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Basic information
- CAS
42228-92-2- Standard SMILES
N[C@H](C(=O)O)[C@@H]1CC(Cl)=NO1- InChIKey
QAWIHIJWNYOLBE-OKKQSCSOSA-N- Molecular formula
- C5H7ClN2O3
- Average molar mass
- 178.57 g/mol
- Monoisotopic mass
- 178.01451976
Overview
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.
Names & identifiers
- Preferred name
- Acivicin
- IUPAC
- (2S)-2-amino-2-[(5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]acetic acid
Names & synonyms
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
Show more names
U-42126NSC163501U-42,126AcivicinaDTXSID0046010U 42,126O0X60K76I6(alpha-S,5S)-alpha-Amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid
Database identifiers
- CAS
42228-92-2- PubChem CID
- 294641
- DTXSID
DTXSID0046010- ChEMBL
CHEMBL1231101- ChEBI
CHEBI:74545- UNII
- O0X60K76I6
- Nikkaji
- J16.742H
Properties
Computed structural propertiesFilling in
- XLogP
- -2.7
- Topological polar surface area
- 84.9 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 206
Experimental & physicochemical properties
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.
Chemistry & industry
Pharmacology
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.
Related reactions
28 records
Compound notes
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