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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:30 UTC
HMDB IDHMDB00897
Secondary Accession NumbersNone
Metabolite Identification
Common Name7-Methylguanine
Description7-Methylguanine is a metabolite of DNA methylation and depurination observed in normal human biofluids; however, it has been found significantly higher in the urine of smokers than in nonsmokers. (PMID 16059882 ).
Structure
Thumb
Synonyms
ValueSource
2-amino-1,7-dihydro-7-Methyl-6H-purin-6-oneChEBI
2-amino-7-MethylhypoxanthineChEBI
7-MethylguanineChEBI
N(7)-MethylguanineChEBI
2-amino-1,7-Dihydroxy-7-methyl-6H-purine-6-oneHMDB
2-amino-6-Hydroxy-7-methylpurineHMDB
7-Methyl-guanineHMDB
7-Methyl-guanine (8ci)HMDB
N-MethylguanineHMDB
N7-MethylguanineHMDB
Chemical FormulaC6H7N5O
Average Molecular Weight165.1527
Monoisotopic Molecular Weight165.065059871
IUPAC Name2-amino-7-methyl-6,7-dihydro-3H-purin-6-one
Traditional Name2-amino-7-methylhypoxanthine
CAS Registry Number578-76-7
SMILES
CN1C=NC2=C1C(=O)N=C(N)N2
InChI Identifier
InChI=1S/C6H7N5O/c1-11-2-8-4-3(11)5(12)10-6(7)9-4/h2H,1H3,(H3,7,9,10,12)
InChI KeyInChIKey=FZWGECJQACGGTI-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
  • N-substituted imidazole
  • 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
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point370 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.12 mg/mLALOGPS
logP-0.62ALOGPS
logP-0.37ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)9.35ChemAxon
pKa (Strongest Basic)2.07ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.8 m3·mol-1ChemAxon
Polarizability15.41 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0900000000-9467edfe6e5fe41d80c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0002-0900000000-248230263bb02a17634dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-64ba12b6ac3ae920980eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-6d69b62500523e3dc3d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-0900000000-37d2717efb3cfd99a3a5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-1900000000-9b6a6193e87ed7391bfdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-2900000000-8bc29ce14fc996e59b37View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-6900000000-b9b860095178bfbd4cd4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00kb-1900000000-0d0f6cc2cd44562b2323View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-9500000000-80f25018b3b2b6146ab0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-9600000000-ab600e6988ac4e56e321View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00dj-9400000000-e929965f6c63f59fcb15View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014j-9000000000-fa82f4a1c9751a539c26View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • White Blood Cells
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.129 +/- 0.024 uMAdult (>18 years old)BothNormal details
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 IDFDB022305
KNApSAcK IDNot Available
Chemspider ID10883
KEGG Compound IDC02242
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00897
Metagene LinkHMDB00897
METLIN IDNot Available
PubChem Compound11361
PDB IDMY6
ChEBI ID28664
References
Synthesis ReferenceAdams, Benjamin L. De-D-ribosylation of 7-alkylpurine D-ribonucleosides by a reduction-displacement procedure. Conversion of 7-methylguanosine into 7-methylguanine. Nucleic Acid Chem. (1978), 2 615-17.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Mustonen R, Hemminki K: 7-Methylguanine levels in DNA of smokers' and non-smokers' total white blood cells, granulocytes and lymphocytes. Carcinogenesis. 1992 Nov;13(11):1951-5. [1423861 ]
  2. Eder E: Intraindividual variations of DNA adduct levels in humans. Mutat Res. 1999 Mar 8;424(1-2):249-61. [10064865 ]
  3. van Delft JH, van den Ende AM, Keizer HJ, Ouwerkerk J, Baan RA: Determination of N7-methylguanine in DNA of white blood cells from cancer patients treated with dacarbazine. Carcinogenesis. 1992 Jul;13(7):1257-9. [1638694 ]
  4. Kumar R, Hemminki K: Separation of 7-methyl- and 7-(2-hydroxyethyl)-guanine adducts in human DNA samples using a combination of TLC and HPLC. Carcinogenesis. 1996 Mar;17(3):485-92. [8631134 ]
  5. Chao MR, Wang CJ, Yang HH, Chang LW, Hu CW: Rapid and sensitive quantification of urinary N7-methylguanine by isotope-dilution liquid chromatography/electrospray ionization tandem mass spectrometry with on-line solid-phase extraction. Rapid Commun Mass Spectrom. 2005;19(17):2427-32. [16059882 ]

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