pemetrexed   Click here for help

GtoPdb Ligand ID: 6837

Synonyms: Alimta® | LY-231514
Approved drug
pemetrexed is an approved drug (FDA (2004), EMA (2009))
Compound class: Synthetic organic
Comment: Inhibits dihydrofolate reductase, GAR transformylase and thymidylate synthase.
Marketed formulations may contain pemetrexed disodium (PubChem CID 46931002).
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 9
Hydrogen bond donors 6
Rotatable bonds 10
Topological polar surface area 191.26
Molecular weight 427.15
XLogP 0.49
No. Lipinski's rules broken 1
Click here for help
Canonical SMILES OC(=O)CCC(C(=O)O)NC(=O)c1ccc(cc1)CCc1c[nH]c2c1c(=O)nc([nH]2)N
Isomeric SMILES OC(=O)CC[C@H](C(=O)O)NC(=O)c1ccc(cc1)CCc1c[nH]c2c1c(=O)nc([nH]2)N
InChI InChI=1S/C20H21N5O6/c21-20-24-16-15(18(29)25-20)12(9-22-16)6-3-10-1-4-11(5-2-10)17(28)23-13(19(30)31)7-8-14(26)27/h1-2,4-5,9,13H,3,6-8H2,(H,23,28)(H,26,27)(H,30,31)(H4,21,22,24,25,29)/t13-/m1/s1
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
dihydrofolate reductase Primary target of this compound Hs Inhibitor Inhibition 8.1 pKi - 1-2
pKi 8.1 (Ki 7x10-9 M) [1-2]
thymidylate synthetase Hs Inhibitor Inhibition 7.0 pKi - 2
pKi 7.0 (Ki 1.09x10-7 M) [2]
phosphoribosylglycinamide formyltransferase, phosphoribosylglycinamide synthetase, phosphoribosylaminoimidazole synthetase Mm Inhibitor Inhibition 5.0 pKi - 2
pKi 5.0 (Ki 9.3x10-6 M) [2]