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Showing metabocard for O6-Benzyl-8-oxoguanine (HMDB0255877)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 15:47:40 UTC
Update Date2022-11-23 22:29:17 UTC
HMDB IDHMDB0255877
Secondary Accession NumbersNone
Metabolite Identification
Common NameO6-Benzyl-8-oxoguanine
Description6-(benzyloxy)-2-imino-3,9-dihydro-2H-purin-8-ol 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-(benzyloxy)-2-imino-3,9-dihydro-2H-purin-8-ol. This compound has been identified in human blood as reported by (PMID: 31557052 ). O6-benzyl-8-oxoguanine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically O6-Benzyl-8-oxoguanine 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0255877 (O6-Benzyl-8-oxoguanine)


  Mrv1652309112117472D          

 19 21  0  0  0  0            999 V2000
    3.9934    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 13 18  1  0  0  0  0
 11 19  1  0  0  0  0
M  END
Download

3D MOL for HMDB0255877 (O6-Benzyl-8-oxoguanine)

HMDB0255877
     RDKit          3D
o6-Benzyl-8-oxoguanine
 30 32  0  0  0  0  0  0  0  0999 V2000
   -1.7336    2.8587   -0.7804 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8027    1.4684   -0.4773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8778    0.8527    0.2953 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9462   -0.4654    0.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0305   -1.1333    1.3605 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0882   -0.5630    1.9641 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9762    0.0030    0.9235 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8534   -0.2199   -0.4279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7135    0.3411   -1.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7340    1.1533   -0.9241 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8935    1.4031    0.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0189    0.8285    1.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0050   -1.1906    0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3154   -2.4943    0.1756 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4414   -2.6796   -0.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0038   -3.8164   -0.6203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8442   -1.5280   -1.0885 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9682   -0.5749   -0.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8196    0.7375   -0.9731 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3839    3.5095   -0.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0671    3.2633   -1.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8004    0.2067    2.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7018   -1.3055    2.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0551   -0.8599   -0.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6157    0.1648   -2.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4017    1.5885   -1.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7038    2.0498    0.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1526    1.0299    2.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7808   -3.2095    0.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6887   -1.4184   -1.6803 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  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  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19  2  1  0
 12  7  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 17 30  1  0
M  END
Download

3D SDF for HMDB0255877 (O6-Benzyl-8-oxoguanine)


  Mrv1652309112117472D          

 19 21  0  0  0  0            999 V2000
    3.9934    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 13 18  1  0  0  0  0
 11 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255877

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC2=C(NC(=O)N2)C(OCC2=CC=CC=C2)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C12H11N5O2/c13-11-15-9-8(14-12(18)16-9)10(17-11)19-6-7-4-2-1-3-5-7/h1-5H,6H2,(H4,13,14,15,16,17,18)

> <INCHI_KEY>
VPMJBCMAJPZWIC-UHFFFAOYSA-N

> <FORMULA>
C12H11N5O2

> <MOLECULAR_WEIGHT>
257.253

> <EXACT_MASS>
257.091274614

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
25.480150795949307

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-amino-6-(benzyloxy)-8,9-dihydro-7H-purin-8-one

> <ALOGPS_LOGP>
1.29

> <JCHEM_LOGP>
1.8274759646666672

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.852166327734025

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.510178309010154

> <JCHEM_PKA_STRONGEST_BASIC>
3.2425983216085705

> <JCHEM_POLAR_SURFACE_AREA>
102.16000000000001

> <JCHEM_REFRACTIVITY>
73.00829999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-6-(benzyloxy)-7,9-dihydropurin-8-one

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0255877 (O6-Benzyl-8-oxoguanine)

HMDB0255877
     RDKit          3D
o6-Benzyl-8-oxoguanine
 30 32  0  0  0  0  0  0  0  0999 V2000
   -1.7336    2.8587   -0.7804 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8027    1.4684   -0.4773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8778    0.8527    0.2953 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9462   -0.4654    0.5807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0305   -1.1333    1.3605 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0882   -0.5630    1.9641 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9762    0.0030    0.9235 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8534   -0.2199   -0.4279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7135    0.3411   -1.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7340    1.1533   -0.9241 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8935    1.4031    0.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0189    0.8285    1.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0050   -1.1906    0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3154   -2.4943    0.1756 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4414   -2.6796   -0.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0038   -3.8164   -0.6203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8442   -1.5280   -1.0885 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9682   -0.5749   -0.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8196    0.7375   -0.9731 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3839    3.5095   -0.2879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0671    3.2633   -1.4693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8004    0.2067    2.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7018   -1.3055    2.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0551   -0.8599   -0.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6157    0.1648   -2.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4017    1.5885   -1.6448 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7038    2.0498    0.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1526    1.0299    2.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7808   -3.2095    0.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6887   -1.4184   -1.6803 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  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  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19  2  1  0
 12  7  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 17 30  1  0
M  END
Download

PDB for HMDB0255877 (O6-Benzyl-8-oxoguanine)

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       7.454   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.788   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.788   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.121   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.121   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.454   4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       7.454   1.540   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       6.121  -0.770   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       3.322   2.016   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.877   0.770   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0       3.322  -0.476   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       8.788  -0.770   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   13                                                       
CONECT   19   11                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END
Download

3D PDB for HMDB0255877 (O6-Benzyl-8-oxoguanine)

COMPND    HMDB0255877
HETATM    1  N1  UNL     1      -1.734   2.859  -0.780  1.00  0.00           N  
HETATM    2  C1  UNL     1      -1.803   1.468  -0.477  1.00  0.00           C  
HETATM    3  N2  UNL     1      -0.878   0.853   0.295  1.00  0.00           N  
HETATM    4  C2  UNL     1      -0.946  -0.465   0.581  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.030  -1.133   1.361  1.00  0.00           O  
HETATM    6  C3  UNL     1       1.088  -0.563   1.964  1.00  0.00           C  
HETATM    7  C4  UNL     1       1.976   0.003   0.924  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.853  -0.220  -0.428  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.714   0.341  -1.353  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.734   1.153  -0.924  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.893   1.403   0.421  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.019   0.829   1.318  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.005  -1.191   0.055  1.00  0.00           C  
HETATM   14  N3  UNL     1      -2.315  -2.494   0.176  1.00  0.00           N  
HETATM   15  C11 UNL     1      -3.441  -2.680  -0.530  1.00  0.00           C  
HETATM   16  O2  UNL     1      -4.004  -3.816  -0.620  1.00  0.00           O  
HETATM   17  N4  UNL     1      -3.844  -1.528  -1.089  1.00  0.00           N  
HETATM   18  C12 UNL     1      -2.968  -0.575  -0.743  1.00  0.00           C  
HETATM   19  N5  UNL     1      -2.820   0.737  -0.973  1.00  0.00           N  
HETATM   20  H1  UNL     1      -2.384   3.509  -0.288  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.067   3.263  -1.469  1.00  0.00           H  
HETATM   22  H3  UNL     1       0.800   0.207   2.720  1.00  0.00           H  
HETATM   23  H4  UNL     1       1.702  -1.306   2.524  1.00  0.00           H  
HETATM   24  H5  UNL     1       1.055  -0.860  -0.774  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.616   0.165  -2.418  1.00  0.00           H  
HETATM   26  H7  UNL     1       4.402   1.588  -1.645  1.00  0.00           H  
HETATM   27  H8  UNL     1       4.704   2.050   0.780  1.00  0.00           H  
HETATM   28  H9  UNL     1       3.153   1.030   2.361  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.781  -3.209   0.712  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.689  -1.418  -1.680  1.00  0.00           H  
CONECT    1    2   20   21
CONECT    2    3    3   19
CONECT    3    4
CONECT    4    5   13   13
CONECT    5    6
CONECT    6    7   22   23
CONECT    7    8    8   12
CONECT    8    9   24
CONECT    9   10   10   25
CONECT   10   11   26
CONECT   11   12   12   27
CONECT   12   28
CONECT   13   14   18
CONECT   14   15   29
CONECT   15   16   16   17
CONECT   17   18   30
CONECT   18   19   19
END
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SMILES for HMDB0255877 (O6-Benzyl-8-oxoguanine)

NC1=NC2=C(NC(=O)N2)C(OCC2=CC=CC=C2)=N1
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INCHI for HMDB0255877 (O6-Benzyl-8-oxoguanine)

InChI=1S/C12H11N5O2/c13-11-15-9-8(14-12(18)16-9)10(17-11)19-6-7-4-2-1-3-5-7/h1-5H,6H2,(H4,13,14,15,16,17,18)
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View in JSmolView Stereo Labels
SynonymsNot Available
Chemical FormulaC12H11N5O2
Average Molecular Weight257.253
Monoisotopic Molecular Weight257.091274614
IUPAC Name2-amino-6-(benzyloxy)-8,9-dihydro-7H-purin-8-one
Traditional Name2-amino-6-(benzyloxy)-7,9-dihydropurin-8-one
CAS Registry NumberNot Available
SMILES
NC1=NC2=C(NC(=O)N2)C(OCC2=CC=CC=C2)=N1
InChI Identifier
InChI=1S/C12H11N5O2/c13-11-15-9-8(14-12(18)16-9)10(17-11)19-6-7-4-2-1-3-5-7/h1-5H,6H2,(H4,13,14,15,16,17,18)
InChI KeyVPMJBCMAJPZWIC-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentHypoxanthines
Alternative Parents
Substituents
  • Hypoxanthine
  • Alkyl aryl ether
  • Aminopyrimidine
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyrimidine
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Urea
  • Ether
  • Azacycle
  • Primary amine
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological location
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP1.29ALOGPS
logP1.83ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)10.51ChemAxon
pKa (Strongest Basic)3.24ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area102.16 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity73.01 m³·mol⁻¹ChemAxon
Polarizability25.48 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+161.09630932474
DeepCCS[M-H]-158.73830932474
DeepCCS[M-2H]-191.62430932474
DeepCCS[M+Na]+167.18930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
o6-Benzyl-8-oxoguanineNC1=NC2=C(NC(=O)N2)C(OCC2=CC=CC=C2)=N13717.6Standard polar33892256
o6-Benzyl-8-oxoguanineNC1=NC2=C(NC(=O)N2)C(OCC2=CC=CC=C2)=N12483.5Standard non polar33892256
o6-Benzyl-8-oxoguanineNC1=NC2=C(NC(=O)N2)C(OCC2=CC=CC=C2)=N12984.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
o6-Benzyl-8-oxoguanine,1TMS,isomer #1C[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)[NH]C2=N12625.8Semi standard non polar33892256
o6-Benzyl-8-oxoguanine,1TMS,isomer #1C[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)[NH]C2=N12658.2Standard non polar33892256
o6-Benzyl-8-oxoguanine,1TMS,isomer #1C[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)[NH]C2=N13716.0Standard polar33892256
o6-Benzyl-8-oxoguanine,1TMS,isomer #2C[Si](C)(C)N1C(=O)[NH]C2=NC(N)=NC(OCC3=CC=CC=C3)=C212658.2Semi standard non polar33892256
o6-Benzyl-8-oxoguanine,1TMS,isomer #2C[Si](C)(C)N1C(=O)[NH]C2=NC(N)=NC(OCC3=CC=CC=C3)=C212611.7Standard non polar33892256
o6-Benzyl-8-oxoguanine,1TMS,isomer #2C[Si](C)(C)N1C(=O)[NH]C2=NC(N)=NC(OCC3=CC=CC=C3)=C213667.0Standard polar33892256
o6-Benzyl-8-oxoguanine,1TMS,isomer #3C[Si](C)(C)N1C(=O)[NH]C2=C(OCC3=CC=CC=C3)N=C(N)N=C212613.8Semi standard non polar33892256
o6-Benzyl-8-oxoguanine,1TMS,isomer #3C[Si](C)(C)N1C(=O)[NH]C2=C(OCC3=CC=CC=C3)N=C(N)N=C212616.9Standard non polar33892256
o6-Benzyl-8-oxoguanine,1TMS,isomer #3C[Si](C)(C)N1C(=O)[NH]C2=C(OCC3=CC=CC=C3)N=C(N)N=C213717.5Standard polar33892256
o6-Benzyl-8-oxoguanine,2TMS,isomer #1C[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)[NH]C2=N1)[Si](C)(C)C2557.6Semi standard non polar33892256
o6-Benzyl-8-oxoguanine,2TMS,isomer #1C[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)[NH]C2=N1)[Si](C)(C)C2738.0Standard non polar33892256
o6-Benzyl-8-oxoguanine,2TMS,isomer #1C[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)[NH]C2=N1)[Si](C)(C)C3487.6Standard polar33892256
o6-Benzyl-8-oxoguanine,2TMS,isomer #2C[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2C(=N1)[NH]C(=O)N2[Si](C)(C)C2600.0Semi standard non polar33892256
o6-Benzyl-8-oxoguanine,2TMS,isomer #2C[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2C(=N1)[NH]C(=O)N2[Si](C)(C)C2554.3Standard non polar33892256
o6-Benzyl-8-oxoguanine,2TMS,isomer #2C[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2C(=N1)[NH]C(=O)N2[Si](C)(C)C3404.4Standard polar33892256
o6-Benzyl-8-oxoguanine,2TMS,isomer #3C[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)N([Si](C)(C)C)C2=N12568.7Semi standard non polar33892256
o6-Benzyl-8-oxoguanine,2TMS,isomer #3C[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)N([Si](C)(C)C)C2=N12588.2Standard non polar33892256
o6-Benzyl-8-oxoguanine,2TMS,isomer #3C[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)N([Si](C)(C)C)C2=N13445.9Standard polar33892256
o6-Benzyl-8-oxoguanine,2TMS,isomer #4C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C2=C(OCC3=CC=CC=C3)N=C(N)N=C212584.7Semi standard non polar33892256
o6-Benzyl-8-oxoguanine,2TMS,isomer #4C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C2=C(OCC3=CC=CC=C3)N=C(N)N=C212566.6Standard non polar33892256
o6-Benzyl-8-oxoguanine,2TMS,isomer #4C[Si](C)(C)N1C(=O)N([Si](C)(C)C)C2=C(OCC3=CC=CC=C3)N=C(N)N=C213446.4Standard polar33892256
o6-Benzyl-8-oxoguanine,3TMS,isomer #1C[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2C(=N1)[NH]C(=O)N2[Si](C)(C)C)[Si](C)(C)C2626.8Semi standard non polar33892256
o6-Benzyl-8-oxoguanine,3TMS,isomer #1C[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2C(=N1)[NH]C(=O)N2[Si](C)(C)C)[Si](C)(C)C2659.4Standard non polar33892256
o6-Benzyl-8-oxoguanine,3TMS,isomer #1C[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2C(=N1)[NH]C(=O)N2[Si](C)(C)C)[Si](C)(C)C3174.7Standard polar33892256
o6-Benzyl-8-oxoguanine,3TMS,isomer #2C[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)N([Si](C)(C)C)C2=N1)[Si](C)(C)C2593.2Semi standard non polar33892256
o6-Benzyl-8-oxoguanine,3TMS,isomer #2C[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)N([Si](C)(C)C)C2=N1)[Si](C)(C)C2669.0Standard non polar33892256
o6-Benzyl-8-oxoguanine,3TMS,isomer #2C[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)N([Si](C)(C)C)C2=N1)[Si](C)(C)C3231.3Standard polar33892256
o6-Benzyl-8-oxoguanine,3TMS,isomer #3C[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2C(=N1)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C2605.4Semi standard non polar33892256
o6-Benzyl-8-oxoguanine,3TMS,isomer #3C[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2C(=N1)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C2550.6Standard non polar33892256
o6-Benzyl-8-oxoguanine,3TMS,isomer #3C[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2C(=N1)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C3244.1Standard polar33892256
o6-Benzyl-8-oxoguanine,4TMS,isomer #1C[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2C(=N1)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)[Si](C)(C)C2676.1Semi standard non polar33892256
o6-Benzyl-8-oxoguanine,4TMS,isomer #1C[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2C(=N1)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)[Si](C)(C)C2671.9Standard non polar33892256
o6-Benzyl-8-oxoguanine,4TMS,isomer #1C[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2C(=N1)N([Si](C)(C)C)C(=O)N2[Si](C)(C)C)[Si](C)(C)C3042.6Standard polar33892256
o6-Benzyl-8-oxoguanine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)[NH]C2=N12784.4Semi standard non polar33892256
o6-Benzyl-8-oxoguanine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)[NH]C2=N12862.6Standard non polar33892256
o6-Benzyl-8-oxoguanine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)[NH]C2=N13761.9Standard polar33892256
o6-Benzyl-8-oxoguanine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=NC(N)=NC(OCC3=CC=CC=C3)=C212825.0Semi standard non polar33892256
o6-Benzyl-8-oxoguanine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=NC(N)=NC(OCC3=CC=CC=C3)=C212806.8Standard non polar33892256
o6-Benzyl-8-oxoguanine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=NC(N)=NC(OCC3=CC=CC=C3)=C213688.9Standard polar33892256
o6-Benzyl-8-oxoguanine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=C(OCC3=CC=CC=C3)N=C(N)N=C212781.2Semi standard non polar33892256
o6-Benzyl-8-oxoguanine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=C(OCC3=CC=CC=C3)N=C(N)N=C212842.6Standard non polar33892256
o6-Benzyl-8-oxoguanine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)[NH]C2=C(OCC3=CC=CC=C3)N=C(N)N=C213717.5Standard polar33892256
o6-Benzyl-8-oxoguanine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)[NH]C2=N1)[Si](C)(C)C(C)(C)C2914.7Semi standard non polar33892256
o6-Benzyl-8-oxoguanine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)[NH]C2=N1)[Si](C)(C)C(C)(C)C3107.6Standard non polar33892256
o6-Benzyl-8-oxoguanine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)[NH]C2=N1)[Si](C)(C)C(C)(C)C3537.9Standard polar33892256
o6-Benzyl-8-oxoguanine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2C(=N1)[NH]C(=O)N2[Si](C)(C)C(C)(C)C2974.3Semi standard non polar33892256
o6-Benzyl-8-oxoguanine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2C(=N1)[NH]C(=O)N2[Si](C)(C)C(C)(C)C2956.4Standard non polar33892256
o6-Benzyl-8-oxoguanine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2C(=N1)[NH]C(=O)N2[Si](C)(C)C(C)(C)C3527.7Standard polar33892256
o6-Benzyl-8-oxoguanine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)N([Si](C)(C)C(C)(C)C)C2=N12940.6Semi standard non polar33892256
o6-Benzyl-8-oxoguanine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)N([Si](C)(C)C(C)(C)C)C2=N13018.3Standard non polar33892256
o6-Benzyl-8-oxoguanine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)N([Si](C)(C)C(C)(C)C)C2=N13542.5Standard polar33892256
o6-Benzyl-8-oxoguanine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C2=C(OCC3=CC=CC=C3)N=C(N)N=C212957.9Semi standard non polar33892256
o6-Benzyl-8-oxoguanine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C2=C(OCC3=CC=CC=C3)N=C(N)N=C212970.0Standard non polar33892256
o6-Benzyl-8-oxoguanine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)C2=C(OCC3=CC=CC=C3)N=C(N)N=C213530.1Standard polar33892256
o6-Benzyl-8-oxoguanine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2C(=N1)[NH]C(=O)N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3150.9Semi standard non polar33892256
o6-Benzyl-8-oxoguanine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2C(=N1)[NH]C(=O)N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3207.0Standard non polar33892256
o6-Benzyl-8-oxoguanine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2C(=N1)[NH]C(=O)N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3397.5Standard polar33892256
o6-Benzyl-8-oxoguanine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)N([Si](C)(C)C(C)(C)C)C2=N1)[Si](C)(C)C(C)(C)C3126.6Semi standard non polar33892256
o6-Benzyl-8-oxoguanine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)N([Si](C)(C)C(C)(C)C)C2=N1)[Si](C)(C)C(C)(C)C3256.4Standard non polar33892256
o6-Benzyl-8-oxoguanine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2[NH]C(=O)N([Si](C)(C)C(C)(C)C)C2=N1)[Si](C)(C)C(C)(C)C3436.3Standard polar33892256
o6-Benzyl-8-oxoguanine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2C(=N1)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C3166.9Semi standard non polar33892256
o6-Benzyl-8-oxoguanine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2C(=N1)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C3142.6Standard non polar33892256
o6-Benzyl-8-oxoguanine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC(OCC2=CC=CC=C2)=C2C(=N1)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C3495.9Standard polar33892256
o6-Benzyl-8-oxoguanine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2C(=N1)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3365.4Semi standard non polar33892256
o6-Benzyl-8-oxoguanine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2C(=N1)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3415.5Standard non polar33892256
o6-Benzyl-8-oxoguanine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=NC(OCC2=CC=CC=C2)=C2C(=N1)N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3344.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - O6-Benzyl-8-oxoguanine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9230000000-ac6fb16104f188e7d51c2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - O6-Benzyl-8-oxoguanine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8598005
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]