Acivicin

HCID 294641

Grundinformationen

CAS
42228-92-2
Standard-SMILES
N[C@H](C(=O)O)[C@@H]1CC(Cl)=NO1
InChIKey
QAWIHIJWNYOLBE-OKKQSCSOSA-N
Summenformel
C5H7ClN2O3
Durchschnittliche Molmasse
178,57 g/mol
Monoisotopische Masse
178,01451976

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Acivicin
IUPAC
(2S)-2-amino-2-[(5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]acetic acid
Englischer Name
ACIVICIN
Summenformel
C5H7ClN2O3
Molmasse
178.57

Namen und Synonyme

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
Weitere Namen anzeigen
(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

Datenbank-Bezeichner

CAS
42228-92-2
PubChem CID
294641
DTXSID
DTXSID0046010
ChEMBL
CHEMBL1231101
ChEBI
CHEBI:74545
UNII
O0X60K76I6
Nikkaji
J16.742H

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-2,7
Polarare Oberfläche (TPSA)
84,9 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
2
Schwere Atome
11

Experimentelle und physikochemische Eigenschaften

Solubility · 6 Einträge

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 Eintrag

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.

Physikochemische Eigenschaften

Schmelzpunkt
200 °C · >200°C (dec.)
Siedepunkt
341.6 · 341.6±48.0 °C(Predicted)
Dichte
1.85 · 1.85±0.1 g/cm3(Predicted)
storage temp.
2 · 2-8°C
Löslichkeit
2 O: · H2O: soluble10mg/mL (warmed)
pka
2.02 · 2.02±0.10(Predicted)

Sicherheit und Regulatorisches

Sicherheitsdaten

wgk
3
ridadr
3172
RTECS-Nr.
NY2103000
risk_code
20/21/22
hazard_code
Xn
safety_code
36

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 5 Einträge

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.

Anwendungen

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

Anbieter43 Anbieter

陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
上海炎泽化工有限公司15345144255 19975051755 · [email protected]
上海优宁维生物科技股份有限公司15921930842 15921930842 · [email protected]
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: 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 lutamate metabolism and several glutamate-dependent synthetic enzymes. It is obtained as a fermentation product of Streptomyces sviceus bacteria.

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