CHEBI:168396 - mycophenolic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name mycophenolic acid
ChEBI ID CHEBI:168396
Definition A member of the class of 2-benzofurans that is 2-benzofuran-1(3H)-one which is substituted at positions 4, 5, 6, and 7 by methyl, methoxy, (2E)-5-carboxy-3-methylpent-2-en-1-yl, and hydroxy groups, respectively. It is an antibiotic produced by Penicillium brevi-compactum, P. stoloniferum, P. echinulatum and related species. An immunosuppressant, it is widely used (partiularly as its sodium salt and as the 2-(morpholin-4-yl)ethyl ester prodrug, mycophenolate mofetil) to prevent tissue rejection following organ transplants and for the treatment of certain autoimmune diseases.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:43973
Supplier Information
Save molfile Download Molfile
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C17H20O6
Net Charge 0
Average Mass 320.33710
Monoisotopic Mass 320.126
InChI InChI=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+
InChIKey HPNSFSBZBAHARI-RUDMXATFSA-N
SMILES COc1c(C)c2COC(=O)c2c(O)c1C\C=C(/C)CCC(O)=O
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): Penicillium metabolite
Any fungal metabolite produced during a metabolic reaction in Penicillium.
mycotoxin
Poisonous substance produced by fungi.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
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.
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.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing mycophenolic acid (CHEBI:168396) has functional parent hex-4-enoic acid (CHEBI:38355)
mycophenolic acid (CHEBI:168396) has role Penicillium metabolite (CHEBI:76964)
mycophenolic acid (CHEBI:168396) has role antimicrobial agent (CHEBI:33281)
mycophenolic acid (CHEBI:168396) has role antineoplastic agent (CHEBI:35610)
mycophenolic acid (CHEBI:168396) has role EC 1.1.1.205 (IMP dehydrogenase) inhibitor (CHEBI:53746)
mycophenolic acid (CHEBI:168396) has role environmental contaminant (CHEBI:78298)
mycophenolic acid (CHEBI:168396) has role immunosuppressive agent (CHEBI:35705)
mycophenolic acid (CHEBI:168396) has role mycotoxin (CHEBI:25442)
mycophenolic acid (CHEBI:168396) has role xenobiotic (CHEBI:35703)
mycophenolic acid (CHEBI:168396) is a γ-lactone (CHEBI:37581)
mycophenolic acid (CHEBI:168396) is a 2-benzofurans (CHEBI:38831)
mycophenolic acid (CHEBI:168396) is a monocarboxylic acid (CHEBI:25384)
mycophenolic acid (CHEBI:168396) is a phenols (CHEBI:33853)
mycophenolic acid (CHEBI:168396) is conjugate acid of mycophenolate (CHEBI:62932)
Incoming mycophenolate mofetil (CHEBI:8764) has functional parent mycophenolic acid (CHEBI:168396)
mycophenolic acid O-acyl-glucuronide (CHEBI:64689) has functional parent mycophenolic acid (CHEBI:168396)
mycophenolate (CHEBI:62932) is conjugate base of mycophenolic acid (CHEBI:168396)
IUPAC Name
(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoic acid
INNs Sources
acide mycophenolique ChemIDplus
acido micofenolico ChemIDplus
acidum mycophenolicum ChemIDplus
mycophenolic acid KEGG DRUG
Synonyms Sources
(E)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic acid ChemIDplus
Micofenolico acido ChemIDplus
Mycophenolate ChemIDplus
Mycophenolsäure ChemIDplus
Database Links Databases
D05096 KEGG DRUG
DB01024 DrugBank
MOA PDBeChem
Mycophenolic_acid Wikipedia
US4753935 Patent
View more database links
Registry Numbers Types Sources
24280-93-1 CAS Registry Number DrugBank
24280-93-1 CAS Registry Number ChemIDplus
24280-93-1 CAS Registry Number KEGG DRUG
318158 Reaxys Registry Number Reaxys
318158 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
11272311 PubMed citation Europe PMC
15470161 PubMed citation Europe PMC
16629948 PubMed citation Europe PMC
16640327 PubMed citation Europe PMC
17482154 PubMed citation Europe PMC
17498396 PubMed citation Europe PMC
18194117 PubMed citation Europe PMC
18611107 PubMed citation Europe PMC
18996104 PubMed citation Europe PMC
19689217 PubMed citation Europe PMC
Last Modified
13 November 2014