	Not Available	169.162	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000138
[M+H]+	Not Available	170.917	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000138

Predicted Molecular Properties

Property	Value	Source
Water Solubility	13.7 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-1.6	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	7.85	ChemAxon
pKa (Strongest Basic)	2.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.44 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	74.26 m³·mol⁻¹	ChemAxon
Polarizability	30.38 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]+	170.078	31661259
DarkChem	[M-H]-	167.322	31661259
DeepCCS	[M+H]+	166.07	30932474
DeepCCS	[M-H]-	163.675	30932474
DeepCCS	[M-2H]-	197.64	30932474
DeepCCS	[M+Na]+	172.655	30932474
AllCCS	[M+H]+	170.8	32859911
AllCCS	[M+H-H2O]+	167.7	32859911
AllCCS	[M+NH4]+	173.6	32859911
AllCCS	[M+Na]+	174.4	32859911
AllCCS	[M-H]-	171.0	32859911
AllCCS	[M+Na-2H]-	170.7	32859911
AllCCS	[M+HCOO]-	170.6	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.	2.67 minutes	32390414
Predicted by Siyang on May 30, 2022	9.7148 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.8 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	98.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1311.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	193.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	91.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	148.4 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	293.7 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	292.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	186.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	610.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	252.9 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	1028.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	185.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	186.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	464.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	204.0 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	134.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N2,N2-Dimethylguanosine	CN(C)C1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O	3301.6	Standard polar	33892256
N2,N2-Dimethylguanosine	CN(C)C1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O	2528.6	Standard non polar	33892256
N2,N2-Dimethylguanosine	CN(C)C1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O	3114.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N2,N2-Dimethylguanosine,1TMS,isomer #1	CN(C)C1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]1O)C=N2	2790.7	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,1TMS,isomer #2	CN(C)C1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]1O)C=N2	2823.0	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,1TMS,isomer #3	CN(C)C1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O[Si](C)(C)C)C=N2	2829.1	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,1TMS,isomer #4	CN(C)C1=NC(=O)C2=C(N([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C=N2)N1[Si](C)(C)C	2797.9	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,2TMS,isomer #1	CN(C)C1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O)C=N2	2724.8	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,2TMS,isomer #2	CN(C)C1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C)C=N2	2735.2	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,2TMS,isomer #3	CN(C)C1=NC(=O)C2=C(N([C@@H]3O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]3O)C=N2)N1[Si](C)(C)C	2765.7	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,2TMS,isomer #4	CN(C)C1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C)C=N2	2739.5	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,2TMS,isomer #5	CN(C)C1=NC(=O)C2=C(N([C@@H]3O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]3O)C=N2)N1[Si](C)(C)C	2804.5	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,2TMS,isomer #6	CN(C)C1=NC(=O)C2=C(N([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O[Si](C)(C)C)C=N2)N1[Si](C)(C)C	2800.0	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,3TMS,isomer #1	CN(C)C1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C)C=N2	2709.4	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,3TMS,isomer #2	CN(C)C1=NC(=O)C2=C(N([C@@H]3O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]3O)C=N2)N1[Si](C)(C)C	2749.6	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,3TMS,isomer #3	CN(C)C1=NC(=O)C2=C(N([C@@H]3O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]3O[Si](C)(C)C)C=N2)N1[Si](C)(C)C	2748.2	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,3TMS,isomer #4	CN(C)C1=NC(=O)C2=C(N([C@@H]3O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]3O[Si](C)(C)C)C=N2)N1[Si](C)(C)C	2766.3	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,4TMS,isomer #1	CN(C)C1=NC(=O)C2=C(N([C@@H]3O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]3O[Si](C)(C)C)C=N2)N1[Si](C)(C)C	2766.0	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,4TMS,isomer #1	CN(C)C1=NC(=O)C2=C(N([C@@H]3O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]3O[Si](C)(C)C)C=N2)N1[Si](C)(C)C	2902.5	Standard non polar	33892256
N2,N2-Dimethylguanosine,4TMS,isomer #1	CN(C)C1=NC(=O)C2=C(N([C@@H]3O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]3O[Si](C)(C)C)C=N2)N1[Si](C)(C)C	3371.9	Standard polar	33892256
N2,N2-Dimethylguanosine,1TBDMS,isomer #1	CN(C)C1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O)C=N2	2991.9	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,1TBDMS,isomer #2	CN(C)C1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O)C=N2	3007.8	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,1TBDMS,isomer #3	CN(C)C1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C)C=N2	3012.0	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,1TBDMS,isomer #4	CN(C)C1=NC(=O)C2=C(N([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C=N2)N1[Si](C)(C)C(C)(C)C	2988.4	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,2TBDMS,isomer #1	CN(C)C1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O)C=N2	3100.4	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,2TBDMS,isomer #2	CN(C)C1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C)C=N2	3103.4	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,2TBDMS,isomer #3	CN(C)C1=NC(=O)C2=C(N([C@@H]3O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]3O)C=N2)N1[Si](C)(C)C(C)(C)C	3121.4	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,2TBDMS,isomer #4	CN(C)C1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C)C=N2	3092.6	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,2TBDMS,isomer #5	CN(C)C1=NC(=O)C2=C(N([C@@H]3O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]3O)C=N2)N1[Si](C)(C)C(C)(C)C	3142.2	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,2TBDMS,isomer #6	CN(C)C1=NC(=O)C2=C(N([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O[Si](C)(C)C(C)(C)C)C=N2)N1[Si](C)(C)C(C)(C)C	3140.6	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,3TBDMS,isomer #1	CN(C)C1=NC(=O)C2=C([NH]1)N([C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C)C=N2	3243.9	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,3TBDMS,isomer #2	CN(C)C1=NC(=O)C2=C(N([C@@H]3O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]3O)C=N2)N1[Si](C)(C)C(C)(C)C	3280.4	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,3TBDMS,isomer #3	CN(C)C1=NC(=O)C2=C(N([C@@H]3O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]3O[Si](C)(C)C(C)(C)C)C=N2)N1[Si](C)(C)C(C)(C)C	3286.3	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,3TBDMS,isomer #4	CN(C)C1=NC(=O)C2=C(N([C@@H]3O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]3O[Si](C)(C)C(C)(C)C)C=N2)N1[Si](C)(C)C(C)(C)C	3286.1	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,4TBDMS,isomer #1	CN(C)C1=NC(=O)C2=C(N([C@@H]3O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]3O[Si](C)(C)C(C)(C)C)C=N2)N1[Si](C)(C)C(C)(C)C	3479.6	Semi standard non polar	33892256
N2,N2-Dimethylguanosine,4TBDMS,isomer #1	CN(C)C1=NC(=O)C2=C(N([C@@H]3O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]3O[Si](C)(C)C(C)(C)C)C=N2)N1[Si](C)(C)C(C)(C)C	3652.0	Standard non polar	33892256
N2,N2-Dimethylguanosine,4TBDMS,isomer #1	CN(C)C1=NC(=O)C2=C(N([C@@H]3O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]3O[Si](C)(C)C(C)(C)C)C=N2)N1[Si](C)(C)C(C)(C)C	3678.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N2,N2-Dimethylguanosine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ac3-9180000000-6b74485ca69b8a0937c1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N2,N2-Dimethylguanosine GC-MS (3 TMS) - 70eV, Positive	splash10-01c0-3391310000-26de80f9bc78e87a644a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N2,N2-Dimethylguanosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N2,N2-Dimethylguanosine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - N2,N2-Dimethylguanosine CE-QTOF-MS system (Agilent 7100 CE + 6550 QTOF) 10V, Positive-QTOF	splash10-001i-0900000000-6033a973f510df066a11	2019-03-07	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 10V, Positive-QTOF	splash10-001i-0901000000-ee7f601ba19e92eb3000	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 30V, Positive-QTOF	splash10-001i-0900000000-1ee81ff6672079088e87	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 40V, Negative-QTOF	splash10-001i-1900000000-d79f213e790ad370a66e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 30V, Negative-QTOF	splash10-0059-0900000000-20a29955f6b438cd3fa1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 20V, Negative-QTOF	splash10-004i-0901000000-1701dcf20f0234b63b6d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 10V, Negative-QTOF	splash10-03di-0309000000-1bbce8944068addfb261	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 40V, Negative-QTOF	splash10-004i-0900000000-95ebcc742789eafc2b3b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 10V, Positive-QTOF	splash10-01q9-0904000000-49681e90d78457e6d0c9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 35V, Positive-QTOF	splash10-001i-0900000000-b320e8e065d43857d0a5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 20V, Negative-QTOF	splash10-03di-0309000000-d555efe7388f8c08d0e5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 20V, Positive-QTOF	splash10-001i-0900000000-8a37caef7033915dada7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 35V, Negative-QTOF	splash10-004i-0900000000-4412ec0093a05d259e3c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 10V, Negative-QTOF	splash10-03di-0009000000-91ed5c716462a0de56ed	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 40V, Positive-QTOF	splash10-001i-0900000000-16a2c20e204fd9a3725c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 0V, Positive-QTOF	splash10-03e9-0709000000-956e2532e241964d69e9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 20V, Positive-QTOF	splash10-001i-0900000000-0138cd5cbbbc494c7b3f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 10V, Positive-QTOF	splash10-001i-0900000000-f21ba6a3e1d687e0fe98	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 30V, Positive-QTOF	splash10-001i-3900000000-b511ad9d8a15f64f7f66	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 10V, Positive-QTOF	splash10-001i-0913000000-0a30a8ffbe4d72e234cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 20V, Positive-QTOF	splash10-001i-0900000000-8d944e0314b44af1f027	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 40V, Positive-QTOF	splash10-01q9-1900000000-ec4fb5d37def9d84c5a5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 10V, Negative-QTOF	splash10-03fr-0759000000-2b4a326aad3ce87ea5e3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 20V, Negative-QTOF	splash10-004i-0910000000-10561e691bbf8dac63d5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N2,N2-Dimethylguanosine 40V, Negative-QTOF	splash10-03di-1900000000-c3a8e7eb56de154adbdb	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.029 +/- 0.09 uM	Adult (>18 years old)	Both	Normal	9607216	details
Blood	Detected and Quantified	0.031 +/- 0.004 uM	Adult (>18 years old)	Both	Normal	2437827	details
Blood	Detected and Quantified	0.0289 +/- 0.0151 uM	Adult (>18 years old)	Both	Normal	12675874	details
Urine	Detected and Quantified	0.360 (0.224-0.496) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15116424	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.44 +/- 0.09 uM	Adult (>18 years old)	Both	Kidney disease	9607216	details
Blood	Detected and Quantified	0.760 +/- 0.288 uM	Adult (>18 years old)	Both	Uremia	12675874	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Kidney disease
Niwa T, Takeda N, Yoshizumi H: RNA metabolism in uremic patients: accumulation of modified ribonucleosides in uremic serum. Technical note. Kidney Int. 1998 Jun;53(6):1801-6. [PubMed:9607216 ]
Uremia
Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023432

KNApSAcK ID

Not Available

Chemspider ID

83878

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

7086

PubChem Compound

92919

PDB ID

Not Available

ChEBI ID

19289

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000454

Good Scents ID

Not Available

References

Synthesis Reference

Gerster, John F.; Robins, Roland K. Purine nucleosides. X. The synthesis of certain naturally occurring 2-substituted amino-9-b-D-ribofuranosylpurin-6(1 H)-ones (N2-substituted guanosines). Journal of the American Chemical Society (1965), 87(16), 3752-9.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Lee SH, Jung BH, Kim SY, Chung BC: A rapid and sensitive method for quantitation of nucleosides in human urine using liquid chromatography/mass spectrometry with direct urine injection. Rapid Commun Mass Spectrom. 2004;18(9):973-7. [PubMed:15116424 ]
Zheng YF, Yang J, Zhao XJ, Feng B, Kong HW, Chen YJ, Lv S, Zheng MH, Xu GW: Urinary nucleosides as biological markers for patients with colorectal cancer. World J Gastroenterol. 2005 Jul 7;11(25):3871-6. [PubMed:15991285 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for N2,N2-Dimethylguanosine (HMDB0004824)

MOL for HMDB0004824 (N2,N2-Dimethylguanosine)

3D MOL for HMDB0004824 (N2,N2-Dimethylguanosine)

3D SDF for HMDB0004824 (N2,N2-Dimethylguanosine)

3D-SDF for HMDB0004824 (N2,N2-Dimethylguanosine)

PDB for HMDB0004824 (N2,N2-Dimethylguanosine)

3D PDB for HMDB0004824 (N2,N2-Dimethylguanosine)

SMILES for HMDB0004824 (N2,N2-Dimethylguanosine)

INCHI for HMDB0004824 (N2,N2-Dimethylguanosine)

Structure for HMDB0004824 (N2,N2-Dimethylguanosine)

3D Structure for HMDB0004824 (N2,N2-Dimethylguanosine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra