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Record Information
Version3.6
Creation Date2013-05-17 01:24:38 UTC
Update Date2017-08-15 23:26:38 UTC
HMDB IDHMDB0060491
Secondary Accession Numbers
  • HMDB60491
Metabolite Identification
Common NameMycophenolic acid O-acyl-glucuronide
DescriptionMycophenolic acid O-acyl-glucuronide is a metabolite of mycophenolate mofetil. Mycophenolate mofetil (MMF) (brand names CellCept, Myfortic) is an immunosuppressant and prodrug of mycophenolic acid, used extensively in transplant medicine. It is a reversible inhibitor of inosine monophosphate dehydrogenase (IMPDH) in purine biosynthesis which is necessary for the growth of T cells and B cells. Other cells are able to recover purines via a separate, scavenger, pathway and are, thus, able to escape the effect. MMF is a less toxic alternative to azathioprine. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
AcMPAGChEBI
Mycophenolic acid acyl glucuronideChEBI
Mycophenolic acid acyl-glucuronideChEBI
Mycophenolic acid-O-acyl-beta-D-glucopyranuronosideChEBI
Mycophenolate O-acyl-glucuronideGenerator
Mycophenolate acyl glucuronideGenerator
Mycophenolate acyl-glucuronideGenerator
Mycophenolate-O-acyl-b-D-glucopyranuronosideGenerator
Mycophenolate-O-acyl-beta-D-glucopyranuronosideGenerator
Mycophenolate-O-acyl-β-D-glucopyranuronosideGenerator
Mycophenolic acid-O-acyl-b-D-glucopyranuronosideGenerator
Mycophenolic acid-O-acyl-β-D-glucopyranuronosideGenerator
Chemical FormulaC23H28O12
Average Molecular Weight496.4612
Monoisotopic Molecular Weight496.15807636
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoyl]oxy}oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoyl]oxy}oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
COC1=C(C)C2=C(C(=O)OC2)C(O)=C1C\C=C(/C)CCC(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C23H28O12/c1-9(4-6-11-15(25)14-12(8-33-22(14)31)10(2)19(11)32-3)5-7-13(24)34-23-18(28)16(26)17(27)20(35-23)21(29)30/h4,16-18,20,23,25-28H,5-8H2,1-3H3,(H,29,30)/b9-4+/t16-,17-,18+,20-,23+/m0/s1
InChI KeyQBMSTEZXAMABFF-UEARNRKISA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentO-glucuronides
Alternative Parents
Substituents
  • 1-o-glucuronide
  • O-glucuronide
  • Isobenzofuranone
  • Phthalide
  • Isocoumaran
  • Tricarboxylic acid or derivatives
  • Anisole
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Fatty acid ester
  • Fatty acyl
  • Hydroxy acid
  • Benzenoid
  • Monosaccharide
  • Pyran
  • Oxane
  • Vinylogous acid
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Acetal
  • Organoheterocyclic compound
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Polyol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 Solubility0.72 mg/mLALOGPS
logP0.91ALOGPS
logP1.58ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.26ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area189.28 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity117.53 m3·mol-1ChemAxon
Polarizability49.24 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00662
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider ID8204343
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB0060491
      METLIN IDNot Available
      PubChem Compound10028772
      PDB IDNot Available
      ChEBI ID64689
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

      Enzymes

      General function:
      Not Available
      Specific function:
      Catalyzes the deglucuronidation of mycophenolic acid acyl-glucuronide, a metabolite of the immunosuppressant drug mycophenolate.
      Gene Name:
      ABHD10
      Uniprot ID:
      Q9NUJ1
      Molecular weight:
      33932.165
      Reactions
      Mycophenolic acid O-acyl-glucuronide + Water → Mycophenolic acid + D-Glucuronic aciddetails