6-diazo-5-oxo-L-norleucine
Basic information
- CAS
157-03-9- Standard SMILES
[N-]=[N+]=CC(=O)CC[C@H](N)C(=O)O- InChIKey
YCWQAMGASJSUIP-YFKPBYRVSA-N- Molecular formula
- C6H9N3O3
- Average molar mass
- 171.15 g/mol
- Monoisotopic mass
- 171.06439116
Overview
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.
Names & identifiers
- Preferred name
- 6-diazo-5-oxo-L-norleucine
- IUPAC
- (2S)-2-amino-6-diazo-5-oxohexanoic acid
- English name
- 6-Diazo-5-oxo-L-norleucine
- Molecular formula
- C6H9N3O3
- Molecular weight
- 171.15
Names & synonyms
6-diazo-5-oxo-L-norleucine157-03-9diazooxonorleucineL-DONNSC-736503J0H273KZCHEBI:138889DTXSID501028846NSC73656 Diazo 5 oxo L norleucineRefChem:132775DTXCID201514482
Show more names
DOND2141H-L-Don-OHdon(pharmaceutical)diazo-oxo-norleucineH-6-DIAZO-5-OXO-NLE-OHH-NLE(6-DIAZO-5-OXO)-OHL-Nle(6-Diazo-5-oxo)-OH
Norleucine, 6-diazo-5-oxo-6-Diazo-5-oxo-L-nor-LeucineL-Norleucine, 6-diazo-5-oxo-MFCD00037218(2S)-2-amino-6-diazo-5-oxohexanoic acidDON (pharmaceutical)(2S)-2-amino-6-diazo-5-oxo-hexanoic acid(S)-2-Amino-6-diazo-5-oxocaproic acid
Database identifiers
- CAS
157-03-9- PubChem CID
- 9087
- DTXSID
DTXSID501028846- ChEMBL
CHEMBL4303391、CHEMBL97485
Properties
Computed structural properties
- XLogP
- -3.5
- Topological polar surface area
- 82.4 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 5
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 232
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
Physicochemical properties
- Melting point
- 145 °C · 145 °C
- Boiling point
- 301.12 °C · 301.12°C (rough estimate)
- Density
- 1.3994 · 1.3994 (rough estimate)
- refractive index
- 1.58 · 1.5800 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- DMSO (Slightly, Heated, Sonicated), Water (Slightly)
- form
- crystalline
- color
- light yellow
- Merck
- 13 · 13,3026
- BRN
- 1725815 · 1725815
- Stability
- Hygroscopic
- InChI
- InChI=1/C6H9N3O3/c7-5(6(11)12)2-1-4(10)3-9-8/h3,5H,1-2,7H2,(H,11,12)/t5-/s3
- InChIKey
- YCWQAMGASJSUIP-GQMHJJTINA-N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Safety data
- F
- 8
- PPE
- Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- RC6340000
- ridadr
- UN 2811 6.1/PG 3
- risk_code
- 23/24/25
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T
- safety_code
- 36/37/39-45
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H301+H311+H331
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 Oral
- Precautionary statements
- P261-P264-P280-P301+P310-P302+P352+P312-P304+P340+P311
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms.
Antimetabolites that are useful in cancer chemotherapy.
Applications
Uses6-Diazo-5-oxo-L-norleucine (DON) has been used as an inhibitor of glutamine synthetase–glutamine(amide)-2-oxoglutarate aminotransferase.
General DescriptionChemical structure: amino acid derivatives
Additional notes
DefinitionChEBI: 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 a bacterial metabolite, an analgesic, an antibacterial agent, an antiviral agent, an antineoplastic agent, 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, an antimetabolite, a glutamine antagonist, an apoptosis inducer, an EC 2.4.2.14 (amidophosphoribosyltransferase) inhibitor, an EC 3.5.1.2 (glutaminase) inhibitor, an EC 6.3.5.1 [NAD(+) synthase (glutamine-hydrolysing)] inhibitor and an EC 6.3.5.4 [asparagine synthase (glutamine-hydrolysing)] inhibitor. It is a non-proteinogenic L-alpha-amino acid, a diazo compound and a ketone. It is a tautomer of a 6-diazo-5-oxo-L-norleucine zwitterion.
Related reactions
0 records
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Compound notes
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