EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:232049 - JHU083

ChEBI IDCHEBI:232049
ChEBI NameJHU083
Stars
DefinitionAn ethyl ester resulting from the formal condensation of the carboxy group of L-leucyl-6-diazo-5-oxo-L-norleucine with ethanol. It is a glutaminase inhibitor and a prodrug of 6-diazo-5-oxo-L-norleucine that exhibits antineoplastic activity.
Last Modified4 October 2024
SubmitterBrianna Xu
DownloadsMolfile
FormulaC14H24N4O4
Net Charge0
Average Mass312.370
Monoisotopic Mass312.17976
SMILESCCOC(=O)[C@H](CCC(=O)C=[N+]=[N-])NC(=O)[C@@H](N)CC(C)C
InChIInChI=1S/C14H24N4O4/c1-4-22-14(21)12(6-5-10(19)8-17-16)18-13(20)11(15)7-9(2)3/h8-9,11-12H,4-7,15H2,1-3H3,(H,18,20)/t11-,12-/m0/s1
InChIKeyYZRCHOFKIPHQBW-RYUDHWBXSA-N
Wikipedia
Roles Classification
Biological Role:
EC 3.5.1.2 (glutaminase) inhibitor  Any EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the activity of a glutaminase (EC 3.5.1.2) and thus the generation of glutamate from glutamine.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
ChEBI Ontology
Outgoing Relation(s)
JHU083 (CHEBI:232049) has role antineoplastic agent (CHEBI:35610)
JHU083 (CHEBI:232049) has role EC 3.5.1.2 (glutaminase) inhibitor (CHEBI:60280)
JHU083 (CHEBI:232049) has role prodrug (CHEBI:50266)
JHU083 (CHEBI:232049) is a L-leucine derivative (CHEBI:25018)
JHU083 (CHEBI:232049) is a diazo compound (CHEBI:39444)
JHU083 (CHEBI:232049) is a ethyl ester (CHEBI:23990)
JHU083 (CHEBI:232049) is a ketone (CHEBI:17087)
JHU083 (CHEBI:232049) is a secondary carboxamide (CHEBI:140325)
IUPAC Name 
ethyl L-leucyl-6-diazo-5-oxo-L-norleucinate
Synonyms  Source
JHU 083SUBMITTER
JHU-083SUBMITTER
ethyl (2S)-2-{[(2S)-2-amino-4-methylpentanoyl]amino}-6-diazo-5-oxohexanoateIUPAC
ethyl (2S)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-6-diazo-5-oxohexanoateSUBMITTER
ethyl (S)-2-((S)-2-amino-4-methylpentanamido)-6-diazo-5-oxohexanoateSUBMITTER
Manual XrefsDatabases
JHU-083Wikipedia
Registry NumbersSources
CAS:1998725-11-3SUBMITTER
Citations