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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-01-29 12:09:56 UTC
Update Date2020-02-26 21:35:27 UTC
HMDB IDHMDB0011599
Secondary Accession Numbers
  • HMDB11599
Metabolite Identification
Common Name1-Methyladenine
Description1-Methyladenine is the product of reaction between 1-methyladenosine and water which is catalyzed by 1-methyladenosine nucleosidase (EC:3.2.2.13). 1-Methyladenine is a product of alkylation damage in DNA which can be repaired by damage reversal by oxidative demethylation, a reaction requiring ferrous iron and 2-oxoglutarate as cofactor and co-substrate, respectively (PMID:15576352 ). 1-Methyladenine is found to be associated with adenosine deaminase (ADA) deficiency, which is an inborn error of metabolism.
Structure
Data?1582752927
Synonyms
ValueSource
N1-MethyladenineChEBI
1, 9-Dihydro-1-methyl-6H-purin-6-imineHMDB
1-Methyl-1H-purin-6-amineHMDB
1-Methyl-1H-purin-6-ylamineHMDB
1-Methyl-adenineHMDB
Chemical FormulaC6H7N5
Average Molecular Weight149.1533
Monoisotopic Molecular Weight149.070145249
IUPAC Name1-methyl-1H-purin-6-amine
Traditional Name1-methyl-1H-purin-6-amine
CAS Registry Number5142-22-3
SMILES
CN1C=NC2=NC=NC2=C1N
InChI Identifier
InChI=1S/C6H7N5/c1-11-3-10-6-4(5(11)7)8-2-9-6/h2-3H,7H2,1H3
InChI KeyHPZMWTNATZPBIH-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. 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-aminopurines
Alternative Parents
Substituents
  • 6-aminopurine
  • Aminopyrimidine
  • Pyrimidine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point> 300 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.91 g/LALOGPS
logP-1.2ALOGPS
logP-0.5ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)0.24ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.62 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.81 m³·mol⁻¹ChemAxon
Polarizability14.43 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dj-4900000000-f072057fd2e79f405bb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-5c8b7b78cfeaed480069Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-43ecee09f3839868d64aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fu-9500000000-25484796e09297895532Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-481001363707d4d47225Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1900000000-527244488c433cfa02fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-8900000000-69922974e3706889c4e7Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.1 (0.0-0.20) umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    BiospecimenStatusValueAgeSexConditionReferenceDetails
    UrineDetected and Quantified3.15 umol/mmol creatinineAdult (>18 years old)FemaleAdenosine deaminase(ADA) deficiency details
    Associated Disorders and Diseases
    Disease References
    Adenosine deaminase deficiency
    1. Mills GC: 1-Methyladenine in urine of an adenosine deaminase-deficient adult without immunodeficiency. Biochem Med Metab Biol. 1989 Dec;42(3):240-7. [PubMed:2597438 ]
    Associated OMIM IDs
    • 102700 (Adenosine deaminase deficiency)
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FooDB IDFDB028310
    KNApSAcK IDNot Available
    Chemspider ID71157
    KEGG Compound IDC02216
    BioCyc ID1-METHYLADENINE
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound78821
    PDB IDNot Available
    ChEBI ID18083
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Falnes PO: Repair of 3-methylthymine and 1-methylguanine lesions by bacterial and human AlkB proteins. Nucleic Acids Res. 2004 Dec 1;32(21):6260-7. Print 2004. [PubMed:15576352 ]