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

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

ChEBI ID	CHEBI:138889
ChEBI Name	6-diazo-5-oxo-L-norleucine
Stars
ASCII Name	6-diazo-5-oxo-L-norleucine
Definition	A 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 Modified	8 November 2017
Submitter	Sandra Orchard
Downloads	Molfile

Formula	C6H9N3O3
Net Charge	0
Average Mass	171.156
Monoisotopic Mass	171.06439
SMILES	[N-]=[N+]=CC(=O)CC[C@H](N)C(=O)O
InChI	InChI=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
InChIKey	YCWQAMGASJSUIP-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:	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. bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria. 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. 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). 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. 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). 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 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). 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 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). glutamine antagonist An antagonist that acts on glutamine receptors. 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. antiviral agent A substance that destroys or inhibits replication of viruses.
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)
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
diazooxonorleucine	ChemIDplus
(S)-2-amino-6-diazo-5-oxocaproic acid	ChEBI
L-DON	ChemIDplus

Manual Xrefs	Databases
24893639	PubChem Compound
6-Diazo-5-oxo-L-norleucine	Wikipedia
CPD0-1627	MetaCyc

Registry Numbers	Sources
Beilstein:1725815	Beilstein
CAS:157-03-9	ChemIDplus

Citations