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Acivicin

Acivicin structure

CAS No:
42228-92-2
Formula:
C5H7ClN2O3
Chemical Name:
Acivicin
Synonyms:
5-Isoxazoleacetic acid,α-amino-3-chloro-4,5-dihydro-,(αS,5S)-;5-Isoxazoleacetic acid,α-amino-3-chloro-4,5-dihydro-,[S-(R*,R*)]-;(αS,5S)-α-Amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid;NSC 163501;AT 125;(α-S,5S)-α-Amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid;U 42126;Antibiotic AT 125;Acivicin
Categories:
Chemical Reagents > Organic Reagents

Description

Acivicin (AT-125), a natural product produced by Streptomyces sviceus is a γ−glutamyl transpeptidase (GGT) inhibitor. Acivicin can across the blood-brain barrier and has anti-cancer, anti-parasitic properties[1][2].

Acivicin is an L-alpha-amino acid that is L-alanine in which the methyl group is replaced by a (5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl group. A glutamine analogue antimetabolite, it interferes with glutamate metabolism and several glutamate-dependent synthetic enzymes. It is obtained as a fermentation product of Streptomyces sviceus bacteria. It has a role as an antimetabolite, a metabolite, an antineoplastic agent, an EC 2.3.2.2 (gamma-glutamyltransferase) inhibitor, an antimicrobial agent, an antileishmanial agent and a glutamine antagonist. It is a member of isoxazoles, an organochlorine compound and a non-proteinogenic L-alpha-amino acid.|Acivicin is a modified amino acid and structural analog of glutamine. Acivicin inhibits glutamine amidotransferases in the purine and pyrimidine biosynthetic pathways, thereby inhibiting tumor growth in cell lines dependent on glutamine metabolism. (NCI04)

Acivicin Basic Attributes

Molecular Weight：

178.57

Exact Mass：

178.57

UNII：

O0X60K76I6

NSC Number：

163501

DSSTox ID：

DTXSID0046010

NCI Thesaurus Code：

C986

Characteristics

PSA：

84.9

XLogP3：

-0.31

Appearance：

white to beige

Density：

1.9±0.1 g/cm3

Melting Point：

>180 °C (decomp) @ Solvent: Methanol

Boiling Point：

341.6±48.0 °C at 760 mmHg

Flash Point：

160.4±29.6 °C

Refractive Index：

1.664

Water Solubility：

soluble in water at 10mg/ml with warming

Storage Conditions：

2-8°C

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

3172

wgk germany：

hazard class code：

20/21/22

safety instructions：

RTECS Number：

NY2103000

Marks：

Stability/Shelf Life：

Bulk: A sample stored at 60 °C for 14 days showed no decomposition as indicated by UV absorption, paper chromatography, or ionic chloride determination. Solution: An aqueous solution (18 mg/mL) which was stored at 28°C for 14 days showed less than 1% decomposition by UV absorption, paper chromatography and ionic chloride measurement.

Drug Information

MeSH：

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)|Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)|Drugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033) (See all compounds classified as Antimetabolites.)|Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)|Antimetabolites that are useful in cancer chemotherapy. (See all compounds classified as Antimetabolites, Antineoplastic.)

MeSH Entry Terms：

acivicin

Acivicin Use and Manufacturing

Azaserine and Acivicin are classical and irreversible inhibitors of γ-Glutamyltranspeptidase

Computed Properties

Molecular Weight:178.57
XLogP3:-2.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:178.0145198
Monoisotopic Mass:178.0145198
Topological Polar Surface Area:84.9
Heavy Atom Count:11
Complexity:206
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes