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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL119
CHEMBL119
Compound Name TRIMETREXATE
ChEMBL Synonyms CI-898 | Neutrexin | Trimetrexate | Trimetrexate Glucuronate
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

Mechanism of Action

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

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

Clinical Data

Number of clinical trials registered at clinicaltrials.gov
Number of reviews at The Cochrane Collaboration
Number of entries at British National Formulary

Structural Alerts

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

Alternate Forms of Compound in ChEMBL


CHEMBL119

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
CHEMBL2902 Dihydrofolate reductase Lactobacillus casei 1.000
CHEMBL1809 Dihydrofolate reductase Escherichia coli K-12 1.000
CHEMBL5441 Dihydrofolate reductase Escherichia coli 1.000
CHEMBL5457 Dihydrofolate reductase Mycobacterium avium 1.000
CHEMBL1926 Dihydrofolate reductase Pneumocystis carinii 1.000
CHEMBL202 Dihydrofolate reductase Homo sapiens 1.000
CHEMBL2425 Dihydrofolate reductase Toxoplasma gondii 1.000
CHEMBL2363 Dihydrofolate reductase Rattus norvegicus 1.000
CHEMBL2329 Dihydrofolate reductase Candida albicans 1.000
CHEMBL1681620 Dihydrofolate reductase Staphylococcus aureus 1.000
CHEMBL4564 Dihydrofolate reductase Mus musculus 1.000
CHEMBL2695 Focal adhesion kinase 1 Homo sapiens 0.994
CHEMBL1939 Dihydrofolate reductase Plasmodium falciparum K1 0.941
CHEMBL4203 Dual specificity protein kinase CLK4 Homo sapiens 0.773
CHEMBL2627 Dihydrofolate reductase type 1 Escherichia coli 0.773
CHEMBL2345 Ribosomal protein S6 kinase alpha 3 Homo sapiens 0.684
CHEMBL3963 Dihydrofolate reductase Plasmodium berghei str. ANKA 0.472
CHEMBL3959 Quinone reductase 2 Homo sapiens 0.435
CHEMBL4045 AMP-activated protein kinase, alpha-1 subunit Homo sapiens 0.350
CHEMBL2292 Dual-specificity tyrosine-phosphorylation regulated kinase 1A Homo sapiens 0.243



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL202 Dihydrofolate reductase Homo sapiens 1.000
CHEMBL1809 Dihydrofolate reductase Escherichia coli K-12 1.000
CHEMBL5441 Dihydrofolate reductase Escherichia coli 1.000
CHEMBL5457 Dihydrofolate reductase Mycobacterium avium 1.000
CHEMBL1926 Dihydrofolate reductase Pneumocystis carinii 1.000
CHEMBL2902 Dihydrofolate reductase Lactobacillus casei 1.000
CHEMBL2425 Dihydrofolate reductase Toxoplasma gondii 1.000
CHEMBL2329 Dihydrofolate reductase Candida albicans 1.000
CHEMBL2363 Dihydrofolate reductase Rattus norvegicus 1.000
CHEMBL1681620 Dihydrofolate reductase Staphylococcus aureus 1.000
CHEMBL4564 Dihydrofolate reductase Mus musculus 1.000
CHEMBL2695 Focal adhesion kinase 1 Homo sapiens 0.999
CHEMBL3394 Tubulin beta chain Bos taurus 0.988
CHEMBL1939 Dihydrofolate reductase Plasmodium falciparum K1 0.936
CHEMBL4203 Dual specificity protein kinase CLK4 Homo sapiens 0.924
CHEMBL4600 Serine/threonine-protein kinase PAK 1 Homo sapiens 0.850
CHEMBL3959 Quinone reductase 2 Homo sapiens 0.827
CHEMBL2627 Dihydrofolate reductase type 1 Escherichia coli 0.615
CHEMBL3835 Serine/threonine-protein kinase NEK2 Homo sapiens 0.509
CHEMBL1952 Thymidylate synthase Homo sapiens 0.499

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

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
BindinDB 18268
DrugBank DB01157
FDA SRS UPN4ITI8T4
Guide to Pharmacology 7613
Human Metabolome Database HMDB15288
IBM Patent System 53221324344C6AEED8B40C70702CADEF
IBM Patents US20090124593 WO2003106646A2 US20100216768 US20040077568 WO2006093677A1 US20070202043 US20100184706 WO2008091798A2 US20050267122 US6534506 US5420276 US20050180975 US20030096772 EP1753416A2 US6025488 US5795909 WO2002009769A2 EP1087770A1 WO2010078514A2 US20040029273 US6399378 US20100022444 WO2006078336A2 WO2007002905A1 US20050245462 EP1963502A2 US20040102395 US20090170799 EP1766052A1 US20040092573 WO2006119643A1 US20090304578 US7465746 US20030096852 WO2003000656A2 EP1871383A2 EP2059536A2 US20030087840 US20070149615 WO2005007825A2 US20040157786 US20060063935 EP0833826B1 US20100216820 US20080050377 EP1104759B1 US20060030547 WO2009065547A2 US6608096 EP1742660A2 EP2051983A1 US20060234239 US5326764 US20060154863 EP1920066A1 WO2009055074A2 US7846691 US20030068307 US20040102621 US20100279291 US20100196362 US20070259830 US20060216265 WO2010080503A1 US7786270 EP1973530A2 US6566385 WO2010123870A1 WO2008079849A2 US20080146652 US20100255013 US7799899 US7775469 EP1765074A2 EP1309589B1 WO2005033112A2 EP1981341A2 US7799807 US20080153858 EP2183232A2 EP0986302A1 US20070105789 WO2010055525A1 US20030144223 WO2009139921A2 EP1987060A2 WO2007089367A2 US6963010 EP2034996A2 US20060063736 WO2003040172A2 US20080193498 US20080286239 US20100324122 EP1871765B1 US20090208500 EP1651599A1 WO2010049454A2 WO2000074667A2 EP2038262A2
KEGG Ligand C11154
Nikkaji J22.060D
PharmGKB PA451790
PubChem 5583
PubChem: Drugs of the Future 12012739
PubChem: Thomson Pharma 14803927
SureChEMBL SCHEMBL3983

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