Showing Compound Card for 1-Methylxanthine (CDB005298)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:29:09 UTC
Updated at2020-12-07 19:11:54 UTC
CannabisDB IDCDB005298
Secondary Accession NumbersNot Available
Cannabis Compound 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. It is also created from xanthosine by purine nucleoside phosphorylase. 1-Methylxanthine is an extremely weak basic (essentially neutral) compound (based on its pKa). 1-Methylxanthine exists in all living organisms, ranging from bacteria to humans. Within humans, 1-methylxanthine participates in a number of enzymatic reactions. 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 the action of the enzyme xanthine dehydrogenase/oxidase. Xanthine is used as a drug precursor for human and animal medications, and is manufactured as a pesticide ingredient. In high doses, they can lead to convulsions that are resistant to anticonvulsants. People with the rare genetic disorders, specifically xanthinuria and Lesch–Nyhan syndrome, lack sufficient xanthine oxidase and cannot convert xanthine to uric acid. In humans, 1-methylxanthine is involved in caffeine metabolism. The therapeutic level is 10-20 micrograms/mL blood; signs of toxicity include tremor, nausea, nervousness, and tachycardia/arrhythmia. Xanthine is subsequently converted to uric acid by the action of the xanthine oxidase enzyme. Several stimulants are derived from xanthine, including caffeine and theobromine. 1-Methylxanthine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC6H6N4O2
Average Molecular Weight166.14
Monoisotopic Molecular Weight166.0491
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
Disposition

Source:

Biological location:

Role

Biological role:

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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS1-Methylxanthine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0apr-3900000000-88bd492326591e730086Spectrum
Predicted GC-MS1-Methylxanthine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1-Methylxanthine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-6fbdd0235ae20be5daa12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-067i-9400000000-26298794cbed4fbcad6b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0aor-3900000000-712a7974e530515b891f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-69924d9d22c49622a32b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - NA , positivesplash10-014i-0900000000-a729acfc9694f20accb02020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-014i-0900000000-6d707d0f8b77fb6f3fcd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-014i-0900000000-a55efb1f01a8ca4a2d952020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-02t9-0900000000-858059d2d9ee8414cafd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-02t9-0900000000-63a50718538a27464c462020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-03di-0900000000-a00013c8cdc36103e8a32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-03di-2900000000-77efece85a8e1b602d5c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-08fr-6900000000-0d9cd06c582f1bf232252020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-0a4i-9300000000-b73bf7301278872b9e262020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-0a4i-9100000000-c05924743c475bbab05b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 17V, positivesplash10-0a4i-9000000000-c01a620479ccd936f5ea2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-03di-0900000000-9fadde7724e8a2f4bab82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-001i-9000000000-5277d916d914013bd1142020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 11V, positivesplash10-00di-0900000000-b32aa806de261f5c0e402020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-03di-1900000000-14f01d07c28c61c920262020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-03di-1900000000-56b961120be01ee887942020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-03di-2900000000-a21b7d715ff67be12f302020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-03di-5900000000-f069376ed73a3dc10f542020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0bt9-9500000000-627f0d2416135b20579b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0a4i-9200000000-693e5185f1cfeede2a4f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-0a4i-9000000000-3a28092a50ffbb7dd36e2020-07-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Xanthine dehydrogenase/oxidaseXDH2p23.1P47989 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Xanthine dehydrogenase/oxidaseXDH2p23.1P47989 details
Cytochrome P450 1A2CYP1A215q24.1P05177 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0010738
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB027885
KNApSAcK IDNot Available
Chemspider ID72464
KEGG Compound IDC16358
BioCyc IDCPD-9025
BiGG IDNot Available
Wikipedia LinkXanthine
METLIN IDNot Available
PubChem Compound80220
PDB IDNot Available
ChEBI ID68444
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Xanthine dehydrogenase/oxidase
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