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MetaCyc Compound: methotrexate

Chemical Formula: C20H20N8O5

Molecular Weight: 452.43 Daltons

Monoisotopic Molecular Weight: 454.1713158583 Daltons

methotrexate compound structure

SMILES: CN(CC1(C=NC2(=NC(N)=NC(N)=C(N=1)2)))C3(C=CC(=CC=3)C(=O)NC(CCC([O-])=O)C(=O)[O-])

InChI: InChI=1S/C20H22N8O5/c1-28(9-11-8-23-17-15(24-11)16(21)26-20(22)27-17)12-4-2-10(3-5-12)18(31)25-13(19(32)33)6-7-14(29)30/h2-5,8,13H,6-7,9H2,1H3,(H,25,31)(H,29,30)(H,32,33)(H4,21,22,23,26,27)/p-2


Unification Links: PubChem:25200568

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): 98.84417Inferred by computational analysis [Latendresse13]

Enzymes inhibited by methotrexate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: dihydrofolate reductase [Baccanari82], dihydrofolate reductase [Giladi03], dihydropteridine reductase [Comment 1] Inhibitor (Mechanism unknown) of: glutathione synthetase [Kato87], dihydrofolate reductase [Neuburger96], dihydrofolate reductase [Wilquet98]


Baccanari82: Baccanari DP, Daluge S, King RW (1982). "Inhibition of dihydrofolate reductase: effect of reduced nicotinamide adenine dinucleotide phosphate on the selectivity and affinity of diaminobenzylpyrimidines." Biochemistry 1982;21(20);5068-75. PMID: 6814484

Giladi03: Giladi M, Altman-Price N, Levin I, Levy L, Mevarech M (2003). "FolM, a new chromosomally encoded dihydrofolate reductase in Escherichia coli." J Bacteriol 185(23);7015-8. PMID: 14617668

Kato87: Kato H, Chihara M, Nishioka T, Murata K, Kimura A, Oda J (1987). "Homology of Escherichia coli B glutathione synthetase with dihydrofolate reductase in amino acid sequence and substrate binding site." J Biochem 101(1);207-15. PMID: 3553173

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Neuburger96: Neuburger M, Rebeille F, Jourdain A, Nakamura S, Douce R (1996). "Mitochondria are a major site for folate and thymidylate synthesis in plants." J Biol Chem 271(16);9466-72. PMID: 8621617

Vasudevan88: Vasudevan SG, Shaw DC, Armarego WL (1988). "Dihydropteridine reductase from Escherichia coli." Biochem J 1988;255(2);581-8. PMID: 3060113

Wilquet98: Wilquet V, Gaspar JA, van de Lande M, Van de Casteele M, Legrain C, Meiering EM, Glansdorff N (1998). "Purification and characterization of recombinant Thermotoga maritima dihydrofolate reductase." Eur J Biochem 1998;255(3);628-37. PMID: 9738902

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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