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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:56 UTC
HMDB IDHMDB01566
Secondary Accession NumbersNone
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 KeyInChIKey=XHBSBNYEHDQRCP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hypoxanthines. These are compounds containing the purine derivative 1H-purin-6(9H)-one. 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 ParentHypoxanthines
Alternative Parents
Substituents
  • Hypoxanthine
  • 6-oxopurine
  • Pyrimidone
  • Pyrimidine
  • Primary aromatic amine
  • Heteroaromatic compound
  • Vinylogous amide
  • Imidazole
  • Azole
  • Azacycle
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.14 m3·mol-1ChemAxon
Polarizability15.33 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
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
NuGOwiki LinkHMDB01566
Metagene LinkHMDB01566
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. [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