Showing metabocard for isoguanine (MMDBc0054516)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-06-05 23:16:30 UTC
Update Date2025-01-15 17:50:43 UTC
Metabolite IDMMDBc0054516
Metabolite Identification
Common Nameisoguanine
Description2-Hydroxyadenine (2-OH-Ade) is formed by hydroxyl radical attack on DNA bases and shows a genotoxicity in human, being the source of the mutations induced by reactive oxygen species. 2-OH-Ade in DNA is miscoding and elicits various mutations, and is a mutagenic in bacterial and mammalian cells. (Recent Research Developments in Biochemistry (2000)2:41-50).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00005645c9ad78d8>

2-Hydroxyadenine.mol
  Mrv0541 02231218302D          

 11 12  0  0  0  0            999 V2000
   -0.6638    0.4466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0507    0.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7652    0.4466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7652   -0.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0507   -0.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6638   -0.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3783   -0.7909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3783   -0.9304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0427   -1.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2222   -1.5979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0507    1.6841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  6  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  2 11  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00005645c9ad78d8>

HMDB0000403
     RDKit          3D
2-Hydroxyadenine
 16 17  0  0  0  0  0  0  0  0999 V2000
   -1.2228   -1.9693   -0.0727 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8430   -0.5984   -0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7270    0.4090   -0.2163 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3666    1.7023   -0.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3387    2.7004   -0.3648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0561    1.9961   -0.1511 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8614    1.0155   -0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2112    1.0232    0.0731 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441   -0.2489    0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6031   -1.0981    0.1163 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5091   -0.3187   -0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5292   -2.3425    0.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2117   -2.5929   -0.8905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8264    3.0504    0.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6744   -0.5693    0.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6182   -2.1588    0.1635 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
  4  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11  2  1  0
 11  7  2  0
  1 12  1  0
  1 13  1  0
  5 14  1  0
  9 15  1  0
 10 16  1  0
M  END
Download

3D SDF for #<Metabolite:0x00005645c9ad78d8>

2-Hydroxyadenine.mol
  Mrv0541 02231218302D          

 11 12  0  0  0  0            999 V2000
   -0.6638    0.4466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0507    0.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7652    0.4466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7652   -0.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0507   -0.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6638   -0.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3783   -0.7909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3783   -0.9304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0427   -1.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2222   -1.5979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0507    1.6841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  6  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  2 11  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054516

> <DATABASE_NAME>
MIME

> <SMILES>
NC1=NC(O)=NC2=C1NC=N2

> <INCHI_IDENTIFIER>
InChI=1S/C5H5N5O/c6-3-2-4(8-1-7-2)10-5(11)9-3/h1H,(H4,6,7,8,9,10,11)

> <INCHI_KEY>
DRAVOWXCEBXPTN-UHFFFAOYSA-N

> <FORMULA>
C5H5N5O

> <MOLECULAR_WEIGHT>
151.1261

> <EXACT_MASS>
151.049409807

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
13.361417514029057

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-amino-7H-purin-2-ol

> <ALOGPS_LOGP>
-0.65

> <JCHEM_LOGP>
-0.1982495303333333

> <ALOGPS_LOGS>
-1.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.811865928730988

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.775155616350027

> <JCHEM_PKA_STRONGEST_BASIC>
2.017194790434338

> <JCHEM_POLAR_SURFACE_AREA>
100.71

> <JCHEM_REFRACTIVITY>
40.14639999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-6-aminopurine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00005645c9ad78d8>

HMDB0000403
     RDKit          3D
2-Hydroxyadenine
 16 17  0  0  0  0  0  0  0  0999 V2000
   -1.2228   -1.9693   -0.0727 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8430   -0.5984   -0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7270    0.4090   -0.2163 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3666    1.7023   -0.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3387    2.7004   -0.3648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0561    1.9961   -0.1511 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8614    1.0155   -0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2112    1.0232    0.0731 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441   -0.2489    0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6031   -1.0981    0.1163 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5091   -0.3187   -0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5292   -2.3425    0.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2117   -2.5929   -0.8905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8264    3.0504    0.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6744   -0.5693    0.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6182   -2.1588    0.1635 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
  4  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11  2  1  0
 11  7  2  0
  1 12  1  0
  1 13  1  0
  5 14  1  0
  9 15  1  0
 10 16  1  0
M  END
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PDB for #<Metabolite:0x00005645c9ad78d8>

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 2-Hydroxyadenine.mol                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      -1.239   0.834   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.095   1.604   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.428   0.834   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.428  -0.706   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.095  -1.476   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.239  -0.706   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -2.573  -1.476   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       2.573  -1.737   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.946  -3.144   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.415  -2.983   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       0.095   3.144   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7    1                                                  
CONECT    7    6                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    2                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END
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3D PDB for #<Metabolite:0x00005645c9ad78d8>

COMPND    HMDB0000403
HETATM    1  N1  UNL     1      -1.223  -1.969  -0.073  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.843  -0.598  -0.102  1.00  0.00           C  
HETATM    3  N2  UNL     1      -1.727   0.409  -0.216  1.00  0.00           N  
HETATM    4  C2  UNL     1      -1.367   1.702  -0.243  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.339   2.700  -0.365  1.00  0.00           O  
HETATM    6  N3  UNL     1      -0.056   1.996  -0.151  1.00  0.00           N  
HETATM    7  C3  UNL     1       0.861   1.016  -0.035  1.00  0.00           C  
HETATM    8  N4  UNL     1       2.211   1.023   0.073  1.00  0.00           N  
HETATM    9  C4  UNL     1       2.644  -0.249   0.163  1.00  0.00           C  
HETATM   10  N5  UNL     1       1.603  -1.098   0.116  1.00  0.00           N  
HETATM   11  C5  UNL     1       0.509  -0.319  -0.005  1.00  0.00           C  
HETATM   12  H1  UNL     1      -1.529  -2.343   0.853  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.212  -2.593  -0.891  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.826   3.050   0.452  1.00  0.00           H  
HETATM   15  H4  UNL     1       3.674  -0.569   0.260  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.618  -2.159   0.164  1.00  0.00           H  
CONECT    1    2   12   13
CONECT    2    3    3   11
CONECT    3    4
CONECT    4    5    6    6
CONECT    5   14
CONECT    6    7
CONECT    7    8   11   11
CONECT    8    9    9
CONECT    9   10   15
CONECT   10   11   16
END
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SMILES for #<Metabolite:0x00005645c9ad78d8>

NC1=NC(O)=NC2=C1NC=N2
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INCHI for #<Metabolite:0x00005645c9ad78d8>

InChI=1S/C5H5N5O/c6-3-2-4(8-1-7-2)10-5(11)9-3/h1H,(H4,6,7,8,9,10,11)
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Synonyms
ValueSource
2-OxoadenineChEBI
6-Amino-1,3-dihydro-2H-purin-2-oneChEBI
6-Amino-3,7-dihydro-purin-2-oneChEBI
6-Amino-3,9-dihydro-2H-purin-2-oneChEBI
6-Amino-7H-purin-2-olChEBI
6-Amino-9H-purin-2-olChEBI
2-Hydroxy-6-aminopurineHMDB
2-OxyadenineHMDB
6-Amino-2-hydroxypurineHMDB
6-Amino-3,7(9)-dihydro-purin-2-oneHMDB
IsoguanineHMDB
2-OH-AdeHMDB
CrotonosideHMDB
2-HydroxyadenineChEBI
Molecular FormulaC5H5N5O
Average Mass151.1261
Monoisotopic Mass151.049409807
IUPAC Name6-amino-7H-purin-2-ol
Traditional Name2-hydroxy-6-aminopurine
CAS Registry NumberNot Available
SMILES
NC1=NC(O)=NC2=C1NC=N2
InChI Identifier
InChI=1S/C5H5N5O/c6-3-2-4(8-1-7-2)10-5(11)9-3/h1H,(H4,6,7,8,9,10,11)
InChI KeyDRAVOWXCEBXPTN-UHFFFAOYSA-N