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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 19:03:53 UTC
HMDB IDHMDB0001566
Secondary Accession Numbers
  • HMDB01566
Metabolite Identification
Common Name3-Methylguanine
Description3-Methylguanine is a methylated purine base. Methylated purine bases are known to be present in normal urine and to change under pathological conditions, in particular in the development of leukemia, tumors and immunodeficiency, by the altered turnover of nucleic acids typical of these diseases. (PMID 9069642 ).
Structure
Thumb
Synonyms
ValueSource
N(3)-MethylguanineChEBI
3-Methyl-guanineHMDB
7-dihydro-3-Methyl-2-amino-3-6H-purin-6-oneHMDB
7-dihydro-3-Methyl-2-amino-3-6H-purin-6-one (9ci)HMDB
N3-MethylguanineHMDB
Chemical FormulaC6H7N5O
Average Molecular Weight165.1527
Monoisotopic Molecular Weight165.065059871
IUPAC Name2-amino-3-methyl-6,7-dihydro-3H-purin-6-one
Traditional NameN(3)-methylguanine
CAS Registry Number2958-98-7
SMILES
CN1C2=C(NC=N2)C(=O)N=C1N
InChI Identifier
InChI=1S/C6H7N5O/c1-11-4-3(8-2-9-4)5(12)10-6(11)7/h2H,1H3,(H,8,9)(H2,7,10,12)
InChI KeyXHBSBNYEHDQRCP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassImidazopyrimidines
Direct ParentPurines and purine derivatives
Alternative Parents
Substituents
  • Purine
  • Hydroxypyrimidine
  • Pyrimidine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.05 g/LALOGPS
logP-0.9ALOGPS
logP-1.2ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)9.01ChemAxon
pKa (Strongest Basic)1.45ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area87.37 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.14 m³·mol⁻¹ChemAxon
Polarizability15.33 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ks-4900000000-89c964e93b806d54b24eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-c4ba0ed5b3ac83a6d773View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0229-0900000000-af571ef129b2b3b3df91View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-4900000000-9ca1b8bbcde0e92e9542View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9200000000-f270ece6f4adfadf299bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kf-9000000000-f60ca01e4c5c004b1e2eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00kb-1900000000-f5ba70dcaf0333618ce0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-9300000000-c9da84dbc7393cd52b91View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dj-9300000000-a69603f1c727d6e9b676View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-006t-9200000000-4fe8bf3a7624361a8258View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00kb-9000000000-c684cc4440c891627e86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-e9b946da74da624a31e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-c6cb6f9878561963a5aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-2086b37308342d3b9796View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-bb41cab24a7d825ed51eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1900000000-708291e89fdfe380eb77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-365be27ae084e43e2c91View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022693
KNApSAcK IDNot Available
Chemspider ID68771
KEGG Compound IDC02230
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound76292
PDB IDNot Available
ChEBI ID27564
References
Synthesis ReferenceItaya, Taisuke; Shioyama, Chieko; Kagatani, Seiya. Improved synthesis of 3-methylguanine. Chemical & Pharmaceutical Bulletin (1982), 30(9), 3392-4.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Hydrolysis of the deoxyribose N-glycosidic bond to excise 3-methyladenine, and 7-methylguanine from the damaged DNA polymer formed by alkylation lesions
Gene Name:
MPG
Uniprot ID:
P29372
Molecular weight:
32868.4