METHOTREXATE

/static/temp/default.svg Search structure
Trade Names
Synonyms
Status
Molecule Category Free-form
ATC L01BA01 L04AX03
UNII YL5FZ2Y5U1
EPA CompTox DTXSID4020822

Structure

InChI Key FBOZXECLQNJBKD-ZDUSSCGKSA-N
Smiles CN(Cc1cnc2nc(N)nc(N)c2n1)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1
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)/t13-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C20H22N8O5
Molecular Weight 454.45
AlogP 0.27
Hydrogen Bond Acceptor 10.0
Hydrogen Bond Donor 5.0
Number of Rotational Bond 9.0
Polar Surface Area 210.54
Molecular species ACID
Aromatic Rings 3.0
Heavy Atoms 33.0

Metabolites Network

visNetwork

Pharmacology

Mechanism of Action Action Reference
Dihydrofolate reductase inhibitor INHIBITOR DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Ligase
- 10 - - -
Enzyme Oxidoreductase
- 0.6-880 0.023-140 5.62e-09-330 1.2e-09-91
Enzyme Transferase
- 0-10 - 600 8e-05-0.00015
Enzyme
- 0.6-880 0.023-140 5.62e-09-330 1.2e-09-91
Membrane receptor
- 106-461 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC19 family of vitamin transporters
- 12-12 - - 60
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - -13.4-27.4
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 26.3
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC46 family of folate transporters
- 120.5-121 - - -
Unclassified protein
- - 24-500 - -
EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Babesia gibsoni
- 68.6 - - -
Bacillus anthracis
- 12.2-15 - - -
Bos taurus
- 1.3-80 - - -
Chlorocebus sabaeus
- 9.2 - - -
Columba livia
- 26-26 - - -
Cricetulus griseus
- 12-461 - - -
Enterococcus faecium
- 0.3-90 - - 1.2e-09-0.15
Escherichia coli
- 2.2-32 0.023-140 0.001-330 -
Gallus gallus
- 19-90 - - -
Homo sapiens
4.5-985 0-990 24-500 0.00034-880 -13.4-102
Lactobacillus casei
- 2e-05-560 - 0.004 1e-08-0.005
Leishmania
- - - 180 -
Leishmania major
- - - 0.1288-39 -
Mus musculus
3.2 0.005-223 - 0.003-0.006 38-98
Mycobacterium avium
- 0.22 - - -
Mycobacterium smegmatis
- - - 0.35 -
Mycobacterium tuberculosis
- 8.25-35 - - -
Mycobacterium tuberculosis H37Rv
- 8.8 - - -
Pediococcus
- 400 - - -
Plasmodium falciparum
- 0.04-84.89 - - -
Plasmodium falciparum 7G8
- 0.11-100 - - -
Plasmodium falciparum D10
- 0.04-31.62 - - -
Plasmodium falciparum HB3
- 0.07-79.43 - - -
Plasmodium falciparum VS/1
- 63 - - -
Pneumocystis carinii
- 1-880 - 0.008 -
Pneumocystis jirovecii
- 5.1 - - -
Rattus norvegicus
- 2.5-85 - 0.073 -
Staphylococcus aureus
- - - 1 -
Toxoplasma gondii
- 1.4-78.3 - - -
Trypanosoma brucei
- - - 152 -
Trypanosoma brucei brucei
- 11 - - -
Trypanosoma cruzi
- - - 0.038 -
Zika virus
280 - - - -
pediococcus cerevisiae
- - - - 190

Target Conservation

Protein: Dihydrofolate reductase
Description: Dihydrofolate reductase
Organism : Homo sapiens
P00374 ENSG00000228716

Related Entries

Cross References

Resources Reference
ChEBI 44185
ChEMBL CHEMBL34259
DrugBank DB00563
DrugCentral 1751
FDA SRS YL5FZ2Y5U1
Human Metabolome Database HMDB0014703
Guide to Pharmacology 4674
KEGG C01937
PDB MTX
PharmGKB PA450428
PubChem 126941
SureChEMBL SCHEMBL3711
ZINC ZINC000001529323
CONTENTS