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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-02-28 10:47:30 UTC
Update Date2017-12-07 01:46:18 UTC
HMDB IDHMDB0001886
Secondary Accession Numbers
  • HMDB01886
Metabolite Identification
Common Name3-Methylxanthine
Description3-Methylxanthine is a caffeine and a theophylline metabolite. (PMID 16870158 , 16678550 ). CYP1A2 probably plays a major role in theophylline 8-hydroxylation at a therapeutic concentration after the full development of CYP1A2 activity in children (after 3 years old). (PMID 9890610 ).
Structure
Thumb
Synonyms
ValueSource
2-oxo-3-MethylhypoxanthineChEBI
3 MXChEBI
3,9-dihydro-3-Methyl-1H-purine-2,6-dioneChEBI
3-Methyl-3,7(9)-dihydro-purine-2,6-dioneChEBI
3-Methyl-3,9-dihydro-2H,6H-purine-2,6-dioneChEBI
2,6-Dihydroxy-3-methylpurineHMDB
3-Methyl xanthineHMDB
3-Methyl-3,9-dihydro-purine-2,6-dioneHMDB
Purine analogHMDB
3-Methylxanthine, monopotassium saltMeSH
3-Methylxanthine, methyl-(13)C-labeledMeSH
3-Methylxanthine, monosodium saltMeSH
Chemical FormulaC6H6N4O2
Average Molecular Weight166.1374
Monoisotopic Molecular Weight166.049075456
IUPAC Name3-methyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional Name3-methylxanthine
CAS Registry Number1076-22-8
SMILES
CN1C2=C(NC=N2)C(=O)NC1=O
InChI Identifier
InChI=1S/C6H6N4O2/c1-10-4-3(7-2-8-4)5(11)9-6(10)12/h2H,1H3,(H,7,8)(H,9,11,12)
InChI KeyGMSNIKWWOQHZGF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassImidazopyrimidines
Direct ParentXanthines
Alternative Parents
Substituents
  • 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
Ontology
Physiological effect

Health effect:

  Health condition:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point> 300 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.50GASPARI,F & BONATI,M (1987)
Predicted Properties
PropertyValueSource
Water Solubility12.7 g/LALOGPS
logP-0.46ALOGPS
logP-0.99ChemAxon
logS-1.1ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01bj-5900000000-e52c5f846a0fa5fe07efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-1900000000-ddc5f6a902d7bbd1fb47View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01b9-1900000000-c8fefaf49ff542098257View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9100000000-e21e77b88dfb9995efddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-014i-1900000000-e5e3ab4240496c2d1174View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-0900000000-18cbc6f55db32d03e9fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-18cbc6f55db32d03e9fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-1900000000-e5e3ab4240496c2d1174View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-c30c1961ecbdf271a24eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1900000000-ab9e73c4012de4c80f38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-8c4dac19316eed77c6dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-ef5279264b1ae3a9f2c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01bc-5900000000-ae2f574c67e566bead1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-1a0783c7fb8ec28a786fView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineDetected but not Quantified Adult (>18 years old)MaleNormal details
    UrineDetected and Quantified10.322 +/- 9.229 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
      • Mordechai, Hien, ...
    details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified4.73 umol/mmol creatinineAdult (>18 years old)Male
    Normal
      • Shaykhutdinov RA,...
    details
    UrineDetected but not Quantified Adult (>18 years old)BothNormal details
    UrineDetected and Quantified4.0 (2.3-6.3) umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified6.2 (1.4-17.8) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected but not Quantified Adult (>18 years old)MaleNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    UrineDetected and Quantified12.755 +/- 12.241 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Eosinophilic esophagitis
      • Mordechai, Hien, ...
    details
    UrineDetected but not Quantified Adult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
    UrineDetected and Quantified8.0 (5.0-14.0) umol/mmol creatinineAdult (>18 years old)Both
    Asthma
    details
    Associated Disorders and Diseases
    Disease References
    Asthma
    1. Zydron M, Baranowski J, Baranowska I: Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples. J Sep Sci. 2004 Oct;27(14):1166-72. [PubMed:15537072 ]
    Associated OMIM IDs
    DrugBank IDNot Available
    DrugBank Metabolite IDDBMET00272
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB022724
    KNApSAcK IDNot Available
    Chemspider ID63805
    KEGG Compound IDC16357
    BioCyc ID3-METHYLXANTHINE
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID2820
    PubChem Compound70639
    PDB IDNot Available
    ChEBI ID62207
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Download (PDF)
    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 ]