Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 09:59:31 UTC
Update Date2021-09-26 23:04:36 UTC
HMDB IDHMDB0252185
Secondary Accession NumbersNone
Metabolite Identification
Common NameFebuxostat
DescriptionFebuxostat, also known as feburic or uloric, belongs to the class of organic compounds known as thiazolecarboxylic acids and derivatives. These are heterocyclic compounds containing a thiazole ring which bears a carboxylic acid group (or a derivative thereof). Febuxostat is a drug which is used for the treatment of hyperuricemia in patients with gout. Febuxostat is an extremely weak basic (essentially neutral) compound (based on its pKa). A 1,3-thiazolemonocarboxylic acid that is 4-methyl-1,3-thiazole-5-carboxylic acid which is substituted by a 3-cyano-4-(2-methylpropoxy)phenyl group at position 2. This compound has been identified in human blood as reported by (PMID: 31557052 ). Febuxostat is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Febuxostat is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
2-(3-Cyano-4-isobutoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylic acidChEBI
AdenuricChEBI
DonifoxateChEBI
FebudayChEBI
FeburicChEBI
FebuxostatumChEBI
GoturicChEBI
GoutexChEBI
TEI 6720ChEBI
TEI-6720ChEBI
TMX 67ChEBI
TMX-67ChEBI
UloricChEBI
ZurigChEBI
2-(3-Cyano-4-isobutoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylateGenerator
Donifoxic acidGenerator
2-(3-cyano-4-Isobutoxyphenyl)-4-methyl-5-thiazolecarboxylic acidMeSH
6720, TEIMeSH
2-[3-Cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylateGenerator
Chemical FormulaC16H16N2O3S
Average Molecular Weight316.375
Monoisotopic Molecular Weight316.088163078
IUPAC Name2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid
Traditional Namefebuxostat
CAS Registry NumberNot Available
SMILES
CC(C)COC1=C(C=C(C=C1)C1=NC(C)=C(S1)C(O)=O)C#N
InChI Identifier
InChI=1S/C16H16N2O3S/c1-9(2)8-21-13-5-4-11(6-12(13)7-17)15-18-10(3)14(22-15)16(19)20/h4-6,9H,8H2,1-3H3,(H,19,20)
InChI KeyBQSJTQLCZDPROO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thiazolecarboxylic acids and derivatives. These are heterocyclic compounds containing a thiazole ring which bears a carboxylic acid group (or a derivative thereof).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassThiazoles
Direct ParentThiazolecarboxylic acids and derivatives
Alternative Parents
Substituents
  • 2,4,5-trisubstituted 1,3-thiazole
  • Phenoxy compound
  • Benzonitrile
  • Thiazolecarboxylic acid or derivatives
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Carboxylic acid derivative
  • Azacycle
  • Carboxylic acid
  • Ether
  • Nitrile
  • Carbonitrile
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot 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
logP3.8ALOGPS
logP3.52ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)3.08ChemAxon
pKa (Strongest Basic)0.39ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.21 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity93.93 m³·mol⁻¹ChemAxon
Polarizability33.88 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+177.51330932474
DeepCCS[M-H]-175.15530932474
DeepCCS[M-2H]-208.94130932474
DeepCCS[M+Na]+184.59930932474
AllCCS[M+H]+170.732859911
AllCCS[M+H-H2O]+167.732859911
AllCCS[M+NH4]+173.532859911
AllCCS[M+Na]+174.332859911
AllCCS[M-H]-173.932859911
AllCCS[M+Na-2H]-173.632859911
AllCCS[M+HCOO]-173.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FebuxostatCC(C)COC1=C(C=C(C=C1)C1=NC(C)=C(S1)C(O)=O)C#N3317.5Standard polar33892256
FebuxostatCC(C)COC1=C(C=C(C=C1)C1=NC(C)=C(S1)C(O)=O)C#N2493.4Standard non polar33892256
FebuxostatCC(C)COC1=C(C=C(C=C1)C1=NC(C)=C(S1)C(O)=O)C#N2798.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Febuxostat GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-4090000000-636b08208913e37cf6c92021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Febuxostat GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Febuxostat GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Febuxostat GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-04Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Febuxostat LC-ESI-qTof , Positive-QTOFsplash10-03xr-0292000000-d8e012f875d1014fe3512017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Febuxostat , positive-QTOFsplash10-03xr-0292000000-d8e012f875d1014fe3512017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Febuxostat 10V, Positive-QTOFsplash10-066s-4089000000-c7acf0318016cd20bec22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Febuxostat 20V, Positive-QTOFsplash10-05fr-3091000000-70fc366c85a87b1108052016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Febuxostat 40V, Positive-QTOFsplash10-0a4i-9220000000-e6f092b19cb56951c75b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Febuxostat 10V, Negative-QTOFsplash10-00di-0092000000-1d9268ebb0d7e9e4ca732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Febuxostat 20V, Negative-QTOFsplash10-00di-0190000000-8c117b3535dd9b43783a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Febuxostat 40V, Negative-QTOFsplash10-01b9-6390000000-029b21a0f25181f7e0812016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Febuxostat 10V, Positive-QTOFsplash10-03xr-2098000000-d7c4d373123c0fe32da12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Febuxostat 20V, Positive-QTOFsplash10-01ox-1090000000-a4e1f7032b3cedd919632021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Febuxostat 40V, Positive-QTOFsplash10-00l6-1290000000-f8dae3e7cfb7130dd2622021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Febuxostat 10V, Negative-QTOFsplash10-014i-0091000000-492981b99c59ea00141b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Febuxostat 20V, Negative-QTOFsplash10-014i-0190000000-ee6d6f385111dcd5aae32021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Febuxostat 40V, Negative-QTOFsplash10-014i-1390000000-27c92224dda6826d4dd32021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04854
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFebuxostat
METLIN IDNot Available
PubChem Compound134018
PDB IDNot Available
ChEBI ID31596
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]