Showing Compound Card for 1-Methyluric acid (CDB005299)

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Record Information
Version1.0
Created at2020-04-17 19:29:15 UTC
Updated at2020-12-07 19:11:55 UTC
CannabisDB IDCDB005299
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name1-Methyluric acid
Description1-Methyluric acid, also known as 1-methylate, 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. An oxopurine that is 7,9-dihydro-1H-purine-2,6,8(3H)-trione substituted by a methyl group at N-1. 1-Methyluric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 1-Methyluric acid exists in all living organisms, ranging from bacteria to humans. 1-methyluric acid can be biosynthesized from 1-methylxanthine through the action of the enzyme xanthine dehydrogenase/oxidase. In humans, 1-methyluric acid is involved in caffeine metabolism. 1-Methyluric acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-MethylateGenerator
1-Methylic acidGenerator
1-MethylurateHMDB, MeSH
Chemical FormulaC6H6N4O3
Average Molecular Weight182.14
Monoisotopic Molecular Weight182.044
IUPAC Name1-methyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
Traditional Name1-methyluric acid
CAS Registry Number708-79-2
SMILES
CN1C(=O)NC2=C(NC(=O)N2)C1=O
InChI Identifier
InChI=1S/C6H6N4O3/c1-10-4(11)2-3(9-6(10)13)8-5(12)7-2/h1H3,(H,9,13)(H2,7,8,12)
InChI KeyQFDRTQONISXGJA-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 Solubility5 mg/mLNot Available
logP-0.57GASPARI,F & BONATI,M (1987)
Predicted Properties
PropertyValueSource
logP-1.2ALOGPS
logP-1.3ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)7.67ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.54 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity50.53 m³·mol⁻¹ChemAxon
Polarizability15.73 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-Methyluric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0far-2900000000-7c88ba8c892ca8263473Spectrum
Predicted GC-MS1-Methyluric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS1-Methyluric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0900000000-f2e42cd67ce1106bed632012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-0900000000-9fd2304504c5787dc2552012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9000000000-6069b457c0c038edb8df2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0006-0900000000-f47eba015e7f8d9f21a72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-001i-0900000000-26da10b11bacabae0d002020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-001i-0900000000-dceee0216914a6ad03492020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-001r-0900000000-cb9d81f2cc810b6a1bf62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-0019-2900000000-79ddb513e243e4fd10542020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-001a-7900000000-aeb7c72625ab71bbfcb32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-000i-0900000000-72f91c756d76768ecc232020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-004i-9000000000-0ae8d2338f48c17984cd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, negativesplash10-001i-9400000000-943dd572fd686e87913d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-03di-0109000000-cf0f38f1f9c792f0404d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-03di-0309000000-9a8aaf68c144b67fbc6e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-01q9-0905000000-d40f59a74d4b8cc4e1d62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-001i-0901000000-265af2cad1ab697d32492020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-001i-0900000000-2b4e4dd83c0bad2269ae2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-001i-0900000000-c37839583f5e4e15cc462020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-001i-0900000000-6254efb7ddc081f6fd0c2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-9fb7b528d968cab88bd32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-1900000000-eb2d1569b5bdfeef979a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000w-9300000000-065aa3463c121bf313122017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1900000000-62dd716e79c8fa6f5ee02017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3900000000-bf85a8ad5b7719f36aba2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-7db60439b29417bbbe0d2017-09-01View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, 5%_DMSO, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)Spectrum
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
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0003099
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023107
KNApSAcK IDNot Available
Chemspider ID62926
KEGG Compound IDC16359
BioCyc IDCPD-14119
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID2821
PubChem Compound69726
PDB IDNot Available
ChEBI ID68441
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