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).
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2D Structure
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Physico-chemical Properties
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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
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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
1. Gangjee A, Zeng Y, McGuire JJ, Kisliuk RL. (2005)
Synthesis of classical, four-carbon bridged 5-substituted furo[2,3-d]pyrimidine and 6-substituted pyrrolo[2,3-d]pyrimidine analogues as antifolates.
J Med Chem, 48 (16): 5329-36. [PMID:16078850]
2. Shih C, Habeck LL, Mendelsohn LG, Chen VJ, Schultz RM. (1998)
Multiple folate enzyme inhibition: mechanism of a novel pyrrolopyrimidine-based antifolate LY231514 (MTA).
Adv Enzyme Regul, 38: 135-52. [PMID:9762351]