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Record Information
Version3.6
Creation Date2013-07-09 16:07:15 UTC
Update Date2016-02-11 08:15:26 UTC
HMDB IDHMDB60919
Secondary Accession NumbersNone
Metabolite Identification
Common NameIbuprofen glucuronide
DescriptionIbuprofen glucuronide 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
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-[2-[4-(2-methylpropyl)phenyl]propanoyloxy]oxane-2-carboxylic acidHMDB
1-(alpha-Methyl-4-(2-methylpropyl)benzeneacetate) b-D-glucopyranuronic acidHMDB
1-(alpha-Methyl-4-(2-methylpropyl)benzeneacetate) b-delta-glucopyranuronic acidHMDB
1-(alpha-Methyl-4-(2-methylpropyl)benzeneacetate) beta-D-glucopyranuronic acidHMDB
1-(alpha-Methyl-4-(2-methylpropyl)benzeneacetate) beta-delta-glucopyranuronic acidHMDB
Ibuprofen acyl glucuronideHMDB
Ibuprofen acyl-beta-D-glucuronideHMDB
Chemical FormulaC19H26O8
Average Molecular Weight382.4049
Monoisotopic Molecular Weight382.162767808
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-[4-(2-methylpropyl)phenyl]propanoyl}oxy)oxane-2-carboxylic acid
Traditional Nameibuprofen acyl glucuronide
CAS Registry NumberNot Available
SMILES
CC(C)CC1=CC=C(C=C1)C(C)C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
InChI Identifier
InChI=1/C19H26O8/c1-9(2)8-11-4-6-12(7-5-11)10(3)18(25)27-19-15(22)13(20)14(21)16(26-19)17(23)24/h4-7,9-10,13-16,19-22H,8H2,1-3H3,(H,23,24)/t10?,13-,14-,15+,16-,19-/s2
InChI KeyInChIKey=ABOLXXZAJIAUGR-JHRQLZMINA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassSugar acids and derivatives
Direct ParentO-glucuronides
Alternative Parents
Substituents
  • O-glucuronide
  • 1-o-glucuronide
  • Phenylacetate
  • Monoterpenoid
  • Monocyclic monoterpenoid
  • Aromatic monoterpenoid
  • P-cymene
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Phenylpropane
  • Beta-hydroxy acid
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • 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 Solubility1.59 mg/mLALOGPS
logP1.37ALOGPS
logP1.9ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.4ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.52 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity93.03 m3·mol-1ChemAxon
Polarizability39.5 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 QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00153
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 LinkHMDB60919
Metagene LinkHMDB60919
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available