Human Metabolome Database Version 3.5

Showing metabocard for 1-(alpha-Methyl-4-(2-methylpropyl)benzeneacetate)-beta-D-Glucopyranuronic acid (HMDB10343)

Record Information
Version 3.5
Creation Date 2008-09-15 11:42:30 -0600
Update Date 2013-02-08 17:24:37 -0700
HMDB ID HMDB10343
Secondary Accession Numbers None
Metabolite Identification
Common Name 1-(alpha-Methyl-4-(2-methylpropyl)benzeneacetate)-beta-D-Glucopyranuronic acid
Description Ibuprofen acyl 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.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-[4-(2-methylpropyl)phenyl]propanoyloxy]oxane-2-carboxylic acid
  2. 1-(alpha-Methyl-4-(2-methylpropyl)benzeneacetate) b-D-Glucopyranuronic acid
  3. 1-(alpha-Methyl-4-(2-methylpropyl)benzeneacetate) b-delta-Glucopyranuronic acid
  4. 1-(alpha-Methyl-4-(2-methylpropyl)benzeneacetate) beta-D-Glucopyranuronic acid
  5. 1-(alpha-Methyl-4-(2-methylpropyl)benzeneacetate) beta-delta-Glucopyranuronic acid
  6. Ibuprofen acyl glucuronide
  7. Ibuprofen acyl-beta-D-glucuronide
Chemical Formula C19H26O8
Average Molecular Weight 382.4049
Monoisotopic Molecular Weight 382.162767808
IUPAC Name (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-[4-(2-methylpropyl)phenyl]propanoyl}oxy)oxane-2-carboxylic acid
Traditional IUPAC Name (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-({2-[4-(2-methylpropyl)phenyl]propanoyl}oxy)oxane-2-carboxylic acid
CAS Registry Number 115075-59-7
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=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 Key ABOLXXZAJIAUGR-JPMMFUSZSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Prenol Lipids
Sub Class Terpene Glycosides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • Aromatic Monoterpene
  • Beta Hydroxy Acid
  • Carboxylic Acid
  • Carboxylic Acid Ester
  • Dicarboxylic Acid Derivative
  • Glucuronic Acid Or Derivative
  • Glycosyl Compound
  • Hexose Monosaccharide
  • O Glycosyl Compound
  • Oxane
  • P Cymene
  • Phenylacetate
  • Saccharide
  • Secondary Alcohol
  • Sugar Acid
Direct Parent Terpene Glycosides
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Waste products
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1.59 g/L ALOGPS
LogP 1.37 ALOGPS
LogP 1.9 ChemAxon
LogS -2.38 ALOGPS
pKa (strongest acidic) 3.4 ChemAxon
pKa (strongest basic) -3.7 ChemAxon
Hydrogen Acceptor Count 7 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 133.52 A2 ChemAxon
Rotatable Bond Count 7 ChemAxon
Refractivity 93.03 ChemAxon
Polarizability 39.5 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
13.0 (0.26-26.16) uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB027495
KNApSAcK ID Not Available
Chemspider ID 143793 Link_out
KEGG Compound ID C03033 Link_out
BioCyc ID Beta-D-Glucuronides Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB10343 Link_out
Metagene Link HMDB10343 Link_out
METLIN ID Not Available
PubChem Compound 163959 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Castillo M, Lam YW, Dooley MA, Stahl E, Smith PC: Disposition and covalent binding of ibuprofen and its acyl glucuronide in the elderly. Clin Pharmacol Ther. 1995 Jun;57(6):636-44. Pubmed: 7781263 Link_out
  2. Castillo M, Smith PC: Disposition and reactivity of ibuprofen and ibufenac acyl glucuronides in vivo in the rhesus monkey and in vitro with human serum albumin. Drug Metab Dispos. 1995 May;23(5):566-72. Pubmed: 7587932 Link_out
  3. Castillo M, Smith PC: Direct determination of ibuprofen and ibuprofen acyl glucuronide in plasma by high-performance liquid chromatography using solid-phase extraction. J Chromatogr. 1993 Apr 21;614(1):109-16. Pubmed: 8496270 Link_out

Enzymes
Name: UDP-glucuronosyltransferase 2B28
Reactions: Not Available
Gene Name: UGT2B28
Uniprot ID: Q9BY64 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B4
Reactions: Not Available
Gene Name: UGT2B4
Uniprot ID: P06133 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-4
Reactions: Not Available
Gene Name: UGT1A4
Uniprot ID: P22310 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B7
Reactions: Not Available
Gene Name: UGT2B7
Uniprot ID: P16662 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B15
Reactions: Not Available
Gene Name: UGT2B15
Uniprot ID: P54855 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2A1
Reactions: Not Available
Gene Name: UGT2A1
Uniprot ID: Q9Y4X1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-1
Reactions: Not Available
Gene Name: UGT1A1
Uniprot ID: P22309 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-9
Reactions: Not Available
Gene Name: UGT1A9
Uniprot ID: O60656 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-3
Reactions: Not Available
Gene Name: UGT1A3
Uniprot ID: P35503 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B17
Reactions: Not Available
Gene Name: UGT2B17
Uniprot ID: O75795 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-6
Reactions: Not Available
Gene Name: UGT1A6
Uniprot ID: P19224 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-5
Reactions: Not Available
Gene Name: UGT1A5
Uniprot ID: P35504 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B11
Reactions: Not Available
Gene Name: UGT2B11
Uniprot ID: O75310 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-glucuronidase
Reactions: Not Available
Gene Name: GUSB
Uniprot ID: P08236 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2A3
Reactions: Not Available
Gene Name: UGT2A3
Uniprot ID: Q6UWM9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: HCG2039726, isoform CRA_f
Reactions: Not Available
Gene Name: UGT1A10
Uniprot ID: Q5DT02 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: HCG2039726, isoform CRA_e
Reactions: Not Available
Gene Name: UGT1A8
Uniprot ID: Q5DSZ6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP glycosyltransferase 1 family polypeptide A7
Reactions: Not Available
Gene Name: UGT1A7
Uniprot ID: Q5DSZ7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA