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Record Information
Version3.6
Creation Date2013-07-09 16:04:46 UTC
Update Date2017-03-02 22:05:31 UTC
HMDB IDHMDB60878
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Hydroxyantipyrine
Description4-Hydroxyantipyrine is a metabolite of antipyrine. Phenazone, phenazon, antipyrine (USAN), or analgesine is an analgesic and antipyretic. It was first synthesized by Ludwig Knorr in 1883.[1] It is formed by reducing diortho- dinitrodiphenyl with sodium amalgam and methyl alcohol, or by heating diphenylene-ortho-dihydrazine with hydrochloric acid to 150 °C. It crystallizes in needles which melt at 156 °C. Potassium permanganate oxidizes it to pyridazine tetracarboxylic acid. Phenazone has an elimination half life of about 12 hours. (Wikipedia)
Structure
Thumb
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
DescriptionThis compound belongs to the class of chemical entities known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassAzoles
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
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility38.2 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity58.38 m3·mol-1ChemAxon
Polarizability21.39 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00004
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB60878
      Metagene LinkHMDB60878
      METLIN IDNot Available
      PubChem Compound98889
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available