mycophenolate mofetil   Click here for help

GtoPdb Ligand ID: 6831

Synonyms: Cellcept® | RS-61443 | RS-61443-190
Approved drug Immunopharmacology Ligand
mycophenolate mofetil is an approved drug (FDA (1995), EMA (1996))
Compound class: Synthetic organic
Comment: Inhibits inosine-5'-monophosphate dehydrogenase (IMPDH)
2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 10
Topological polar surface area 94.53
Molecular weight 433.21
XLogP 1.98
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES COc1c(CC=C(CCC(=O)OCCN2CCOCC2)C)c(O)c2c(c1C)COC2=O
Isomeric SMILES COc1c(C/C=C(/CCC(=O)OCCN2CCOCC2)\C)c(O)c2c(c1C)COC2=O
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+
InChI Key RTGDFNSFWBGLEC-SYZQJQIISA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1995), EMA (1996))
Is prodrug? Yes
Active form mycophenolic acid
IUPAC Name Click here for help
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 Click here for help
Cellcept® | RS-61443 | RS-61443-190
Database Links Click here for help
CAS Registry No. 128794-94-5
ChEMBL Ligand CHEMBL1456
DrugBank Ligand DB00688
DrugCentral Ligand 1859
GtoPdb PubChem SID 178103437
Immunopaedia Search mycophenolate mofetil
PubChem CID 5281078
Search Google for chemical match using the InChIKey RTGDFNSFWBGLEC-SYZQJQIISA-N
Search Google for chemicals with the same backbone RTGDFNSFWBGLEC
UniChem Compound Search for chemical match using the InChIKey RTGDFNSFWBGLEC-SYZQJQIISA-N
UniChem Connectivity Search for chemical match using the InChIKey RTGDFNSFWBGLEC-SYZQJQIISA-N
Wikipedia Mycophenolate_mofetil