| Stereochemistry | ABSOLUTE |
| Molecular Formula | C40H68O11 |
| Molecular Weight | 724.9613 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 19 / 19 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(C[C@H](C)[C@@]([H])(O1)[C@]2(C)CC[C@@]([H])(O2)[C@]3(C)C[C@@H](C)[C@]4(O3)O[C@]([H])(C[C@@]5([H])CC[C@H](C)[C@@]([H])(O5)[C@@H](C)C(O)=O)C[C@@H](OC)[C@H]4C)[C@@]6([H])O[C@@](O)(CO)[C@H](C)C[C@@H]6C
InChI
InChIKey=DANUORFCFTYTSZ-SJSJOXFOSA-N
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
| Molecular Formula | C40H68O11 |
| Molecular Weight | 724.9613 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 19 / 19 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Nigericin is an antibiotic derived from Streptomyces “Nig-1”. It is the potassium ionophore and H+/K+ exchanger. It is shown to be highly effective as an ionophore for Pb(2+). Thus, nigericin may be more useful than monensin in the treatment of Pb intoxication. Nigericin induced mitochondrial membrane hyperpolarization. Malignant characteristics of human glioma cells were markedly suppressed by nigericin treatment in vivo. Nigericin induces cell death and promotes the maturation and release of IL-1beta in lipopolysaccharide (LPS)-primed monocytes and macrophages. The mechanism of induction of apoptosis by nigericin is most probably to decrease intracellular pH.
Originator
Approval Year
PubMed
Patents
Sample Use Guides
Nigericin inhibits gram-positive bacteria at levels below 0.5 ug/ml, but levels above 60 ug/ml are required to inhibit gram-negative bacteria such as Escherichia coli. Mycobacterium smegmatis and Candida albicans are inhibited at 2 ug/ml, and fungi are inhibited at somewhat higher concentrations. The antibiotic is not active against bacteriophages at 500 ug/ml.