ALAMETHICIN

Synonyms. Alamethicin; Antibiotic U-22324; N-Acetyl-2-methylalanyl-L-prolyl- 2-methylalanyl-L-alanyl-2- methylalanyl-L-alanyl-L-glutaminyl- 2-methylalanyl-L-valyl-2-methylalanylglycyl- D-leucyl-2- methylalanyl- L -prolyl-L-valyl- 2-methylalanyl- 2-methylalanyl-L-alpha-glutamyl-N1-((1S)-1-benzyl- 2-hydroxyethyl)-L-glutamamide; Ac-Aib-Pro-Aib-Ala-Aib-Ala-Gln-Aib-Val-Aib-Gly-Leu-Aib-Pro-Val- Aib-Aib- Glu-Gln-Phl (Ac = acetyl, Phl = phenylalaninol, Aib = 2-Aminoisobutyric acid);

ALAMETHICIN

Click for original image

 

PRODUCT IDENTIFICATION

CAS RN

27061-78-5

EINECS RN

 

FORMULA

C92H150N22O25

MOLE WEIGHT

1964.31

H.S CODE

 2941.90.1050

SMILES

 N(C(C)(C(=O)N[C@@H](C)C(=O)NC(C)(C(=O)N[C@@H](C)C(=O) N[C@H] (C (=O)NC(C)(C(=O)N[C@H](C(=O)NC(C)(C(=O)NCC (=O)N[C@H](C (=O) NC (C)(C(=O)N1[C@H](C (=O)N[C@H](C(=O)NC(C)(C(=O)NC(C) (C(=O)N [C@H] (C(=O)N[C@H](C(=O)N[C@H](CO)Cc2ccccc2)CCC(=O)N) CCC(= O)O)C)C) [C@@H](C)C)CCC1)C)CC(C)C)C)[C@@H](C)C)C)CCC (=O)N)C) C) C(=O)[C@H]1N(CCC1)C(=O)C(NC(=O)C)(C)C

CLASSIFICATION

Antibacterial, Anti-Infective, Ionophore, Polypeptide antibiotic

EXTRA NOTES

A cyclic nonadecapeptide antibiotic that can act as an ionophore and is produced by strains of Trichoderma viride. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed) [MeSH]

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE.

off-white to beige powder

MELTING POINT

265 ~ 270 C

BOILING POINT

 

DENSITY

 

SOLUBILITY IN WATER

Insoluble

SOLVENT SOLUBILITY

Soluble in DMSO, methanol, and ethanol

VAPOR DENSITY

 

log P(octanol-water)

  

VAPOR PRESSURE

  

AUTOIGNITION TEMP

  
pK

 

REFRACTIVE INDEX

 

FLASH POINT

 

 

STABILITY AND REACTIVITY
STABILITY Stable under normal conditions.

INCOMPATIBLE MATERIALS

Strong oxidizing agents

POLYMERIZATION

Has not been reported

NFPA RATINGS

Health: 2, Flammability: 0, Reactivity: 0

 

EXTERNAL LINKS & GENERAL DESCRIPTION

USA.gov - Alamethicin

Wikipedia Linking - Alamethicin

Google Scholar Search - Alamethicin

U.S. National Library of Medicine - Alamethicin

PubChem Compound Summary - Alamethicin

http://www.ebi.ac.uk/ (ChEMBL) -  Alamethicin

http://www.ncbi.nlm.nih.gov/ -  Alamethicin

http://www.sigmaaldrich.com/content/
Alamethicin is a 20-amino acid channel-forming peptide antibiotic (~2 kDa) isolated from the fungus Trichoderma viride. It consists of several isoforms, for which structural information has been published. This product is a mixture of alamethicin isoforms. Alamethicin catalyzes the exchange of protons for monovalent cations with little difference in affinities and has the ability to transport cations through biological and artificial lipid membranes. Its function is similar to Gramicidin A in that it forms pores or channels in the membrane in a voltage-dependent manner.

 

SALES SPECIFICATION

APPEARANCE

off-white to beige powder

ASSAY

97% min

MELTING POINT

265 ~ 270 C

HEAVY METALS

10ppm max

 

TRANSPORT & REGULATORY INFORMATION

UN NO.

3462

HAZARD CLASS

6.1

PACKING GROUP III

 

SAFETY INFORMATION

HAZARD OVERVIEW

GHS (Globally Harmonised System) Classification: Acute toxicity (Oral). Hazard statements: Toxic if swallowed. Potential Health Effects: Eyes - May cause eye irritation. Skin - May be harmful if absorbed through skin. May cause skin irritation. Ingestion - Toxic if swallowed. Inhalation - May be harmful if inhaled. May cause respiratory tract irritation.

SIGNAL WORD Danger

PICTOGRAMS

PICTOGRAM_GHS06_skull.jpg

HAZARD STATEMENTS

H301

P STATEMENTS

P301 + P310

EC DIRECTIVES

 

HAZARD CODES

CODE_T_T+_toxic_very_toxic.gif

RISK PHRASES

25

SAFETY PHRASES

45

 

PACKING

Preserved in light-resistant and well-closed bottles