You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2009-01-29 12:14:58 UTC
Update Date2017-03-02 21:31:53 UTC
HMDB IDHMDB11600
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Methyladenine
Description3-Methyladenine is one of the purines damaged by alkylation and oxidation which can be recognized and excised by the human 3-methyladenine DNA glycosylase (AAG) (EC: EC 3.2.2.21).
Structure
Thumb
Synonyms
ValueSource
3-Methyl-3H-adenineChEBI
3-METHYL-3H-purin-6-ylamineChEBI
6-amino-3-MethylpurineChEBI
3-Methyl-3H-purin-6-amineHMDB
3-Methyl-3H-purin-6-amine (acd/name 4.0)HMDB
3-Methyl-3H-purin-6-ylamine (acd/name 4.0)HMDB
3-Methyl-adenineHMDB
3-MA nucleobaseMeSH
N(3)-MethyladenineMeSH
Chemical FormulaC6H7N5
Average Molecular Weight149.1533
Monoisotopic Molecular Weight149.070145249
IUPAC Name3-methyl-3H-purin-6-amine
Traditional Name3-methyladenine
CAS Registry Number5142-23-4
SMILES
CN1C=NC(N)=C2N=CN=C12
InChI Identifier
InChI=1S/C6H7N5/c1-11-3-10-5(7)4-6(11)9-2-8-4/h2-3H,7H2,1H3
InChI KeyFSASIHFSFGAIJM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassImidazopyrimidines
Direct Parent6-aminopurines
Alternative Parents
Substituents
  • 6-aminopurine
  • Aminopyrimidine
  • Primary aromatic amine
  • Pyrimidine
  • Imidolactam
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Azacycle
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 Solubility1.81 mg/mLALOGPS
logP-1.1ALOGPS
logP-0.31ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)17.3ChemAxon
pKa (Strongest Basic)3.03ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.62 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.5 m3·mol-1ChemAxon
Polarizability14.48 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-0a4i-4980000000-d3e94e4150e2b870d9b2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-0a4i-3890000000-235f39119df7c967e9baView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0a4i-2980000000-251ceed13f156eff1fc4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-0ab9-9760000000-e3d1a7f774e6bfb718aeView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-0900000000-b32577a48ebafc94ae9aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0udi-1900000000-485f684fffa023d0050eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0udi-4900000000-6b3b3dd2f2f2d875bf14View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a59-9800000000-fe6c9700b9c081b8697aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0udi-1900000000-b4a28f0f1bd551992615View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0900000000-8db506e73a05ea922d94View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0udi-0900000000-f67b128eb2b6ac7139b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-4900000000-49dc94a0b10083c8230fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0900000000-e564522269418ab462fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-53161ff2cee1a6ff34d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-1ab536fe3bbb9bdfde76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0giv-9600000000-a22dc2c9e956ce0b2b86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-31965d8430668c1cef72View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006t-2900000000-1c6ebd899170870682a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pc0-5900000000-23b69a04a094c620fe7fView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified2.53 +/- 1.65 umol/mmol creatinineChildren (1-13 years old)BothNormal details
    UrineDetected and Quantified1.48 +/- 0.17 umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
    UrineDetected and Quantified0.86 +/- 0.29 umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    UrineDetected and Quantified3.96 +/- 1.44 umol/mmol creatinineAdult (>18 years old)BothCanavan disease details
    Associated Disorders and Diseases
    Disease References
    Canavan disease
    1. Tavazzi B, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B: Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism. Clin Biochem. 2005 Nov;38(11):997-1008. Epub 2005 Sep 1. [PubMed:16139832 ]
    Associated OMIM IDs
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB028311
    KNApSAcK IDNot Available
    Chemspider ID1610
    KEGG Compound IDC00913
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB11600
    Metagene LinkHMDB11600
    METLIN IDNot Available
    PubChem Compound1673
    PDB IDADK
    ChEBI ID38635
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Download (PDF)
    General ReferencesNot Available

    Enzymes

    General function:
    Involved in catalytic activity
    Specific function:
    Hydrolysis of the deoxyribose N-glycosidic bond to excise 3-methyladenine, and 7-methylguanine from the damaged DNA polymer formed by alkylation lesions
    Gene Name:
    MPG
    Uniprot ID:
    P29372
    Molecular weight:
    32868.4