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Record Information
Version3.6
Creation Date2013-06-15 18:19:33 UTC
Update Date2016-02-11 08:09:44 UTC
HMDB IDHMDB60634
Secondary Accession NumbersNone
Metabolite Identification
Common NameMycophenolic acid glucuronide
DescriptionMycophenolic acid 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
SynonymsNot Available
Chemical FormulaC23H28O12
Average Molecular Weight496.4612
Monoisotopic Molecular Weight496.15807636
IUPAC Name6-({5-[(2Z)-5-carboxy-3-methylpent-2-en-1-yl]-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name6-({5-[(2Z)-5-carboxy-3-methylpent-2-en-1-yl]-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
COC1=C(C)C2=C(C(=O)OC2)C(OC2OC(C(O)C(O)C2O)C(O)=O)=C1C\C=C(\C)CCC(O)=O
InChI Identifier
InChI=1/C23H28O12/c1-9(5-7-13(24)25)4-6-11-18(32-3)10(2)12-8-33-22(31)14(12)19(11)34-23-17(28)15(26)16(27)20(35-23)21(29)30/h4,15-17,20,23,26-28H,5-8H2,1-3H3,(H,24,25)(H,29,30)/b9-4-
InChI KeyInChIKey=BYFGTSAYQQIUCN-WTKPLQERNA-N
Chemical Taxonomy
ClassificationNot classified
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 Solubility0.89 mg/mLALOGPS
logP0.3ALOGPS
logP0.93ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)2.74ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area189.28 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity117.25 m3·mol-1ChemAxon
Polarizability47.96 Å3ChemAxon
Number of Rings3ChemAxon
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 IDDBMET00916
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 LinkHMDB60634
Metagene LinkHMDB60634
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