Record Information
Version3.6
Creation Date2008-09-15 17:19:14 UTC
Update Date2013-06-10 17:06:25 UTC
HMDB IDHMDB10334
Secondary Accession NumbersNone
Metabolite Identification
Common NameKetoprofen glucuronide
DescriptionKetoprofen glucuronide is a natural human metabolite of ketoprofen 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.
Structure
Thumb
Synonyms
  1. 1-(3-Benzoyl-alpha-methylbenzeneacetate) beta-D-glucopyranuronic acid
  2. 1-(3-Benzoyl-alpha-methylbenzeneacetate) beta-delta-glucopyranuronic acid
  3. DL-Ketoprofen glucuronide
  4. Ketoprofen glucuronide
Chemical FormulaC22H22O9
Average Molecular Weight430.4047
Monoisotopic Molecular Weight430.126382302
IUPAC Name(2S,3S,4S,5R,6S)-6-{[2-(3-benzoylphenyl)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional IUPAC Name(2S,3S,4S,5R,6S)-6-{[2-(3-benzoylphenyl)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry Number76690-94-3
SMILES
CC(C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C1=CC(=CC=C1)C(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C22H22O9/c1-11(13-8-5-9-14(10-13)15(23)12-6-3-2-4-7-12)21(29)31-22-18(26)16(24)17(25)19(30-22)20(27)28/h2-11,16-19,22,24-26H,1H3,(H,27,28)/t11?,16-,17-,18+,19-,22-/m0/s1
InChI KeyPBTXSZZKPHBHMA-LYFYOZKASA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassBenzophenones
Sub ClassN/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Diphenylmethanes
  • Glucuronic Acid Derivatives
  • Glucuronides
  • O-glycosyl Compounds
Substituents
  • 1,2 Diol
  • Benzoyl
  • Beta Hydroxy Acid
  • Carboxylic Acid
  • Carboxylic Acid Ester
  • Dicarboxylic Acid Derivative
  • Hexose Monosaccharide
  • Ketone
  • Oxane
  • Phenylacetate
  • Saccharide
  • Secondary Alcohol
  • Sugar Acid
Direct ParentBenzophenones
Ontology
StatusExpected and Not Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility0.6 g/LALOGPS
logP1.26ALOGPS
logP1.67ChemAxon
logS-2.9ALOGPS
pKa (strongest acidic)3.24ChemAxon
pKa (strongest basic)-3.7ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count8ChemAxon
hydrogen donor count4ChemAxon
polar surface area150.59ChemAxon
rotatable bond count7ChemAxon
refractivity104.81ChemAxon
polarizability42.93ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00589
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB027486
KNApSAcK IDNot Available
Chemspider ID116053
KEGG Compound IDNot Available
BioCyc IDBeta-D-Glucuronides
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB10334
Metagene LinkHMDB10334
METLIN IDNot Available
PubChem Compound131281
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
UGT2B28
Uniprot ID:
Q9BY64
Gene Name:
UGT2B4
Uniprot ID:
P06133
Gene Name:
UGT1A4
Uniprot ID:
P22310
Gene Name:
UGT2B7
Uniprot ID:
P16662
Gene Name:
UGT2B15
Uniprot ID:
P54855
Gene Name:
UGT2A1
Uniprot ID:
Q9Y4X1
Gene Name:
UGT1A1
Uniprot ID:
P22309
Gene Name:
UGT1A9
Uniprot ID:
O60656
Gene Name:
UGT1A3
Uniprot ID:
P35503
Gene Name:
UGT2B17
Uniprot ID:
O75795
Gene Name:
UGT1A6
Uniprot ID:
P19224
Gene Name:
UGT1A5
Uniprot ID:
P35504
Gene Name:
UGT2B11
Uniprot ID:
O75310
Gene Name:
GUSB
Uniprot ID:
P08236
Gene Name:
UGT2A3
Uniprot ID:
Q6UWM9
Gene Name:
UGT1A10
Uniprot ID:
Q5DT02
Gene Name:
UGT1A8
Uniprot ID:
Q5DSZ6