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Record Information
Created at2006-02-28 10:47:30 UTC
Updated at2021-10-07 20:38:45 UTC
NP-MRD IDNP0000293
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Methylxanthine
Description3-Methyl-9H-xanthine is a 3-methylxanthine tautomer where the imidazole proton is located at the 9-position. It has a role as a metabolite. It is a tautomer of a 3-methyl-7H-xanthine. 3-Methylxanthine, also known as 3 MX or purine analog, belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
3-Methylxanthine, methyl-(13)C-labeledHMDB
3-Methylxanthine, monosodium saltHMDB
3-Methylxanthine, monopotassium saltHMDB
3-Methyl xanthineHMDB
Purine analogHMDB
Chemical FormulaC6H6N4O2
Average Mass166.1374 Da
Monoisotopic Mass166.04908 Da
IUPAC Name3-methyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional Name3-methylxanthine
CAS Registry Number1076-22-8
InChI Identifier
Spectrum TypeDescriptionDepositor IDDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)V.dorna832021-08-08View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)V.dorna832021-09-06View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)V.dorna832021-09-06View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)V.dorna832021-09-06View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)V.dorna832021-09-06View Spectrum
Species of Origin
Species NameSourceReference
Camellia assamicaKNApSAcK Database
Camellia irrawadiensisiaKNApSAcK Database
Camellia kissiKNApSAcK Database
Camellia ptilophyllaKNApSAcK Database
Camellia sinensisKNApSAcK Database
Camellia taliensisKNApSAcK Database
Camellia toliensisKNApSAcK Database
Citrus maximaKNApSAcK Database
Coffea arabicaKNApSAcK Database
Coffea canephoraKNApSAcK Database
Coffea dewevreiKNApSAcK Database
Coffea eugeniodesKNApSAcK Database
Coffea kianjavatensisKNApSAcK Database
Coffea libericaKNApSAcK Database
Coffea racemosaKNApSAcK Database
Coffea salvatrixKNApSAcK Database
Cola sp.KNApSAcK Database
Ilex paraguariensisKNApSAcK Database
Paullinia cupanaKNApSAcK Database
Theobroma cacaoKNApSAcK Database
Theobroma grandiflorumKNApSAcK Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents
  • Xanthine
  • Purinone
  • Alkaloid or derivatives
  • Pyrimidone
  • Hydroxypyrimidine
  • Pyrimidine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
Experimental Properties
Melting Point> 300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility8394 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.50Gaspari, F., Vigano, G., Orisio, S., Bonati, M., Livio, M., & Remuzzi, G. (1987). Aspirin prolongs bleeding time in uremia by a mechanism distinct from platelet cyclooxygenase inhibition. The Journal of clinical investigation, 79(6), 1788-1797.
Predicted Properties
Water Solubility12.7 g/LALOGPS
pKa (Strongest Acidic)7.86ChemAxon
pKa (Strongest Basic)-0.76ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area78.09 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity40.04 m³·mol⁻¹ChemAxon
Polarizability14.75 ųChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022724
KNApSAcK IDC00043196
Chemspider ID63805
KEGG Compound IDC16357
BioCyc IDRXN-11546
BiGG IDNot Available
Wikipedia LinkXanthine
PubChem Compound70639
PDB IDNot Available
ChEBI ID62207
Good Scents IDrw1192211
General References
  1. Orlando R, Padrini R, Perazzi M, De Martin S, Piccoli P, Palatini P: Liver dysfunction markedly decreases the inhibition of cytochrome P450 1A2-mediated theophylline metabolism by fluvoxamine. Clin Pharmacol Ther. 2006 May;79(5):489-99. [PubMed:16678550 ]
  2. Knoppert DC, Spino M, Beck R, Thiessen JJ, MacLeod SM: Cystic fibrosis: enhanced theophylline metabolism may be linked to the disease. Clin Pharmacol Ther. 1988 Sep;44(3):254-64. [PubMed:3046811 ]
  3. Miller M, Opheim KE, Raisys VA, Motulsky AG: Theophylline metabolism: variation and genetics. Clin Pharmacol Ther. 1984 Feb;35(2):170-82. [PubMed:6362955 ]
  4. Desiraju RK, Sugita ET, Mayock RL: Determination of theophylline and its metabolites by liquid chromatography. J Chromatogr Sci. 1977 Dec;15(12):563-8. [PubMed:591601 ]
  5. Tarka SM Jr, Arnaud MJ, Dvorchik BH, Vesell ES: Theobromine kinetics and metabolic disposition. Clin Pharmacol Ther. 1983 Oct;34(4):546-55. [PubMed:6617078 ]
  6. Tateishi T, Asoh M, Yamaguchi A, Yoda T, Okano YJ, Koitabashi Y, Kobayashi S: Developmental changes in urinary elimination of theophylline and its metabolites in pediatric patients. Pediatr Res. 1999 Jan;45(1):66-70. [PubMed:9890610 ]
  7. Geraets L, Moonen HJ, Wouters EF, Bast A, Hageman GJ: Caffeine metabolites are inhibitors of the nuclear enzyme poly(ADP-ribose)polymerase-1 at physiological concentrations. Biochem Pharmacol. 2006 Sep 28;72(7):902-10. Epub 2006 Jul 25. [PubMed:16870158 ]