Uric acid (YMDB01494)

Identification
YMDB IDYMDB01494
NameUric acid
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionUric acid is a heterocyclic compound produced by xanthine oxidase from xanthine and hypoxanthine, which in turn are produced from purine. In humans and higher primates, uric acid is the final oxidation product of purine metabolism and is excreted in urine. In birds and reptiles, and in some desert dwelling mammals (e.g., the kangaroo rat), uric acid also is the end product of purine metabolism, but it is excreted in feces as a dry mass.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1H-Purine-2, 6,8-triol
  • 1H-Purine-2,6,8-triol
  • 1H-Purine-2,6,8(3H)-trione, 7,9-dihydro-
  • 2,6-dihydroxy-7,9-dihydro-8H-purin-8-one
  • 2,6, 8-Trioxypurine
  • 2,6,8-Trihydroxypurine
  • 2,6,8-Trioxopurine
  • 2,6,8-trioxypurine
  • 7,9-Dihydro-1H-purine-2,6,8(3H)-trione
  • 8-hydroxyxanthine
  • Diohippuric acid I 125 (USAN)
  • Lithate
  • lithic acid
  • Purine-2,6,8-triol
  • Purine-2,6,8(1H,3H,9H)-trione
  • Purine-3,6,8(1H,3H,9H)-trione
  • Urate
  • URIC ACID
  • uric oxide
  • Acid urate, ammonium
  • Ammonium acid urate
  • Monohydrate, sodium urate
  • Urate, ammonium acid
  • Urate, monosodium
  • Acid, uric
  • Monosodium urate monohydrate
  • Sodium acid urate
  • Sodium urate
  • Trioxopurine
  • Urate, sodium acid
  • Monohydrate, monosodium urate
  • Monosodium urate
  • Potassium urate
  • Sodium acid urate monohydrate
  • Urate monohydrate, sodium
  • Acid urate, sodium
  • Sodium urate monohydrate
  • Urate monohydrate, monosodium
  • Urate, potassium
  • Urate, sodium
CAS number69-93-2
WeightAverage: 168.1103
Monoisotopic: 168.028340014
InChI KeyLEHOTFFKMJEONL-UHFFFAOYSA-N
InChIInChI=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)
IUPAC Name2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
Traditional IUPAC Nameuric acid
Chemical FormulaC5H4N4O3
SMILESO=C1NC2=C(N1)C(=O)NC(=O)N2
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
Physical Properties
StateSolid
Charge0
Melting point>300 °C
Experimental Properties
PropertyValueReference
Water Solubility0.06 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-2.17 [NAHUM,A & HORVATH,C (1980)]PhysProp
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Purine metabolismec00230 Map00230
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot 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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
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
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0006-9000000000-ed929369da80ee084e89JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-dae78aaa83fc4120e56fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00r7-9500000000-120c639f57df45d23153JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-96d2ee50d279f8056671JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00xr-4900000000-1d613278865ada2e6457JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-01b9-2900000000-a8460af7fe6f1d23fbfeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0btc-9000000000-d9b1f657e4c7e43bd776JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-02na-9500000000-7dddbc2120455b19bba9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-01c0-3900000000-95ebf9c951d7085b85e3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-1900000000-029e9b2adfbb2e0d26d8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-88f140dfad19d2f058f6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0gcc-6900000000-d9540bd8f38fac1e92b0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-9200000000-80997201350d0752fbbfJSpectraViewer | 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-e82d2b9a4cad815cef76JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-002f-9200000000-e5abb655836214cc56b3JSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Yannai S. Dictionary of food compounds with CD-ROM: additives, flavors, and ingredients. Chapman & Hall/CRC; 2004.
Synthesis Reference:Brenner-Holzach, O.; Leuthardt, F. Uric acid formation from glucose carbon in Drosophila melanogaster. Preliminary report. Helvetica Chimica Acta (1963), 46(4), 1426-8.
External Links:
ResourceLink
CHEBI ID17775
HMDB IDHMDB00289
Pubchem Compound ID1175
Kegg IDC00366
ChemSpider ID1142
FOODB IDFDB015350
WikipediaUric_acid
BioCyc IDURATE