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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:34:45 UTC
Update Date2022-09-22 18:35:09 UTC
HMDB IDHMDB0030097
Secondary Accession Numbers
  • HMDB30097
Metabolite Identification
Common Name5-Hydroxyisourate
Description5-Hydroxyisourate (CAS: 6960-30-1) 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. 5-Hydroxyisourate is an extremely weak basic (essentially neutral) compound (based on its pKa). 5-Hydroxyisourate exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 5-hydroxyisourate has been detected, but not quantified in, several different foods, such as soybeans, common thymes, poppies, blackcurrants, black elderberries, and rapes. This could make 5-hydroxyisourate a potential biomarker for the consumption of these foods. 5-Hydroxyisourate is the product of the oxidation of uric acid by urate oxidase.
Structure
Data?1583778041
Synonyms
ValueSource
5-Hydroxyisouric acidGenerator
(S)-5-Hydroxyisouric acidHMDB
5,7-Dihydro-5-hydroxy-1H-purine-2,6,8(3H)-trioneHMDB
5H-Purine-2,5,6,8-tetrolHMDB
5-HydroxyisourateHMDB
Chemical FormulaC5H4N4O4
Average Molecular Weight184.111
Monoisotopic Molecular Weight184.023254625
IUPAC Name(5S)-5,6,8-trihydroxy-5,7-dihydro-2H-purin-2-one
Traditional Name(5S)-5,6,8-trihydroxy-7H-purin-2-one
CAS Registry Number151359-24-9
SMILES
O[C@@]12NC(=O)NC1=NC(=O)NC2=O
InChI Identifier
InChI=1S/C5H4N4O4/c10-2-5(13)1(6-3(11)8-2)7-4(12)9-5/h13H,(H3,6,7,8,9,10,11,12)/t5-/m0/s1
InChI KeyLTQYPAVLAYVKTK-YFKPBYRVSA-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
  • Purinone
  • Alpha-amino acid or derivatives
  • Alkaloid or derivatives
  • Ureide
  • Pyrimidone
  • N-acyl urea
  • Pyrimidine
  • 1,3-diazinane
  • 3-imidazoline
  • Dicarboximide
  • Urea
  • Carbonic acid derivative
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Carboxylic acid derivative
  • Carboxylic acid amidine
  • Amidine
  • Alkanolamine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility10.6 g/LALOGPS
logP-1.2ALOGPS
logP-2.8ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)-1.6ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area126.87 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity36.43 m³·mol⁻¹ChemAxon
Polarizability14.31 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-168.25330932474
DeepCCS[M+Na]+142.9930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-HydroxyisourateO[C@@]12NC(=O)NC1=NC(=O)NC2=O3914.3Standard polar33892256
5-HydroxyisourateO[C@@]12NC(=O)NC1=NC(=O)NC2=O1887.2Standard non polar33892256
5-HydroxyisourateO[C@@]12NC(=O)NC1=NC(=O)NC2=O2259.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Hydroxyisourate,1TMS,isomer #1C[Si](C)(C)O[C@@]12NC(=O)NC1=NC(=O)NC2=O2176.3Semi standard non polar33892256
5-Hydroxyisourate,1TMS,isomer #2C[Si](C)(C)N1C(=O)NC2=NC(=O)NC(=O)[C@@]21O2204.6Semi standard non polar33892256
5-Hydroxyisourate,1TMS,isomer #3C[Si](C)(C)N1C(=O)N[C@@]2(O)C(=O)NC(=O)N=C122144.7Semi standard non polar33892256
5-Hydroxyisourate,1TMS,isomer #4C[Si](C)(C)N1C(=O)N=C2NC(=O)N[C@@]2(O)C1=O2151.3Semi standard non polar33892256
5-Hydroxyisourate,2TMS,isomer #1C[Si](C)(C)O[C@]12C(=O)NC(=O)N=C1NC(=O)N2[Si](C)(C)C2163.5Semi standard non polar33892256
5-Hydroxyisourate,2TMS,isomer #1C[Si](C)(C)O[C@]12C(=O)NC(=O)N=C1NC(=O)N2[Si](C)(C)C1992.6Standard non polar33892256
5-Hydroxyisourate,2TMS,isomer #2C[Si](C)(C)O[C@@]12NC(=O)N([Si](C)(C)C)C1=NC(=O)NC2=O2175.0Semi standard non polar33892256
5-Hydroxyisourate,2TMS,isomer #2C[Si](C)(C)O[C@@]12NC(=O)N([Si](C)(C)C)C1=NC(=O)NC2=O1919.5Standard non polar33892256
5-Hydroxyisourate,2TMS,isomer #3C[Si](C)(C)O[C@@]12NC(=O)NC1=NC(=O)N([Si](C)(C)C)C2=O2133.7Semi standard non polar33892256
5-Hydroxyisourate,2TMS,isomer #3C[Si](C)(C)O[C@@]12NC(=O)NC1=NC(=O)N([Si](C)(C)C)C2=O1924.9Standard non polar33892256
5-Hydroxyisourate,2TMS,isomer #4C[Si](C)(C)N1C(=O)N([Si](C)(C)C)[C@@]2(O)C(=O)NC(=O)N=C122046.6Semi standard non polar33892256
5-Hydroxyisourate,2TMS,isomer #4C[Si](C)(C)N1C(=O)N([Si](C)(C)C)[C@@]2(O)C(=O)NC(=O)N=C121986.1Standard non polar33892256
5-Hydroxyisourate,2TMS,isomer #5C[Si](C)(C)N1C(=O)N=C2NC(=O)N([Si](C)(C)C)[C@@]2(O)C1=O2090.6Semi standard non polar33892256
5-Hydroxyisourate,2TMS,isomer #5C[Si](C)(C)N1C(=O)N=C2NC(=O)N([Si](C)(C)C)[C@@]2(O)C1=O2035.1Standard non polar33892256
5-Hydroxyisourate,2TMS,isomer #6C[Si](C)(C)N1C(=O)N=C2N([Si](C)(C)C)C(=O)N[C@@]2(O)C1=O2077.6Semi standard non polar33892256
5-Hydroxyisourate,2TMS,isomer #6C[Si](C)(C)N1C(=O)N=C2N([Si](C)(C)C)C(=O)N[C@@]2(O)C1=O1961.7Standard non polar33892256
5-Hydroxyisourate,3TMS,isomer #1C[Si](C)(C)O[C@]12C(=O)N([Si](C)(C)C)C(=O)N=C1NC(=O)N2[Si](C)(C)C2094.7Semi standard non polar33892256
5-Hydroxyisourate,3TMS,isomer #1C[Si](C)(C)O[C@]12C(=O)N([Si](C)(C)C)C(=O)N=C1NC(=O)N2[Si](C)(C)C2058.7Standard non polar33892256
5-Hydroxyisourate,3TMS,isomer #2C[Si](C)(C)O[C@]12C(=O)NC(=O)N=C1N([Si](C)(C)C)C(=O)N2[Si](C)(C)C2066.4Semi standard non polar33892256
5-Hydroxyisourate,3TMS,isomer #2C[Si](C)(C)O[C@]12C(=O)NC(=O)N=C1N([Si](C)(C)C)C(=O)N2[Si](C)(C)C2026.1Standard non polar33892256
5-Hydroxyisourate,3TMS,isomer #3C[Si](C)(C)O[C@@]12NC(=O)N([Si](C)(C)C)C1=NC(=O)N([Si](C)(C)C)C2=O2113.2Semi standard non polar33892256
5-Hydroxyisourate,3TMS,isomer #3C[Si](C)(C)O[C@@]12NC(=O)N([Si](C)(C)C)C1=NC(=O)N([Si](C)(C)C)C2=O2029.6Standard non polar33892256
5-Hydroxyisourate,3TMS,isomer #4C[Si](C)(C)N1C(=O)N=C2N([Si](C)(C)C)C(=O)N([Si](C)(C)C)[C@@]2(O)C1=O1913.8Semi standard non polar33892256
5-Hydroxyisourate,3TMS,isomer #4C[Si](C)(C)N1C(=O)N=C2N([Si](C)(C)C)C(=O)N([Si](C)(C)C)[C@@]2(O)C1=O2014.8Standard non polar33892256
5-Hydroxyisourate,4TMS,isomer #1C[Si](C)(C)O[C@]12C(=O)N([Si](C)(C)C)C(=O)N=C1N([Si](C)(C)C)C(=O)N2[Si](C)(C)C1965.0Semi standard non polar33892256
5-Hydroxyisourate,4TMS,isomer #1C[Si](C)(C)O[C@]12C(=O)N([Si](C)(C)C)C(=O)N=C1N([Si](C)(C)C)C(=O)N2[Si](C)(C)C2062.3Standard non polar33892256
5-Hydroxyisourate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@]12NC(=O)NC1=NC(=O)NC2=O2334.0Semi standard non polar33892256
5-Hydroxyisourate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(=O)NC2=NC(=O)NC(=O)[C@@]21O2442.3Semi standard non polar33892256
5-Hydroxyisourate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(=O)N[C@@]2(O)C(=O)NC(=O)N=C122375.3Semi standard non polar33892256
5-Hydroxyisourate,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C(=O)N=C2NC(=O)N[C@@]2(O)C1=O2316.2Semi standard non polar33892256
5-Hydroxyisourate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@]12C(=O)NC(=O)N=C1NC(=O)N2[Si](C)(C)C(C)(C)C2542.0Semi standard non polar33892256
5-Hydroxyisourate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@]12C(=O)NC(=O)N=C1NC(=O)N2[Si](C)(C)C(C)(C)C2432.4Standard non polar33892256
5-Hydroxyisourate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@]12NC(=O)N([Si](C)(C)C(C)(C)C)C1=NC(=O)NC2=O2547.0Semi standard non polar33892256
5-Hydroxyisourate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@]12NC(=O)N([Si](C)(C)C(C)(C)C)C1=NC(=O)NC2=O2348.2Standard non polar33892256
5-Hydroxyisourate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@]12NC(=O)NC1=NC(=O)N([Si](C)(C)C(C)(C)C)C2=O2456.4Semi standard non polar33892256
5-Hydroxyisourate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@]12NC(=O)NC1=NC(=O)N([Si](C)(C)C(C)(C)C)C2=O2364.2Standard non polar33892256
5-Hydroxyisourate,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)[C@@]2(O)C(=O)NC(=O)N=C122459.4Semi standard non polar33892256
5-Hydroxyisourate,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C(=O)N([Si](C)(C)C(C)(C)C)[C@@]2(O)C(=O)NC(=O)N=C122422.7Standard non polar33892256
5-Hydroxyisourate,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N1C(=O)N=C2NC(=O)N([Si](C)(C)C(C)(C)C)[C@@]2(O)C1=O2500.1Semi standard non polar33892256
5-Hydroxyisourate,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)N1C(=O)N=C2NC(=O)N([Si](C)(C)C(C)(C)C)[C@@]2(O)C1=O2474.1Standard non polar33892256
5-Hydroxyisourate,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)N1C(=O)N=C2N([Si](C)(C)C(C)(C)C)C(=O)N[C@@]2(O)C1=O2508.9Semi standard non polar33892256
5-Hydroxyisourate,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)N1C(=O)N=C2N([Si](C)(C)C(C)(C)C)C(=O)N[C@@]2(O)C1=O2373.1Standard non polar33892256
5-Hydroxyisourate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@]12C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N=C1NC(=O)N2[Si](C)(C)C(C)(C)C2649.2Semi standard non polar33892256
5-Hydroxyisourate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@]12C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N=C1NC(=O)N2[Si](C)(C)C(C)(C)C2664.7Standard non polar33892256
5-Hydroxyisourate,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@]12C(=O)NC(=O)N=C1N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C2642.3Semi standard non polar33892256
5-Hydroxyisourate,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@]12C(=O)NC(=O)N=C1N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C2660.0Standard non polar33892256
5-Hydroxyisourate,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@]12NC(=O)N([Si](C)(C)C(C)(C)C)C1=NC(=O)N([Si](C)(C)C(C)(C)C)C2=O2665.9Semi standard non polar33892256
5-Hydroxyisourate,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@]12NC(=O)N([Si](C)(C)C(C)(C)C)C1=NC(=O)N([Si](C)(C)C(C)(C)C)C2=O2619.3Standard non polar33892256
5-Hydroxyisourate,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C(=O)N=C2N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)[C@@]2(O)C1=O2546.1Semi standard non polar33892256
5-Hydroxyisourate,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C(=O)N=C2N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)[C@@]2(O)C1=O2619.7Standard non polar33892256
5-Hydroxyisourate,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@]12C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N=C1N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C2754.2Semi standard non polar33892256
5-Hydroxyisourate,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@]12C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N=C1N([Si](C)(C)C(C)(C)C)C(=O)N2[Si](C)(C)C(C)(C)C2845.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxyisourate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyisourate 10V, Positive-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyisourate 20V, Positive-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyisourate 40V, Positive-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyisourate 10V, Negative-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyisourate 20V, Negative-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyisourate 40V, Negative-QTOFNot Available2020-06-30Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyisourate 10V, Positive-QTOFsplash10-000i-0900000000-328b63432fd0a39eb0e52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyisourate 20V, Positive-QTOFsplash10-000i-0900000000-4a932f6bd3d7cb44cda62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyisourate 40V, Positive-QTOFsplash10-00kf-9400000000-54d06916085174c7255d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyisourate 10V, Negative-QTOFsplash10-001i-0900000000-e57f31b0eb96d36850fa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyisourate 20V, Negative-QTOFsplash10-01q9-1900000000-cf516e4e59e8401013272021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxyisourate 40V, Negative-QTOFsplash10-0006-9400000000-713a9fe71f0f504af4972021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001616
KNApSAcK IDC00007531
Chemspider IDNot Available
KEGG Compound IDC11821
BioCyc ID5-HYDROXYISOURATE
BiGG IDNot Available
Wikipedia Link5-Hydroxyisourate
METLIN IDNot Available
PubChem Compound101957720
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDC11821
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Afendi FM, Okada T, Yamazaki M, Hirai-Morita A, Nakamura Y, Nakamura K, Ikeda S, Takahashi H, Altaf-Ul-Amin M, Darusman LK, Saito K, Kanaya S. (2012) KNApSAcK family databases: integrated metabolite-plant species databases for multifaceted plant research. Plant Cell Physiol. 2012 Feb;53(2):e1.. .