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

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ChEBI Name 6-diazo-5-oxo-L-norleucine
ChEBI ID CHEBI:138889
ChEBI 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Sandra Orchard
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Formula C6H9N3O3
Net Charge 0
Average Mass 171.154
Monoisotopic Mass 171.06439
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
SMILES C(=O)(O)[C@H](CCC(C=[N+]=[N-])=O)N
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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.
glutamine antagonist
An antagonist that acts on glutamine receptors.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
EC 6.3.4.2 [CTP synthase (glutamine hydrolyzing)] inhibitor
Any EC 6.3.4.* (other carbonnitrogen ligases) inhibitor that interferes with the action of CTP synthase (glutamine hydrolyzing) (EC 6.3.4.2).
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 6.3.5.2 [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).
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
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.
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
antiviral agent
A substance that destroys or inhibits replication of viruses.
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).
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 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.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
(via L-alpha-amino acid )
Application(s): 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.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing 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)
IUPAC Name
6-diazo-5-oxo-L-norleucine
Synonyms Sources
(S)-2-amino-6-diazo-5-oxocaproic acid ChEBI
diazooxonorleucine ChemIDplus
L-DON ChemIDplus
Manual Xrefs Databases
24893639 PubChem
6-Diazo-5-oxo-L-norleucine Wikipedia
CPD0-1627 MetaCyc
View more database links
Registry Numbers Types Sources
157-03-9 CAS Registry Number ChemIDplus
1725815 Beilstein Registry Number SUBMITTER
Citations Waiting for Citations Types Sources
1412455 PubMed citation Europe PMC
2108451 PubMed citation Europe PMC
25584882 PubMed citation Europe PMC
26425550 PubMed citation Europe PMC
27489275 PubMed citation Europe PMC
27560860 PubMed citation Europe PMC
28454342 PubMed citation Europe PMC
28552037 PubMed citation Europe PMC
28759224 PubMed citation Europe PMC
909432 PubMed citation Europe PMC
Last Modified
08 November 2017