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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-04-12 21:01:07 UTC
Update Date2017-12-07 01:55:38 UTC
HMDB IDHMDB0006040
Secondary Accession Numbers
  • HMDB06040
Metabolite Identification
Common NameN2-Methylguanine
DescriptionN2-Methylguanine is a modified nucleoside. N2-Methylguanine is an endogenous methylated nucleoside found in human fluids; methylated purine bases are present in higher amounts in tumor-bearing patients compared to healthy controls. Human exposure to carcinogenic alkylating agents can lead to the formation of covalently bound adducts in DNA, some of which are excreted in urine as alkylated purines following DNA degrdn. and repair; the N2 position of guanine is one of the major sites for DNA modification by various carcinogens. Measurements of RNA or DNA catabolites in urine can be used as a measure for the metabolism of each of the three major species of RNA. An accumulation of modified ribonucleosides appears in the serum of uremic patients. (PMID: 16527824 , 16061253 , 8043914 , 2428556 , 7159514 , 9607216 ).
Structure
Thumb
Synonyms
ValueSource
1, 7-dihydro-2-(methylamino)-6H-Purin-6-oneHMDB
1,7-dihydro-2-(methylamino)-6H-Purin-6-oneHMDB
2-(methylamino)-9H-Purin-6-olHMDB
2-methylamino-1,9-dihydro-Purin-6-oneHMDB
2-methylamino-6-OxopurineHMDB
2-MethylguanineHMDB
2-monomethylamino-6-HydroxypurineHMDB
6-Hydroxy-2-methylamino-purineHMDB
6-Hydroxy-2-methylaminopurineHMDB
N-Methyl-guanineHMDB
7-MethylguanineMeSH
N7-Me-gMeSH
7-Methylguanine, 14C-labeledMeSH
N(2)-MethylguanineMeSH
N7-MethylguanineMeSH
Chemical FormulaC6H7N5O
Average Molecular Weight165.1527
Monoisotopic Molecular Weight165.065059871
IUPAC Name2-(methylamino)-6,7-dihydro-3H-purin-6-one
Traditional Name2-(methylamino)-3,7-dihydropurin-6-one
CAS Registry Number10030-78-1
SMILES
CNC1=NC(=O)C2=C(N1)N=CN2
InChI Identifier
InChI=1S/C6H7N5O/c1-7-6-10-4-3(5(12)11-6)8-2-9-4/h2H,1H3,(H3,7,8,9,10,11,12)
InChI KeySGSSKEDGVONRGC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassImidazopyrimidines
Direct ParentHypoxanthines
Alternative Parents
Substituents
  • 6-oxopurine
  • Hypoxanthine
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Imidazole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

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 Solubility0.81 g/LALOGPS
logP-0.71ALOGPS
logP-0.31ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)8.92ChemAxon
pKa (Strongest Basic)2.22ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area82.17 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.68 m³·mol⁻¹ChemAxon
Polarizability15.5 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, Positivesplash10-00li-2900000000-539ed57cd0169be157e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-c5b4249fffca3d4d371fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-e0e61dd036c1eeb8c7cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000b-9700000000-bc35e49ab2b1f81d19f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-18f6ed24aee9629d2b71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dr-1900000000-3647b625be48894ded97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9200000000-eb014bf17054735890c3View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.20 (0.16-0.23) umol/mmol creatinineAdult (>18 years old)BothNormal
      • Geigy Scientific ...
    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 IDFDB023816
    KNApSAcK IDNot Available
    Chemspider ID23213
    KEGG Compound IDC04153
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound24828
    PDB IDNot Available
    ChEBI IDNot Available
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Niwa T, Takeda N, Yoshizumi H: RNA metabolism in uremic patients: accumulation of modified ribonucleosides in uremic serum. Technical note. Kidney Int. 1998 Jun;53(6):1801-6. [PubMed:9607216 ]
    2. Choi JY, Guengerich FP: Adduct size limits efficient and error-free bypass across bulky N2-guanine DNA lesions by human DNA polymerase eta. J Mol Biol. 2005 Sep 9;352(1):72-90. [PubMed:16061253 ]
    3. Kanduc D, Sapia G: Origin of 1,7-dimethylguanosine in tRNA chemical and enzymatic methylation. Boll Soc Ital Biol Sper. 1982 Oct 15;58(19):1221-5. [PubMed:7159514 ]
    4. Choi JY, Guengerich FP: Kinetic evidence for inefficient and error-prone bypass across bulky N2-guanine DNA adducts by human DNA polymerase iota. J Biol Chem. 2006 May 5;281(18):12315-24. Epub 2006 Mar 8. [PubMed:16527824 ]
    5. Porcelli B, Pagani R, Lorenzini L, De Martino A, Catinella S, Traldi P: Different mass spectrometric approaches in the identification of endogenous methylated purine bases in urine extracts. Rapid Commun Mass Spectrom. 1994 Jun;8(6):443-50. [PubMed:8043914 ]
    6. Sander G, Topp H, Heller-Schoch G, Wieland J, Schoch G: Ribonucleic acid turnover in man:RNA catabolites in urine as measure for the metabolism of each of the three major species of RNA. Clin Sci (Lond). 1986 Oct;71(4):367-74. [PubMed:2428556 ]