CHEBI:8764 - mycophenolate mofetil

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name mycophenolate mofetil
ChEBI ID CHEBI:8764
Definition A carboxylic ester resulting from the formal condensation between the carboxylic acid group of mycophenolic acid and the hydroxy group of 2-(morpholin-4-yl)ethanol. In the liver, it is metabolised to mycophenolic acid, an immunosuppressant for which it is a prodrug. It is widely used to prevent tissue rejection following organ transplants as well as for the treatment of certain autoimmune diseases.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C23H31NO7
Net Charge 0
Average Mass 433.49470
Monoisotopic Mass 433.210
InChI InChI=1S/C23H31NO7/c1-15(5-7-19(25)30-13-10-24-8-11-29-12-9-24)4-6-17-21(26)20-18(14-31-23(20)27)16(2)22(17)28-3/h4,26H,5-14H2,1-3H3/b15-4+
InChIKey RTGDFNSFWBGLEC-SYZQJQIISA-N
SMILES COc1c(C)c2COC(=O)c2c(O)c1C\C=C(/C)CCC(=O)OCCN1CCOCC1
Roles Classification
Biological Role(s): immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
EC 1.1.1.205 (IMP dehydrogenase) inhibitor
An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of IMP dehydrogenase (EC 1.1.1.205), so blocking de novo biosynthesis of purine nucleotides.
Application(s): immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing mycophenolate mofetil (CHEBI:8764) has functional parent 2-(morpholin-4-yl)ethanol (CHEBI:67144)
mycophenolate mofetil (CHEBI:8764) has functional parent mycophenolic acid (CHEBI:168396)
mycophenolate mofetil (CHEBI:8764) has role EC 1.1.1.205 (IMP dehydrogenase) inhibitor (CHEBI:53746)
mycophenolate mofetil (CHEBI:8764) has role immunosuppressive agent (CHEBI:35705)
mycophenolate mofetil (CHEBI:8764) has role prodrug (CHEBI:50266)
mycophenolate mofetil (CHEBI:8764) is a γ-lactone (CHEBI:37581)
mycophenolate mofetil (CHEBI:8764) is a carboxylic ester (CHEBI:33308)
mycophenolate mofetil (CHEBI:8764) is a ether (CHEBI:25698)
mycophenolate mofetil (CHEBI:8764) is a phenols (CHEBI:33853)
mycophenolate mofetil (CHEBI:8764) is a tertiary amino compound (CHEBI:50996)
IUPAC Name
2-(morpholin-4-yl)ethyl (4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoate
Synonyms Sources
2-morpholinoethyl (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoate ChemIDplus
MMF ChEBI
mycophenolic acid morpholinoethyl ester ChemIDplus
RS 61443 KEGG COMPOUND
RS 61443 KEGG COMPOUND
Brand Name Source
Cellcept KEGG DRUG
Database Links Databases
1859 DrugCentral
C07908 KEGG COMPOUND
D00752 KEGG DRUG
DB00688 DrugBank
HMDB0014826 HMDB
Mycophenolate_mofetil Wikipedia
View more database links
Registry Numbers Types Sources
128794-94-5 CAS Registry Number ChemIDplus
7500599 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11099793 PubMed citation Europe PMC
11490743 PubMed citation Europe PMC
15572389 PubMed citation Europe PMC
15992049 PubMed citation Europe PMC
16979992 PubMed citation Europe PMC
19858585 PubMed citation Europe PMC
21180633 PubMed citation Europe PMC
21710356 PubMed citation Europe PMC
22081165 PubMed citation Europe PMC
22294686 PubMed citation Europe PMC
22310598 PubMed citation Europe PMC
22417996 PubMed citation Europe PMC
22460418 PubMed citation Europe PMC
22560143 PubMed citation Europe PMC
8826401 PubMed citation Europe PMC
9274835 PubMed citation Europe PMC
Last Modified
22 February 2017