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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL225072
CHEMBL225072
Compound Name PEMETREXED
ChEMBL Synonyms PEMETREXED TROMETHAMINE | Alimta | LY-2315 | LY-231514 | PEMETREXED | PEMETREXED DISODIUM | ALIMTA
Max Phase 4 (Approved)
Trade Names ALIMTA | Alimta
Molecular Formula C20H21N5O6

Additional synonyms for CHEMBL225072 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES NC1=Nc2[nH]cc(CCc3ccc(cc3)C(=O)N[C@@H](CCC(=O)O)C(=O)O)c2C(= ...
Download SMILES
Standard InChI InChI=1S/C20H21N5O6/c21-20-24-16-15(18(29)25-20)12(9-22-16)6 ...
Download InChI
Standard InChI Key WBXPDJSOTKVWSJ-ZDUSSCGKSA-N

Sources

  • BindingDB Database
  • British National Formulary
  • 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


CHEMBL225072

Molecule Features

CHEMBL225072 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:N First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:N Parenteral:Y Topical:N Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Dihydrofolate reductase inhibitor Dihydrofolate reductase DailyMed
GAR transformylase inhibitor GAR transformylase DailyMed
Thymidylate synthase inhibitor Thymidylate synthase DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma3ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ATC

Clinical Data

ClinicalTrials.gov PEMETREXED
The Cochrane Collaboration PEMETREXED

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 CHEMBL225072. 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
CHEMBL202 Dihydrofolate reductase Homo sapiens 1.000
CHEMBL1952 Thymidylate synthase Homo sapiens 1.000
CHEMBL3160 Thymidylate synthase Mus musculus 1.000
CHEMBL3972 GAR transformylase Homo sapiens 1.000
CHEMBL4564 Dihydrofolate reductase Mus musculus 1.000
CHEMBL5328 Thymidylate synthase Lactobacillus casei 1.000
CHEMBL2902 Dihydrofolate reductase Lactobacillus casei 1.000
CHEMBL6137 Thymidylate synthase Escherichia coli 1.000
CHEMBL2425 Dihydrofolate reductase Toxoplasma gondii 1.000
CHEMBL1892 Glutamate carboxypeptidase II Homo sapiens 1.000
CHEMBL5441 Dihydrofolate reductase Escherichia coli 1.000
CHEMBL2363 Dihydrofolate reductase Rattus norvegicus 0.999
CHEMBL4270 Matrix metalloproteinase 10 Homo sapiens 0.998
CHEMBL4393 Matrix metalloproteinase 12 Homo sapiens 0.979
CHEMBL5098 Glutamate carboxypeptidase II Rattus norvegicus 0.956
CHEMBL325 Histone deacetylase 1 Homo sapiens 0.918
CHEMBL1937 Histone deacetylase 2 Homo sapiens 0.911
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.592
CHEMBL209 Trypsin I Homo sapiens 0.472
CHEMBL1865 Histone deacetylase 6 Homo sapiens 0.406



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL202 Dihydrofolate reductase Homo sapiens 1.000
CHEMBL1952 Thymidylate synthase Homo sapiens 1.000
CHEMBL3160 Thymidylate synthase Mus musculus 1.000
CHEMBL2902 Dihydrofolate reductase Lactobacillus casei 1.000
CHEMBL3972 GAR transformylase Homo sapiens 1.000
CHEMBL4564 Dihydrofolate reductase Mus musculus 1.000
CHEMBL5328 Thymidylate synthase Lactobacillus casei 1.000
CHEMBL6137 Thymidylate synthase Escherichia coli 1.000
CHEMBL2425 Dihydrofolate reductase Toxoplasma gondii 1.000
CHEMBL5441 Dihydrofolate reductase Escherichia coli 1.000
CHEMBL1892 Glutamate carboxypeptidase II Homo sapiens 1.000
CHEMBL2363 Dihydrofolate reductase Rattus norvegicus 1.000
CHEMBL4393 Matrix metalloproteinase 12 Homo sapiens 1.000
CHEMBL4270 Matrix metalloproteinase 10 Homo sapiens 0.998
CHEMBL2693 Cystinyl aminopeptidase Homo sapiens 0.992
CHEMBL5098 Glutamate carboxypeptidase II Rattus norvegicus 0.990
CHEMBL5043 Endoplasmic reticulum aminopeptidase 2 Homo sapiens 0.981
CHEMBL2288 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Homo sapiens 0.970
CHEMBL209 Trypsin I Homo sapiens 0.826
CHEMBL325 Histone deacetylase 1 Homo sapiens 0.770

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
427.4 427.1492 0.67 9 191.26 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
6 6 1 11 7 2


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
3.58 5.27 .36 -4.32 3 31 0.29

Structural Alerts

There are 2 structural alerts for CHEMBL225072. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01B - ANTIMETABOLITES
L01BA - Folic acid analogues
L01BA04 - pemetrexed

ChemSpider ChemSpider:WBXPDJSOTKVWSJ-ZDUSSCGKSA-N
DailyMed pemetrexed disodium
PubChem SID: 124893263 SID: 124950689 SID: 525786
Wikipedia Pemetrexed

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL225072



ACToR 137281-23-3
BindingDB 18796 50027656
Brenda 125093 56903 1155
ChEBI 63616
ChemicalBook CB4170583
DrugBank DB00642
DrugCentral 2073
eMolecules 37036813 30513153
EPA CompTox Dashboard DTXSID2048329
FDA SRS 04Q9AIZ7NO
IBM Patent System C3D00F1F5D48BD7D649BC389B13E57F9
LINCS LSM-6353
MolPort MolPort-016-638-470 MolPort-020-179-988
Nikkaji J696.080D
PDBe LYA
PubChem 446556
PubChem: Thomson Pharma 14758615 15378661
SureChEMBL SCHEMBL7968
ZINC ZINC000001540998

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