6-Diazo-5-oxo-L-norleucine
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6-Diazo-5-oxo-L-norleucine
structure -
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CAS No:
157-03-9
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Formula:
C6H9N3O3
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Chemical Name:
6-Diazo-5-oxo-L-norleucine
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Synonyms:
L-Norleucine,6-diazo-5-oxo-;Norleucine,6-diazo-5-oxo-,L-;6-Diazo-5-oxo-L-norleucine;DON;NSC 7365;DON (pharmaceutical);L-DON;L-6-Diazo-5-oxonorleucine;(2S)-2-Amino-6-diazo-5-oxohexanoic acid;543-31-7;15440-70-7;945678-45-5;2180165-45-9
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CAS No:
Description
Slightly yellow powder
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.|An amino acid that inhibits phosphate-activated glutaminase and interferes with glutamine metabolism. It is an antineoplastic antibiotic produced by an unidentified species of Streptomyces from Peruvian soil. (From Merck Index, 11th ed)
Characteristics
117.78000
light yellow crystalline
1.3994 (rough estimate)
145-155 °C (decomp)
301.12°C (rough estimate)
1.5800 (estimate)
−20°C
Safety Information
UN 2811 6.1/PG 3
3
23/24/25
36/37/39-45
RC6340000
T
P261-P280-P301 + P310-P311
H301-H311-H331
|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P311, P312, P321, P322, P330, P361, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 40 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Drug Information
Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)|Antimetabolites that are useful in cancer chemotherapy. (See all compounds classified as Antimetabolites, Antineoplastic.)
6 Diazo 5 oxo L norleucine
Computed Properties
Molecular Weight:171.15
XLogP3:-3.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:5
Exact Mass:171.06439116
Monoisotopic Mass:171.06439116
Topological Polar Surface Area:82.4
Heavy Atom Count:12
Complexity:232
Defined Atom Stereocenter Count:1
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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