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6-Diazo-5-oxo-L-norleucine

6-Diazo-5-oxo-L-norleucine structure

CAS No:
157-03-9
Formula:
C6H9N3O3
Chemical Name:
6-Diazo-5-oxo-L-norleucine
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
Categories:
Biochemical Engineering > Amino Acids and Derivatives

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)

6-Diazo-5-oxo-L-norleucine Basic Attributes

Molecular Weight：

171.15

Exact Mass：

171.06400

UNII：

03J0H273KZ

HScode：

2927000090

Characteristics

PSA：

117.78000

Appearance：

light yellow crystalline

Density：

1.3994 (rough estimate)

Melting Point：

145-155 °C (decomp)

Boiling Point：

301.12°C (rough estimate)

Refractive Index：

1.5800 (estimate)

Storage Conditions：

−20°C

Safety Information

Transport codes：

UN 2811 6.1/PG 3

wgk germany：

hazard class code：

23/24/25

safety instructions：

36/37/39-45

RTECS Number：

RC6340000

Marks：

Precautionary statement(s)：

P261-P280-P301 + P310-P311

Hazard Statements：

H301-H311-H331

GHS Classification：

|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

MeSH：

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.)

MeSH Entry Terms：

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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Guide of 6-Diazo-5-oxo-L-norleucine

Description
Basic Attributes
Characteristics
Safety Information
Drug Information
Computed Properties
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