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CHEBI:138889 - 6-diazo-5-oxo-L-norleucine

ChEBI IDCHEBI:138889
ChEBI Name6-diazo-5-oxo-L-norleucine
Stars
ASCII Name6-diazo-5-oxo-L-norleucine
DefinitionA non-proteinogenic L-α-amino acid that is L-norleucine which is substituted at position 5 by an oxo group and at position 6 by a diazo group. It is as inhibitor of various glutamine-utilising enzymes.
Last Modified8 November 2017
SubmitterSandra Orchard
DownloadsMolfile
FormulaC6H9N3O3
Net Charge0
Average Mass171.156
Monoisotopic Mass171.06439
SMILES[N-]=[N+]=CC(=O)CC[C@H](N)C(=O)O
InChIInChI=1S/C6H9N3O3/c7-5(6(11)12)2-1-4(10)3-9-8/h3,5H,1-2,7H2,(H,11,12)/t5-/m0/s1
InChIKeyYCWQAMGASJSUIP-YFKPBYRVSA-N
Wikipedia
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
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.
glutamine antagonist  An antagonist that acts on glutamine receptors.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
EC 2.4.2.14 (amidophosphoribosyltransferase) inhibitor  Any EC 2.4.2.* (pentosyltransferase) inhibitor that interferes with the action of amidophosphoribosyltransferase (EC 2.4.2.14).
antiviral agent  A substance that destroys or inhibits replication of viruses.
EC 6.3.5.3 (phosphoribosylformylglycinamidine synthase) inhibitor  Any EC 6.3.5.* (carbon-nitrogen ligases with glutamine as amido-N-donor) inhibitor that interferes with the action of phosphoribosylformylglycinamidine synthase (EC 6.3.5.3).
EC 6.3.4.2 [CTP synthase (glutamine hydrolyzing)] inhibitor  Any EC 6.3.4.* (other carbon—nitrogen ligases) inhibitor that interferes with the action of CTP synthase (glutamine hydrolyzing) (EC 6.3.4.2).
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.
EC 6.3.5.1 [NAD(+) synthase (glutamine-hydrolysing)] inhibitor  Any EC 6.3.5.* (carbon-nitrogen ligases with glutamine as amido-N-donor) inhibitor that interferes with the action of NAD+ synthase (glutamine-hydrolysing) (EC 6.3.5.1).
EC 6.3.5.4 [asparagine synthase (glutamine-hydrolysing)] inhibitor  Any EC 6.3.5.* (carbon-nitrogen ligases with glutamine as amido-N-donor) inhibitor that interferes with the action of asparagine synthase (glutamine-hydrolysing), EC 6.3.5.4.
EC 6.3.5.5 [carbamoyl-phosphate synthase (glutamine-hydrolysing)] inhibitor  An EC 6.3.5.* (carbon-nitrogen ligases with glutamine as amido-N-donor) inhibitor that interferes with the action of carbamoyl-phosphate synthase (glutamine-hydrolysing) (EC 6.3.5.5).
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
EC 6.3.5.2 [GMP synthase (glutamine-hydrolysing)] inhibitor  An EC 6.3.5.* (carbon-nitrogen ligases with glutamine as amido-N-donor) inhibitor that interferes with the action of GMP synthase (glutamine-hydrolysing) (EC 6.3.5.2).
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
ChEBI Ontology
Outgoing Relation(s)
6-diazo-5-oxo-L-norleucine (CHEBI:138889) has role analgesic (CHEBI:35480)
6-diazo-5-oxo-L-norleucine (CHEBI:138889) has role antibacterial agent (CHEBI:33282)
6-diazo-5-oxo-L-norleucine (CHEBI:138889) has role antimetabolite (CHEBI:35221)
6-diazo-5-oxo-L-norleucine (CHEBI:138889) has role antineoplastic agent (CHEBI:35610)
6-diazo-5-oxo-L-norleucine (CHEBI:138889) has role antiviral agent (CHEBI:22587)
6-diazo-5-oxo-L-norleucine (CHEBI:138889) has role apoptosis inducer (CHEBI:68495)
6-diazo-5-oxo-L-norleucine (CHEBI:138889) has role bacterial metabolite (CHEBI:76969)
6-diazo-5-oxo-L-norleucine (CHEBI:138889) has role EC 2.4.2.14 (amidophosphoribosyltransferase) inhibitor (CHEBI:138952)
6-diazo-5-oxo-L-norleucine (CHEBI:138889) has role EC 3.5.1.2 (glutaminase) inhibitor (CHEBI:60280)
6-diazo-5-oxo-L-norleucine (CHEBI:138889) has role EC 6.3.4.2 [CTP synthase (glutamine hydrolyzing)] inhibitor (CHEBI:138925)
6-diazo-5-oxo-L-norleucine (CHEBI:138889) has role EC 6.3.5.1 [NAD+ synthase (glutamine-hydrolysing)] inhibitor (CHEBI:138953)
6-diazo-5-oxo-L-norleucine (CHEBI:138889) has role EC 6.3.5.2 [GMP synthase (glutamine-hydrolysing)] inhibitor (CHEBI:138928)
6-diazo-5-oxo-L-norleucine (CHEBI:138889) has role EC 6.3.5.3 (phosphoribosylformylglycinamidine synthase) inhibitor (CHEBI:138927)
6-diazo-5-oxo-L-norleucine (CHEBI:138889) has role EC 6.3.5.4 [asparagine synthase (glutamine-hydrolysing)] inhibitor (CHEBI:138956)
6-diazo-5-oxo-L-norleucine (CHEBI:138889) has role EC 6.3.5.5 [carbamoyl-phosphate synthase (glutamine-hydrolysing)] inhibitor (CHEBI:138921)
6-diazo-5-oxo-L-norleucine (CHEBI:138889) has role glutamine antagonist (CHEBI:138931)
6-diazo-5-oxo-L-norleucine (CHEBI:138889) is a diazo compound (CHEBI:39444)
6-diazo-5-oxo-L-norleucine (CHEBI:138889) is a ketone (CHEBI:17087)
6-diazo-5-oxo-L-norleucine (CHEBI:138889) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
6-diazo-5-oxo-L-norleucine (CHEBI:138889) is tautomer of 6-diazo-5-oxo-L-norleucine zwitterion (CHEBI:183231)
Incoming Relation(s)
6-diazo-5-oxo-L-norleucine zwitterion (CHEBI:183231) is tautomer of 6-diazo-5-oxo-L-norleucine (CHEBI:138889)
IUPAC Name 
6-diazo-5-oxo-L-norleucine
Synonyms  Source
(S)-2-amino-6-diazo-5-oxocaproic acidChEBI
diazooxonorleucineChemIDplus
L-DONChemIDplus
Manual XrefsDatabases
24893639PubChem Compound
6-Diazo-5-oxo-L-norleucineWikipedia
CPD0-1627MetaCyc
Registry NumbersSources
Beilstein:1725815Beilstein
CAS:157-03-9ChemIDplus
Citations