Nigericin

Nigericin

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Names
IUPAC name (2R)-2-[(2R,3S,6R)-6-[[(2S,4R,5R,7R,9R,10R)- 2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6R)-6-hydroxy- 6-(hydroxymethyl)-3,5-dimethyl-2-tetrahydropyranyl]-3-methyl- 2-tetrahydrofuranyl]-5-methyl-2-tetrahydrofuranyl]-9-methoxy- 2,4,10-trimethyl-1,6-dioxaspiro[4.5]decan-7-yl]methyl]-3-methyl- 2-tetrahydropyranyl]propanoic acid
Other names Polyetherin A, Azalomycin M, Helixin C, Helix C
Identifiers
CAS Number	28380-24-7 N
ChEBI	CHEBI:7569 Y
ChEMBL	ChEMBL405862 Y
ChemSpider	10196461 Y
Jmol 3D model	Interactive image
PubChem	34230
InChI InChI=1S/C40H68O11/c1-21-11-12-28(46-33(21)26(6)36(42)43)17-29-18-30(45-10)27(7)40(48-29)25(5)19-38(9,51-40)32-13-14-37(8,49-32)35-23(3)16-31(47-35)34-22(2)15-24(4)39(44,20-41)50-34/h21-35,41,44H,11-20H2,1-10H3,(H,42,43)/t21-,22-,23-,24+,25+,26+,27+,28+,29+,30+,31+,32+,33+,34-,35+,37-,38-,39-,40+/m0/s1 Y Key: DANUORFCFTYTSZ-SJSJOXFOSA-N Y InChI=1/C40H68O11/c1-21-11-12-28(46-33(21)26(6)36(42)43)17-29-18-30(45-10)27(7)40(48-29)25(5)19-38(9,51-40)32-13-14-37(8,49-32)35-23(3)16-31(47-35)34-22(2)15-24(4)39(44,20-41)50-34/h21-35,41,44H,11-20H2,1-10H3,(H,42,43)/t21-,22-,23-,24+,25+,26+,27+,28+,29+,30+,31+,32+,33+,34-,35+,37-,38-,39-,40+/m0/s1 Key: DANUORFCFTYTSZ-SJSJOXFOBS
SMILES OC(=O)[C@H](C)[C@@H]1O[C@H](CC[C@@H]1C)C[C@H]6O[C@]2(O[C@@](C)(C[C@H]2C)[C@H]3CC[C@](C)(O3)[C@@H]4O[C@H](C[C@@H]4C)[C@H]5O[C@@](O)(CO)[C@H](C)C[C@@H]5C)[C@H](C)[C@H](OC)C6
Properties
Chemical formula	C40H68O11
Molar mass	724.96132 g/mol
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Nigericin is an antibiotic derived from Streptomyces hygroscopicus. Its isolation was described in the 1950s, and in 1968 the structure could be elucidated by X-ray crystallography. The structure and properties of nigericin are similar to the antibiotic monensin. Commercially it is obtained as a byproduct, or contaminant, at the fermentation of Geldanamycin. It is also called Polyetherin A, Azalomycin M, Helixin C, Antibiotic K178, Antibiotic X-464.

Nigericin acts as an H⁺, K⁺, Pb²⁺ ionophore. Most commonly it is an antiporter of H⁺ and K⁺.

In the past nigericin was used as an antibiotic active against gram positive bacteria. It inhibits the Golgi functions in Eukaryotic cells.

External links

• Commercial supplier of nigericin sodium