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Record Information
Version1.0
Creation Date2016-07-13 19:42:58 UTC
Update Date2016-09-23 18:44:44 UTC
LmdbLMDB00128
Secondary Accession NumbersNone
Metabolite Identification
Common NameUric acid
DescriptionUric acid is a heterocyclic purine derivative that is the final oxidation product of purine metabolism. It is produced by the enzyme xanthine oxidase, which oxidizes oxypurines such as xanthine into uric acid. In most mammals, except animals and higher primates, the enzyme uricase further oxidizes uric acid to allantoin. Uric acid is also the end product of nitrogen metabolism in birds and reptiles. In such species, it is excreted in feces as a dry mass. Humans produce only small quantities of uric acid with excess accumulation leading to a type of arthritis known as gout. The loss of uricase in higher primates parallels the similar loss of the ability to synthesize ascorbic acid vitamin C. This may be because in higher primates uric acid partially replaces ascorbic acid.
Structure
Thumb
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 Weight168.1103
Monoisotopic Molecular Weight168.028340014
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
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0537-0913400000-bd24364053510c462adeSpectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-052f-0603900000-8c1224738bed2608c262Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0g59-5917000000-4b28946431495667844bSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0537-0913400000-bd24364053510c462adeSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-052f-0603900000-8c1224738bed2608c262Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0g59-5917000000-4b28946431495667844bSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052g-0902500000-05851611f4bbf0745b81Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00os-4900000000-54b6de73b60ab2faad65Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0900000000-0525c12dc3951f55a2c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-006w-9500000000-fe10d491ad634ca46332Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0gbd-9100000000-d48a3e7919c385949313Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-01c0-3900000000-b3b3f0a20aaac71095d7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0f6x-0900000000-a6699ab18f69b21b3823Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-971b5c8c5d975d306fedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016r-1900000000-72edb3607fe9beb9b805Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zgi-9500000000-753be769a0b48fc2960bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-a4f5b18495486c5a1d5aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-1900000000-bc9e45f168dafb0d874cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-e01e386869d687364c61Spectrum
MSMass Spectrum (Electron Ionization)splash10-002f-9200000000-e5abb655836214cc56b3Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Follicular Fluid
  • Milk
  • Plasma
  • Serum
  • Whole blood
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Follicular FluidDetected and Quantified5.948 +/- 0 uMNot AvailablePorcine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Kurt J. Boudonck,...
details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected and Quantified4.759 +/- 3.569 uMNot AvailablePorcine details
Whole bloodDetected and Quantified91.0117-191.541 uMNot AvailableBovine
    • Arthur K. Anderso...
details
DrugBank IDDB08844
HMDB IDHMDB0000289
FooDB IDFDB015350
Phenol Explorer IDNot Available
KNApSAcK IDC00007301
BiGG ID34768
BioCyc IDURATE
METLIN ID88
PDB IDNot Available
Wikipedia LinkUric_acid
Chemspider ID1142
ChEBI ID17775
PubChem Compound ID1175
Kegg Compound IDC00366
YMDB IDYMDB01494
ECMDB IDECMDB00289
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available