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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2013-06-15 16:53:44 UTC
Update Date2021-09-14 15:45:17 UTC
HMDB IDHMDB0060565
Secondary Accession Numbers
  • HMDB60565
Metabolite Identification
Common Name1-Hydroxyibuprofen
Description1-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
Data?1563866076
SynonymsNot Available
Chemical FormulaC13H18O3
Average Molecular Weight222.2802
Monoisotopic Molecular Weight222.125594442
IUPAC Name2-[4-(1-hydroxy-2-methylpropyl)phenyl]propanoic acid
Traditional Name2-[4-(1-hydroxy-2-methylpropyl)phenyl]propanoic acid
CAS Registry NumberNot Available
SMILES
CC(C)C(O)C1=CC=C(C=C1)C(C)C(O)=O
InChI Identifier
InChI=1S/C13H18O3/c1-8(2)12(14)11-6-4-10(5-7-11)9(3)13(15)16/h4-9,12,14H,1-3H3,(H,15,16)
InChI KeyRMOQYHYFRKTDRI-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
  • P-cymene
  • Aromatic monoterpenoid
  • Monoterpenoid
  • Monocyclic monoterpenoid
  • Phenylpropane
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organooxygen compound
  • Aromatic alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • 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 Solubility0.51 g/LALOGPS
logP2.47ALOGPS
logP2.69ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)4.55ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity62.17 m³·mol⁻¹ChemAxon
Polarizability24.64 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]+152.64331661259
DarkChem[M-H]-150.92631661259
DeepCCS[M+H]+152.74630932474
DeepCCS[M-H]-150.38830932474
DeepCCS[M-2H]-183.94430932474
DeepCCS[M+Na]+158.94330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-HydroxyibuprofenCC(C)C(O)C1=CC=C(C=C1)C(C)C(O)=O3316.9Standard polar33892256
1-HydroxyibuprofenCC(C)C(O)C1=CC=C(C=C1)C(C)C(O)=O1738.8Standard non polar33892256
1-HydroxyibuprofenCC(C)C(O)C1=CC=C(C=C1)C(C)C(O)=O1792.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-Hydroxyibuprofen,1TMS,isomer #1CC(C(=O)O)C1=CC=C(C(O[Si](C)(C)C)C(C)C)C=C11788.7Semi standard non polar33892256
1-Hydroxyibuprofen,1TMS,isomer #2CC(C(=O)O[Si](C)(C)C)C1=CC=C(C(O)C(C)C)C=C11814.6Semi standard non polar33892256
1-Hydroxyibuprofen,2TMS,isomer #1CC(C(=O)O[Si](C)(C)C)C1=CC=C(C(O[Si](C)(C)C)C(C)C)C=C11790.1Semi standard non polar33892256
1-Hydroxyibuprofen,1TBDMS,isomer #1CC(C(=O)O)C1=CC=C(C(O[Si](C)(C)C(C)(C)C)C(C)C)C=C12067.1Semi standard non polar33892256
1-Hydroxyibuprofen,1TBDMS,isomer #2CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(C(O)C(C)C)C=C12079.7Semi standard non polar33892256
1-Hydroxyibuprofen,2TBDMS,isomer #1CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(C(O[Si](C)(C)C(C)(C)C)C(C)C)C=C12254.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-Hydroxyibuprofen GC-MS (Non-derivatized) - 70eV, Positivesplash10-003f-3900000000-d627e94eac15f3611bdf2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Hydroxyibuprofen GC-MS (2 TMS) - 70eV, Positivesplash10-05ic-9173000000-f7072ba58ae502c6792f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Hydroxyibuprofen 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 - 1-Hydroxyibuprofen 10V, Positive-QTOFsplash10-0a4i-0490000000-01a67313138061083c4a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxyibuprofen 20V, Positive-QTOFsplash10-0a4i-1930000000-7cf2dc02a84f96e83c6c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxyibuprofen 40V, Positive-QTOFsplash10-0pc0-3900000000-2a098a67b36af13d126a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxyibuprofen 10V, Negative-QTOFsplash10-00di-0390000000-4990bd9c561ddedb88132017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxyibuprofen 20V, Negative-QTOFsplash10-05i0-0950000000-795aa4686b1320e66e3d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxyibuprofen 40V, Negative-QTOFsplash10-0a6r-7900000000-ad8c4f5d595fd15516e52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxyibuprofen 10V, Negative-QTOFsplash10-00di-0190000000-38098f72da632f1549482021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxyibuprofen 20V, Negative-QTOFsplash10-0a6r-0920000000-9d98bdc8d63bf137688f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxyibuprofen 40V, Negative-QTOFsplash10-0a4i-5900000000-25ac6d7d6c239231541f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxyibuprofen 10V, Positive-QTOFsplash10-0a4i-0890000000-34bec3d9fec40ffc684a2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxyibuprofen 20V, Positive-QTOFsplash10-0bu9-0930000000-3340e057c4521ddccb5b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Hydroxyibuprofen 40V, Positive-QTOFsplash10-0a4i-2900000000-3e52998a12ad24bea05b2021-10-12Wishart 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
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
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 Compound45117195
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 ReferencesNot Available

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
1-Hydroxyibuprofen → 2-{4-[2-methyl-1-(sulfooxy)propyl]phenyl}propanoic aciddetails
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
1-Hydroxyibuprofen → 6-{1-[4-(1-carboxyethyl)phenyl]-2-methylpropoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
1-Hydroxyibuprofen → 3,4,5-trihydroxy-6-({2-[4-(1-hydroxy-2-methylpropyl)phenyl]propanoyl}oxy)oxane-2-carboxylic aciddetails