Record Information
Version1.0
Creation date2010-04-08 22:11:47 UTC
Update date2019-11-26 03:11:29 UTC
Primary IDFDB015350
Secondary Accession Numbers
  • FDB031247
Chemical Information
FooDB NameUric acid
DescriptionOccurs as phosphate in yeast and meat products For example, some researchers propose that hyperuricemia-induced oxidative stress is a cause of metabolic syndrome. On the other hand, plasma uric acid levels correlate with longevity in primates and other mammals. This is presumably a function of urate's antioxidant properties.; Uric acid (or urate) is an organic compound of carbon, nitrogen, oxygen and hydrogen with the formula C5H4N4O3.; Uric 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 humans 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. Uric acid is found in many foods, some of which are common oregano, yellow zucchini, watermelon, and other bread.
CAS Number69-93-2
Structure
Thumb
Synonyms
SynonymSource
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
1H-Purine-2, 6,8-triolbiospider
1H-Purine-2,6,8-triol 2,6,8-Trihydroxypurinebiospider
1H-Purine-2,6,8(3H)-trione, 7,9-dihydro-biospider
1H-Purine-2,6,8(3H)-trione, 7,9-dihydro- (9CI)biospider
2,6-dihydroxy-7,9-dihydro-8H-purin-8-onebiospider
2,6, 8-Trioxypurinebiospider
2,6,8(1H,3H,9H)-Purinetrionedb_source
6,8-Dioxo-6,7,8,9-tetrahydro-1H-purin-2-olatebiospider
7,9-Dihydro-1H-purine-2,6,8(3H)-trionebiospider
7,9-Dihydro-1H-purine-2,6,8(3H)-trione, 9CIdb_source
7,9-dihydro-3H-purine-2,6,8-trionebiospider
7H-purine-2,6,8-triolbiospider
8-Hydroxyxanthinebiospider
9H-purine-2,6,8-triolbiospider
Acidum Uricum-Injeel Forte Liq (D6-D200)biospider
purine-2,6,8-(1H,3H,9H)-trionebiospider
Purine-2,6,8-triolbiospider
Purine-3,6,8(1H,3H,9H)-trionebiospider
URCbiospider
Uric acid (8CI)biospider
Uric oxidebiospider
Uricum acidumbiospider
Uricum Acidum 3-30chbiospider
Predicted Properties
PropertyValueSource
Water Solubility1.76 g/LALOGPS
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H4N4O3
IUPAC name2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
InChI IdentifierInChI=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
Isomeric SMILESO=C1NC2=C(N1)C(=O)NC(=O)N2
Average Molecular Weight168.1103
Monoisotopic Molecular Weight168.028340014
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 35.72%; H 2.40%; N 33.33%; O 28.55%DFC
Melting Point> 300 oC
Boiling PointNot Available
Experimental Water Solubility0.06 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-2.17NAHUM,A & HORVATH,C (1980)
Experimental pKapKa2 10.6DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
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-bd24364053510c462adeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-052f-0603900000-8c1224738bed2608c262JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0g59-5917000000-4b28946431495667844bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0537-0913400000-bd24364053510c462adeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-052f-0603900000-8c1224738bed2608c262JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0g59-5917000000-4b28946431495667844bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052g-0902500000-05851611f4bbf0745b81JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00os-4900000000-54b6de73b60ab2faad65JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0900000000-0525c12dc3951f55a2c8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-006w-9500000000-fe10d491ad634ca46332JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0gbd-9100000000-d48a3e7919c385949313JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-01c0-3900000000-b3b3f0a20aaac71095d7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0f6x-0900000000-a6699ab18f69b21b3823JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-971b5c8c5d975d306fedJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016r-1900000000-72edb3607fe9beb9b805JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zgi-9500000000-753be769a0b48fc2960bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-a4f5b18495486c5a1d5aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-1900000000-bc9e45f168dafb0d874cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-e01e386869d687364c61JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-002f-9200000000-e5abb655836214cc56b3JSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID1142
ChEMBL IDCHEMBL792
KEGG Compound IDC00366
Pubchem Compound ID1175
Pubchem Substance IDNot Available
ChEBI ID17775
Phenol-Explorer IDNot Available
DrugBank IDDB01696
HMDB IDHMDB00289
CRC / DFC (Dictionary of Food Compounds) IDJZR60-K:JZR60-K
EAFUS IDNot Available
Dr. Duke IDURIC-ACID
BIGG ID34768
KNApSAcK IDC00007301
HET IDURC
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDUric acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Glycogen phosphorylase, liver formPYGLP06737
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050 map00230
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).