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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:36 UTC
Update Date2023-02-21 17:16:09 UTC
HMDB IDHMDB0002099
Secondary Accession Numbers
  • HMDB02099
Metabolite Identification
Common Name6-Methyladenine
Description6-Methyladenine is a methylated adenine residue. The formation of internal 6-methyladenine (m6A) residues in eucaryotic messenger RNA (mRNA) is a postsynthetic modification in which S-adenosyl-L-methionine (SAM) serves as the methyl donor. 6-Methyladenine residues have also been localized to heterogeneous nuclear RNA (HnRNA), and for the most part these residues are conserved during mRNA processing. Although the biological significance of internal adenine methylation in eucaryotic mRNA remains unclear, a great deal of research has indicated that this modification may be required for mRNA transport to the cytoplasm, the selection of splice sites or other RNA processing reactions. The presence of m6A residues increases the in vitro translation efficiency of dihydrofolate reductase; an inhibition of m6A residues in dihydrofolate reductase transcripts significantly alters their rate of translation. m6A is found in many human fluids: oviductal fluid, blood plasma and urine (PMID:1551452 , 8925412 , 10481270 , 16083005 , 16684535 , 3506820 , 3728186 ).
Structure
Data?1676999769
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 Weight149.1533
Monoisotopic Molecular Weight149.070145249
IUPAC NameN-methyl-7H-purin-6-amine
Traditional Name6-(methylamino)purine
CAS Registry Number443-72-1
SMILES
CNC1=NC=NC2=C1NC=N2
InChI Identifier
InChI=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
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 Solubility1.18 mg/mL at 20 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
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]+131.41131661259
DarkChem[M-H]-130.82931661259
DeepCCS[M+H]+129.030932474
DeepCCS[M-H]-126.31430932474
DeepCCS[M-2H]-163.10930932474
DeepCCS[M+Na]+137.89830932474
AllCCS[M+H]+132.732859911
AllCCS[M+H-H2O]+128.032859911
AllCCS[M+NH4]+137.032859911
AllCCS[M+Na]+138.232859911
AllCCS[M-H]-128.632859911
AllCCS[M+Na-2H]-129.632859911
AllCCS[M+HCOO]-130.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6-MethyladenineCNC1=NC=NC2=C1NC=N22364.6Standard polar33892256
6-MethyladenineCNC1=NC=NC2=C1NC=N21774.3Standard non polar33892256
6-MethyladenineCNC1=NC=NC2=C1NC=N21851.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
6-Methyladenine,1TMS,isomer #1CN(C1=NC=NC2=C1[NH]C=N2)[Si](C)(C)C1835.8Semi standard non polar33892256
6-Methyladenine,1TMS,isomer #1CN(C1=NC=NC2=C1[NH]C=N2)[Si](C)(C)C1792.5Standard non polar33892256
6-Methyladenine,1TMS,isomer #1CN(C1=NC=NC2=C1[NH]C=N2)[Si](C)(C)C2688.1Standard polar33892256
6-Methyladenine,1TMS,isomer #2CNC1=NC=NC2=C1N([Si](C)(C)C)C=N21901.7Semi standard non polar33892256
6-Methyladenine,1TMS,isomer #2CNC1=NC=NC2=C1N([Si](C)(C)C)C=N21719.9Standard non polar33892256
6-Methyladenine,1TMS,isomer #2CNC1=NC=NC2=C1N([Si](C)(C)C)C=N22752.0Standard polar33892256
6-Methyladenine,2TMS,isomer #1CN(C1=NC=NC2=C1N([Si](C)(C)C)C=N2)[Si](C)(C)C1876.6Semi standard non polar33892256
6-Methyladenine,2TMS,isomer #1CN(C1=NC=NC2=C1N([Si](C)(C)C)C=N2)[Si](C)(C)C1823.2Standard non polar33892256
6-Methyladenine,2TMS,isomer #1CN(C1=NC=NC2=C1N([Si](C)(C)C)C=N2)[Si](C)(C)C2351.1Standard polar33892256
6-Methyladenine,1TBDMS,isomer #1CN(C1=NC=NC2=C1[NH]C=N2)[Si](C)(C)C(C)(C)C2068.3Semi standard non polar33892256
6-Methyladenine,1TBDMS,isomer #1CN(C1=NC=NC2=C1[NH]C=N2)[Si](C)(C)C(C)(C)C1988.9Standard non polar33892256
6-Methyladenine,1TBDMS,isomer #1CN(C1=NC=NC2=C1[NH]C=N2)[Si](C)(C)C(C)(C)C2802.3Standard polar33892256
6-Methyladenine,1TBDMS,isomer #2CNC1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C=N22116.6Semi standard non polar33892256
6-Methyladenine,1TBDMS,isomer #2CNC1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C=N21903.7Standard non polar33892256
6-Methyladenine,1TBDMS,isomer #2CNC1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C=N22831.2Standard polar33892256
6-Methyladenine,2TBDMS,isomer #1CN(C1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2)[Si](C)(C)C(C)(C)C2274.8Semi standard non polar33892256
6-Methyladenine,2TBDMS,isomer #1CN(C1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2)[Si](C)(C)C(C)(C)C2237.7Standard non polar33892256
6-Methyladenine,2TBDMS,isomer #1CN(C1=NC=NC2=C1N([Si](C)(C)C(C)(C)C)C=N2)[Si](C)(C)C(C)(C)C2519.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 6-Methyladenine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dj-1900000000-4388236e2ed64fa864852017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6-Methyladenine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Methyladenine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-0002-0900000000-ebccac10312d914083da2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Methyladenine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-0002-0900000000-acd38df5c1893ac9af762012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Methyladenine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-001i-0900000000-f9139c5b6ccbec800e532012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Methyladenine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-001i-1900000000-7a5ba4a964d60f60ecb02012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Methyladenine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-00lr-6900000000-006dc8e68d6ad96440902012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Methyladenine LC-ESI-QQ , negative-QTOFsplash10-0002-0900000000-ebccac10312d914083da2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Methyladenine LC-ESI-QQ , negative-QTOFsplash10-0002-0900000000-306d0a3a86a82c8e9c2d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Methyladenine LC-ESI-QQ , negative-QTOFsplash10-001i-0900000000-f9139c5b6ccbec800e532017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Methyladenine LC-ESI-QQ , negative-QTOFsplash10-001i-1900000000-7a5ba4a964d60f60ecb02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 6-Methyladenine LC-ESI-QQ , negative-QTOFsplash10-00lr-6900000000-a9aecd02881bc63a44cf2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methyladenine 10V, Positive-QTOFsplash10-0udi-0900000000-95e5ff9c45c5436136462017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methyladenine 20V, Positive-QTOFsplash10-0udi-0900000000-d725eaa6bb993c0825d12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methyladenine 40V, Positive-QTOFsplash10-0q34-9500000000-1d36feb5463dedb4b9392017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methyladenine 10V, Negative-QTOFsplash10-0002-0900000000-d994d99b1fbee490b9c12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methyladenine 20V, Negative-QTOFsplash10-0002-0900000000-0219b6e174726015e92e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methyladenine 40V, Negative-QTOFsplash10-0a4i-9500000000-bdc2edc9722c931b492d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methyladenine 10V, Negative-QTOFsplash10-0002-0900000000-0fdae69660ea9759916e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methyladenine 20V, Negative-QTOFsplash10-0002-0900000000-91ca82897e368d4072852021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methyladenine 40V, Negative-QTOFsplash10-066s-4900000000-13a3c96e59d3df0511ab2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methyladenine 10V, Positive-QTOFsplash10-0udi-0900000000-18eefbc35459f26a65702021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methyladenine 20V, Positive-QTOFsplash10-0udi-0900000000-18eefbc35459f26a65702021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-Methyladenine 40V, Positive-QTOFsplash10-0006-9100000000-42405660fb0f8bcc5c232021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)2012-12-05Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)2012-12-05Wishart 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 LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022845
KNApSAcK IDNot Available
Chemspider ID61270
KEGG Compound IDC08434
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound67955
PDB IDNot Available
ChEBI ID28871
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceElion, Gertrude B. Some new N-methylpurines. Ciba Foundation Symposium, Chem. and Biol. Purines (1957), 39-49.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:3506820 ]
  2. Tuck MT: The formation of internal 6-methyladenine residues in eucaryotic messenger RNA. Int J Biochem. 1992 Mar;24(3):379-86. [PubMed:1551452 ]
  3. 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. [PubMed:8925412 ]
  4. 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. [PubMed:10481270 ]
  5. Baniushin BF: [Methylation of adenine residues in DNA of eukaryotes]. Mol Biol (Mosk). 2005 Jul-Aug;39(4):557-66. [PubMed:16083005 ]
  6. 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. [PubMed:16684535 ]
  7. 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. [PubMed:3728186 ]