Record Information
Version1.0
Creation date2010-04-08 22:11:47 UTC
Update date2020-09-17 15:38:33 UTC
Primary IDFDB015350
Secondary Accession Numbers
  • FDB031247
Chemical Information
FooDB 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.
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-002f-9200000000-e5abb655836214cc56b3Spectrum
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
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0900000000-0525c12dc3951f55a2c8Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-006w-9500000000-fe10d491ad634ca46332Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0gbd-9100000000-d48a3e7919c385949313Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-01c0-3900000000-b3b3f0a20aaac71095d7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0f6x-0900000000-a6699ab18f69b21b3823Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-971b5c8c5d975d306fedSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016r-1900000000-72edb3607fe9beb9b805Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zgi-9500000000-753be769a0b48fc2960bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-a4f5b18495486c5a1d5aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-1900000000-bc9e45f168dafb0d874cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-e01e386869d687364c61Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR SpectrumSpectrum
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).