Mycophenolic-acid

Mycophenolic acid (MPA) is a fungal natural product. Mycophenolic Acid is an antineoplastic antibiotic derived from various Penicillium fungal species. Mycophenolic acid is an active metabolite of the prodrug mycophenolate mofetil. Mycophenolic acid inhibits inosine monophosphate dehydrogenase (IMPDH), preventing the formation of guanosine monophosphate and synthesis of lymphocyte DNA that results in inhibition of lymphocyte proliferation, antibody production, cellular adhesion, and migration of T and B lymphocytes. Mycophenolic acid also has antibacterial, antifungal, and antiviral activities. In the compartmentalized biosynthesis of MPA, the acyl-coenzyme A (CoA) hydrolase MpaH' located in peroxisomes catalyzes the highly specific hydrolysis of MPA-CoA to produce the final product MPA

General

Type : Natural, Benzofuran

Chemical_Nomenclature : (E)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoic acid

Canonical SMILES : CC1=C2COC(=O)C2=C(C(=C1OC)CC=C(C)CCC(=O)O)O

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

Other name(s) : mycophenolic acid  ||  Mycophenolate  ||  Myfortic  ||  Melbex  ||  MPA  ||  MOA  ||  CHEMBL866  ||  CHEBI:168396  ||  SCHEMBL4549  ||  CHEBI:92545


MW : 320.3

Formula : C17H20O6

CAS_number : 24280-93-1

PubChem : 446541

UniChem : HPNSFSBZBAHARI-RUDMXATFSA-N

Target

Families : Mycophenolic-acid ligand of proteins in family
MpaH

Structure :
7DBL

Protein :
penbr-mpaH

References (2)

Title : Structural basis for substrate specificity of the peroxisomal acyl-CoA hydrolase MpaH' involved in mycophenolic acid biosynthesis - You_2021_FEBS.J_288_5768
Author(s) : You C , Li F , Zhang X , Ma L , Zhang YZ , Zhang W , Li S
Ref : Febs J , 288 :5768 , 2021
Abstract :
PubMedSearch : You_2021_FEBS.J_288_5768
PubMedID: 33843134
Gene_locus related to this paper: penbr-mpaH

Title : Mycophenolic Acid: a one hundred year odyssey from antibiotic to immunosuppressant -
Author(s) : Bentley R
Ref : Chem Rev , 100 :3801 , 2000
PubMedID: 11749328