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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-01-29 12:14:58 UTC
Update Date2020-11-09 23:18:25 UTC
HMDB IDHMDB0011600
Secondary Accession Numbers
  • HMDB11600
Metabolite Identification
Common Name3-Methyladenine
Description3-Methyladenine, also known as 3-ma nucleobase, 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. 3-Methyladenine is a strong basic compound (based on its pKa). 3-Methyladenine exists in all living species, ranging from bacteria to humans. Outside of the human body, 3-Methyladenine has been detected, but not quantified in, several different foods, such as soft-necked garlics, chinese bayberries, burbots, amaranths, and tea. This could make 3-methyladenine a potential biomarker for the consumption of these foods. 3-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: EC3.2.2.21).
Structure
Data?1582752927
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 nucleobaseHMDB
N(3)-MethyladenineHMDB
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
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
  • Imidolactam
  • 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

Route of exposure:

Biological location:

Source:

Role

Industrial application:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.5 m³·mol⁻¹ChemAxon
Polarizability14.48 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-0a4i-4980000000-d3e94e4150e2b870d9b2Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-0a4i-3890000000-235f39119df7c967e9baSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0a4i-2980000000-251ceed13f156eff1fc4Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-0ab9-9760000000-e3d1a7f774e6bfb718aeSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-4980000000-d3e94e4150e2b870d9b2Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-3890000000-235f39119df7c967e9baSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-2980000000-251ceed13f156eff1fc4Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ab9-9760000000-e3d1a7f774e6bfb718aeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dj-6900000000-26ef3d4c1c9edc2697efSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-0900000000-b32577a48ebafc94ae9aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0udi-1900000000-485f684fffa023d0050eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0udi-4900000000-6b3b3dd2f2f2d875bf14Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a59-9800000000-fe6c9700b9c081b8697aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0udi-1900000000-b4a28f0f1bd551992615Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0900000000-8db506e73a05ea922d94Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0udi-0900000000-f67b128eb2b6ac7139b4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0900000000-b32577a48ebafc94ae9aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-1900000000-485f684fffa023d0050eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-4900000000-49dc94a0b10083c8230fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a59-9800000000-fe6c9700b9c081b8697aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-1900000000-b4a28f0f1bd551992615Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-8db506e73a05ea922d94Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0900000000-f67b128eb2b6ac7139b4Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0900000000-e564522269418ab462fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-53161ff2cee1a6ff34d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-1ab536fe3bbb9bdfde76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0giv-9600000000-a22dc2c9e956ce0b2b86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-31965d8430668c1cef72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006t-2900000000-1c6ebd899170870682a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pc0-5900000000-23b69a04a094c620fe7fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
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
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal 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
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 IDDB04104
Phenol Explorer Compound IDNot Available
FooDB IDFDB028311
KNApSAcK IDNot Available
Chemspider ID1610
KEGG Compound IDC00913
BioCyc ID3-Methyl-Adenines
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1673
PDB IDADK
ChEBI ID38635
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000844
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  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 ]
  2. Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C: Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Anal Chem. 2012 Aug 7;84(15):6429-37. doi: 10.1021/ac300829f. Epub 2012 Jul 17. [PubMed:22770225 ]
  3. Li M, Yang X, Wang H, Xu E, Xi Z: Inhibition of androgen induces autophagy in benign prostate epithelial cells. Int J Urol. 2014 Feb;21(2):195-9. doi: 10.1111/iju.12210. Epub 2013 Jul 2. [PubMed:23819759 ]
  4. Huang YT, Cheng CC, Lin TC, Chiu TH, Lai PC: Therapeutic potential of sepantronium bromide YM155 in gemcitabine-resistant human urothelial carcinoma cells. Oncol Rep. 2014 Feb;31(2):771-80. doi: 10.3892/or.2013.2882. Epub 2013 Nov 28. [PubMed:24297644 ]
  5. Pickard RD, Spencer BH, McFarland AJ, Bernaitis N, Davey AK, Perkins AV, Chess-Williams R, McDermott CM, Forbes A, Christie D, Anoopkumar-Dukie S: Paradoxical effects of the autophagy inhibitor 3-methyladenine on docetaxel-induced toxicity in PC-3 and LNCaP prostate cancer cells. Naunyn Schmiedebergs Arch Pharmacol. 2015 Jul;388(7):793-9. doi: 10.1007/s00210-015-1104-7. Epub 2015 Feb 24. [PubMed:25708950 ]

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