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Showing NP-Card for 1-Methylguanine (NP0000273)

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Record Information
Version2.0
Created at2006-05-22 15:12:47 UTC
Updated at2021-08-19 23:57:59 UTC
NP-MRD IDNP0000273
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-Methylguanine
Description1-Methylguanine is a naturally occurring modified purine derived from tRNA, found in elevated levels in the serum and urine of cancer patients (PMID: 2413515 ). Increase of 1-methylguanine in the urine of colorectal tumor bearing patients, has been justified either by a more rapid turnover of nucleic acids in tumor tissue or by an increase in the extent of their methylation (PMID: 9069642 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000273 (1-Methylguanine)


  Mrv1652305261923512D          

 12 13  0  0  0  0            999 V2000
   28.7018  -13.5650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2728  -16.0401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9873  -14.8025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.1969  -14.5512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.7018  -16.0401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.1969  -15.8789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2728  -14.3900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9873  -15.6276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7018  -14.3900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4163  -15.6276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4163  -14.8025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6784  -15.2151    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
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4 11  1  0  0  0  0
  4 12  1  0  0  0  0
  5  8  2  0  0  0  0
  5 10  1  0  0  0  0
  6 10  1  0  0  0  0
  6 12  2  0  0  0  0
  9 11  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
Download

3D MOL for NP0000273 (1-Methylguanine)

HMDB0003282
     RDKit          3D
1-Methylguanine
 19 20  0  0  0  0  0  0  0  0999 V2000
   -2.3114   -0.7974   -0.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9900   -0.2146   -0.0601 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8744    1.0233    0.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0610    1.7476    0.6917 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3560    1.5862    0.5670 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4635    0.8586    0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7812    1.0884    0.3181 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4805    0.0167   -0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5524   -0.9170   -0.4144 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3237   -0.4306   -0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0708   -1.0006   -0.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0873   -2.1759   -0.8069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9811   -0.0535   -0.7128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7169   -1.0292    0.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2714   -1.7596   -0.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2822    2.0228    1.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7454    2.0281   -0.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5635   -0.1115   -0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7296   -1.8818   -0.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11  2  1  0
 10  6  2  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  4 17  1  0
  8 18  1  0
  9 19  1  0
M  END
Download

3D SDF for NP0000273 (1-Methylguanine)


  Mrv1652305261923512D          

 12 13  0  0  0  0            999 V2000
   28.7018  -13.5650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2728  -16.0401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9873  -14.8025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.1969  -14.5512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.7018  -16.0401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.1969  -15.8789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2728  -14.3900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9873  -15.6276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7018  -14.3900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4163  -15.6276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4163  -14.8025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6784  -15.2151    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
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4 11  1  0  0  0  0
  4 12  1  0  0  0  0
  5  8  2  0  0  0  0
  5 10  1  0  0  0  0
  6 10  1  0  0  0  0
  6 12  2  0  0  0  0
  9 11  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000273

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(N)=NC2=C(NC=N2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H7N5O/c1-11-5(12)3-4(9-2-8-3)10-6(11)7/h2H,1H3,(H2,7,10)(H,8,9)

> <INCHI_KEY>
RFLVMTUMFYRZCB-UHFFFAOYSA-N

> <FORMULA>
C6H7N5O

> <MOLECULAR_WEIGHT>
165.1527

> <EXACT_MASS>
165.065059871

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.360458747348375

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-1-methyl-6,7-dihydro-1H-purin-6-one

> <ALOGPS_LOGP>
-0.88

> <JCHEM_LOGP>
-0.8832736693333332

> <ALOGPS_LOGS>
-1.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.260245839599168

> <JCHEM_PKA_STRONGEST_BASIC>
0.2844112059186009

> <JCHEM_POLAR_SURFACE_AREA>
87.37

> <JCHEM_REFRACTIVITY>
44.231199999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.94e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-1-methyl-7H-purin-6-one

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000273 (1-Methylguanine)

HMDB0003282
     RDKit          3D
1-Methylguanine
 19 20  0  0  0  0  0  0  0  0999 V2000
   -2.3114   -0.7974   -0.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9900   -0.2146   -0.0601 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8744    1.0233    0.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0610    1.7476    0.6917 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3560    1.5862    0.5670 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4635    0.8586    0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7812    1.0884    0.3181 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4805    0.0167   -0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5524   -0.9170   -0.4144 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3237   -0.4306   -0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0708   -1.0006   -0.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0873   -2.1759   -0.8069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9811   -0.0535   -0.7128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7169   -1.0292    0.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2714   -1.7596   -0.7861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2822    2.0228    1.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7454    2.0281   -0.0430 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5635   -0.1115   -0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7296   -1.8818   -0.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11  2  1  0
 10  6  2  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  4 17  1  0
  8 18  1  0
  9 19  1  0
M  END
Download

PDB for NP0000273 (1-Methylguanine)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0      53.577 -25.321   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      50.909 -29.942   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      52.243 -27.631   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      56.368 -27.162   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      53.577 -29.942   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      56.368 -29.641   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      50.909 -26.861   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      52.243 -29.172   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      53.577 -26.861   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      54.910 -29.172   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      54.910 -27.631   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      57.266 -28.402   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2    8                                                            
CONECT    3    7    8    9                                                  
CONECT    4   11   12                                                       
CONECT    5    8   10                                                       
CONECT    6   10   12                                                       
CONECT    7    3                                                            
CONECT    8    2    3    5                                                  
CONECT    9    1    3   11                                                  
CONECT   10    5    6   11                                                  
CONECT   11    4    9   10                                                  
CONECT   12    4    6                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END
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3D PDB for NP0000273 (1-Methylguanine)

COMPND    HMDB0003282
HETATM    1  C1  UNL     1      -2.311  -0.797  -0.239  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.990  -0.215  -0.060  1.00  0.00           N  
HETATM    3  C2  UNL     1      -0.874   1.023   0.393  1.00  0.00           C  
HETATM    4  N2  UNL     1      -2.061   1.748   0.692  1.00  0.00           N  
HETATM    5  N3  UNL     1       0.356   1.586   0.567  1.00  0.00           N  
HETATM    6  C3  UNL     1       1.464   0.859   0.269  1.00  0.00           C  
HETATM    7  N4  UNL     1       2.781   1.088   0.318  1.00  0.00           N  
HETATM    8  C4  UNL     1       3.480   0.017  -0.096  1.00  0.00           C  
HETATM    9  N5  UNL     1       2.552  -0.917  -0.414  1.00  0.00           N  
HETATM   10  C5  UNL     1       1.324  -0.431  -0.202  1.00  0.00           C  
HETATM   11  C6  UNL     1       0.071  -1.001  -0.378  1.00  0.00           C  
HETATM   12  O1  UNL     1      -0.087  -2.176  -0.807  1.00  0.00           O  
HETATM   13  H1  UNL     1      -2.981  -0.054  -0.713  1.00  0.00           H  
HETATM   14  H2  UNL     1      -2.717  -1.029   0.773  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.271  -1.760  -0.786  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.282   2.023   1.673  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.745   2.028  -0.043  1.00  0.00           H  
HETATM   18  H6  UNL     1       4.564  -0.111  -0.172  1.00  0.00           H  
HETATM   19  H7  UNL     1       2.730  -1.882  -0.775  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   11
CONECT    3    4    5    5
CONECT    4   16   17
CONECT    5    6
CONECT    6    7   10   10
CONECT    7    8    8
CONECT    8    9   18
CONECT    9   10   19
CONECT   10   11
CONECT   11   12   12
END
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SMILES for NP0000273 (1-Methylguanine)

CN1C(N)=NC2=C(NC=N2)C1=O
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INCHI for NP0000273 (1-Methylguanine)

InChI=1S/C6H7N5O/c1-11-5(12)3-4(9-2-8-3)10-6(11)7/h2H,1H3,(H2,7,10)(H,8,9)
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View in JSmol
Synonyms
ValueSource
N1-MethylguanineChEBI
1-Methyl-(8ci)-guanineHMDB
1-Methyl-guanineHMDB
RRNA containing N1-methylguanineHMDB
Chemical FormulaC6H7N5O
Average Mass165.1527 Da
Monoisotopic Mass165.06506 Da
IUPAC Name2-amino-1-methyl-6,7-dihydro-1H-purin-6-one
Traditional Name2-amino-1-methyl-7H-purin-6-one
CAS Registry Number938-85-2
SMILES
CN1C(N)=NC2=C(NC=N2)C1=O
InChI Identifier
InChI=1S/C6H7N5O/c1-11-5(12)3-4(9-2-8-3)10-6(11)7/h2H,1H3,(H2,7,10)(H,8,9)
InChI KeyRFLVMTUMFYRZCB-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica chinensisKNApSAcK Database
Brassica rapa ssp. chinensisPlant
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 6-oxopurines. These are purines that carry a C=O group at position 6. 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 Parent6-oxopurines
Alternative Parents
Substituents
  • 6-oxopurine
  • Pyrimidone
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility64310 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.94 g/LALOGPS
logP-0.88ALOGPS
logP-0.88ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)8.26ChemAxon
pKa (Strongest Basic)0.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area87.37 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.23 m³·mol⁻¹ChemAxon
Polarizability15.36 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003282
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014518
KNApSAcK IDC00055389
Chemspider ID63498
KEGG Compound IDC04152
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethylguanine
METLIN ID3778
PubChem Compound70315
PDB IDNot Available
ChEBI ID21803
Good Scents IDrw1851531
References
General References
  1. Mills GC, Schmalstieg FC, Goldblum RM: Urinary excretion of modified purines and nucleosides in immunodeficient children. Biochem Med. 1985 Aug;34(1):37-51. [PubMed:4052062 ]
  2. Porcelli B, Muraca LF, Frosi B, Marinello E, Vernillo R, De Martino A, Catinella S, Traldi P: Fast-atom bombardment mass spectrometry for mapping of endogenous methylated purine bases in urine extracts. Rapid Commun Mass Spectrom. 1997;11(4):398-404. [PubMed:9069642 ]
  3. Kerr SJ: Induction of adipocyte formation in 10T1/2 cells by 1-methylguanine and 7-methylguanine. Tumour Biol. 1985;6(2):115-21. [PubMed:2413515 ]
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