Showing metabocard for 8-oxoguanine (MMDBc0054310)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-06-05 23:06:21 UTC
Update Date2024-04-30 20:52:29 UTC
Metabolite IDMMDBc0054310
Metabolite Identification
Common Name8-oxoguanine
DescriptionFormation of 8-hydroxyguanine (8-OHG), a mutagenic base which is a marker for OH-mediated DNA damage, requires peroxidase and halides and occurs in the presence of transition metal chelators (DTPA +/- desferrioxamine), and is inhibited by catalase, superoxide dismutase (SOD), and scavengers of hypohalous acids. (PMID 10820020 ). 8-Hydroxyguanine is an oxidative stress marker for diagnosis of Alzheimer's disease (AD). (PMID 15977989 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f9208ef2cd8>


  Mrv0541 02231219192D          

 12 13  0  0  0  0            999 V2000
   15.6957  -10.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2832   -9.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5207  -10.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6957   -9.2679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9333   -9.9824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5207   -9.2679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4762  -10.1540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3900  -10.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1436  -11.3100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9333   -8.5534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9333  -11.4114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6754  -11.3870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  2  0  0  0  0
  5  6  1  0  0  0  0
  8  7  1  0  0  0  0
  2  7  1  0  0  0  0
  9  8  1  0  0  0  0
  1  2  2  0  0  0  0
  1  9  1  0  0  0  0
 10  6  1  0  0  0  0
 11  3  2  0  0  0  0
 12  8  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f9208ef2cd8>

HMDB0002032
     RDKit          3D
8-Hydroxyguanine
 17 18  0  0  0  0  0  0  0  0999 V2000
    3.0974   -0.7992    0.0238 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7532   -0.3453   -0.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138   -1.0866    0.3922 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5657   -0.6640    0.3415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7511   -1.1997    0.6938 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7584   -0.3510    0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0037   -0.5308    0.6371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1830    0.7428   -0.0980 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8512    0.5854   -0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1940    1.3477   -0.6024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0419    2.5006   -1.0745 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4532    0.8819   -0.5311 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8130   -0.6169   -0.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3958   -1.3531    0.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8290   -2.1552    1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7124    1.5987   -0.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2759    1.4447   -0.8578 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  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12  2  1  0
  9  4  2  0
  1 13  1  0
  1 14  1  0
  5 15  1  0
  8 16  1  0
 12 17  1  0
M  END
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3D SDF for #<Metabolite:0x00007f9208ef2cd8>


  Mrv0541 02231219192D          

 12 13  0  0  0  0            999 V2000
   15.6957  -10.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2832   -9.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5207  -10.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6957   -9.2679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9333   -9.9824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5207   -9.2679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4762  -10.1540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3900  -10.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1436  -11.3100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9333   -8.5534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9333  -11.4114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6754  -11.3870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  2  0  0  0  0
  5  6  1  0  0  0  0
  8  7  1  0  0  0  0
  2  7  1  0  0  0  0
  9  8  1  0  0  0  0
  1  2  2  0  0  0  0
  1  9  1  0  0  0  0
 10  6  1  0  0  0  0
 11  3  2  0  0  0  0
 12  8  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054310

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H5N5O2/c6-4-8-2-1(3(11)10-4)7-5(12)9-2/h(H5,6,7,8,9,10,11,12)

> <INCHI_KEY>
CLGFIVUFZRGQRP-UHFFFAOYSA-N

> <FORMULA>
C5H5N5O2

> <MOLECULAR_WEIGHT>
167.1255

> <EXACT_MASS>
167.044324429

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
14.264250400689727

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-6,7,8,9-tetrahydro-1H-purine-6,8-dione

> <ALOGPS_LOGP>
-1.57

> <JCHEM_LOGP>
-1.4743647556666666

> <ALOGPS_LOGS>
-1.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.498329511148071

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.3478292672007814

> <JCHEM_PKA_STRONGEST_BASIC>
3.9470355681440923

> <JCHEM_POLAR_SURFACE_AREA>
108.60999999999999

> <JCHEM_REFRACTIVITY>
47.80779999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.94e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxyguanine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f9208ef2cd8>

HMDB0002032
     RDKit          3D
8-Hydroxyguanine
 17 18  0  0  0  0  0  0  0  0999 V2000
    3.0974   -0.7992    0.0238 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7532   -0.3453   -0.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138   -1.0866    0.3922 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5657   -0.6640    0.3415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7511   -1.1997    0.6938 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7584   -0.3510    0.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0037   -0.5308    0.6371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1830    0.7428   -0.0980 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8512    0.5854   -0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1940    1.3477   -0.6024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0419    2.5006   -1.0745 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4532    0.8819   -0.5311 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8130   -0.6169   -0.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3958   -1.3531    0.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8290   -2.1552    1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7124    1.5987   -0.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2759    1.4447   -0.8578 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  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12  2  1  0
  9  4  2  0
  1 13  1  0
  1 14  1  0
  5 15  1  0
  8 16  1  0
 12 17  1  0
M  END
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PDB for #<Metabolite:0x00007f9208ef2cd8>

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      29.299 -19.968   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.529 -18.634   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      30.839 -19.968   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      29.299 -17.300   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      31.609 -18.634   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      30.839 -17.300   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      27.022 -18.954   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      26.861 -20.486   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      28.268 -21.112   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      31.609 -15.966   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      31.609 -21.301   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      25.527 -21.256   0.000  0.00  0.00           O+0
CONECT    1    3    2    9                                                  
CONECT    2    4    7    1                                                  
CONECT    3    1    5   11                                                  
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5   10                                                  
CONECT    7    8    2                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8    1                                                       
CONECT   10    6                                                            
CONECT   11    3                                                            
CONECT   12    8                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END
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3D PDB for #<Metabolite:0x00007f9208ef2cd8>

COMPND    HMDB0002032
HETATM    1  N1  UNL     1       3.097  -0.799   0.024  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.753  -0.345  -0.034  1.00  0.00           C  
HETATM    3  N2  UNL     1       0.714  -1.087   0.392  1.00  0.00           N  
HETATM    4  C2  UNL     1      -0.566  -0.664   0.342  1.00  0.00           C  
HETATM    5  N3  UNL     1      -1.751  -1.200   0.694  1.00  0.00           N  
HETATM    6  C3  UNL     1      -2.758  -0.351   0.432  1.00  0.00           C  
HETATM    7  O1  UNL     1      -4.004  -0.531   0.637  1.00  0.00           O  
HETATM    8  N4  UNL     1      -2.183   0.743  -0.098  1.00  0.00           N  
HETATM    9  C4  UNL     1      -0.851   0.585  -0.167  1.00  0.00           C  
HETATM   10  C5  UNL     1       0.194   1.348  -0.602  1.00  0.00           C  
HETATM   11  O2  UNL     1      -0.042   2.501  -1.075  1.00  0.00           O  
HETATM   12  N5  UNL     1       1.453   0.882  -0.531  1.00  0.00           N  
HETATM   13  H1  UNL     1       3.813  -0.617  -0.708  1.00  0.00           H  
HETATM   14  H2  UNL     1       3.396  -1.353   0.852  1.00  0.00           H  
HETATM   15  H3  UNL     1      -1.829  -2.155   1.113  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.712   1.599  -0.412  1.00  0.00           H  
HETATM   17  H5  UNL     1       2.276   1.445  -0.858  1.00  0.00           H  
CONECT    1    2   13   14
CONECT    2    3    3   12
CONECT    3    4
CONECT    4    5    9    9
CONECT    5    6   15
CONECT    6    7    7    8
CONECT    8    9   16
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   17
END
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SMILES for #<Metabolite:0x00007f9208ef2cd8>

NC1=NC2=C(NC(=O)N2)C(=O)N1
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INCHI for #<Metabolite:0x00007f9208ef2cd8>

InChI=1S/C5H5N5O2/c6-4-8-2-1(3(11)10-4)7-5(12)9-2/h(H5,6,7,8,9,10,11,12)
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Synonyms
ValueSource
8-OxoguanineChEBI
1H-Purine-6,8-dione, 2-amino-7,9-dihydro-1H-purine-6,8-dioneHMDB
2-amino-6,8-DihydroxypurineHMDB, MeSH
2-amino-7,9-dihydro-1H-Purine-6,8-dioneHMDB
2-amino-Purine-6,8-diolHMDB
2-Aminopurine-6,8-diolHMDB
7,8-dihydro-8-OxoguanineHMDB
oxo-8-GuaMeSH, HMDB
8-oxo-7,8-DihydroguanineMeSH, HMDB
8-HydroxyguanineChEBI
Molecular FormulaC5H5N5O2
Average Mass167.1255
Monoisotopic Mass167.044324429
IUPAC Name2-amino-6,7,8,9-tetrahydro-1H-purine-6,8-dione
Traditional Name8-hydroxyguanine
CAS Registry NumberNot Available
SMILES
NC1=NC2=C(NC(=O)N2)C(=O)N1
InChI Identifier
InChI=1S/C5H5N5O2/c6-4-8-2-1(3(11)10-4)7-5(12)9-2/h(H5,6,7,8,9,10,11,12)
InChI KeyCLGFIVUFZRGQRP-UHFFFAOYSA-N