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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: methotrexate

Chemical Formula: C20H20N8O5

Molecular Weight: 452.43 Daltons

Monoisotopic Molecular Weight: 454.1713158583 Daltons

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

InChIKey: InChIKey=FBOZXECLQNJBKD-UHFFFAOYSA-L

Unification Links: PubChem:25200568

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 98.84417 Inferred 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]


References

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


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Fri Nov 28, 2014, BIOCYC14B.