mycophenolic acid
(E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoic acid
Molecular Identity
mycophenolic acid
(E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoic acid
PubChem CID: 446541
Mycophenolic acid is 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. It has a role as an anticoronaviral agent, a mycotoxin, an antimicrobial agent, an antineoplastic agent, a xenobiotic, an immunosuppressive agent, an EC 1.1.1.205 (IMP dehydrogenase) inhibitor, a Penicillium metabolite and an environmental contaminant. It is a monocarboxylic acid, a member of phenols, a gamma-lactone and a member of 2-benzofurans. It is functionally related to a hex-4-enoic acid. It is a conjugate acid of a mycophenolate.
2D Structure
Properties
C17H20O6
Molecular Formula
320.30
Molecular Weight
g/mol
320.1260
Exact Mass
Da
3.2
XLogP
Drug-like (Lipinski: < 5)
93.1
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
6
H-Bond Acceptors
485
Complexity
SMILES
Canonical SMILES
SMILES: Synonyms(20)
mycophenolic acid24280-93-1MelbexMycophenolsaeureLilly-68618Acido micofenolicoAcide mycophenoliqueNSC-129185(4E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-4-methylhex-4-enoic acidMicofenolico acidoAcidum mycophenolicum(E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoic acidLy 68618(E)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic acidHU9DX48N0T
Data from PubChem (NCBI)
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