CHEBI:63616 - pemetrexed

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ChEBI Name pemetrexed
ChEBI ID CHEBI:63616
Definition An N-acylglutamic acid in which the N-acyl group is specified as 4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl. Inhibits thymidylate synthase (TS), 421 dihydrofolate reductase (DHFR), and glycinamide ribonucleotide formyltransferase (GARFT).
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
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Formula C20H21N5O6
Net Charge 0
Average Mass 427.41060
Monoisotopic Mass 427.149
InChI InChI=1S/C20H21N5O6/c21-20-24-16-15(18(29)25-20)12(9-22-16)6-3-10-1-4-11(5-2-10)17(28)23-13(19(30)31)7-8-14(26)27/h1-2,4-5,9,13H,3,6-8H2,(H,23,28)(H,26,27)(H,30,31)(H4,21,22,24,25,29)/t13-/m0/s1
InChIKey WBXPDJSOTKVWSJ-ZDUSSCGKSA-N
SMILES Nc1nc(=O)c2c(CCc3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)c[nH]c2[nH]1
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): antimetabolite
A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
EC 2.1.1.45 (thymidylate synthase) inhibitor
An EC 2.1.1.* (methyltransferases) inhibitor that interferes with the action of thymidylate synthase (EC 2.1.1.45).
EC 1.5.1.3 (dihydrofolate reductase) inhibitor
An EC 1.5.1.* (oxidoreductase acting on donor CH-NH group, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of dihydrofolate reductase (EC 1.5.1.3).
EC 2.1.2.2 (phosphoribosylglycinamide formyltransferase) inhibitor
An EC 2.1.2.* (hydroxymethyl-, formyl- and related transferases) inhibitor that interferes with the action of phosphoribosylglycinamide formyltransferase (EC 2.1.2.2).
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing pemetrexed (CHEBI:63616) has role antimetabolite (CHEBI:35221)
pemetrexed (CHEBI:63616) has role antineoplastic agent (CHEBI:35610)
pemetrexed (CHEBI:63616) has role EC 1.5.1.3 (dihydrofolate reductase) inhibitor (CHEBI:50683)
pemetrexed (CHEBI:63616) has role EC 2.1.1.45 (thymidylate synthase) inhibitor (CHEBI:63720)
pemetrexed (CHEBI:63616) has role EC 2.1.2.2 (phosphoribosylglycinamide formyltransferase) inhibitor (CHEBI:63721)
pemetrexed (CHEBI:63616) is a N-acyl-L-glutamic acid (CHEBI:21650)
pemetrexed (CHEBI:63616) is a pyrrolopyrimidine (CHEBI:38670)
pemetrexed (CHEBI:63616) is conjugate acid of pemetrexed(2−) (CHEBI:63724)
Incoming pemetrexed(2−) (CHEBI:63724) is conjugate base of pemetrexed (CHEBI:63616)
IUPAC Name
N-{4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid
INN Source
pemetrexed KEGG DRUG
Manual Xrefs Databases
D07472 KEGG DRUG
DB00642 DrugBank
EP432677 Patent
LSM-6353 LINCS
Pemetrexed Wikipedia
US5344932 Patent
View more database links
Registry Numbers Types Sources
137281-23-3 CAS Registry Number ChemIDplus
137281-23-3 CAS Registry Number KEGG DRUG
9097855 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
25 February 2016