CAS 42228-92-2 Acivicin (HCID 294641)

基本情報

CAS: 42228-92-2
標準SMILES: N[C@H](C(=O)O)[C@@H]1CC(Cl)=NO1
InChIKey: QAWIHIJWNYOLBE-OKKQSCSOSA-N
分子式: C5H7ClN2O3
平均分子量: 178.57 g/mol
単同位体質量: 178.01451976

概要

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 a glutamine antagonist, a metabolite, an antimicrobial agent, an antimetabolite, an antineoplastic agent, an antileishmanial agent and an EC 2.3.2.2 (gamma-glutamyltransferase) inhibitor. It is an organochlorine compound, a member of isoxazoles and a non-proteinogenic L-alpha-amino acid.

名称と識別子

優先名称: Acivicin
IUPAC: (2S)-2-amino-2-[(5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]acetic acid
現地名: アシビシン
英語名: ACIVICIN
分子式: C5H7ClN2O3
分子量: 178.57

名称と別名

acivicin42228-92-2Antibiotic AT 125AcivicineAT-125AcivicinoAcivicinumNSC-163501AT 125NSC 163501(2S)-2-Amino-2-[(5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]acetic acidU 42126

名称をさらに表示

抗生物質U-42126(5S,αS)-α-アミノ-3-クロロ-4,5-ジヒドロ-5-イソオキサゾール酢酸アシビシン(αS,5S)-α-アミノ-3-クロロ-4,5-ジヒドロ-5-イソオキサゾール酢酸(S)-α-アミノ-α-[[(S)-3-クロロ-4,5-ジヒドロイソオキサゾール]-5-イル]酢酸(2S)-2-アミノ-2-[(5S)-3-クロロ-4,5-ジヒドロ-1,2-オキサゾール-5-イル]酢酸(αS,5S)-antibioticat125AcivicinAcivicinAntibiotic U-42126DIHYDROXY-5-ISOXAZOLEACETICACID

U-42126NSC163501U-42,126AcivicinaDTXSID0046010U 42,126O0X60K76I6(alpha-S,5S)-alpha-Amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid

データベース識別子

CAS: 42228-92-2
PubChem CID: 294641
DTXSID

物性

構造計算による物性

XLogP: -2.7
極性表面積: 84.9 Å²
水素結合供与体数: 2
水素結合受容体数: 5
回転可能結合数: 2
重原子数: 11
形式電荷: 0
複雑度: 206

実験および物理化学的性質

Solubility · 6 件

Water 17.9 - 18.2 (mg/mL)

0.1 M Citrate buffer pH 4.3 17.1 - 25.7 (mg/mL)

0.1 M Borate buffer pH 9.0 8.7 - 13.0 (mg/mL)

0.1 N HCl 31 - 35 (mg/mL)

0.1 N NaOH 34.4 - 36.8 (mg/mL)

95% Ethanol 0.8 (mg/mL)

Stability/Shelf Life · 1 件

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.

物理化学的性質

融点: 200 °C · >200°C (dec.)
沸点: 341.6 · 341.6±48.0 °C(Predicted)
比重(密度): 1.85 · 1.85±0.1 g/cm3(Predicted)
貯蔵温度: 2 · 2-8°C
溶解性: 2 O: · H2O: ソリュブル10mg/mL (加温)
酸解離定数(Pka): 2.02 · 2.02±0.10(Predicted)
外見: 白い固体。
色: 白からベージュ
水溶解度: 10 mg/mlで水に溶ける · 温めると10mg/mlで水に溶ける
安定性: 吸湿性

安全と法規制

安全データ

wgk: 3
rtecs: NY2103000
ridadr: 3172
risk_code: 20/21/22
hazard_code: Xn
safety_code: 36
hazard_class: 6.1(b)
packing_group: III

化学と産業

薬理情報

MeSH Pharmacological Classification · 5 件

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms.

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.

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)

Antimetabolites that are useful in cancer chemotherapy.

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.