You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Bovine Metabolome Database.

Showing metabocard for 7-Methylxanthine (BMDB0001991)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:49:40 UTC
Update Date2020-05-11 20:22:59 UTC
BMDB IDBMDB0001991
Secondary Accession Numbers
  • BMDB01991
Metabolite Identification
Common Name7-Methylxanthine
Description7-Methylxanthine, also known as 7-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. 7-Methylxanthine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 7-Methylxanthine exists in all living organisms, ranging from bacteria to humans. 7-Methylxanthine participates in a number of enzymatic reactions, within cattle. In particular, 7-Methylxanthine and formaldehyde can be biosynthesized from paraxanthine; which is catalyzed by the enzyme cytochrome P450 1A2. In addition, 7-Methylxanthine can be converted into 7-methyluric acid; which is mediated by the enzyme xanthine dehydrogenase/oxidase. In cattle, 7-methylxanthineee is involved in the metabolic pathway called the caffeine metabolism pathway.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3,7-Dihydro-7-methyl-1H-purine-2,6-dioneChEBI
7-MethylxanthinChEBI
HeteroxanthinChEBI
HeteroxanthineChEBI
7-Methylxanthine, 7-(13)C-labeledMeSH
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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00rb-4900000000-5a121544b907c24f5972View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-014i-0900000000-30f6b1fe21e6924b4408View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-00xr-6900000000-f5c1b1369f226330b60eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-014i-9000000000-3b1edad37f3a300fd3b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-014i-0900000000-3c4effaf7fee8c2b61eaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-014i-0900000000-e2df10d0ab191cf48ad3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-007k-9000000000-b0fa1ce6138138a94167View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-0fk9-0900000000-45a47f7201f1b1cc4c0aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 2V, positivesplash10-004i-3900000000-6b031051442287925863View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-0059-7900000000-8472e8c51cabdb800b2bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-001i-9100000000-68f333821040ae2d706cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 12V, positivesplash10-001i-9100000000-3c01ab92dda7a36ca993View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 14V, positivesplash10-001i-9100000000-92ec6b69d4cfe4cd2a3dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 16V, positivesplash10-001i-9200000000-1a9b42f2cd8d64ed5d47View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 18V, positivesplash10-001i-9000000000-e26454dd03e8fe73c4a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 26V, positivesplash10-001i-9000000000-9e6003927514a8801358View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-001i-9000000000-fa3240e26cb87ab70fa4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-001l-9000000000-9419618135a9b903f29cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-001l-9000000000-2aa69c9cec10c58e1b56View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-014i-0900000000-ce6eec4ee9efe1c5a732View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-d0d15cf114e854cb9389View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01b9-1900000000-a22c299c1d6da4639631View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kg-9200000000-5a65dfd385a5e35051c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-1fd502b43c7af78c68adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9400000000-93978f7127dd2e954aa0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-212eeb1212b80abd05ebView in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, 5%_DMSO, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001991
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
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)Not Available
General ReferencesNot Available