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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:47:44 UTC

Update Date

2022-11-23 22:29:17 UTC

HMDB ID

HMDB0255878

Secondary Accession Numbers

None

Metabolite Identification

Common Name

O(6)-Benzylguanine

Description

6-O-benzylguanine, also known as O(6)-bgua, belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. Based on a literature review very few articles have been published on 6-O-benzylguanine. This compound has been identified in human blood as reported by (PMID: 31557052 ). O(6)-benzylguanine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically O(6)-Benzylguanine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0255878
     RDKit          3D
o6-Benzylguanine
 29 31  0  0  0  0  0  0  0  0999 V2000
   -3.5481   -2.8543    0.0704 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0812   -1.6367    0.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7615   -1.3947    0.0400 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2886   -0.1462    0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0652    0.1689    0.0127 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9671   -0.9110   -0.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3735   -0.4347   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6906    0.9120   -0.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9951    1.3558   -0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0435    0.4680   -0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7248   -0.8723   -0.3263 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4203   -1.3242   -0.2712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2001    0.8884    0.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0789    2.2339    0.2535 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3033    2.7784    0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1963    1.7788    0.3579 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5406    0.6076    0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9958   -0.6618    0.2150 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8683   -3.6338   -0.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8049   -1.6885    0.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7642   -1.3773   -1.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8571    1.6256   -0.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1936    2.4175   -0.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0837    0.8111   -0.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5200   -1.5822   -0.4126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1849   -2.3964   -0.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5495    3.8511    0.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2418    1.8863    0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0343   -0.8693    0.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 12  7  1  0
 17 13  2  0
  1 19  1  0
  6 20  1  0
  6 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 15 27  1  0
 16 28  1  0
 18 29  1  0
M  END

  Mrv0541 05041408522D          

 18 20  0  0  0  0            999 V2000
    2.0701    3.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    2.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  8  6  1  0  0  0  0
 10  9  2  0  0  0  0
 11  9  1  0  0  0  0
 13 12  2  0  0  0  0
 14  7  2  0  0  0  0
 14  9  1  0  0  0  0
 15  7  1  0  0  0  0
 15 10  1  0  0  0  0
 16 10  1  0  0  0  0
 16 12  1  0  0  0  0
 17 11  2  0  0  0  0
 17 12  1  0  0  0  0
 18  6  1  0  0  0  0
 18 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255878

> <DATABASE_NAME>
hmdb

> <SMILES>
N=C1NC2=C(N=CN2)C(OCC2=CC=CC=C2)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C12H11N5O/c13-12-16-10-9(14-7-15-10)11(17-12)18-6-8-4-2-1-3-5-8/h1-5,7H,6H2,(H3,13,14,15,16,17)

> <INCHI_KEY>
KRWMERLEINMZFT-UHFFFAOYSA-N

> <FORMULA>
C12H11N5O

> <MOLECULAR_WEIGHT>
241.2486

> <EXACT_MASS>
241.096359999

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
24.548049332022586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(benzyloxy)-3,9-dihydro-2H-purin-2-imine

> <ALOGPS_LOGP>
0.90

> <JCHEM_LOGP>
1.3873817133333337

> <ALOGPS_LOGS>
-3.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.860562657397779

> <JCHEM_PKA_STRONGEST_BASIC>
5.206676086402932

> <JCHEM_POLAR_SURFACE_AREA>
86.15

> <JCHEM_REFRACTIVITY>
77.9697

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(benzyloxy)-3,9-dihydropurin-2-imine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255878
     RDKit          3D
o6-Benzylguanine
 29 31  0  0  0  0  0  0  0  0999 V2000
   -3.5481   -2.8543    0.0704 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0812   -1.6367    0.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7615   -1.3947    0.0400 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2886   -0.1462    0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0652    0.1689    0.0127 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9671   -0.9110   -0.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3735   -0.4347   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6906    0.9120   -0.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9951    1.3558   -0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0435    0.4680   -0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7248   -0.8723   -0.3263 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4203   -1.3242   -0.2712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2001    0.8884    0.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0789    2.2339    0.2535 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3033    2.7784    0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1963    1.7788    0.3579 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5406    0.6076    0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9958   -0.6618    0.2150 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8683   -3.6338   -0.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8049   -1.6885    0.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7642   -1.3773   -1.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8571    1.6256   -0.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1936    2.4175   -0.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0837    0.8111   -0.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5200   -1.5822   -0.4126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1849   -2.3964   -0.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5495    3.8511    0.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2418    1.8863    0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0343   -0.8693    0.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 12  7  1  0
 17 13  2  0
  1 19  1  0
  6 20  1  0
  6 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 15 27  1  0
 16 28  1  0
 18 29  1  0
M  END

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3    8                                                       
CONECT    6    8   18                                                       
CONECT    7   14   15                                                       
CONECT    8    4    5    6                                                  
CONECT    9   10   11   14                                                  
CONECT   10    9   15   16                                                  
CONECT   11    9   17   18                                                  
CONECT   12   13   16   17                                                  
CONECT   13   12                                                            
CONECT   14    7    9                                                       
CONECT   15    7   10                                                       
CONECT   16   10   12                                                       
CONECT   17   11   12                                                       
CONECT   18    6   11                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0255878
HETATM    1  N1  UNL     1      -3.548  -2.854   0.070  1.00  0.00           N  
HETATM    2  C1  UNL     1      -3.081  -1.637   0.107  1.00  0.00           C  
HETATM    3  N2  UNL     1      -1.762  -1.395   0.040  1.00  0.00           N  
HETATM    4  C2  UNL     1      -1.289  -0.146   0.078  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.065   0.169   0.013  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.967  -0.911  -0.100  1.00  0.00           C  
HETATM    7  C4  UNL     1       2.374  -0.435  -0.160  1.00  0.00           C  
HETATM    8  C5  UNL     1       2.691   0.912  -0.107  1.00  0.00           C  
HETATM    9  C6  UNL     1       3.995   1.356  -0.163  1.00  0.00           C  
HETATM   10  C7  UNL     1       5.043   0.468  -0.274  1.00  0.00           C  
HETATM   11  C8  UNL     1       4.725  -0.872  -0.326  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.420  -1.324  -0.271  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.200   0.888   0.189  1.00  0.00           C  
HETATM   14  N3  UNL     1      -2.079   2.234   0.254  1.00  0.00           N  
HETATM   15  C11 UNL     1      -3.303   2.778   0.357  1.00  0.00           C  
HETATM   16  N4  UNL     1      -4.196   1.779   0.358  1.00  0.00           N  
HETATM   17  C12 UNL     1      -3.541   0.608   0.255  1.00  0.00           C  
HETATM   18  N5  UNL     1      -3.996  -0.662   0.215  1.00  0.00           N  
HETATM   19  H1  UNL     1      -2.868  -3.634  -0.013  1.00  0.00           H  
HETATM   20  H2  UNL     1       0.805  -1.689   0.644  1.00  0.00           H  
HETATM   21  H3  UNL     1       0.764  -1.377  -1.107  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.857   1.626  -0.018  1.00  0.00           H  
HETATM   23  H5  UNL     1       4.194   2.417  -0.118  1.00  0.00           H  
HETATM   24  H6  UNL     1       6.084   0.811  -0.319  1.00  0.00           H  
HETATM   25  H7  UNL     1       5.520  -1.582  -0.413  1.00  0.00           H  
HETATM   26  H8  UNL     1       3.185  -2.396  -0.314  1.00  0.00           H  
HETATM   27  H9  UNL     1      -3.549   3.851   0.430  1.00  0.00           H  
HETATM   28  H10 UNL     1      -5.242   1.886   0.427  1.00  0.00           H  
HETATM   29  H11 UNL     1      -5.034  -0.869   0.267  1.00  0.00           H  
CONECT    1    2    2   19
CONECT    2    3   18
CONECT    3    4    4
CONECT    4    5   13
CONECT    5    6
CONECT    6    7   20   21
CONECT    7    8    8   12
CONECT    8    9   22
CONECT    9   10   10   23
CONECT   10   11   24
CONECT   11   12   12   25
CONECT   12   26
CONECT   13   14   17   17
CONECT   14   15   15
CONECT   15   16   27
CONECT   16   17   28
CONECT   17   18
CONECT   18   29
END

HMDB0255878
     RDKit          3D
o6-Benzylguanine
 29 31  0  0  0  0  0  0  0  0999 V2000
   -3.5481   -2.8543    0.0704 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0812   -1.6367    0.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7615   -1.3947    0.0400 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2886   -0.1462    0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0652    0.1689    0.0127 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9671   -0.9110   -0.1000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3735   -0.4347   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6906    0.9120   -0.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9951    1.3558   -0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0435    0.4680   -0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7248   -0.8723   -0.3263 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4203   -1.3242   -0.2712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2001    0.8884    0.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0789    2.2339    0.2535 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3033    2.7784    0.3571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1963    1.7788    0.3579 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5406    0.6076    0.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9958   -0.6618    0.2150 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8683   -3.6338   -0.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8049   -1.6885    0.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7642   -1.3773   -1.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8571    1.6256   -0.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1936    2.4175   -0.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0837    0.8111   -0.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5200   -1.5822   -0.4126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1849   -2.3964   -0.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5495    3.8511    0.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2418    1.8863    0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0343   -0.8693    0.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 12  7  1  0
 17 13  2  0
  1 19  1  0
  6 20  1  0
  6 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 15 27  1  0
 16 28  1  0
 18 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
O(6)-BGua	MeSH
O(6)-Benzylguanine	MeSH
O6-Benzylguanine	ChEMBL
6-O-Benzylguanine	MeSH

Chemical Formula

C₁₂H₁₁N₅O

Average Molecular Weight

241.2486

Monoisotopic Molecular Weight

241.096359999

IUPAC Name

6-(benzyloxy)-3,9-dihydro-2H-purin-2-imine

Traditional Name

6-(benzyloxy)-3,9-dihydropurin-2-imine

CAS Registry Number

Not Available

SMILES

N=C1NC2=C(N=CN2)C(OCC2=CC=CC=C2)=N1

InChI Identifier

InChI=1S/C12H11N5O/c13-12-16-10-9(14-7-15-10)11(17-12)18-6-8-4-2-1-3-5-8/h1-5,7H,6H2,(H3,13,14,15,16,17)

InChI Key

KRWMERLEINMZFT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Hypoxanthines

Alternative Parents

Substituents

Hypoxanthine
Alkyl aryl ether
Aminopyrimidine
Monocyclic benzene moiety
Pyrimidine
Benzenoid
Azole
Imidazole
Heteroaromatic compound
Ether
Azacycle
Organooxygen compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Primary amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.9	ALOGPS
logP	1.39	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	12.86	ChemAxon
pKa (Strongest Basic)	5.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.15 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	77.97 m³·mol⁻¹	ChemAxon
Polarizability	24.55 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DeepCCS	[M+H]+	155.864	30932474
DeepCCS	[M-H]-	153.506	30932474
DeepCCS	[M-2H]-	186.415	30932474
DeepCCS	[M+Na]+	161.957	30932474
AllCCS	[M+H]+	154.5	32859911
AllCCS	[M+H-H2O]+	150.5	32859911
AllCCS	[M+NH4]+	158.3	32859911
AllCCS	[M+Na]+	159.3	32859911
AllCCS	[M-H]-	156.5	32859911
AllCCS	[M+Na-2H]-	156.0	32859911
AllCCS	[M+HCOO]-	155.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
o6-Benzylguanine	N=C1NC2=C(N=CN2)C(OCC2=CC=CC=C2)=N1	3504.0	Standard polar	33892256
o6-Benzylguanine	N=C1NC2=C(N=CN2)C(OCC2=CC=CC=C2)=N1	2565.4	Standard non polar	33892256
o6-Benzylguanine	N=C1NC2=C(N=CN2)C(OCC2=CC=CC=C2)=N1	2720.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
o6-Benzylguanine,1TMS,isomer #1	C[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C([NH]C=N2)[NH]1	2391.9	Semi standard non polar	33892256
o6-Benzylguanine,1TMS,isomer #1	C[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C([NH]C=N2)[NH]1	2547.0	Standard non polar	33892256
o6-Benzylguanine,1TMS,isomer #1	C[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C([NH]C=N2)[NH]1	3545.4	Standard polar	33892256
o6-Benzylguanine,1TMS,isomer #2	C[Si](C)(C)N1C(=N)N=C(OCC2=CC=CC=C2)C2=C1[NH]C=N2	2477.4	Semi standard non polar	33892256
o6-Benzylguanine,1TMS,isomer #2	C[Si](C)(C)N1C(=N)N=C(OCC2=CC=CC=C2)C2=C1[NH]C=N2	2498.8	Standard non polar	33892256
o6-Benzylguanine,1TMS,isomer #2	C[Si](C)(C)N1C(=N)N=C(OCC2=CC=CC=C2)C2=C1[NH]C=N2	3571.8	Standard polar	33892256
o6-Benzylguanine,1TMS,isomer #3	C[Si](C)(C)N1C=NC2=C1[NH]C(=N)N=C2OCC1=CC=CC=C1	2547.6	Semi standard non polar	33892256
o6-Benzylguanine,1TMS,isomer #3	C[Si](C)(C)N1C=NC2=C1[NH]C(=N)N=C2OCC1=CC=CC=C1	2492.1	Standard non polar	33892256
o6-Benzylguanine,1TMS,isomer #3	C[Si](C)(C)N1C=NC2=C1[NH]C(=N)N=C2OCC1=CC=CC=C1	3496.5	Standard polar	33892256
o6-Benzylguanine,2TMS,isomer #1	C[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C([NH]1)N([Si](C)(C)C)C=N2	2439.2	Semi standard non polar	33892256
o6-Benzylguanine,2TMS,isomer #1	C[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C([NH]1)N([Si](C)(C)C)C=N2	2565.2	Standard non polar	33892256
o6-Benzylguanine,2TMS,isomer #1	C[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C([NH]1)N([Si](C)(C)C)C=N2	3301.3	Standard polar	33892256
o6-Benzylguanine,2TMS,isomer #2	C[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C([NH]C=N2)N1[Si](C)(C)C	2448.0	Semi standard non polar	33892256
o6-Benzylguanine,2TMS,isomer #2	C[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C([NH]C=N2)N1[Si](C)(C)C	2509.0	Standard non polar	33892256
o6-Benzylguanine,2TMS,isomer #2	C[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C([NH]C=N2)N1[Si](C)(C)C	3271.5	Standard polar	33892256
o6-Benzylguanine,2TMS,isomer #3	C[Si](C)(C)N1C=NC2=C1N([Si](C)(C)C)C(=N)N=C2OCC1=CC=CC=C1	2489.6	Semi standard non polar	33892256
o6-Benzylguanine,2TMS,isomer #3	C[Si](C)(C)N1C=NC2=C1N([Si](C)(C)C)C(=N)N=C2OCC1=CC=CC=C1	2537.1	Standard non polar	33892256
o6-Benzylguanine,2TMS,isomer #3	C[Si](C)(C)N1C=NC2=C1N([Si](C)(C)C)C(=N)N=C2OCC1=CC=CC=C1	3309.5	Standard polar	33892256
o6-Benzylguanine,3TMS,isomer #1	C[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C(N([Si](C)(C)C)C=N2)N1[Si](C)(C)C	2483.8	Semi standard non polar	33892256
o6-Benzylguanine,3TMS,isomer #1	C[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C(N([Si](C)(C)C)C=N2)N1[Si](C)(C)C	2511.3	Standard non polar	33892256
o6-Benzylguanine,3TMS,isomer #1	C[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C(N([Si](C)(C)C)C=N2)N1[Si](C)(C)C	3108.6	Standard polar	33892256
o6-Benzylguanine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C([NH]C=N2)[NH]1	2640.4	Semi standard non polar	33892256
o6-Benzylguanine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C([NH]C=N2)[NH]1	2712.0	Standard non polar	33892256
o6-Benzylguanine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C([NH]C=N2)[NH]1	3613.6	Standard polar	33892256
o6-Benzylguanine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=N)N=C(OCC2=CC=CC=C2)C2=C1[NH]C=N2	2655.6	Semi standard non polar	33892256
o6-Benzylguanine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=N)N=C(OCC2=CC=CC=C2)C2=C1[NH]C=N2	2694.1	Standard non polar	33892256
o6-Benzylguanine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(=N)N=C(OCC2=CC=CC=C2)C2=C1[NH]C=N2	3553.3	Standard polar	33892256
o6-Benzylguanine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=NC2=C1[NH]C(=N)N=C2OCC1=CC=CC=C1	2720.2	Semi standard non polar	33892256
o6-Benzylguanine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=NC2=C1[NH]C(=N)N=C2OCC1=CC=CC=C1	2707.7	Standard non polar	33892256
o6-Benzylguanine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=NC2=C1[NH]C(=N)N=C2OCC1=CC=CC=C1	3552.3	Standard polar	33892256
o6-Benzylguanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C([NH]1)N([Si](C)(C)C(C)(C)C)C=N2	2844.3	Semi standard non polar	33892256
o6-Benzylguanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C([NH]1)N([Si](C)(C)C(C)(C)C)C=N2	2915.9	Standard non polar	33892256
o6-Benzylguanine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C([NH]1)N([Si](C)(C)C(C)(C)C)C=N2	3430.4	Standard polar	33892256
o6-Benzylguanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C([NH]C=N2)N1[Si](C)(C)C(C)(C)C	2840.5	Semi standard non polar	33892256
o6-Benzylguanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C([NH]C=N2)N1[Si](C)(C)C(C)(C)C	2856.4	Standard non polar	33892256
o6-Benzylguanine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C([NH]C=N2)N1[Si](C)(C)C(C)(C)C	3364.8	Standard polar	33892256
o6-Benzylguanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=N)N=C2OCC1=CC=CC=C1	2858.8	Semi standard non polar	33892256
o6-Benzylguanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=N)N=C2OCC1=CC=CC=C1	2913.9	Standard non polar	33892256
o6-Benzylguanine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=NC2=C1N([Si](C)(C)C(C)(C)C)C(=N)N=C2OCC1=CC=CC=C1	3412.5	Standard polar	33892256
o6-Benzylguanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C(N([Si](C)(C)C(C)(C)C)C=N2)N1[Si](C)(C)C(C)(C)C	3062.9	Semi standard non polar	33892256
o6-Benzylguanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C(N([Si](C)(C)C(C)(C)C)C=N2)N1[Si](C)(C)C(C)(C)C	3056.3	Standard non polar	33892256
o6-Benzylguanine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1N=C(OCC2=CC=CC=C2)C2=C(N([Si](C)(C)C(C)(C)C)C=N2)N1[Si](C)(C)C(C)(C)C	3359.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - O(6)-Benzylguanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9230000000-f1734d97cbf2bbe3917a	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O(6)-Benzylguanine 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 - O(6)-Benzylguanine LC-ESI-qTof , Positive-QTOF	splash10-0006-9511000001-e6a03ce9bd4d7464a377	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - O(6)-Benzylguanine , positive-QTOF	splash10-0006-9511000001-e6a03ce9bd4d7464a377	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O(6)-Benzylguanine 10V, Positive-QTOF	splash10-0006-0090000000-bf959d134bc5b078c6f0	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O(6)-Benzylguanine 20V, Positive-QTOF	splash10-0006-5590000000-ce3df04e82cff16a5a60	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O(6)-Benzylguanine 40V, Positive-QTOF	splash10-053u-8900000000-bfb8fd6f7a8be3f3a77b	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O(6)-Benzylguanine 10V, Negative-QTOF	splash10-0006-0290000000-47bafa4842508ab7927c	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O(6)-Benzylguanine 20V, Negative-QTOF	splash10-0006-5890000000-435df1558322e1711fb7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O(6)-Benzylguanine 40V, Negative-QTOF	splash10-05r3-9300000000-a2fde32033bd158ab6ae	2017-07-26	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB11919

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4417

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4578

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for O(6)-Benzylguanine (HMDB0255878)

MOL for HMDB0255878 (O(6)-Benzylguanine)

3D MOL for HMDB0255878 (O(6)-Benzylguanine)

3D SDF for HMDB0255878 (O(6)-Benzylguanine)

3D-SDF for HMDB0255878 (O(6)-Benzylguanine)

PDB for HMDB0255878 (O(6)-Benzylguanine)

3D PDB for HMDB0255878 (O(6)-Benzylguanine)

SMILES for HMDB0255878 (O(6)-Benzylguanine)

INCHI for HMDB0255878 (O(6)-Benzylguanine)

Structure for HMDB0255878 (O(6)-Benzylguanine)

3D Structure for HMDB0255878 (O(6)-Benzylguanine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra