ChemFOnt: Showing chemical card for Mycophenolate mofetil (CFc000009163)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:13 UTC

Chemfont ID

CFc000009163

Molecule Identification

Common Name

Mycophenolate mofetil

Definition

Mycophenolate mofetil is only found in individuals that have used or taken this drug. It is the 2-morpholinoethyl ester of mycophenolic acid (MPA), an immunosuppressive agent, inosine monophosphate dehydrogenase (IMPDH) inhibitor.Mycophenolate mofetil is hydrolyzed to form mycophenolic acid (MPA), which is the active metabolite. MPA 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, MPA has potent cytostatic effects on lymphocytes. MPA inhibits proliferative responses of T- and B-lymphocytes to both mitogenic and allospecific stimulation. Addition of guanosine or deoxyguanosine reverses the cytostatic effects of MPA on lymphocytes. MPA also suppresses antibody formation by B-lymphocytes. MPA 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. Mycophenolate mofetil did not inhibit early events in the activation of human peripheral blood mononuclear cells, such as the production of interleukin-1 (IL-1) and interleukin-2 (IL-2), but did block the coupling of these events to DNA synthesis and proliferation.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Morpholinoethyl (e)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoate	ChEBI
Cellcept	ChEBI
MMF	ChEBI
Mycophenolic acid morpholinoethyl ester	ChEBI
RS 61443	ChEBI
2-Morpholinoethyl (e)-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-5-phthalanyl)-4-methyl-4-hexenoic acid	Generator
Mycophenolate morpholinoethyl ester	Generator
Mycophenolic acid mofetil	Generator
Mycophenylate mofetil	HMDB
Mycophenolate sodium	HMDB
Myfortic	HMDB
Sodium mycophenolate	HMDB
Mycophenolate mofetil hydrochloride	HMDB
Mofetil hydrochloride, mycophenolate	HMDB
Mofetil, mycophenolate	HMDB
Mycophenolate, sodium	HMDB
Mycophenolic acid	HMDB

Chemical Formula

C₂₃H₃₁NO₇

Average Molecular Weight

433.4947

Monoisotopic Molecular Weight

433.210052351

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

Traditional Name

mycophenolate mofetil

CAS Registry Number

128794-94-5

SMILES

COC1=C(C\C=C(/C)CCC(=O)OCCN2CCOCC2)C(O)=C2C(=O)OCC2=C1C

InChI Identifier

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+

InChI Key

RTGDFNSFWBGLEC-SYZQJQIISA-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,.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isocoumarans

Sub Class

Isobenzofuranones

Direct Parent

Phthalides

Alternative Parents

Substituents

Phthalide
Anisole
Alkyl aryl ether
Fatty acid ester
Dicarboxylic acid or derivatives
Morpholine
Oxazinane
Fatty acyl
Benzenoid
Vinylogous acid
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary amine
Tertiary aliphatic amine
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Amine
Carbonyl group
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:8764 )
carboxylic ester (CHEBI:8764 )
phenols (CHEBI:8764 )
ether (CHEBI:8764 )
gamma-lactone (CHEBI:8764 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014826)

Source

Exogenous

Exogenous (HMDB: HMDB0014826)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Mycophenolic Acid Metabolism Pathway (PathBank: SMP0000652)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.095 g/L	ALOGPS
logP	2.17	ALOGPS
logP	3.47	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.76	ChemAxon
pKa (Strongest Basic)	6.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	94.53 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	117.1 m³·mol⁻¹	ChemAxon
Polarizability	45.55 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon