2-(6-{6-[2-(5-ethyl-5-hydroxy-6-methyloxan-2-yl)-15-hydroxy-2,10,12-trimethyl-1,6,8-trioxadispiro[4.1.57.35]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl}-3,5-dimethyloxan-2-yl)butanoic acid

• ChemBase ID: 132805
• Molecular Formular: C43H72O11
• Molecular Mass: 765.02518
• Monoisotopic Mass: 764.50746312
• SMILES: CCC(C1C(CC(C(O1)C(C)C(C(C)C(=O)C(CC)C1C(CC(C2(O1)C=CC(C1(O2)CCC(O1)(C)C1CCC(C(O1)C)(CC)O)O)C)C)O)C)C)C(=O)O
• Canonical SMILES: CCC(C1OC2(C=CC(C3(O2)CCC(O3)(C)C2CCC(C(O2)C)(O)CC)O)C(CC1C)C)C(=O)C(C(C(C1OC(C(CC1C)C)C(C(=O)O)CC)C)O)C
• InChI: InChI=1S/C43H72O11/c1-12-30(35(46)27(8)34(45)28(9)36-23(4)21-24(5)37(51-36)31(13-2)39(47)48)38-25(6)22-26(7)42(52-38)18-15-32(44)43(54-42)20-19-40(11,53-43)33-16-17-41(49,14-3)29(10)50-33/h15,18,23-34,36-38,44-45,49H,12-14,16-17,19-22H2,1-11H3,(H,47,48)
• InChIKey: VHKXXVVRRDYCIK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(6-{6-[2-(5-ethyl-5-hydroxy-6-methyloxan-2-yl)-15-hydroxy-2,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5^7.3^5]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl}-3,5-dimethyloxan-2-yl)butanoic acid
• IUPAC Traditional name: 2-(6-{6-[2-(5-ethyl-5-hydroxy-6-methyloxan-2-yl)-15-hydroxy-2,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5^7.3^5]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl}-3,5-dimethyloxan-2-yl)butanoic acid
• Synonyms: Narasin from Streptomyces auriofaciens

Database IDs

• CAS Number: 55134-13-9
• MDL Number: MFCD00133653
• PubChem SID: 162227082; 24897476
• PubChem CID: 4264204

CALCULATED PROPERTIES

• Acid pKa: 4.4974623
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): 6.834408
• LogD (pH = 7.4): 5.0657854
• Log P: 7.8768196
• Molar Refractivity: 204.5379 cm^3
• Polarizability: 81.99842 Å^3
• Polar Surface Area: 161.21 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: VO8640000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 28
• Safety Statements: 28-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - N1271

Application
Narasin is a growth-promoting ionophoric antibacterial agent for Enterococci, specifically Enterococcus faecium and Enterococcus faecalis1,2. It inhibits coccidial infection in poultry and mammals and is used in studies involving sodium calcium ion exchange.
Biochem/physiol Actions
Narasin administration in swine results in improved nitrogen digestibility, which decreases fecal nitrogen and increases the relative concentrations of propionic acid in the large intestine. Polyether ionophores, such as Narasin, have a hydrophilic interior and a hydrophobic exterior. The lipophilic ionophore attaches to the lipid rich cell membranes of Gram-positive bacteria. Ionophores bind Na+, K+, and H+ and facilitate their transfer across the bacterial cell membrane, resulting in an increase in H+ concentration on the inside of the Gram-positive cell. Therefore, the H+ ATPase pump is activated to transport out excess H+. The cell is depleted of its energy resources and reduces fermentative functions and cell division 3.