CHEBI:71223 - pralatrexate

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ChEBI Name pralatrexate
ChEBI ID CHEBI:71223
Definition A pteridine that is the N-4-[1-(2,4-diaminopteridin-6-yl)pent-4-yn-2-yl]benzoyl derivative of L-glutamic acid. Used for treatment of Peripheral T-Cell Lymphoma, an aggressive form of non-Hodgkins lymphoma.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C23H23N7O5
Net Charge 0
Average Mass 477.47260
Monoisotopic Mass 477.17607
InChI InChI=1S/C23H23N7O5/c1-2-3-14(10-15-11-26-20-18(27-15)19(24)29-23(25)30-20)12-4-6-13(7-5-12)21(33)28-16(22(34)35)8-9-17(31)32/h1,4-7,11,14,16H,3,8-10H2,(H,28,33)(H,31,32)(H,34,35)(H4,24,25,26,29,30)/t14?,16-/m0/s1
InChIKey OGSBUKJUDHAQEA-WMCAAGNKSA-N
SMILES Nc1nc(N)c2nc(CC(CC#C)c3ccc(cc3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)cnc2n1
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 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).
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing pralatrexate (CHEBI:71223) has role antimetabolite (CHEBI:35221)
pralatrexate (CHEBI:71223) has role antineoplastic agent (CHEBI:35610)
pralatrexate (CHEBI:71223) has role EC 1.5.1.3 (dihydrofolate reductase) inhibitor (CHEBI:50683)
pralatrexate (CHEBI:71223) is a N-acyl-L-glutamic acid (CHEBI:21650)
pralatrexate (CHEBI:71223) is a pteridines (CHEBI:26373)
pralatrexate (CHEBI:71223) is a terminal acetylenic compound (CHEBI:73477)
IUPAC Name
N-{4-[1-(2,4-diaminopteridin-6-yl)pent-4-yn-2-yl]benzoyl}-L-glutamic acid
INNs Sources
pralatrexate WHO MedNet
pralatrexate KEGG DRUG
pralatrexato WHO MedNet
pralatrexatum WHO MedNet
Synonyms Sources
(2S)-2-((4-((1RS)-1-((2,4-Diaminopteridin-6-yl)methyl)but-3-ynyl)benzoyl)amino)pentanedioic acid ChemIDplus
(2S)-2-({4-[1-(2,4-diaminopteridin-6-yl)pent-4-yn-2-yl]benzoyl}amino)pentanedioic acid IUPAC
10-Propargyl-10-deazaaminopterin KEGG DRUG
HSDB 7786 ChemIDplus
N-(4-(1-((2,4-Diamino-6-pteridinyl)methyl)-3-butynyl)benzoyl)-L-glutamic acid ChemIDplus
Brand Name Source
Folotyn ChemIDplus
Manual Xrefs Databases
4117 DrugCentral
D05589 KEGG DRUG
Pralatrexate Wikipedia
US2005267117 Patent
US2011190305 Patent
US6028071 Patent
US6323205 Patent
WO2007023243 Patent
View more database links
Registry Numbers Types Sources
146464-95-1 CAS Registry Number ChemIDplus
146464-95-1 CAS Registry Number KEGG DRUG
6624234 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017