emvododstat   Click here for help

GtoPdb Ligand ID: 11421

Synonyms: PTC-299 | PTC299
Compound class: Synthetic organic
Comment: Emvododstat (PTC299) is an orally bioavailable inhibitor of dihydroorotate dehydrogenase (DHODH) that was developed by PTC Therapeutics [1] for anti-cancer potential. It inhibits de novo pyrimidine nucleotide (UMP) biosynthesis and exhibits broad activity against leukemia in vitro and in vivo.

SARS-CoV-2: Emvododstat inhibits replication of SARS-CoV-2 in vitro (EC50 2.0-31.6 nM) and other RNA viruses [2]. It blocks production of inflammatory cytokines in infected cell cultures.
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 54.56
Molecular weight 466.09
XLogP 6.27
No. Lipinski's rules broken 1
Click here for help
Canonical SMILES COc1ccc(cc1)[C@@H]1N(CCc2c1[nH]c1c2cc(cc1)Cl)C(=O)Oc1ccc(cc1)Cl
Isomeric SMILES COc1ccc(cc1)[C@@H]1N(CCc2c1[nH]c1c2cc(cc1)Cl)C(=O)Oc1ccc(cc1)Cl
InChI InChI=1S/C25H20Cl2N2O3/c1-31-18-7-2-15(3-8-18)24-23-20(21-14-17(27)6-11-22(21)28-23)12-13-29(24)25(30)32-19-9-4-16(26)5-10-19/h2-11,14,24,28H,12-13H2,1H3/t24-/m0/s1
1. Cao L, Weetall M, Trotta C, Cintron K, Ma J, Kim MJ, Furia B, Romfo C, Graci JD, Li W et al.. (2019)
Targeting of Hematologic Malignancies with PTC299, A Novel Potent Inhibitor of Dihydroorotate Dehydrogenase with Favorable Pharmaceutical Properties.
Mol Cancer Ther, 18 (1): 3-16. [PMID:30352802]
2. Luban J, Sattler RA, Mühlberger E, Graci JD, Cao L, Weetall M, Trotta C, Colacino JM, Bavari S, Strambio-De-Castillia C et al.. (2021)
The DHODH inhibitor PTC299 arrests SARS-CoV-2 replication and suppresses induction of inflammatory cytokines.
Virus Res, 292: 198246. [PMID:33249060]