Showing metabocard for Guanine (MMDBc0000037)

Not Available
Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:28:04 UTC
Update Date2024-10-09 23:16:54 UTC
Metabolite IDMMDBc0000037
Metabolite Identification
Common NameGuanine
DescriptionGuanine is one of the five main nucleobases found in the nucleic acids DNA and RNA. Guanine is a derivative of purine, consisting of a fused pyrimidine-imidazole ring system with conjugated double bonds. Being unsaturated, the bicyclic molecule is planar. The guanine nucleoside is called guanosine. The first isolation of guanine was reported in 1844 from the excreta of sea birds, known as guano, which was used as a source of fertilizer. High affinity binding of guanine nucleotides and the ability to hydrolyze bound GTP to GDP are characteristics of an extended family of intracellular proteins. Guanine nucleotide-binding regulatory proteins may be involved in the activation of phospholipases C and A2 by hormones and other ligands. The binding of hormones to receptors that activate phospholipase C is decreased by guanine nucleotides and these hormones also stimulate a high-affinity GTPase activity in cell membranes. Effects of hormones on phospholipase C activity in cell-free preparations are dependent on the presence of guanine nucleotides. Hypoxanthine-guanine phosphoribosyltransferase (HPRT, EC 2.4.2.8) is a purine salvage enzyme that catalyses the conversion of hypoxanthine and guanine to their respective mononucleotides. Partial deficiency of this enzyme can result in the overproduction of uric acid leading to a severe form of gout, whilst a virtual absence of HPRT activity causes the Lesch-Nyhan syndrome, an inborn error of metabolism, which is characterised by hyperuricaemia, mental retardation, choreoathetosis and compulsive self-mutilation. Peroxynitrite induces DNA base damage predominantly at guanine (G) and 8-oxoguanine (8-oxoG) nucleobases via oxidation reactions. G and 8-oxoG are the most reactive bases toward Peroxynitrite and possibly the major contributors to peroxynitrite-derived genotoxic and mutagenic lesions. The neutral G radical, reacts with NO2 to yield 8-nitroguanine and 5-nitro-4-guanidinohydantoin (PMID: 16352449 , 2435586 , 2838362 , 1487231 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdb0a82ab08>


  Mrv1652309032023532D          

 11 12  0  0  0  0            999 V2000
   12.1750  -11.7106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1750  -14.1857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6701  -12.6968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6701  -14.0245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4605  -12.9481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7460  -14.1857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8895  -12.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8895  -13.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1750  -12.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4605  -13.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1516  -13.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0  0  0  0
  2  8  1  0  0  0  0
  2 10  1  0  0  0  0
  3  7  1  0  0  0  0
  3 11  1  0  0  0  0
  4  8  1  0  0  0  0
  4 11  2  0  0  0  0
  5  9  1  0  0  0  0
  5 10  2  0  0  0  0
  6 10  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fdb0a82ab08>

HMDB0000132
     RDKit          3D
Guanine
 16 17  0  0  0  0  0  0  0  0999 V2000
    3.1014   -0.1322    0.1736 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7090    0.1117    0.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2043    1.3199   -0.2709 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1148    1.5401   -0.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6033    2.6655   -0.6850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0058    0.4986   -0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3455    0.4047   -0.2080 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6489   -0.8697    0.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5156   -1.5565    0.3129 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4513   -0.7408    0.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8750   -0.9050    0.2619 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5928    0.2111    1.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125   -0.6438   -0.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9880    1.1942   -0.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6706   -1.2622    0.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2488   -1.8356    0.5082 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  2  0
  4  6  1  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
 10  6  2  0
  1 12  1  0
  1 13  1  0
  7 14  1  0
  8 15  1  0
 11 16  1  0
M  END
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3D SDF for #<Metabolite:0x00007fdb0a82ab08>


  Mrv1652309032023532D          

 11 12  0  0  0  0            999 V2000
   12.1750  -11.7106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1750  -14.1857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6701  -12.6968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6701  -14.0245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4605  -12.9481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7460  -14.1857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8895  -12.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8895  -13.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1750  -12.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4605  -13.7732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1516  -13.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0  0  0  0
  2  8  1  0  0  0  0
  2 10  1  0  0  0  0
  3  7  1  0  0  0  0
  3 11  1  0  0  0  0
  4  8  1  0  0  0  0
  4 11  2  0  0  0  0
  5  9  1  0  0  0  0
  5 10  2  0  0  0  0
  6 10  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000037

> <DATABASE_NAME>
MIME

> <SMILES>
NC1=NC(=O)C2=C(N1)N=CN2

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

> <INCHI_KEY>
UYTPUPDQBNUYGX-UHFFFAOYSA-N

> <FORMULA>
C5H5N5O

> <MOLECULAR_WEIGHT>
151.1261

> <EXACT_MASS>
151.049409807

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
13.339986140369138

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-6,7-dihydro-3H-purin-6-one

> <ALOGPS_LOGP>
-0.92

> <JCHEM_LOGP>
-0.5893389343333332

> <ALOGPS_LOGS>
-1.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.536910677452525

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.949155880456997

> <JCHEM_PKA_STRONGEST_BASIC>
2.2167738264968646

> <JCHEM_POLAR_SURFACE_AREA>
96.16

> <JCHEM_REFRACTIVITY>
38.9011

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-aminohypoxanthine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fdb0a82ab08>

HMDB0000132
     RDKit          3D
Guanine
 16 17  0  0  0  0  0  0  0  0999 V2000
    3.1014   -0.1322    0.1736 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7090    0.1117    0.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2043    1.3199   -0.2709 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1148    1.5401   -0.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6033    2.6655   -0.6850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0058    0.4986   -0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3455    0.4047   -0.2080 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6489   -0.8697    0.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5156   -1.5565    0.3129 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4513   -0.7408    0.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8750   -0.9050    0.2619 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5928    0.2111    1.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125   -0.6438   -0.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9880    1.1942   -0.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6706   -1.2622    0.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2488   -1.8356    0.5082 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  2  0
  4  6  1  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
 10  6  2  0
  1 12  1  0
  1 13  1  0
  7 14  1  0
  8 15  1  0
 11 16  1  0
M  END
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PDB for #<Metabolite:0x00007fdb0a82ab08>

HEADER    PROTEIN                                 03-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-20         0                                  
HETATM    1  O   UNK     0      22.727 -21.860   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      22.727 -26.480   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      25.518 -23.701   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      25.518 -26.179   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      21.393 -24.170   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      20.059 -26.480   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      24.060 -24.170   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.060 -25.710   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.727 -23.400   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.393 -25.710   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      26.416 -24.940   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2    8   10                                                       
CONECT    3    7   11                                                       
CONECT    4    8   11                                                       
CONECT    5    9   10                                                       
CONECT    6   10                                                            
CONECT    7    3    8    9                                                  
CONECT    8    2    4    7                                                  
CONECT    9    1    5    7                                                  
CONECT   10    2    5    6                                                  
CONECT   11    3    4                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END
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3D PDB for #<Metabolite:0x00007fdb0a82ab08>

COMPND    HMDB0000132
HETATM    1  N1  UNL     1       3.101  -0.132   0.174  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.709   0.112   0.050  1.00  0.00           C  
HETATM    3  N2  UNL     1       1.204   1.320  -0.271  1.00  0.00           N  
HETATM    4  C2  UNL     1      -0.115   1.540  -0.385  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.603   2.666  -0.685  1.00  0.00           O  
HETATM    6  C3  UNL     1      -1.006   0.499  -0.170  1.00  0.00           C  
HETATM    7  N3  UNL     1      -2.346   0.405  -0.208  1.00  0.00           N  
HETATM    8  C4  UNL     1      -2.649  -0.870   0.092  1.00  0.00           C  
HETATM    9  N4  UNL     1      -1.516  -1.557   0.313  1.00  0.00           N  
HETATM   10  C5  UNL     1      -0.451  -0.741   0.161  1.00  0.00           C  
HETATM   11  N5  UNL     1       0.875  -0.905   0.262  1.00  0.00           N  
HETATM   12  H1  UNL     1       3.593   0.211   1.023  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.612  -0.644  -0.573  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.988   1.194  -0.432  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.671  -1.262   0.142  1.00  0.00           H  
HETATM   16  H5  UNL     1       1.249  -1.836   0.508  1.00  0.00           H  
CONECT    1    2   12   13
CONECT    2    3    3   11
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   10   10
CONECT    7    8   14
CONECT    8    9    9   15
CONECT    9   10
CONECT   10   11
CONECT   11   16
END
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SMILES for #<Metabolite:0x00007fdb0a82ab08>

NC1=NC(=O)C2=C(N1)N=CN2
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INCHI for #<Metabolite:0x00007fdb0a82ab08>

InChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
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Synonyms
ValueSource
2-Amino-6-hydroxypurineChEBI
2-Amino-6-oxopurineChEBI
GChEBI
GuaChEBI
2-Amino-1,7-dihydro-6H-purin-6-oneHMDB
2-Amino-1,9-dihydro-6H-purin-6-oneHMDB
2-Amino-1,9-dihydro-purin-6-oneHMDB
2-Amino-3,7-dihydro-6H-purin-6-oneHMDB
2-Amino-6-hydroxy-1H-purineHMDB
2-Amino-6-purinolHMDB
2-Amino-hypoxanthineHMDB
2-AminohypoxanthineHMDB
6-Hydroxy-2-aminopurineHMDB
C.I. natural white 1HMDB
CI natural white 1HMDB
Dew pearlHMDB
GuaninHMDB
Guanine enolHMDB
GUNHMDB
MearlmaidHMDB
Mearlmaid aaHMDB
Natural pearl essenceHMDB
Natural white 1HMDB
NaturonHMDB
PathocidinHMDB
Pearl essenceHMDB
Stella polarisHMDB
Molecular FormulaC5H5N5O
Average Mass151.1261
Monoisotopic Mass151.049409807
IUPAC Name2-amino-6,7-dihydro-3H-purin-6-one
Traditional Name2-aminohypoxanthine
CAS Registry Number73-40-5
SMILES
NC1=NC(=O)C2=C(N1)N=CN2
InChI Identifier
InChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
InChI KeyUYTPUPDQBNUYGX-UHFFFAOYSA-N