Acivicin
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
Weitere Namen anzeigen
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
- Formalladung
- 0
- Komplexität
- 206
Experimentelle und physikochemische Eigenschaften
Solubility
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
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)
- Aggregatzustand
- White solid.
- Farbe
- white to beige
- Wasserlöslichkeit
- 10 mg/ml · Soluble in water at 10mg/ml with warming
- Stabilität
- Hygroscopic
Sicherheit und Regulatorisches
Sicherheitsdaten
- wgk
- 3
- ridadr
- 3172
- RTECS-Nr.
- NY2103000
- risk_code
- 20/21/22
- hazard_code
- Xn
- safety_code
- 36
- hazard_class
- 6.1(b)
- packing_group
- III
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological Classification
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
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter43 Anbieter
Ergänzende Hinweise
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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