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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2013-07-09 16:07:18 UTC
Update Date2018-03-28 16:46:54 UTC
HMDB IDHMDB0060920
Secondary Accession Numbers
  • HMDB0060698
  • HMDB60698
  • HMDB60920
Metabolite Identification
Common Name2-Hydroxyibuprofen
Description2-Hydroxyibuprofen is a metabolite of ibuprofen. Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID) used for relief of symptoms of arthritis, fever, as an analgesic (pain reliever), especially where there is an inflammatory component, and dysmenorrhea. Ibuprofen is known to have an antiplatelet effect, though it is relatively mild and somewhat short-lived when compared with aspirin or other better-known antiplatelet drugs. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
2,4'-(2-Hydroxy-2-methylpropyl)phenylpropionic acidChEBI
HydroxyibuprofenChEBI
Ibuprofen OHChEBI
2,4'-(2-Hydroxy-2-methylpropyl)phenylpropionateGenerator
Chemical FormulaC13H18O3
Average Molecular Weight222.2802
Monoisotopic Molecular Weight222.125594442
IUPAC Name2-[4-(2-hydroxy-2-methylpropyl)phenyl]propanoic acid
Traditional Name2-[4-(2-hydroxy-2-methylpropyl)phenyl]propanoic acid
CAS Registry NumberNot Available
SMILES
CC(C(O)=O)C1=CC=C(CC(C)(C)O)C=C1
InChI Identifier
InChI=1S/C13H18O3/c1-9(12(14)15)11-6-4-10(5-7-11)8-13(2,3)16/h4-7,9,16H,8H2,1-3H3,(H,14,15)
InChI KeyUJHKVYPPCJBOSG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 2-phenylpropanoic-acid
  • P-cymene
  • Aromatic monoterpenoid
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • Phenylpropane
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

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 Solubility0.3 g/LALOGPS
logP2.41ALOGPS
logP2.37ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)4.63ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity62.57 m³·mol⁻¹ChemAxon
Polarizability24.48 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aor-4910000000-230705a3b25bc8d2bbd7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00ai-9682000000-0111491ba4a88d97341eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0690000000-9318a4a4877cd81cd175View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0930000000-ea94bba1900c2d2c4529View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0900000000-d16bf512545d34c8d478View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0590000000-ad78ab3a996915e1bec9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0629-1940000000-3d114bfd3f6171882588View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-6900000000-3ca6784a37e019ab2e84View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Ibuprofen Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Ibuprofen Metabolism PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    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
      Phenol Explorer Compound IDNot Available
      FoodDB 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 Compound10443535
      PDB IDNot Available
      ChEBI ID133197
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available

      Enzymes

      General function:
      Involved in transferase activity, transferring hexosyl groups
      Specific function:
      UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
      Gene Name:
      UGT1A1
      Uniprot ID:
      P22309
      Molecular weight:
      59590.91
      Reactions
      2-Hydroxyibuprofen → 6-({1-[4-(1-carboxyethyl)phenyl]-2-methylpropan-2-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
      2-Hydroxyibuprofen → 3,4,5-trihydroxy-6-({2-[4-(2-hydroxy-2-methylpropyl)phenyl]propanoyl}oxy)oxane-2-carboxylic aciddetails