ChEMBL logo

ChEMBL

spacer
ChEMBL Statistics
  Loading Statistics...
spacer

Compound Report Card

Compound Name and Classification

Compound ID CHEMBL119
CHEMBL119
Compound Name TRIMETREXATE
ChEMBL Synonyms TRIMETREXATE GLUCURONATE | Neutrexin | CI-898 | NEUTREXIN | Trimetrexate
Max Phase 4 (Approved)
Trade Names NEUTREXIN
Molecular Formula C19H23N5O3

Additional synonyms for CHEMBL119 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES COc1cc(NCc2ccc3nc(N)nc(N)c3c2C)cc(OC)c1OC
Standard InChI InChI=1S/C19H23N5O3/c1-10-11(5-6-13-16(10)18(20)24-19(21)23- ...
Download InChI
Standard InChI Key NOYPYLRCIDNJJB-UHFFFAOYSA-N

Sources

  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL119

Molecule Features

CHEMBL119 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:N Parenteral:Y Topical:N Black Box:N Availability Type:Discontinued

Mechanism of Action

Mechanism of Action ChEMBL Target References
Dihydrofolate reductase inhibitor Dihydrofolate reductase DailyMed

Clinical Data

ClinicalTrials.gov TRIMETREXATE
The Cochrane Collaboration TRIMETREXATE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL119. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL2329 Dihydrofolate reductase Candida albicans 1.000
CHEMBL1926 Dihydrofolate reductase Pneumocystis carinii 1.000
CHEMBL2363 Dihydrofolate reductase Rattus norvegicus 1.000
CHEMBL2425 Dihydrofolate reductase Toxoplasma gondii 1.000
CHEMBL5457 Dihydrofolate reductase Mycobacterium avium 1.000
CHEMBL5441 Dihydrofolate reductase Escherichia coli 1.000
CHEMBL2902 Dihydrofolate reductase Lactobacillus casei 1.000
CHEMBL202 Dihydrofolate reductase Homo sapiens 1.000
CHEMBL1809 Dihydrofolate reductase Escherichia coli K-12 1.000
CHEMBL1681620 Dihydrofolate reductase Staphylococcus aureus 1.000
CHEMBL4564 Dihydrofolate reductase Mus musculus 1.000
CHEMBL2535 Glucose transporter Homo sapiens 0.980
CHEMBL1939 Dihydrofolate reductase Plasmodium falciparum K1 0.947
CHEMBL4203 Dual specificity protein kinase CLK4 Homo sapiens 0.810
CHEMBL2627 Dihydrofolate reductase type 1 Escherichia coli 0.792
CHEMBL3963 Dihydrofolate reductase Plasmodium berghei str. ANKA 0.500
CHEMBL3959 Quinone reductase 2 Homo sapiens 0.385
CHEMBL4045 AMP-activated protein kinase, alpha-1 subunit Homo sapiens 0.376
CHEMBL1952 Thymidylate synthase Homo sapiens 0.214



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2329 Dihydrofolate reductase Candida albicans 1.000
CHEMBL5441 Dihydrofolate reductase Escherichia coli 1.000
CHEMBL2363 Dihydrofolate reductase Rattus norvegicus 1.000
CHEMBL5457 Dihydrofolate reductase Mycobacterium avium 1.000
CHEMBL2902 Dihydrofolate reductase Lactobacillus casei 1.000
CHEMBL2425 Dihydrofolate reductase Toxoplasma gondii 1.000
CHEMBL202 Dihydrofolate reductase Homo sapiens 1.000
CHEMBL1926 Dihydrofolate reductase Pneumocystis carinii 1.000
CHEMBL1809 Dihydrofolate reductase Escherichia coli K-12 1.000
CHEMBL1681620 Dihydrofolate reductase Staphylococcus aureus 1.000
CHEMBL4564 Dihydrofolate reductase Mus musculus 1.000
CHEMBL4697 Hexose transporter 1 Plasmodium falciparum 1.000
CHEMBL2535 Glucose transporter Homo sapiens 1.000
CHEMBL3394 Tubulin beta chain Bos taurus 0.987
CHEMBL1939 Dihydrofolate reductase Plasmodium falciparum K1 0.930
CHEMBL4203 Dual specificity protein kinase CLK4 Homo sapiens 0.923
CHEMBL6194 Pteridine reductase 1 Leishmania major 0.855
CHEMBL3959 Quinone reductase 2 Homo sapiens 0.654
CHEMBL2627 Dihydrofolate reductase type 1 Escherichia coli 0.593
CHEMBL4375 Serine/threonine-protein kinase SRPK1 Homo sapiens 0.506

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
369.4 369.1801 2.78 6 117.54 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
8 3 0 8 5 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 8.09 1.76 .73 3 27 0.61

Structural Alerts

There are 1 structural alerts for CHEMBL119. To view alerts please click here.

Compound Cross References

ATC P - ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
P01 - ANTIPROTOZOALS
P01A - AGENTS AGAINST AMOEBIASIS AND OTHER PROTOZOAL DISEASES
P01AX - Other agents against amoebiasis and other protozoal diseases
P01AX07 - trimetrexate

ChemSpider ChemSpider:NOYPYLRCIDNJJB-UHFFFAOYSA-N
PubChem SID: 26755046 SID: 50110873
Wikipedia Trimetrexate

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL119



ACToR 52128-35-5
BindingDB 18268
DrugBank DB01157
DrugCentral 2757
EPA CompTox Dashboard DTXSID3023714
FDA SRS UPN4ITI8T4
Guide to Pharmacology 7613
Human Metabolome Database HMDB0015288
IBM Patent System 53221324344C6AEED8B40C70702CADEF
KEGG Ligand C11154
Nikkaji J22.060D
PharmGKB PA451790
PubChem 5583
PubChem: Drugs of the Future 12012739
PubChem: Thomson Pharma 14803927
SureChEMBL SCHEMBL3983
ZINC ZINC000000598852

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/NOYPYLRCIDNJJB-UHFFFAOYSA-N spacer
spacer