NP-MRD: Showing NP-Card for 7-Methylguanosine (NP0000848)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2020-11-24 22:18:47 UTC

NP-MRD ID

NP0000848

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-Methylguanosine

Description

7-Methylguanosine is an endogenous methylated nucleoside found in human fluids; methylated purine bases are present in higher amounts in tumor-bearing patients compared to healthy controls.DNA hypermethylation is a common finding in malignant cells and has been explored as a therapeutic target for hypomethylating agents. When chemical bonds to DNA, the DNA becomes damaged and proper and complete replication cannot occur to make the normal intended cell. A DNA adduct is an abnormal piece of DNA covalently-bonded to a cancer-causing chemical. This has shown to be the start of a cancerous cell, or carcinogenesis. DNA adducts in scientific experiments are used as bio-markers and as such are themselves measured to reflect quantitatively, for comparison, the amount of cancer in the subject. 7-Methylguanosine is a substrate for purine-nucleoside phosphorylase and Eukaryotic translation initiation factor 4E. (PMID: 3506820 , 17044778 , 17264127 , 16799933 ).

Structure

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

HMDB0001107
     RDKit          3D
7-Methylguanosine
 37 39  0  0  0  0  0  0  0  0999 V2000
   -3.5358   -2.8002   -1.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5120   -1.7886   -0.7329 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1919   -2.0118   -0.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5391   -0.8681   -0.3173 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.8776   -0.7577   -0.1105 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1935   -0.0647    1.0729 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5885   -0.0833    0.9838 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2367    0.7042    2.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6163    0.6196    1.9090 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8050    0.5607   -0.3699 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9824    0.1556   -0.9513 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5861    0.0526   -1.1494 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9969   -0.8427   -2.1597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4750    0.0976   -0.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3610    1.4007   -0.0487 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4568    2.1857   -0.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3311    3.5958    0.1878 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6567    1.6342   -0.3150 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8278    0.3223   -0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9513   -0.1921   -0.7913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7066   -0.4708   -0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2979   -2.3761   -1.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9759   -3.1593   -0.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0072   -3.6716   -1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7681   -3.0209   -0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3432   -1.7379   -0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8872   -1.1480    0.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9232    1.7515    2.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9814    0.2237    3.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9100   -0.3175    1.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7471    1.6582   -0.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6414    0.8825   -0.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0109    0.8855   -1.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2699   -1.4655   -2.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4136    1.8026    0.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5988    3.9952    0.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9906    4.2488   -0.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  4 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21  2  1  0
 12  5  1  0
 21 14  2  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  5 26  1  1
  7 27  1  6
  8 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  1
 11 32  1  0
 12 33  1  6
 13 34  1  0
 15 35  1  0
 17 36  1  0
 17 37  1  0
M  CHG  1   4   1
M  END


  Mrv1652305271900012D          

 21 23  0  0  1  0            999 V2000
    0.5576   -2.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3027   -1.6349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7876   -0.9674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3027   -0.3000    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.4819   -0.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4819   -1.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1964   -1.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1964   -2.6174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9109   -1.3799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9109   -0.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1964   -0.1424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6253   -0.1424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5576    0.4846    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3423    0.7396    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3423    1.5646    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5576    1.8195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0727    1.1521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3027    2.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8547    3.2172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0097    2.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0097    0.2547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 10 12  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  6  0  0  0
 16 18  1  6  0  0  0
 18 19  1  0  0  0  0
 15 20  1  1  0  0  0
 14 21  1  1  0  0  0
M  CHG  1   4   1
M  END
> <DATABASE_ID>
NP0000848

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C=[N+]([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C2=C1C(=O)N=C(N)N2

> <INCHI_IDENTIFIER>
InChI=1S/C11H15N5O5/c1-15-3-16(8-5(15)9(20)14-11(12)13-8)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2-,12,13,14,20)/p+1/t4-,6-,7-,10-/m1/s1

> <INCHI_KEY>
OGHAROSJZRTIOK-KQYNXXCUSA-O

> <FORMULA>
C11H16N5O5

> <MOLECULAR_WEIGHT>
298.2752

> <EXACT_MASS>
298.115143647

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
28.471549334789664

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-methyl-6-oxo-6,7-dihydro-3H-9lambda5-purin-9-ylium

> <ALOGPS_LOGP>
-1.43

> <JCHEM_LOGP>
-6.202784917138413

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.720656395523086

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.008217314888612

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9841648924777244

> <JCHEM_POLAR_SURFACE_AREA>
146.21

> <JCHEM_REFRACTIVITY>
69.38040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-methyl-6-oxo-3H-9lambda5-purin-9-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001107
     RDKit          3D
7-Methylguanosine
 37 39  0  0  0  0  0  0  0  0999 V2000
   -3.5358   -2.8002   -1.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5120   -1.7886   -0.7329 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1919   -2.0118   -0.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5391   -0.8681   -0.3173 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.8776   -0.7577   -0.1105 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1935   -0.0647    1.0729 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5885   -0.0833    0.9838 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2367    0.7042    2.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6163    0.6196    1.9090 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8050    0.5607   -0.3699 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9824    0.1556   -0.9513 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5861    0.0526   -1.1494 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9969   -0.8427   -2.1597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4750    0.0976   -0.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3610    1.4007   -0.0487 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4568    2.1857   -0.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3311    3.5958    0.1878 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6567    1.6342   -0.3150 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8278    0.3223   -0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9513   -0.1921   -0.7913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7066   -0.4708   -0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2979   -2.3761   -1.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9759   -3.1593   -0.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0072   -3.6716   -1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7681   -3.0209   -0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3432   -1.7379   -0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8872   -1.1480    0.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9232    1.7515    2.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9814    0.2237    3.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9100   -0.3175    1.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7471    1.6582   -0.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6414    0.8825   -0.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0109    0.8855   -1.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2699   -1.4655   -2.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4136    1.8026    0.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5988    3.9952    0.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9906    4.2488   -0.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  4 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21  2  1  0
 12  5  1  0
 21 14  2  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  5 26  1  1
  7 27  1  6
  8 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  1
 11 32  1  0
 12 33  1  6
 13 34  1  0
 15 35  1  0
 17 36  1  0
 17 37  1  0
M  CHG  1   4   1
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       1.041  -4.516   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.565  -3.052   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.470  -1.806   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       0.565  -0.560   0.000  0.00  0.00           N+1
HETATM    5  C   UNK     0      -0.900  -1.036   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.900  -2.576   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.233  -3.346   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.233  -4.886   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      -3.567  -2.576   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -3.567  -1.036   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -2.233  -0.266   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      -4.901  -0.266   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       1.041   0.905   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.506   1.381   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.506   2.921   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.041   3.396   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.136   2.151   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.565   4.861   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.595   6.005   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.751   3.826   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.751   0.475   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    2    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10    5                                                       
CONECT   12   10                                                            
CONECT   13    4   14   17                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   13                                                       
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   15                                                            
CONECT   21   14                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0001107
HETATM    1  C1  UNL     1      -3.536  -2.800  -1.037  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.512  -1.789  -0.733  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.192  -2.012  -0.595  1.00  0.00           C  
HETATM    4  N2  UNL     1      -0.539  -0.868  -0.317  1.00  0.00           N1+
HETATM    5  C3  UNL     1       0.878  -0.758  -0.111  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.193  -0.065   1.073  1.00  0.00           O  
HETATM    7  C4  UNL     1       2.589  -0.083   0.984  1.00  0.00           C  
HETATM    8  C5  UNL     1       3.237   0.704   2.093  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.616   0.620   1.909  1.00  0.00           O  
HETATM   10  C6  UNL     1       2.805   0.561  -0.370  1.00  0.00           C  
HETATM   11  O3  UNL     1       3.982   0.156  -0.951  1.00  0.00           O  
HETATM   12  C7  UNL     1       1.586   0.053  -1.149  1.00  0.00           C  
HETATM   13  O4  UNL     1       1.997  -0.843  -2.160  1.00  0.00           O  
HETATM   14  C8  UNL     1      -1.475   0.098  -0.281  1.00  0.00           C  
HETATM   15  N3  UNL     1      -1.361   1.401  -0.049  1.00  0.00           N  
HETATM   16  C9  UNL     1      -2.457   2.186  -0.064  1.00  0.00           C  
HETATM   17  N4  UNL     1      -2.331   3.596   0.188  1.00  0.00           N  
HETATM   18  N5  UNL     1      -3.657   1.634  -0.315  1.00  0.00           N  
HETATM   19  C10 UNL     1      -3.828   0.322  -0.556  1.00  0.00           C  
HETATM   20  O5  UNL     1      -4.951  -0.192  -0.791  1.00  0.00           O  
HETATM   21  C11 UNL     1      -2.707  -0.471  -0.539  1.00  0.00           C  
HETATM   22  H1  UNL     1      -4.298  -2.376  -1.717  1.00  0.00           H  
HETATM   23  H2  UNL     1      -3.976  -3.159  -0.075  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.007  -3.672  -1.474  1.00  0.00           H  
HETATM   25  H4  UNL     1      -0.768  -3.021  -0.706  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.343  -1.738  -0.032  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.887  -1.148   0.994  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.923   1.751   2.016  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.981   0.224   3.049  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.910  -0.317   1.802  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.747   1.658  -0.212  1.00  0.00           H  
HETATM   32  H11 UNL     1       4.641   0.882  -0.840  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.011   0.885  -1.558  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.270  -1.466  -2.385  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.414   1.803   0.144  1.00  0.00           H  
HETATM   36  H15 UNL     1      -1.599   3.995   0.811  1.00  0.00           H  
HETATM   37  H16 UNL     1      -2.991   4.249  -0.265  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   21
CONECT    3    4    4   25
CONECT    4    5   14
CONECT    5    6   12   26
CONECT    6    7
CONECT    7    8   10   27
CONECT    8    9   28   29
CONECT    9   30
CONECT   10   11   12   31
CONECT   11   32
CONECT   12   13   33
CONECT   13   34
CONECT   14   15   21   21
CONECT   15   16   35
CONECT   16   17   18   18
CONECT   17   36   37
CONECT   18   19
CONECT   19   20   20   21
END

HMDB0001107
     RDKit          3D
7-Methylguanosine
 37 39  0  0  0  0  0  0  0  0999 V2000
   -3.5358   -2.8002   -1.0374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5120   -1.7886   -0.7329 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1919   -2.0118   -0.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5391   -0.8681   -0.3173 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.8776   -0.7577   -0.1105 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1935   -0.0647    1.0729 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5885   -0.0833    0.9838 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2367    0.7042    2.0928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6163    0.6196    1.9090 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8050    0.5607   -0.3699 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9824    0.1556   -0.9513 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5861    0.0526   -1.1494 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9969   -0.8427   -2.1597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4750    0.0976   -0.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3610    1.4007   -0.0487 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4568    2.1857   -0.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3311    3.5958    0.1878 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6567    1.6342   -0.3150 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8278    0.3223   -0.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9513   -0.1921   -0.7913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7066   -0.4708   -0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2979   -2.3761   -1.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9759   -3.1593   -0.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0072   -3.6716   -1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7681   -3.0209   -0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3432   -1.7379   -0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8872   -1.1480    0.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9232    1.7515    2.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9814    0.2237    3.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9100   -0.3175    1.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7471    1.6582   -0.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6414    0.8825   -0.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0109    0.8855   -1.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2699   -1.4655   -2.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4136    1.8026    0.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5988    3.9952    0.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9906    4.2488   -0.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  4 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21  2  1  0
 12  5  1  0
 21 14  2  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  5 26  1  1
  7 27  1  6
  8 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  1
 11 32  1  0
 12 33  1  6
 13 34  1  0
 15 35  1  0
 17 36  1  0
 17 37  1  0
M  CHG  1   4   1
M  END

View in JSmol

Synonyms

Value	Source
G	ChEBI
m7g	ChEBI
N(7)-Methylguanosine	ChEBI
2-Amino-6,9-dihydro-7-methyl-6-oxo-9-beta-D-ribofuranosyl-1H-purinium	HMDB
2-Amino-6,9-dihydro-7-methyl-6-oxo-9-beta-delta-ribofuranosyl-1H-purinium	HMDB
N(2)-Methylguanosine	HMDB
2-Methylguanosine	HMDB

Chemical Formula

C₁₁H₁₆N₅O₅

Average Mass

298.2752 Da

Monoisotopic Mass

298.11514 Da

IUPAC Name

2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-methyl-6-oxo-6,7-dihydro-3H-9lambda5-purin-9-ylium

Traditional Name

2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-methyl-6-oxo-3H-9lambda5-purin-9-ylium

CAS Registry Number

20244-86-4

SMILES

CN1C=[N+]([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C2=C1C(=O)N=C(N)N2

InChI Identifier

InChI=1S/C11H15N5O5/c1-15-3-16(8-5(15)9(20)14-11(12)13-8)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2-,12,13,14,20)/p+1/t4-,6-,7-,10-/m1/s1

InChI Key

OGHAROSJZRTIOK-KQYNXXCUSA-O

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, simulated)	Varshavi.d26			2021-08-11	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Camellia assamica	KNApSAcK Database	22123792
Camellia irrawadiensisia	KNApSAcK Database	22123792
Camellia kissi	KNApSAcK Database	22123792
Camellia ptilophylla	KNApSAcK Database	22123792
Camellia sinensis	KNApSAcK Database	22123792
Camellia taliensis	KNApSAcK Database	22123792
Camellia toliensis	KNApSAcK Database	22123792
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Citrus maxima	KNApSAcK Database	22123792
Coffea arabica	KNApSAcK Database	22123792
Coffea canephora	KNApSAcK Database	22123792
Coffea dewevrei	KNApSAcK Database	22123792
Coffea eugeniodes	KNApSAcK Database	22123792
Coffea kianjavatensis	KNApSAcK Database	22123792
Coffea liberica	KNApSAcK Database	22123792
Coffea racemosa	KNApSAcK Database	22123792
Coffea salvatrix	KNApSAcK Database	22123792
Cola sp.	KNApSAcK Database	22123792
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Ilex paraguariensis	KNApSAcK Database	22123792
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Paullinia cupana	KNApSAcK Database	22123792
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Theobroma cacao	KNApSAcK Database	22123792
Theobroma grandiflorum	KNApSAcK Database	22123792

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Not Available

Direct Parent

Purine nucleosides

Alternative Parents

Substituents

Purine nucleoside
Glycosyl compound
N-glycosyl compound
6-oxopurine
Hypoxanthine
Pentose monosaccharide
Imidazopyrimidine
Purine
Aminopyrimidine
Pyrimidone
Monosaccharide
N-substituted imidazole
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Azacycle
Primary alcohol
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Amine
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Primary amine
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic cation (CHEBI:20794 )
methylguanosine (CHEBI:20794 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	155 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	5.61 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-6.2	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	6.01	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	146.21 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	69.38 m³·mol⁻¹	ChemAxon
Polarizability	28.47 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

External Links

HMDB ID

HMDB0001107

DrugBank ID

DB03493

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022428

KNApSAcK ID

C00051958

Chemspider ID

393054

KEGG Compound ID

Not Available

BioCyc ID

CPD0-1041

BiGG ID

Not Available

Wikipedia Link

7-Methylguanosine

METLIN ID

6008

PubChem Compound

445404

PDB ID

Not Available

ChEBI ID

20794

Good Scents ID

Not Available

References

General References

Reynaud C, Bruno C, Boullanger P, Grange J, Barbesti S, Niveleau A: Monitoring of urinary excretion of modified nucleosides in cancer patients using a set of six monoclonal antibodies. Cancer Lett. 1992 Jan 31;61(3):255-62. [PubMed:1739950 ]
Topp H, Sander G, Heller-Schoch G, Schoch G: Determination of 7-methylguanine, N2,N2-dimethylguanosine, and pseudouridine in ultrafiltrated serum of healthy adults by high-performance liquid chromatography. Anal Biochem. 1987 Feb 15;161(1):49-56. [PubMed:2437827 ]
Tebib JG, Reynaud C, Cedoz JP, Letroublon MC, Niveleau A: Relationship between urinary excretion of modified nucleosides and rheumatoid arthritis process. Br J Rheumatol. 1997 Sep;36(9):990-5. [PubMed:9376997 ]
Morris GS, Simmonds HA, Davies PM: Use of biological fluids for the rapid diagnosis of potentially lethal inherited disorders of human purine and pyrimidine metabolism. Biomed Chromatogr. 1986 Jun;1(3):109-18. [PubMed:3506820 ]
Cho SH, Jung BH, Lee SH, Lee WY, Kong G, Chung BC: Direct determination of nucleosides in the urine of patients with breast cancer using column-switching liquid chromatography-tandem mass spectrometry. Biomed Chromatogr. 2006 Nov;20(11):1229-36. [PubMed:16799933 ]
Yang TH, Hu ML: Intracellular levels of S-adenosylhomocysteine but not homocysteine are highly correlated to the expression of nm23-H1 and the level of 5-methyldeoxycytidine in human hepatoma cells with different invasion activities. Nutr Cancer. 2006;55(2):224-31. [PubMed:17044778 ]
Liu Z, Liu S, Xie Z, Blum W, Perrotti D, Paschka P, Klisovic R, Byrd J, Chan KK, Marcucci G: Characterization of in vitro and in vivo hypomethylating effects of decitabine in acute myeloid leukemia by a rapid, specific and sensitive LC-MS/MS method. Nucleic Acids Res. 2007;35(5):e31. Epub 2007 Jan 30. [PubMed:17264127 ]

Showing NP-Card for 7-Methylguanosine (NP0000848)

MOL for NP0000848 (7-Methylguanosine)

3D MOL for NP0000848 (7-Methylguanosine)

3D SDF for NP0000848 (7-Methylguanosine)

3D-SDF for NP0000848 (7-Methylguanosine)

PDB for NP0000848 (7-Methylguanosine)

3D PDB for NP0000848 (7-Methylguanosine)

SMILES for NP0000848 (7-Methylguanosine)

INCHI for NP0000848 (7-Methylguanosine)

Structure for NP0000848 (7-Methylguanosine)

3D Structure for NP0000848 (7-Methylguanosine)