Compound: 6-diazo-5-oxo-L-norleucine
SMILES: O=C(O)[C@@H](N)CCC(=O)C=[N+]=[N-]
InChIKey: YCWQAMGASJSUIP-YFKPBYRVSA-N
Synonyms: 6-diazo-5-oxo-L-norleucine, 157-03-9, diazooxonorleucine, L-DON, NSC-7365, 03J0H273KZ, CHEBI:138889, DTXSID501028846, NSC7365, 6 Diazo 5 oxo L norleucine, RefChem:132775, DTXCID201514482, Norleucine, 6-diazo-5-oxo-, 6-Diazo-5-oxo-L-nor-Leucine, L-Norleucine, 6-diazo-5-oxo-, MFCD00037218, L-Norleucine,6-diazo-5-oxo-, (2S)-2-amino-6-diazo-5-oxohexanoic acid, DON (pharmaceutical), (2S)-2-amino-6-diazo-5-oxo-hexanoic acid, (S)-2-Amino-6-diazo-5-oxocaproic acid, H-6-Diazo-5-oxo-Nle-OH, NSC 7365, L-6-Diazo-5-oxonorleucine, BRN 1725815, Norleucine,6-diazo-5-oxo-, UNII-03J0H273KZ, AI3-26441, Norleucine, 6-diazo-5-oxo, L-, (S)-2-amino-6-diazo-5-oxohexanoic acid, NCIMech_000302, SCHEMBL9295, NCIStruc1_000220, NCIStruc2_000175, (L)-DON, 4-04-00-03278 (Beilstein Handbook Reference), CHEMBL97485, L-Nle(6-Diazo-5-oxo)-OH, orb1685388, CHEMBL4303391, L-DON;H-Glu(diazomethylketone)-OH;6-Diazo-5-oxo-L-2-aminohexanoic acid, SCHEMBL15349013, SCHEMBL15349015, KMX-010, NCI7365, YCWQAMGASJSUIP-YFKPBYRVSA-N, EX-A1965, CCG-35449, CCG-37571, NCGC00013078, NSC823855, AKOS030213039, 6-Diazo-5-oxo-L-2-aminohexanoic acid, EBC-616896, FD49029, NSC-823855, NCGC00013078-02, NCGC00096202-01, 6-Diazo-5-oxo-L-norleucine, crystalline, SY264659, 6-DIAZO-5-OXO-L-NORLEUCINE [MI], HY-108357, CS-0028442, NS00011811, C22429, F82153, Q245487
Theoretical properties:
molecular_formula: C6H9N3O3
molecular_weight: 171.15 g/mol
exact_mass: 171.06439116 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 5
heavy_atom_count: 12
topological_polar_surface_area: 82.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "6-diazo-5-oxo-L-norleucine is a non-proteinogenic L-alpha-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. It has a role as an EC 6.3.5.5 [carbamoyl-phosphate synthase (glutamine-hydrolysing)] inhibitor, an EC 6.3.4.2 [CTP synthase (glutamine hydrolyzing)] inhibitor, an EC 6.3.5.3 (phosphoribosylformylglycinamidine synthase) inhibitor, an EC 6.3.5.2 [GMP synthase (glutamine-hydrolysing)] inhibitor, a glutamine antagonist, an EC 2.4.2.14 (amidophosphoribosyltransferase) inhibitor, an EC 6.3.5.1 [NAD(+) synthase (glutamine-hydrolysing)] inhibitor, an EC 6.3.5.4 [asparagine synthase (glutamine-hydrolysing)] inhibitor, an antiviral agent, an antibacterial agent, an antimetabolite, an analgesic, an antineoplastic agent, an EC 3.5.1.2 (glutaminase) inhibitor, an apoptosis inducer and a bacterial metabolite. It is a ketone, a diazo compound and a non-proteinogenic L-alpha-amino acid. It is a tautomer of a 6-diazo-5-oxo-L-norleucine zwitterion.", "chebi": "A non-proteinogenic <small>L</small>-\u03b1-amino acid that is <small>L</small>-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.", "chembl": "6-DIAZO-5-OXO-L-NORLEUCINE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "6-Diazo-5-oxo-L-norleucine (DON) is a glutamine antagonist, which was isolated originally from Streptomyces in a sample of Peruvian soil. This diazo compound is biosynthesized from lysine by three enzymes in bacteria. It is one of the most famous non-proteinogenic amino acid and was characterized in 1956 by Henry W Dion et al., who suggested a possible use in cancer therapy. This antitumoral efficacy was confirmed in different animal models. DON was tested as chemotherapeutic agent in different clinical studies, but was never approved. In 2019, DON was shown to kill tumor cells while reversing disease symptoms and improve overall survival in late-stage experimental glioblastoma in mice, when combined with calorie-restricted ketogenic diet."}