Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120576
Identification
Name: 3-methyladenine
Description:A methyladenine that is adenine substituted with a methyl group at position N-3.
Structure
Thumb
Synonyms:
  • 3-methyl-3H-adenine
  • 3-METHYL-3H-PURIN-6-YLAMINE
  • 3-Methyladenine
  • 6-amino-3-methylpurine
Chemical Formula: C6H7N5
Average Molecular Weight: 149.155
Monoisotopic Molecular Weight: 149.07014
InChI Key: FSASIHFSFGAIJM-UHFFFAOYSA-N
InChI:InChI=1S/C6H7N5/c1-11-3-10-5(7)4-6(11)9-2-8-4/h2-3H,7H2,1H3
CAS number: 5142-23-4
IUPAC Name:3-methyl-3H-purin-6-amine
Traditional IUPAC Name: 3-methyladenine
SMILES:CN1(C2(=NC=NC(=C(N)N=C1)2))
Chemical Taxonomy
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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organoheterocyclic compounds
Sub ClassImidazopyrimidines
Direct Parent 6-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 Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
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
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways: Not Available
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
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
References
References:
  • Tavazzi B, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B (2005)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. Clinical biochemistry 38, Pubmed: 16139832
  • Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C (2012)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. Analytical chemistry 84, Pubmed: 22770225
  • Li M, Yang X, Wang H, Xu E, Xi Z (2014)Inhibition of androgen induces autophagy in benign prostate epithelial cells. International journal of urology : official journal of the Japanese Urological Association 21, Pubmed: 23819759
  • Huang YT, Cheng CC, Lin TC, Chiu TH, Lai PC (2014)Therapeutic potential of sepantronium bromide YM155 in gemcitabine-resistant human urothelial carcinoma cells. Oncology reports 31, Pubmed: 24297644
  • Pickard RD, Spencer BH, McFarland AJ, Bernaitis N, Davey AK, Perkins AV, Chess-Williams R, McDermott CM, Forbes A, Christie D, Anoopkumar-Dukie S (2015)Paradoxical effects of the autophagy inhibitor 3-methyladenine on docetaxel-induced toxicity in PC-3 and LNCaP prostate cancer cells. Naunyn-Schmiedeberg's archives of pharmacology 388, Pubmed: 25708950
  • Tran AT, Ramalinga M, Kedir H, Clarke R, Kumar D (2015)Autophagy inhibitor 3-methyladenine potentiates apoptosis induced by dietary tocotrienols in breast cancer cells. European journal of nutrition 54, Pubmed: 24830781
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
METABOLIGHTSMTBLC38635
HMDBHMDB11600
DRUGBANKDB04104
CHEBI38635