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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:04:46 UTC
Update Date2023-02-21 17:30:16 UTC
HMDB IDHMDB0060878
Secondary Accession Numbers
  • HMDB60878
Metabolite Identification
Common Name4-Hydroxyantipyrine
Description4-Hydroxyantipyrine, a major metabolite of the drug antipyrine. Antypyrene is an analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver (PMID: 6121894 , 8735513 ). In man, 30–40% of an antipyrine dose is typically oxidized to 4-hydroxyantipyrine. In addition to its use for monitoring drug metabolism, 4-hydroxyantipyrine has also been used as a drug biodistribution promoter (PMID: 11767111 ). 4-Hydroxyantipyrine is only found in individuals who have taken or received the drug antipyrine.
Structure
Data?1677000616
SynonymsNot Available
Chemical FormulaC11H12N2O2
Average Molecular Weight204.2252
Monoisotopic Molecular Weight204.089877638
IUPAC Name4-hydroxy-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one
Traditional Name4-hydroxy-1,5-dimethyl-2-phenylpyrazol-3-one
CAS Registry NumberNot Available
SMILES
CN1N(C(=O)C(O)=C1C)C1=CC=CC=C1
InChI Identifier
InChI=1S/C11H12N2O2/c1-8-10(14)11(15)13(12(8)2)9-6-4-3-5-7-9/h3-7,14H,1-2H3
InChI KeySKVPTPMWXJSBTF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassPyrazoles
Direct ParentPhenylpyrazoles
Alternative Parents
Substituents
  • Phenylpyrazole
  • Monocyclic benzene moiety
  • Pyrazolinone
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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 Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available141.435http://allccs.zhulab.cn/database/detail?ID=AllCCS00001099
Predicted Molecular Properties
PropertyValueSource
Water Solubility38.2 g/LALOGPS
logP0.47ALOGPS
logP0.97ChemAxon
logS-0.73ALOGPS
pKa (Strongest Acidic)7.35ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.78 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity58.38 m³·mol⁻¹ChemAxon
Polarizability21.39 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]+144.48730932474
DeepCCS[M-H]-142.09230932474
DeepCCS[M-2H]-175.54930932474
DeepCCS[M+Na]+150.430932474
AllCCS[M+H]+143.932859911
AllCCS[M+H-H2O]+139.732859911
AllCCS[M+NH4]+147.932859911
AllCCS[M+Na]+149.032859911
AllCCS[M-H]-145.732859911
AllCCS[M+Na-2H]-145.832859911
AllCCS[M+HCOO]-146.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-HydroxyantipyrineCN1N(C(=O)C(O)=C1C)C1=CC=CC=C12971.2Standard polar33892256
4-HydroxyantipyrineCN1N(C(=O)C(O)=C1C)C1=CC=CC=C11874.2Standard non polar33892256
4-HydroxyantipyrineCN1N(C(=O)C(O)=C1C)C1=CC=CC=C11944.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxyantipyrine,1TMS,isomer #1CC1=C(O[Si](C)(C)C)C(=O)N(C2=CC=CC=C2)N1C1857.8Semi standard non polar33892256
4-Hydroxyantipyrine,1TBDMS,isomer #1CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)N(C2=CC=CC=C2)N1C2115.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyantipyrine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fbi-3910000000-c98f07a419260f2ebee52017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyantipyrine GC-MS (1 TMS) - 70eV, Positivesplash10-0229-6970000000-4157d8ad16409897e7292017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyantipyrine 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 - 4-Hydroxyantipyrine 10V, Positive-QTOFsplash10-0a4i-0190000000-292149064e355d5990d22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyantipyrine 20V, Positive-QTOFsplash10-0a6r-9730000000-b226bb7edf212df27cf62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyantipyrine 40V, Positive-QTOFsplash10-00di-3900000000-4bd99b951eeadc20b6a92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyantipyrine 10V, Negative-QTOFsplash10-0udi-1390000000-af26936060dbf3af58ff2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyantipyrine 20V, Negative-QTOFsplash10-0uk9-1910000000-efa28afb9a3d7ad219332017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyantipyrine 40V, Negative-QTOFsplash10-0006-9300000000-75bff330553ba4a233d12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyantipyrine 10V, Positive-QTOFsplash10-0a4i-0090000000-82053d3e7735d22e65cf2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyantipyrine 20V, Positive-QTOFsplash10-0a4i-3790000000-62d9b91b90f6c4a97eec2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyantipyrine 40V, Positive-QTOFsplash10-004i-9000000000-586628bded880a48b8d82021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyantipyrine 10V, Negative-QTOFsplash10-0udi-0090000000-9b41106fc25a17d1b2b22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyantipyrine 20V, Negative-QTOFsplash10-00kf-9510000000-5e0092c6cf3b99537c962021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyantipyrine 40V, Negative-QTOFsplash10-0006-9300000000-1c735bb91571d85a98be2021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
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 LinkNot Available
METLIN IDNot Available
PubChem Compound98889
PDB IDNot Available
ChEBI IDNot Available
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. Bottcher J, Bassmann H, Schuppel R: Quantitation and urinary pattern of 4,4'-dihydroxy-antipyrine, 4-hydroxy-antipyrine and 3-hydroxymethyl-antipyrine, as main metabolites of antipyrine in man and rat. J Pharm Pharmacol. 1982 Mar;34(3):168-75. doi: 10.1111/j.2042-7158.1982.tb04215.x. [PubMed:6121894 ]
  2. Janus K, Suszycka J: Effect of age on the pharmacokinetics of antipyrine in calves. Res Vet Sci. 1996 May;60(3):234-7. doi: 10.1016/s0034-5288(96)90045-4. [PubMed:8735513 ]
  3. Ohkawa Y, Kiyohara Y, Asoh T, Maeda H, Kurumi M, Sasaki K, Kurosaki Y, Matsumura M, Nakayama T: Application of 4-hydroxyantipyrine and acetaminophen O-sulfate as biodistribution promoter. Biol Pharm Bull. 2001 Dec;24(12):1404-10. doi: 10.1248/bpb.24.1404. [PubMed:11767111 ]