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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-06-15 16:53:40 UTC
Update Date2017-12-07 17:17:31 UTC
HMDB IDHMDB0060564
Secondary Accession Numbers
  • HMDB60564
Metabolite Identification
Common NameCarboxy-ibuprofen
DescriptionCarboxy-ibuprofen 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-Carboxypropyl)phenylpropionic acidChEBI
2-(4-(2-Carboxypropyl)phenyl)propionic acidChEBI
Carboxy-ibuprofenChEBI
Ibuprofen COOHChEBI
2,4'-(2-Carboxypropyl)phenylpropionateGenerator
2-(4-(2-Carboxypropyl)phenyl)propionateGenerator
Chemical FormulaC13H16O4
Average Molecular Weight236.2637
Monoisotopic Molecular Weight236.104859
IUPAC Name3-[4-(1-carboxyethyl)phenyl]-2-methylpropanoic acid
Traditional Name3-[4-(1-carboxyethyl)phenyl]-2-methylpropanoic acid
CAS Registry NumberNot Available
SMILES
CC(CC1=CC=C(C=C1)C(C)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C13H16O4/c1-8(12(14)15)7-10-3-5-11(6-4-10)9(2)13(16)17/h3-6,8-9H,7H2,1-2H3,(H,14,15)(H,16,17)
InChI KeyDIVLBIVDYADZPL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassPhenylpropanoic acids
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 2-phenylpropanoic-acid
  • 3-phenylpropanoic-acid
  • P-cymene
  • Aromatic monoterpenoid
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • Phenylpropane
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

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
logP2.29ALOGPS
logP2.78ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)3.97ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity62.42 m³·mol⁻¹ChemAxon
Polarizability24.7 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-029y-9000000000-c80bec974f28638c0ef3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kg-1910000000-67160596c417008327e9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-022m-9283000000-0efcd729a3f3c7d7edf2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ku-0890000000-09c6cf9139f4b24b5595View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014l-1920000000-840272a444f21fad8bd7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-1900000000-8142fc0197c65242ac9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0590000000-ef703bcd0ae31b3c6858View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000g-0920000000-6adff5ecdf1de0c84c84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xs-7900000000-13b3f512d747eb0400e9View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Ibuprofen Metabolism PathwayPw000566Pw000566 greyscalePw000566 simpleNot Available
Ibuprofen PathwayPw000131Pw000131 greyscalePw000131 simpleNot 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 IDDBMET00808
      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
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI ID133199
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Tan SC, Baker JA, Stevens N, deBiasi V, Salter C, Chalaux M, Afarinkia K, Hutt AJ: Synthesis, chromatographic resolution and chiroptical properties of carboxyibuprofen stereoisomers: major metabolites of ibuprofen in man. Chirality. 1997;9(1):75-87. [PubMed:9094205 ]