1-(alpha-Methyl-4-(2-methylpropyl)benzeneacetate)-beta-D-Glucopyranuronic acid (CHEM039586)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 18:00:50 UTC
Update Date2016-11-09 01:22:06 UTC
Accession NumberCHEM039586
Identification
Common Name1-(alpha-Methyl-4-(2-methylpropyl)benzeneacetate)-beta-D-Glucopyranuronic acid
ClassSmall Molecule
DescriptionIbuprofen-beta-D-glucuronide is a natural human metabolite of Ibuprofen generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Ibuprofen-b-D-glucuronideGenerator
Ibuprofen-β-D-glucuronideGenerator
(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
Ibuprofen acyl glucuronide, (R)-isomerHMDB
Ibuprofen acyl glucuronide, (S)-isomerHMDB
1-(a-Methyl-4-(2-methylpropyl)benzeneacetate)-b-D-glucopyranuronateGenerator
1-(a-Methyl-4-(2-methylpropyl)benzeneacetic acid)-b-D-glucopyranuronic acidGenerator
1-(alpha-Methyl-4-(2-methylpropyl)benzeneacetate)-beta-D-glucopyranuronateGenerator
1-(alpha-Methyl-4-(2-methylpropyl)benzeneacetic acid)-beta-D-glucopyranuronic acidGenerator
1-(Α-methyl-4-(2-methylpropyl)benzeneacetate)-β-D-glucopyranuronateGenerator
1-(Α-methyl-4-(2-methylpropyl)benzeneacetic acid)-β-D-glucopyranuronic acidGenerator
Chemical FormulaC19H26O8
Average Molecular Mass382.405 g/mol
Monoisotopic Mass382.163 g/mol
CAS Registry Number115075-59-7
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
SMILESCC(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 IdentifierInChI=1S/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-/m0/s1
InChI KeyABOLXXZAJIAUGR-JPMMFUSZSA-N
Chemical Taxonomy
Description 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 ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glucuronides
Alternative Parents
Substituents
  • 1-o-glucuronide
  • O-glucuronide
  • P-cymene
  • Aromatic monoterpenoid
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • Phenylpropane
  • Beta-hydroxy acid
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Monosaccharide
  • Benzenoid
  • Pyran
  • Oxane
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Acetal
  • Oxacycle
  • Polyol
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.59 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity93.03 m³·mol⁻¹ChemAxon
Polarizability39.5 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-07fu-8911000000-2dc2074267d41b490a39Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0aor-4900226000-f431985ff3b3d42b3fbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ap0-0944000000-bbc92191eed30be9a0a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-1921000000-71a3ad99af07efac05abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06s9-2900000000-e525ec23abd2c857f7d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a5i-1769000000-51e4a9238f7d6ffa854fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-3952000000-ec476851e7bdd9ccbaebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bu0-8940000000-86bb9bbc996839d2b68cSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0060919
FooDB IDFDB027495
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDBeta-D-Glucuronides
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID143793
ChEBI ID88735
PubChem Compound ID163959
Kegg Compound IDC03033
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available