Record Information
Creation date2011-09-21 01:31:26 UTC
Update date2020-09-17 15:41:42 UTC
Primary IDFDB027885
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1-Methylxanthine
Description1-Methylxanthine 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. It is also created from xanthosine by purine nucleoside phosphorylase. 1-Methylxanthine is an extremely weak basic (essentially neutral) compound (based on its pKa). 1-Methylxanthine exists in all living organisms, ranging from bacteria to humans. Within humans, 1-methylxanthine participates in a number of enzymatic reactions. In particular, 1-methylxanthine and formaldehyde can be biosynthesized from theophylline; which is mediated by the enzyme cytochrome P450 1A2. In addition, 1-methylxanthine can be converted into 1-methyluric acid through the action of the enzyme xanthine dehydrogenase/oxidase. Xanthine is used as a drug precursor for human and animal medications, and is manufactured as a pesticide ingredient. In high doses, they can lead to convulsions that are resistant to anticonvulsants. People with the rare genetic disorders, specifically xanthinuria and Lesch–Nyhan syndrome, lack sufficient xanthine oxidase and cannot convert xanthine to uric acid. In humans, 1-methylxanthine is involved in caffeine metabolism. The therapeutic level is 10-20 micrograms/mL blood; signs of toxicity include tremor, nausea, nervousness, and tachycardia/arrhythmia. Xanthine is subsequently converted to uric acid by the action of the xanthine oxidase enzyme. Several stimulants are derived from xanthine, including caffeine and theobromine.
CAS Number6136-37-4
Predicted Properties
Water Solubility11.7 g/LALOGPS
pKa (Strongest Acidic)3.11ChemAxon
pKa (Strongest Basic)1.67ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area81.58 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.26 m³·mol⁻¹ChemAxon
Polarizability14.92 ųChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H6N4O2
IUPAC name2-hydroxy-1-methyl-6,9-dihydro-1H-purin-6-one
InChI IdentifierInChI=1S/C6H6N4O2/c1-10-5(11)3-4(8-2-7-3)9-6(10)12/h2H,1H3,(H,7,8)(H,9,12)
Isomeric SMILESCN1C(=O)NC2=C(NC=N2)C1=O
Average Molecular Weight166.1374
Monoisotopic Molecular Weight166.049075456
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
  • 6-oxopurine
  • Purinone
  • Alkaloid or derivatives
  • Pyrimidone
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors


Biological location:


Naturally occurring process:


Biological role:

  • Cocoa and cocoa products
  • Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionNot Available
    Melting PointNot Available
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    TypeDescriptionSplash KeyView
    Predicted GC-MS1-Methylxanthine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0apr-3900000000-88bd492326591e730086Spectrum
    Predicted GC-MS1-Methylxanthine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS1-Methylxanthine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - NA , positivesplash10-014i-0900000000-a729acfc9694f20accb0Spectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-014i-0900000000-6d707d0f8b77fb6f3fcdSpectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-014i-0900000000-a55efb1f01a8ca4a2d95Spectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-02t9-0900000000-858059d2d9ee8414cafdSpectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-02t9-0900000000-63a50718538a27464c46Spectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-03di-0900000000-a00013c8cdc36103e8a3Spectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-03di-2900000000-77efece85a8e1b602d5cSpectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-08fr-6900000000-0d9cd06c582f1bf23225Spectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-0a4i-9300000000-b73bf7301278872b9e26Spectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-0a4i-9100000000-c05924743c475bbab05bSpectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 17V, positivesplash10-0a4i-9000000000-c01a620479ccd936f5eaSpectrum
    MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-03di-0900000000-9fadde7724e8a2f4bab8Spectrum
    MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-001i-9000000000-5277d916d914013bd114Spectrum
    MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-00di-0900000000-b32aa806de261f5c0e40Spectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-03di-1900000000-14f01d07c28c61c92026Spectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-03di-1900000000-56b961120be01ee88794Spectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-03di-2900000000-a21b7d715ff67be12f30Spectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-03di-5900000000-f069376ed73a3dc10f54Spectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0bt9-9500000000-627f0d2416135b20579bSpectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-870901373643f9963bf5Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xr-0900000000-54540cdf9de1abed31f9Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02u0-9400000000-df69b5d77ae7adac9ed5Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1900000000-f6dc4dabad421c556050Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-3900000000-82481c42feeeb1737775Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-9200000000-c5e7b6ee0ee1354a37acSpectrum
    NMRNot Available
    ChemSpider ID72464
    KEGG Compound IDC16358
    Pubchem Compound ID80220
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer IDNot Available
    DrugBank IDNot Available
    HMDB IDHMDB10738
    CRC / DFC (Dictionary of Food Compounds) IDNot Available
    EAFUS IDNot Available
    Dr. Duke IDNot Available
    BIGG IDNot Available
    KNApSAcK IDNot Available
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite IDNot Available
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    EnzymesNot Available
    NameSMPDB LinkKEGG Link
    Caffeine MetabolismSMP00028 map00232
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    MSDSNot Available
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference