Showing Compound Card for Uric acid (CDB004839)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-04-17 18:42:06 UTC
Updated at2022-12-13 23:36:29 UTC
CannabisDB IDCDB004839
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameUric acid
DescriptionUric acid, also known as urate or lithate, 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 in which the purine ring is substituted by oxo groups at positions 2, 6, and 8. Uric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Uric acid exists in all living species, ranging from bacteria to humans. uric acid can be biosynthesized from xanthine through its interaction with the enzyme xanthine dehydrogenase/oxidase. In humans, uric acid is involved in the metabolic disorder called the purine nucleoside phosphorylase deficiency pathway. Outside of the human body, Uric acid is found, on average, in the highest concentration within milk (cow) and garden cress. Uric acid has also been detected, but not quantified in, several different foods, such as mamey sapotes, american pokeweeds, horned melons, towel gourds, and mammee apples. This could make uric acid a potential biomarker for the consumption of these foods. Uric acid is a potentially toxic compound. Uric acid, with regard to humans, has been found to be associated with several diseases such as bacterial meningitis, gout, and nucleotide depletion syndrome; uric acid has also been linked to several inborn metabolic disorders including primary hypomagnesemia and 3-methyl-crotonyl-glycinuria. Uric acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,6,8-TrioxopurineChEBI
2,6,8-TrioxypurineChEBI
Purine-2,6,8(1H,3H,9H)-trioneChEBI
UrateChEBI
1H-Purine-2,6,8-triolHMDB
2,6,8-TrihydroxypurineHMDB
LithateHMDB
Lithic acidHMDB
Acid urate, ammoniumHMDB
Ammonium acid urateHMDB
Monohydrate, sodium urateHMDB
Urate, ammonium acidHMDB
Urate, monosodiumHMDB
Acid, uricHMDB
Monosodium urate monohydrateHMDB
Sodium acid urateHMDB
Sodium urateHMDB
TrioxopurineHMDB
Urate, sodium acidHMDB
Monohydrate, monosodium urateHMDB
Monosodium urateHMDB
Potassium urateHMDB
Sodium acid urate monohydrateHMDB
Urate monohydrate, sodiumHMDB
Acid urate, sodiumHMDB
Sodium urate monohydrateHMDB
Urate monohydrate, monosodiumHMDB
Urate, potassiumHMDB
Urate, sodiumHMDB
Chemical FormulaC5H4N4O3
Average Molecular Weight168.11
Monoisotopic Molecular Weight168.0283
IUPAC Name2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
Traditional Nameuric acid
CAS Registry Number69-93-2
SMILES
O=C1NC2=C(N1)C(=O)NC(=O)N2
InChI Identifier
InChI=1S/C5H4N4O3/c10-3-1-2(7-4(11)6-1)8-5(12)9-3/h(H4,6,7,8,9,10,11,12)
InChI KeyLEHOTFFKMJEONL-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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point> 300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.06 mg/mLNot Available
logP-2.17NAHUM,A & HORVATH,C (1980)
Predicted Properties
PropertyValueSource
logP-1.1ALOGPS
logP-1.5ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)7.25ChemAxon
pKa (Strongest Basic)-6.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.33 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity45.63 m³·mol⁻¹ChemAxon
Polarizability13.61 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-002f-9200000000-e5abb655836214cc56b32014-09-20View Spectrum
GC-MSUric acid, non-derivatized, GC-MS Spectrumsplash10-0537-0913400000-bd24364053510c462adeSpectrum
GC-MSUric acid, 4 TMS, GC-MS Spectrumsplash10-052f-0603900000-8c1224738bed2608c262Spectrum
GC-MSUric acid, 3 TMS, GC-MS Spectrumsplash10-0g59-5917000000-4b28946431495667844bSpectrum
GC-MSUric acid, non-derivatized, GC-MS Spectrumsplash10-0537-0913400000-bd24364053510c462adeSpectrum
GC-MSUric acid, non-derivatized, GC-MS Spectrumsplash10-052f-0603900000-8c1224738bed2608c262Spectrum
GC-MSUric acid, non-derivatized, GC-MS Spectrumsplash10-0g59-5917000000-4b28946431495667844bSpectrum
GC-MSUric acid, non-derivatized, GC-MS Spectrumsplash10-052g-0902500000-05851611f4bbf0745b81Spectrum
Predicted GC-MSUric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00os-4900000000-54b6de73b60ab2faad65Spectrum
Predicted GC-MSUric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSUric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0900000000-0525c12dc3951f55a2c82012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-006w-9500000000-fe10d491ad634ca463322012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0gbd-9100000000-d48a3e7919c3859493132012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-01c0-3900000000-b3b3f0a20aaac71095d72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0f6x-0900000000-a6699ab18f69b21b38232017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0006-9000000000-ed929369da80ee084e892021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-dae78aaa83fc4120e56f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00r7-9500000000-120c639f57df45d231532021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-96d2ee50d279f80566712021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00xr-4900000000-1d613278865ada2e64572021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-01b9-2900000000-a8460af7fe6f1d23fbfe2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0btc-9000000000-d9b1f657e4c7e43bd7762021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-02na-9500000000-7dddbc2120455b19bba92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-01c0-3900000000-95ebf9c951d7085b85e32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-1900000000-029e9b2adfbb2e0d26d82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-88f140dfad19d2f058f62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0gcc-6900000000-d9540bd8f38fac1e92b02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-9200000000-80997201350d0752fbbf2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-971b5c8c5d975d306fed2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016r-1900000000-72edb3607fe9beb9b8052015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zgi-9500000000-753be769a0b48fc2960b2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-a4f5b18495486c5a1d5a2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-1900000000-bc9e45f168dafb0d874c2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-e01e386869d687364c612015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-e82d2b9a4cad815cef762021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Xanthine dehydrogenase/oxidaseXDH2p23.1P47989 details
Glycogen phosphorylase, liver formPYGL14q21-q22P06737 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Xanthine dehydrogenase/oxidaseXDH2p23.1P47989 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.0218 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.0240 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.0299 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.0195 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.0110 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.0149 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0000289
DrugBank IDDB08844
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015350
KNApSAcK IDC00007301
Chemspider ID1142
KEGG Compound IDC00366
BioCyc IDURATE
BiGG ID34768
Wikipedia LinkUric_acid
METLIN ID88
PubChem Compound1175
PDB IDNot Available
ChEBI ID17775
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
Enzyme Details
2. Glycogen phosphorylase, liver form
General function:
Involved in phosphorylase activity
Specific function:
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known phosphorylases share catalytic and structural properties.
Gene Name:
PYGL
Uniprot ID:
P06737
Molecular weight:
93133.25