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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2013-06-15 16:53:40 UTC
Update Date2021-09-14 15:29:55 UTC
HMDB IDHMDB0060564
Secondary Accession Numbers
  • HMDB60564
Metabolite Identification
Common NameCarboxy-ibuprofen
DescriptionCarboxy-ibuprofen, also known as ibuprofen COOH, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Carboxy-ibuprofen is a weakly acidic compound (based on its pKa). carboxy-ibuprofen can be biosynthesized from 3-hydroxyibuprofen; which is mediated by the enzyme cytochrome P450 2C9. In humans, carboxy-ibuprofen is involved in ibuprofen metabolism pathway. 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. Carboxy-ibuprofen is a metabolite of ibuprofen. 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.
Structure
Data?1563866076
Synonyms
ValueSource
2,4'-(2-Carboxypropyl)phenylpropionic acidChEBI
2-(4-(2-Carboxypropyl)phenyl)propionic acidChEBI
Ibuprofen COOHChEBI
2,4'-(2-Carboxypropyl)phenylpropionateGenerator
2-(4-(2-Carboxypropyl)phenyl)propionateGenerator
Carboxy-ibuprofenChEBI
CarboxyibuprofenMeSH
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
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids 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
  • 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
Disposition

Biological location

Process

Naturally occurring process

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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+156.33631661259
DarkChem[M-H]-152.37631661259
DeepCCS[M+H]+153.14130932474
DeepCCS[M-H]-150.78330932474
DeepCCS[M-2H]-183.8230932474
DeepCCS[M+Na]+159.23430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Carboxy-ibuprofenCC(CC1=CC=C(C=C1)C(C)C(O)=O)C(O)=O3371.8Standard polar33892256
Carboxy-ibuprofenCC(CC1=CC=C(C=C1)C(C)C(O)=O)C(O)=O1837.4Standard non polar33892256
Carboxy-ibuprofenCC(CC1=CC=C(C=C1)C(C)C(O)=O)C(O)=O2005.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Carboxy-ibuprofen,1TMS,isomer #1CC(CC1=CC=C(C(C)C(=O)O[Si](C)(C)C)C=C1)C(=O)O1949.0Semi standard non polar33892256
Carboxy-ibuprofen,1TMS,isomer #2CC(CC1=CC=C(C(C)C(=O)O)C=C1)C(=O)O[Si](C)(C)C1964.8Semi standard non polar33892256
Carboxy-ibuprofen,2TMS,isomer #1CC(CC1=CC=C(C(C)C(=O)O[Si](C)(C)C)C=C1)C(=O)O[Si](C)(C)C1981.4Semi standard non polar33892256
Carboxy-ibuprofen,1TBDMS,isomer #1CC(CC1=CC=C(C(C)C(=O)O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O2200.5Semi standard non polar33892256
Carboxy-ibuprofen,1TBDMS,isomer #2CC(CC1=CC=C(C(C)C(=O)O)C=C1)C(=O)O[Si](C)(C)C(C)(C)C2235.6Semi standard non polar33892256
Carboxy-ibuprofen,2TBDMS,isomer #1CC(CC1=CC=C(C(C)C(=O)O[Si](C)(C)C(C)(C)C)C=C1)C(=O)O[Si](C)(C)C(C)(C)C2465.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Carboxy-ibuprofen EI-B (Non-derivatized)splash10-029y-9000000000-c80bec974f28638c0ef32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Carboxy-ibuprofen EI-B (Non-derivatized)splash10-029y-9000000000-c80bec974f28638c0ef32018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carboxy-ibuprofen GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kg-1910000000-67160596c417008327e92017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carboxy-ibuprofen GC-MS (2 TMS) - 70eV, Positivesplash10-022m-9283000000-0efcd729a3f3c7d7edf22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carboxy-ibuprofen GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Carboxy-ibuprofen 35V, Positive-QTOFsplash10-0006-0910000000-c2827168498a4962ac862021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carboxy-ibuprofen 35V, Negative-QTOFsplash10-00di-9100000000-5383e1959b406038f21a2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxy-ibuprofen 10V, Positive-QTOFsplash10-00ku-0890000000-09c6cf9139f4b24b55952016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxy-ibuprofen 20V, Positive-QTOFsplash10-014l-1920000000-840272a444f21fad8bd72016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxy-ibuprofen 40V, Positive-QTOFsplash10-00kb-1900000000-8142fc0197c65242ac9c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxy-ibuprofen 10V, Negative-QTOFsplash10-000i-0590000000-ef703bcd0ae31b3c68582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxy-ibuprofen 20V, Negative-QTOFsplash10-000g-0920000000-6adff5ecdf1de0c84c842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxy-ibuprofen 40V, Negative-QTOFsplash10-00xs-7900000000-13b3f512d747eb0400e92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxy-ibuprofen 10V, Positive-QTOFsplash10-014i-0890000000-661f246b92748cdf71ad2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxy-ibuprofen 20V, Positive-QTOFsplash10-015d-0920000000-78e23a387b076915da3e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxy-ibuprofen 40V, Positive-QTOFsplash10-0gb9-1900000000-da77016d411c40f246202021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxy-ibuprofen 10V, Negative-QTOFsplash10-000l-0790000000-6d8f4e25e001b41245122021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxy-ibuprofen 20V, Negative-QTOFsplash10-0002-0900000000-d35ab8e1327b17e568e92021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carboxy-ibuprofen 40V, Negative-QTOFsplash10-014i-0900000000-7aaf8622cd9f39155d7f2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal 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 Compound10444113
PDB IDNot Available
ChEBI ID133199
Food Biomarker OntologyNot Available
VMH IDCARIBUP_R
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]