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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-04-12 21:01:07 UTC
Update Date2023-02-21 17:17:13 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
Data?1676999833
Synonyms
ValueSource
1,7-Dihydro-2-(methylamino)-6H-purin-6-oneChEBI
2-Methylamino-6-oxopurineChEBI
2-MethylguanineChEBI
N-Methyl-guanineChEBI
1, 7-dihydro-2-(methylamino)-6H-Purin-6-oneHMDB
2-(methylamino)-9H-Purin-6-olHMDB
2-methylamino-1,9-dihydro-Purin-6-oneHMDB
2-monomethylamino-6-HydroxypurineHMDB
6-Hydroxy-2-methylamino-purineHMDB
6-Hydroxy-2-methylaminopurineHMDB
7-MethylguanineMeSH, HMDB
N7-Me-gMeSH, HMDB
7-Methylguanine, 14C-labeledMeSH, HMDB
N(2)-MethylguanineMeSH, HMDB
N7-MethylguanineMeSH, HMDB
N2-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
Description Belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines 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
  • 6-oxopurine
  • Hypoxanthine
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Imidazole
  • Azole
  • Azacycle
  • Secondary amine
  • Organic nitrogen compound
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.54331661259
DarkChem[M-H]-134.91331661259
DeepCCS[M+H]+133.96630932474
DeepCCS[M-H]-130.99230932474
DeepCCS[M-2H]-167.64330932474
DeepCCS[M+Na]+143.00430932474
AllCCS[M+H]+136.132859911
AllCCS[M+H-H2O]+131.632859911
AllCCS[M+NH4]+140.332859911
AllCCS[M+Na]+141.532859911
AllCCS[M-H]-132.732859911
AllCCS[M+Na-2H]-133.432859911
AllCCS[M+HCOO]-134.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N2-MethylguanineCNC1=NC(=O)C2=C(N1)N=CN22939.8Standard polar33892256
N2-MethylguanineCNC1=NC(=O)C2=C(N1)N=CN22048.6Standard non polar33892256
N2-MethylguanineCNC1=NC(=O)C2=C(N1)N=CN22170.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N2-Methylguanine,1TMS,isomer #1CN(C1=NC(=O)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C2016.8Semi standard non polar33892256
N2-Methylguanine,1TMS,isomer #1CN(C1=NC(=O)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C2113.5Standard non polar33892256
N2-Methylguanine,1TMS,isomer #1CN(C1=NC(=O)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C3098.3Standard polar33892256
N2-Methylguanine,1TMS,isomer #2CNC1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C1961.5Semi standard non polar33892256
N2-Methylguanine,1TMS,isomer #2CNC1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C2108.2Standard non polar33892256
N2-Methylguanine,1TMS,isomer #2CNC1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C3118.7Standard polar33892256
N2-Methylguanine,1TMS,isomer #3CNC1=NC(=O)C2=C(N=CN2[Si](C)(C)C)[NH]12065.3Semi standard non polar33892256
N2-Methylguanine,1TMS,isomer #3CNC1=NC(=O)C2=C(N=CN2[Si](C)(C)C)[NH]12058.1Standard non polar33892256
N2-Methylguanine,1TMS,isomer #3CNC1=NC(=O)C2=C(N=CN2[Si](C)(C)C)[NH]13043.0Standard polar33892256
N2-Methylguanine,2TMS,isomer #1CN(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C)[NH]1)[Si](C)(C)C2044.0Semi standard non polar33892256
N2-Methylguanine,2TMS,isomer #1CN(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C)[NH]1)[Si](C)(C)C2106.2Standard non polar33892256
N2-Methylguanine,2TMS,isomer #1CN(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C)[NH]1)[Si](C)(C)C2623.0Standard polar33892256
N2-Methylguanine,2TMS,isomer #2CN(C1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C)[Si](C)(C)C1993.2Semi standard non polar33892256
N2-Methylguanine,2TMS,isomer #2CN(C1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C)[Si](C)(C)C2173.7Standard non polar33892256
N2-Methylguanine,2TMS,isomer #2CN(C1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C)[Si](C)(C)C2707.6Standard polar33892256
N2-Methylguanine,2TMS,isomer #3CNC1=NC(=O)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C1982.5Semi standard non polar33892256
N2-Methylguanine,2TMS,isomer #3CNC1=NC(=O)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C2042.5Standard non polar33892256
N2-Methylguanine,2TMS,isomer #3CNC1=NC(=O)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C2687.0Standard polar33892256
N2-Methylguanine,3TMS,isomer #1CN(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C)[Si](C)(C)C2028.2Semi standard non polar33892256
N2-Methylguanine,3TMS,isomer #1CN(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C)[Si](C)(C)C2110.7Standard non polar33892256
N2-Methylguanine,3TMS,isomer #1CN(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C)N1[Si](C)(C)C)[Si](C)(C)C2390.6Standard polar33892256
N2-Methylguanine,1TBDMS,isomer #1CN(C1=NC(=O)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C(C)(C)C2207.7Semi standard non polar33892256
N2-Methylguanine,1TBDMS,isomer #1CN(C1=NC(=O)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C(C)(C)C2323.5Standard non polar33892256
N2-Methylguanine,1TBDMS,isomer #1CN(C1=NC(=O)C2=C(N=C[NH]2)[NH]1)[Si](C)(C)C(C)(C)C3173.7Standard polar33892256
N2-Methylguanine,1TBDMS,isomer #2CNC1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C2176.0Semi standard non polar33892256
N2-Methylguanine,1TBDMS,isomer #2CNC1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C2327.2Standard non polar33892256
N2-Methylguanine,1TBDMS,isomer #2CNC1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C3090.0Standard polar33892256
N2-Methylguanine,1TBDMS,isomer #3CNC1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]12270.0Semi standard non polar33892256
N2-Methylguanine,1TBDMS,isomer #3CNC1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]12236.3Standard non polar33892256
N2-Methylguanine,1TBDMS,isomer #3CNC1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]13101.2Standard polar33892256
N2-Methylguanine,2TBDMS,isomer #1CN(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]1)[Si](C)(C)C(C)(C)C2421.1Semi standard non polar33892256
N2-Methylguanine,2TBDMS,isomer #1CN(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]1)[Si](C)(C)C(C)(C)C2525.6Standard non polar33892256
N2-Methylguanine,2TBDMS,isomer #1CN(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)[NH]1)[Si](C)(C)C(C)(C)C2737.1Standard polar33892256
N2-Methylguanine,2TBDMS,isomer #2CN(C1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2354.5Semi standard non polar33892256
N2-Methylguanine,2TBDMS,isomer #2CN(C1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2569.7Standard non polar33892256
N2-Methylguanine,2TBDMS,isomer #2CN(C1=NC(=O)C2=C(N=C[NH]2)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2747.3Standard polar33892256
N2-Methylguanine,2TBDMS,isomer #3CNC1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C2408.6Semi standard non polar33892256
N2-Methylguanine,2TBDMS,isomer #3CNC1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C2471.8Standard non polar33892256
N2-Methylguanine,2TBDMS,isomer #3CNC1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C2754.3Standard polar33892256
N2-Methylguanine,3TBDMS,isomer #1CN(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2583.5Semi standard non polar33892256
N2-Methylguanine,3TBDMS,isomer #1CN(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2785.6Standard non polar33892256
N2-Methylguanine,3TBDMS,isomer #1CN(C1=NC(=O)C2=C(N=CN2[Si](C)(C)C(C)(C)C)N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2633.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N2-Methylguanine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00li-2900000000-539ed57cd0169be157e12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N2-Methylguanine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N2-Methylguanine 10V, Positive-QTOFsplash10-014i-0900000000-c5b4249fffca3d4d371f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N2-Methylguanine 20V, Positive-QTOFsplash10-014i-0900000000-e0e61dd036c1eeb8c7cd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N2-Methylguanine 40V, Positive-QTOFsplash10-000b-9700000000-bc35e49ab2b1f81d19f22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N2-Methylguanine 10V, Negative-QTOFsplash10-03di-0900000000-18f6ed24aee9629d2b712016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N2-Methylguanine 20V, Negative-QTOFsplash10-03dr-1900000000-3647b625be48894ded972016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N2-Methylguanine 40V, Negative-QTOFsplash10-00kf-9200000000-eb014bf17054735890c32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N2-Methylguanine 10V, Negative-QTOFsplash10-03di-0900000000-11e5406fb2e0acd600c02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N2-Methylguanine 20V, Negative-QTOFsplash10-03el-1900000000-3dab99342f0796ffff0a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N2-Methylguanine 40V, Negative-QTOFsplash10-0006-9000000000-568aee5531b232c430162021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N2-Methylguanine 10V, Positive-QTOFsplash10-014i-0900000000-7f20cf9333bbb1eb98e12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N2-Methylguanine 20V, Positive-QTOFsplash10-014i-1900000000-2641d6f2b8a5684157402021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N2-Methylguanine 40V, Positive-QTOFsplash10-0002-9300000000-58b99541aa08fb42a8382021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
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
Phenol Explorer Compound IDNot Available
FooDB 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 ID21818
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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 ]