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Record Information
Version1.0
Creation Date2016-10-03 18:12:49 UTC
Update Date2020-05-11 20:25:31 UTC
BMDB IDBMDB0010738
Secondary Accession Numbers
  • BMDB10738
Metabolite Identification
Common 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. 1-Methylxanthine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 1-Methylxanthine exists in all living organisms, ranging from bacteria to humans. 1-Methylxanthine participates in a number of enzymatic reactions, within cattle. 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 its interaction with the enzyme xanthine dehydrogenase/oxidase. In cattle, 1-methylxanthine is involved in the metabolic pathway called the caffeine metabolism pathway.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC6H6N4O2
Average Molecular Weight166.1374
Monoisotopic Molecular Weight166.049075456
IUPAC Name2-hydroxy-1-methyl-6,9-dihydro-1H-purin-6-one
Traditional Name1-methylxanthine
CAS Registry Number6136-37-4
SMILES
CN1C(=O)NC2=C(NC=N2)C1=O
InChI Identifier
InChI=1S/C6H6N4O2/c1-10-5(11)3-4(8-2-7-3)9-6(10)12/h2H,1H3,(H,7,8)(H,9,12)
InChI KeyMVOYJPOZRLFTCP-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
  • 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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.46ALOGPS
logP-0.4ChemAxon
logS-1.2ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0apr-3900000000-88bd492326591e730086View in MoNA
LC-MS/MSLC-MS/MS Spectrum - NA , positivesplash10-014i-0900000000-a729acfc9694f20accb0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-014i-0900000000-6d707d0f8b77fb6f3fcdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-014i-0900000000-a55efb1f01a8ca4a2d95View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-02t9-0900000000-858059d2d9ee8414cafdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-02t9-0900000000-63a50718538a27464c46View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-03di-0900000000-a00013c8cdc36103e8a3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-03di-2900000000-77efece85a8e1b602d5cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-08fr-6900000000-0d9cd06c582f1bf23225View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-0a4i-9300000000-b73bf7301278872b9e26View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-0a4i-9100000000-c05924743c475bbab05bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 17V, positivesplash10-0a4i-9000000000-c01a620479ccd936f5eaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-03di-0900000000-9fadde7724e8a2f4bab8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-001i-9000000000-5277d916d914013bd114View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-00di-0900000000-b32aa806de261f5c0e40View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-03di-1900000000-14f01d07c28c61c92026View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-03di-1900000000-56b961120be01ee88794View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-03di-2900000000-a21b7d715ff67be12f30View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-03di-5900000000-f069376ed73a3dc10f54View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0bt9-9500000000-627f0d2416135b20579bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-870901373643f9963bf5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xr-0900000000-54540cdf9de1abed31f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02u0-9400000000-df69b5d77ae7adac9ed5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1900000000-f6dc4dabad421c556050View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-3900000000-82481c42feeeb1737775View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mo-9200000000-c5e7b6ee0ee1354a37acView in MoNA
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 IDHMDB0010738
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027885
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC16358
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkXanthine
METLIN IDNot Available
PubChem Compound80220
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available