Record Information
Version1.0
Creation date2010-04-08 22:05:11 UTC
Update date2020-09-17 15:41:41 UTC
Primary IDFDB001978
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name7-Methylxanthine
Description7-Methylxanthine, also known as heteroxanthin, 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. 7-Methylxanthine is an extremely weak basic (essentially neutral) compound (based on its pKa). 7-Methylxanthine exists in all living organisms, ranging from bacteria to humans. Within humans, 7-methylxanthine participates in a number of enzymatic reactions. In particular, 7-methylxanthine and formaldehyde can be biosynthesized from paraxanthine through the action of the enzyme cytochrome P450 1A2. In addition, 7-methylxanthine can be converted into 7-methyluric acid through the action of the enzyme xanthine dehydrogenase/oxidase. In humans, 7-methylxanthine is involved in caffeine metabolism. Outside of the human body, 7-Methylxanthine has been detected, but not quantified in, arabica coffee. This could make 7-methylxanthine a potential biomarker for the consumption of these foods.
CAS Number552-62-5
Structure
Thumb
Synonyms
SynonymSource
3,7-Dihydro-7-methyl-1H-purine-2,6-dioneChEBI
7-MethylxanthinChEBI
HeteroxanthinChEBI
HeteroxanthineChEBI
7-Methylxanthine, 7-(13)C-labeledHMDB
2,6-Dihydroxy-7-methylpurineHMDB
7-Methyl-3,7-dihydro-1H-purine-2,6-dioneHMDB
7-Methyl-7H-purine-2,6-diolHMDB
MethylxanthineHMDB
3,7-dihydro-7-Methyl-1H-purine-2,6-dioneChEBI
3,7-Dihydro-7-methyl-1H-purine-2,6-dione, 9CIdb_source
7-Methylxanthinedb_source
Predicted Properties
PropertyValueSource
Water Solubility7 g/LALOGPS
logP-0.59ALOGPS
logP0.017ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)9.31ChemAxon
pKa (Strongest Basic)-0.85ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area76.02 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.82 m³·mol⁻¹ChemAxon
Polarizability14.77 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H6N4O2
IUPAC name7-methyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
InChI IdentifierInChI=1S/C6H6N4O2/c1-10-2-7-4-3(10)5(11)9-6(12)8-4/h2H,1H3,(H2,8,9,11,12)
InChI KeyPFWLFWPASULGAN-UHFFFAOYSA-N
Isomeric SMILESCN1C=NC2=C1C(=O)NC(=O)N2
Average Molecular Weight166.1374
Monoisotopic Molecular Weight166.049075456
Classification
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
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • Alkaloid or derivatives
  • Hydroxypyrimidine
  • Pyrimidine
  • N-substituted imidazole
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Foods
  • Cocoa and cocoa products
  • Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 43.38%; H 3.64%; N 33.72%; O 19.26%DFC
    Melting PointMp 380° dec.DFC
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logP-0.89GASPARI,F & BONATI,M (1987)
    Experimental pKa8.33
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    Predicted GC-MS7-Methylxanthine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00rb-4900000000-5a121544b907c24f5972Spectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-014i-0900000000-30f6b1fe21e6924b4408Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-00xr-6900000000-f5c1b1369f226330b60eSpectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-014i-9000000000-3b1edad37f3a300fd3b7Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-014i-0900000000-3c4effaf7fee8c2b61eaSpectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-014i-0900000000-e2df10d0ab191cf48ad3Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-007k-9000000000-b0fa1ce6138138a94167Spectrum
    MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-0fk9-0900000000-45a47f7201f1b1cc4c0aSpectrum
    MS/MSLC-MS/MS Spectrum - QTOF 2V, positivesplash10-004i-3900000000-6b031051442287925863Spectrum
    MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-0059-7900000000-8472e8c51cabdb800b2bSpectrum
    MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-001i-9100000000-68f333821040ae2d706cSpectrum
    MS/MSLC-MS/MS Spectrum - QTOF 12V, positivesplash10-001i-9100000000-3c01ab92dda7a36ca993Spectrum
    MS/MSLC-MS/MS Spectrum - QTOF 14V, positivesplash10-001i-9100000000-92ec6b69d4cfe4cd2a3dSpectrum
    MS/MSLC-MS/MS Spectrum - QTOF 16V, positivesplash10-001i-9200000000-1a9b42f2cd8d64ed5d47Spectrum
    MS/MSLC-MS/MS Spectrum - QTOF 18V, positivesplash10-001i-9000000000-e26454dd03e8fe73c4a8Spectrum
    MS/MSLC-MS/MS Spectrum - QTOF 26V, positivesplash10-001i-9000000000-9e6003927514a8801358Spectrum
    MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-001i-9000000000-fa3240e26cb87ab70fa4Spectrum
    MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-001l-9000000000-9419618135a9b903f29cSpectrum
    MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-001l-9000000000-2aa69c9cec10c58e1b56Spectrum
    MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-014i-0900000000-ce6eec4ee9efe1c5a732Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-d0d15cf114e854cb9389Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01b9-1900000000-a22c299c1d6da4639631Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kg-9200000000-5a65dfd385a5e35051c8Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-1fd502b43c7af78c68adSpectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9400000000-93978f7127dd2e954aa0Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-212eeb1212b80abd05ebSpectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR SpectrumSpectrum
    2D NMR[1H,13C] 2D NMR SpectrumSpectrum
    ChemSpider ID61660
    ChEMBL IDCHEMBL321248
    KEGG Compound IDC16353
    Pubchem Compound ID68374
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer IDNot Available
    DrugBank IDNot Available
    HMDB IDHMDB01991
    CRC / DFC (Dictionary of Food Compounds) IDCBV75-B:CBV79-F
    EAFUS IDNot Available
    Dr. Duke IDNot Available
    BIGG IDNot Available
    KNApSAcK IDC00007326
    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
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    EnzymesNot Available
    Pathways
    NameSMPDB LinkKEGG Link
    Caffeine MetabolismSMP00028 map00232
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.