(N-6)-Methyladenine (CHEM016349)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:28:27 UTC
Update Date2016-11-09 01:15:23 UTC
Accession NumberCHEM016349
Identification
Common Name(N-6)-Methyladenine
ClassSmall Molecule
DescriptionA methyladenine that is 9H-purin-6-amine substituted by a methyl group at the amino nitrogen.
Contaminant Sources
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
6-MAPChEBI
6-MethylaminopurineChEBI
N6-MethyladenineChEBI
N6-MonomethyladenineChEBI
(N-6)-MethyladenineHMDB
6-(methylamino)PurineHMDB
6-MonomethylaminopurineHMDB
Methyl(purin-6-yl)amineHMDB
N-6-MethyladenineHMDB
N-Methyl-9H-purin-6-amineHMDB
N-Methyl-adenineHMDB
N-Methyl-N-(9H-purin-6-yl)amineHMDB
N-MethyladenineHMDB
N(6)-MethyladenineMeSH, HMDB
6-MethyladenineChEBI
Chemical FormulaC6H7N5
Average Molecular Mass149.153 g/mol
Monoisotopic Mass149.070 g/mol
CAS Registry Number443-72-1
IUPAC NameN-methyl-7H-purin-6-amine
Traditional Name6-(methylamino)purine
SMILESCNC1=NC=NC2=C1NC=N2
InChI IdentifierInChI=1S/C6H7N5/c1-7-5-4-6(10-2-8-4)11-3-9-5/h2-3H,1H3,(H2,7,8,9,10,11)
InChI KeyCKOMXBHMKXXTNW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 6-alkylaminopurines. 6-alkylaminopurines are compounds that contain an alkylamine group attached at the 6-position of a purine. 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 Parent6-alkylaminopurines
Alternative Parents
Substituents
  • 6-alkylaminopurine
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • Pyrimidine
  • Imidolactam
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.94 g/LALOGPS
logP0.19ALOGPS
logP-0.27ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)10.24ChemAxon
pKa (Strongest Basic)3.49ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.49 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.71 m³·mol⁻¹ChemAxon
Polarizability14.43 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dj-1900000000-4388236e2ed64fa86485Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-ebccac10312d914083daSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-0900000000-acd38df5c1893ac9af76Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-0900000000-f9139c5b6ccbec800e53Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-1900000000-7a5ba4a964d60f60ecb0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00lr-6900000000-006dc8e68d6ad9644090Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-ebccac10312d914083daSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-306d0a3a86a82c8e9c2dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-f9139c5b6ccbec800e53Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-1900000000-7a5ba4a964d60f60ecb0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00lr-6900000000-a9aecd02881bc63a44cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-95e5ff9c45c543613646Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-d725eaa6bb993c0825d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0q34-9500000000-1d36feb5463dedb4b939Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-d994d99b1fbee490b9c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-0219b6e174726015e92eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9500000000-bdc2edc9722c931b492dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-0fdae69660ea9759916eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-91ca82897e368d407285Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066s-4900000000-13a3c96e59d3df0511abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-18eefbc35459f26a6570Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-18eefbc35459f26a6570Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-42405660fb0f8bcc5c23Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002099
FooDB IDFDB022845
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID61270
ChEBI ID28871
PubChem Compound ID67955
Kegg Compound IDC08434
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23547775
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=25936836
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=26158636
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=26211457
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=26293475
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=7433124
7. Elion, Gertrude B. Some new N-methylpurines. Ciba Foundation Symposium, Chem. and Biol. Purines (1957), 39-49.
8. Elion, Gertrude B. Some new N-methylpurines. Ciba Foundation Symposium, Chem. and Biol. Purines (1957), 39-49.
9. Tuck MT: The formation of internal 6-methyladenine residues in eucaryotic messenger RNA. Int J Biochem. 1992 Mar;24(3):379-86.
10. Heilman KL, Leach RA, Tuck MT: Internal 6-methyladenine residues increase the in vitro translation efficiency of dihydrofolate reductase messenger RNA. Int J Biochem Cell Biol. 1996 Jul;28(7):823-9.
11. Tuck MT, Wiehl PE, Pan T: Inhibition of 6-methyladenine formation decreases the translation efficiency of dihydrofolate reductase transcripts. Int J Biochem Cell Biol. 1999 Aug;31(8):837-51.
12. Baniushin BF: [Methylation of adenine residues in DNA of eukaryotes]. Mol Biol (Mosk). 2005 Jul-Aug;39(4):557-66.
13. Ratel D, Ravanat JL, Charles MP, Platet N, Breuillaud L, Lunardi J, Berger F, Wion D: Undetectable levels of N6-methyl adenine in mouse DNA: Cloning and analysis of PRED28, a gene coding for a putative mammalian DNA adenine methyltransferase. FEBS Lett. 2006 May 29;580(13):3179-84. Epub 2006 May 3.
14. Morris GS, Simmonds HA, Davies PM: Use of biological fluids for the rapid diagnosis of potentially lethal inherited disorders of human purine and pyrimidine metabolism. Biomed Chromatogr. 1986 Jun;1(3):109-18.
15. Morris GS, Simmonds HA: A single system for the evaluation of purine and pyrimidine nucleosides and bases together with their analogues in biological fluids. Adv Exp Med Biol. 1986;195 Pt A:593-9.