Ligand id: 4815

Name: methotrexate

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: methotrexate

Structure and Physico-chemical Properties

2D Structure
Click here for structure editor
Calculated Physico-chemical Properties
Hydrogen bond acceptors 13
Hydrogen bond donors 5
Rotatable bonds 10
Topological polar surface area 210.54
Molecular weight 454.17
XLogP -2.67
No. Lipinski's rules broken 1

Molecular properties generated using the CDK

1. Cronstein BN. (2005)
Low-dose methotrexate: a mainstay in the treatment of rheumatoid arthritis.
Pharmacol. Rev., 57 (2): 163-72. [PMID:15914465]
2. Dervieux T, Furst D, Lein DO, Capps R, Smith K, Walsh M, Kremer J. (2004)
Polyglutamation of methotrexate with common polymorphisms in reduced folate carrier, aminoimidazole carboxamide ribonucleotide transformylase, and thymidylate synthase are associated with methotrexate effects in rheumatoid arthritis.
Arthritis Rheum., 50 (9): 2766-74. [PMID:15457444]
3. Lee YH, Bae SC. (2016)
Association of the ATIC 347 C/G polymorphism with responsiveness to and toxicity of methotrexate in rheumatoid arthritis: a meta-analysis.
Rheumatol. Int., 36 (11): 1591-1599. [PMID:27379764]
4. Qiu A, Jansen M, Sakaris A, Min SH, Chattopadhyay S, Tsai E, Sandoval C, Zhao R, Akabas MH, Goldman ID. (2006)
Identification of an intestinal folate transporter and the molecular basis for hereditary folate malabsorption.
Cell, 127 (5): 917-28. [PMID:17129779]
5. Rosowsky A, Forsch RA, Wright JE. (2004)
Synthesis and in vitro antifolate activity of rotationally restricted aminopterin and methotrexate analogues.
J. Med. Chem., 47 (27): 6958-63. [PMID:15615544]
6. Rosowsky A, Mota CE, Queener SF, Waltham M, Ercikan-Abali E, Bertino JR. (1995)
2,4-Diamino-5-substituted-quinazolines as inhibitors of a human dihydrofolate reductase with a site-directed mutation at position 22 and of the dihydrofolate reductases from Pneumocystis carinii and Toxoplasma gondii.
J. Med. Chem., 38 (5): 745-52. [PMID:7877140]
7. Zhong W, Zhao L, Liu T, Jiang Z. (2017)
IL-22-producing CD4+T cells in the treatment response of rheumatoid arthritis to combination therapy with methotrexate and leflunomide.
Sci Rep, 7: 41143. [PMID:28117352]