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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-15 18:19:33 UTC
Update Date2021-09-14 14:58:56 UTC
HMDB IDHMDB0060634
Secondary Accession Numbers
  • HMDB60634
Metabolite Identification
Common NameMycophenolic acid glucuronide
DescriptionMycophenolic acid glucuronide belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Mycophenolic acid glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, mycophenolic acid glucuronide participates in a number of enzymatic reactions. In particular, mycophenolic acid glucuronide and uridine 5'-diphosphate can be biosynthesized from mycophenolic acid and uridine diphosphate glucuronic acid through its interaction with the enzymes UDP-glucuronosyltransferase 1-8 and UDP-glucuronosyltransferase 1-9. In addition, mycophenolic acid glucuronide and uridine 5'-diphosphate can be biosynthesized from mycophenolic acid and uridine diphosphate glucuronic acid; which is mediated by the enzymes UDP-glucuronosyltransferase 1-7 and UDP-glucuronosyltransferase 1-9. In humans, mycophenolic acid glucuronide is involved in mycophenolic acid metabolism pathway. Mycophenolic 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. MMF is a less toxic alternative to azathioprine. 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.
Structure
Data?1563866085
Synonyms
ValueSource
Mycophenolate glucuronideGenerator
MPAG CPDMeSH
Mycophenolic acid 7-O-glucuronideMeSH
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=1S/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 KeyBYFGTSAYQQIUCN-WTKPLQERSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • O-glycosyl compound
  • Isobenzofuranone
  • Phthalide
  • Isocoumaran
  • Tricarboxylic acid or derivatives
  • Anisole
  • Beta-hydroxy acid
  • Alkyl aryl ether
  • Pyran
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Carboxylic acid ester
  • Secondary alcohol
  • Lactone
  • Acetal
  • Ether
  • Carboxylic acid
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131769923
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available