Mycophenolic acid (CHEM002323)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (5)XML
Record Information
Version1.0
Creation Date2009-07-21 20:28:11 UTC
Update Date2026-05-14 16:56:08 UTC
Accession NumberCHEM002323
Identification
Common NameMycophenolic acid
ClassSmall Molecule
DescriptionMycophenolic acid is an an immunosuppresant drug and potent anti-proliferative, and can be used in place of the older anti-proliferative azathioprine. It is usually used as part of triple therapy including a calcineurin inhibitor (ciclosporin or tacrolimus) and prednisolone. It is also useful in research for the selection of animal cells that express the E. coli gene coding for XGPRT (xanthine guanine phosphoribosyltransferase).
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Antibiotic, Antineoplastic
  • Drug
  • Enzyme Inhibitor
  • Ester
  • Ether
  • Human Neurotoxin
  • Metabolite
  • Mycotoxin
  • Organic Compound
  • PFAS
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(e)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic acidChEBI
Acide mycophenoliqueChEBI
Acido micofenolicoChEBI
Acidum mycophenolicumChEBI
Micofenolico acidoChEBI
MycophenolateChEBI
MycophenolsaeureChEBI
(e)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoateGenerator
Mycophenoic acidHMDB
Acid, mycophenolicHMDB
CellceptHMDB
Mofetil hydrochloride, mycophenolateHMDB
Mofetil, mycophenolateHMDB
Mycophenolate sodiumHMDB
Mycophenolate, sodiumHMDB
Sodium mycophenolateHMDB
Mycophenolate mofetilHMDB
Mycophenolate mofetil hydrochlorideHMDB
Mycophenolic acid morpholinoethyl esterHMDB
MyforticHMDB
Chemical FormulaC17H20O6
Average Molecular Mass320.337 g/mol
Monoisotopic Mass320.126 g/mol
CAS Registry Number24280-93-1
IUPAC Name(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoic acid
Traditional Namemycophenolic acid
SMILESCOC1=C(C\C=C(/C)CCC(O)=O)C(O)=C2C(=O)OCC2=C1C
InChI IdentifierInChI=1S/C17H20O6/c1-9(5-7-13(18)19)4-6-11-15(20)14-12(8-23-17(14)21)10(2)16(11)22-3/h4,20H,5-8H2,1-3H3,(H,18,19)/b9-4+
InChI KeyHPNSFSBZBAHARI-RUDMXATFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phthalides. Phthalides are compounds containing a 3-hydrocarbylidene-2-benzofuran-1(3H)-one moiety,.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsocoumarans
Sub ClassIsobenzofuranones
Direct ParentPhthalides
Alternative Parents
Substituents
  • Phthalide
  • Anisole
  • Medium-chain fatty acid
  • Alkyl aryl ether
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Fatty acid
  • Benzenoid
  • Unsaturated fatty acid
  • Vinylogous acid
  • Carboxylic acid ester
  • Lactone
  • Ether
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Kidney
  • Liver
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point141°C
Boiling PointNot Available
SolubilityInsoluble
Predicted Properties
PropertyValueSource
Water Solubility0.036 g/LALOGPS
logP2.36ALOGPS
logP3.53ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)3.57ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity85.23 m³·mol⁻¹ChemAxon
Polarizability32.95 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bvm-0091000000-bb41ce2ccd5996f6c67cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-002b-3128900000-5379558b00ac276e7fc2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0udi-0019000000-01d925bb1f9079308d85Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4i-0091000000-22fc916594dbab851293Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4i-0940000000-84f4c65c2cd8b7358b78Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4i-0593000000-1fed07ad435ca0bd7249Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0udi-0249000000-bd1d2df9c9ae8a17841fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-002r-0490000000-99420edc8894323b59c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-0009000000-b99d88ff2ddeb6977c4aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-0149000000-ed6b854b4f9af495c8d8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0972000000-12d0e80f109d1fa6eb11Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0950000000-2e6c3543fe3f9f4e0790Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0930000000-e7a74fbe76e7141ec5f3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-022c-0910000000-27f7c0023a8b7e5b4d66Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-0009000000-4aba5ee4ba77899b36fbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-014i-0149000000-497b49ab395f3319c943Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0971000000-68634f04b665bb0e68a3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0006-0950000000-37f2ee0320d2ec560b93Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0f6x-0930000000-500359a3fd82c686ff99Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-006x-0900000000-6d04c3395aae26f88529Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-002r-0590000000-fe2f27357ba775714c5aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0169000000-8ac1fec528501fa1c885Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0rmi-4192000000-ec1fc3aacbfa34ce9caaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9250000000-93b72d09ba1c362a0809Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0039000000-c3557e0d3c1a6aeeb587Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0690-2197000000-4c49dc321b035b072f67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9381000000-0998ac034d01d840f5deSpectrum
Toxicity Profile
Route of ExposureBioavailability following oral administration of Myfortic delayed-release tablet ranges from 70-95%
Mechanism of ToxicityMycophenolic acid is a potent, selective, uncompetitive, and reversible inhibitor of inosine monophosphate dehydrogenase (IMPDH), and therefore inhibits the de novo pathway of guanosine nucleotide synthesis without incorporation into DNA. Because T- and B-lymphocytes are critically dependent for their proliferation on de novo synthesis of purines, whereas other cell types can utilize salvage pathways, mycophenolic acid has potent cytostatic effects on lymphocytes. Mycophenolic acid inhibits proliferative responses of T- and B-lymphocytes to both mitogenic and allospecific stimulation. Addition of guanosine or deoxyguanosine reverses the cytostatic effects of mycophenolic acid on lymphocytes. Mycophenolic acid also suppresses antibody formation by B-lymphocytes. Mycophenolic acid prevents the glycosylation of lymphocyte and monocyte glycoproteins that are involved in intercellular adhesion to endothelial cells and may inhibit recruitment of leukocytes into sites of inflammation and graft rejection.
MetabolismMycophenolic acid is metabolized mainly by glucuronyl transferase to glucuronidated metabolites, predominantly the phenolic glucuronide, mycophenolic acid glucuronide (MPAG). MPAG does not manifest pharmacological activity. The acyl glucuronide minor metabolite has pharmacological activity similar to mycophenolic acid. The AUC ratio of Mycophenolic acid:MPAG:acyl glucuronide is approximately 1:24:0.28 at steady state. Half Life: The mean elimination half-life for mycophenolic acid ranges from 8-16 hours, while that of the MPAG metabolite ranges from 13-17 hours.
Toxicity ValuesLD50: 352 mg/kg (Oral, Rat) (1) LD50: 1000 mg/kg (Oral, Mouse) (1) LD50: >6000 mg/kg (Oral, Rabbit) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the prophylaxis of organ rejection in patients receiving allogeneic renal transplants, administered in combination with cyclosporine and corticosteroids.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsPossible signs and symptoms of acute overdose could include the following: hematological abnormalities such as leukopenia and neutropenia, and gastrointestinal symptoms such as abdominal pain, diarrhea, nausea and vomiting, and dyspepsia.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01024
HMDB IDHMDB0015159
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDMOA
Wikipedia LinkMycophenolic_acid
Chemspider ID393865
ChEBI ID168396
PubChem Compound ID446541
Kegg Compound IDC20380
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Bernard J. Abbott, John G. Whitney, “Method of preparing mycophenolic acid glucoside.” U.S. Patent US4234684, issued January, 1976.

MSDSLink
General References
1. Woodroffe R, Yao GL, Meads C, Bayliss S, Ready A, Raftery J, Taylor RS: Clinical and cost-effectiveness of newer immunosuppressive regimens in renal transplantation: a systematic review and modelling study. Health Technol Assess. 2005 May;9(21):1-179, iii-iv.
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11272311
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15470161
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=16629948
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=16640327
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=17482154
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=17498396
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=18194117
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=18611107
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=18996104
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=19689217