Nigericin Na+ salt, K+ ionophore

Key facts

CAS number

28643-80-3

Purity

>98%

Form

Solid

form

Source

Streptomyces hygroscopicus

Molecular weight

746.9 Da

Molecular formula

C₄₀H₆₇NaO₁₁

PubChem

16760591

Nature

Native

Solubility

Soluble in ethanol to 100 mM

Biochemical name

Nigericin sodium

Biological description

K+ ionophore; exchanges K+ for H+ across most biological membranes. Stimulates mitochondrial ATPase activity, and exchanges H+ for K+>Rb+>Cs+>>Na+. Reported to inhibit Poliovirus and influenza virus replication.

Canonical smiles

CC1CCC(OC1C(C)C(=O)[O-])CC2CC(C(C3(O2)C(CC(O3)(C)C4CCC(O4)(C)C5C(CC(O5)C6C(CC(C(O6)(CO)O)C)C)C)C)C)OC.[Na+]

Isomeric smiles

C[C@H]1CC[C@@H](O[C@H]1[C@@H](C)C(=O)[O-])C[C@@H]2C[C@H]([C@H]([C@@]3(O2)[C@@H](C[C@@](O3)(C)[C@H]4CC[C@@](O4)(C)[C@H]5[C@H](C[C@@H](O5)[C@@H]6[C@H](C[C@H]([C@@](O6)(CO)O)C)C)C)C)C)OC.[Na+]

InChi

InChI=1S/C40H68O11.Na/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);/q;+1/p-1/t21-,22-,23-,24+,25+,26+,27+,28+,29+,30+,31+,32+,33+,34-,35+,37-,38-,39-,40+;/m0./s1

InChiKey

MOYOTUKECQMGHE-PDEFJWSRSA-M

IUPAC Name

sodium;(2R)-2-[(2R,3S,6R)-6-[[(2S,4R,5R,6R,7R,9R)-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-7-methoxy-2,4,6-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]methyl]-3-methyloxan-2-yl]propanoate