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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:30 UTC
Update Date2020-11-09 23:16:21 UTC
HMDB IDHMDB0001991
Secondary Accession Numbers
  • HMDB01991
Metabolite Identification
Common Name7-Methylxanthine
Description7-Methylxanthine is a methyl derivative of xanthine, found occasionally in human urine. 7-Methylxanthine is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline and theobromine). Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase or N-acetyltransferase-2 to give 14 different metabolites, including 7-methylxanthine. CYP1A2 activity shows an inter-individual variability among the population. CYP1A2, an isoform of the CYP1A cytochrome P450 super-family, is involved in the metabolism of many drugs and plays a potentially important role in the induction of chemical carcinogenesis. Purine derivatives in urinary calculi could be considered markers of abnormal purine metabolism. The content of a purine derivative in stone depends on its average urinary excretion in the general population, similarity to the chemical structure of uric acid, and content of the latter in stone. This suggests that purines in stones represent a solid solution with uric acid as solvent. It is also plausible that methylxanthines, ubiquitous components of the diet and drugs, are involved in the pathogenesis of urolithiasis. (PMID: 11712316 , 15833286 , 3506820 , 15013152 ).
Structure
Data?1582752222
Synonyms
ValueSource
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
Chemical FormulaC6H6N4O2
Average Molecular Weight166.1374
Monoisotopic Molecular Weight166.049075456
IUPAC Name7-methyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
Traditional Name7-methylxanthine
CAS Registry Number552-62-5
SMILES
CN1C=NC2=C1C(=O)NC(=O)N2
InChI Identifier
InChI=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
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
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point> 300 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-0.89GASPARI,F & BONATI,M (1987)
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00rb-4900000000-5a121544b907c24f5972Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-014i-0900000000-30f6b1fe21e6924b4408Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-00xr-6900000000-f5c1b1369f226330b60eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-014i-9000000000-3b1edad37f3a300fd3b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-014i-0900000000-3c4effaf7fee8c2b61eaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-014i-0900000000-e2df10d0ab191cf48ad3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-007k-9000000000-b0fa1ce6138138a94167Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-0fk9-0900000000-45a47f7201f1b1cc4c0aSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 2V, positivesplash10-004i-3900000000-6b031051442287925863Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-0059-7900000000-8472e8c51cabdb800b2bSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-001i-9100000000-68f333821040ae2d706cSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 12V, positivesplash10-001i-9100000000-3c01ab92dda7a36ca993Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 14V, positivesplash10-001i-9100000000-92ec6b69d4cfe4cd2a3dSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 16V, positivesplash10-001i-9200000000-1a9b42f2cd8d64ed5d47Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 18V, positivesplash10-001i-9000000000-e26454dd03e8fe73c4a8Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 26V, positivesplash10-001i-9000000000-9e6003927514a8801358Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-001i-9000000000-fa3240e26cb87ab70fa4Spectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-001l-9000000000-9419618135a9b903f29cSpectrum
LC-MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-001l-9000000000-2aa69c9cec10c58e1b56Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-014i-0900000000-ce6eec4ee9efe1c5a732Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-d0d15cf114e854cb9389Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01b9-1900000000-a22c299c1d6da4639631Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kg-9200000000-5a65dfd385a5e35051c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-1fd502b43c7af78c68adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9400000000-93978f7127dd2e954aa0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-212eeb1212b80abd05ebSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified10.0 (6.7-14.6) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified10.0(3.9-16.1) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified10.0 (2.7-17.8) umol/mmol creatinineAdult (>18 years old)Both
Asthma
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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
Phenol Explorer Compound IDNot Available
FooDB IDFDB001978
KNApSAcK IDC00007326
Chemspider ID61660
KEGG Compound IDC16353
BioCyc ID7-METHYLXANTHINE
BiGG IDNot Available
Wikipedia LinkXanthine
METLIN IDNot Available
PubChem Compound68374
PDB IDNot Available
ChEBI ID48991
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceHutzenlaub, Wolfgang; Pfleiderer, Wolfgang. Purines. XIII. Simplified syntheses of 7-methyl- and 1,7-dimethylxanthines and -uric acids. Liebigs Annalen der Chemie (1979), (11), 1847-54.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Safranow K: [Identification and quantitation of purine derivatives in urinary calculi as markers of abnormal purine metabolism by using high-performance liquid chromatography (HPLC)]. Ann Acad Med Stetin. 2000;46:35-49. [PubMed:11712316 ]
  2. Safranow K, Machoy Z: Simultaneous determination of 16 purine derivatives in urinary calculi by gradient reversed-phase high-performance liquid chromatography with UV detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 May 25;819(2):229-35. [PubMed:15833286 ]
  3. Morris GS, Simmonds HA, Davies PM: Use of biological fluids for the rapid diagnosis of potentially lethal inherited disorders of human purine and pyrimidine metabolism. Biomed Chromatogr. 1986 Jun;1(3):109-18. [PubMed:3506820 ]
  4. Caubet MS, Comte B, Brazier JL: Determination of urinary 13C-caffeine metabolites by liquid chromatography-mass spectrometry: the use of metabolic ratios to assess CYP1A2 activity. J Pharm Biomed Anal. 2004 Feb 4;34(2):379-89. [PubMed:15013152 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular weight:
146422.99
Reactions
7-Methylxanthine + Oxygen + Water → 7-Methyluric acid + Hydrogen peroxidedetails