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Nigericin

CAT: 0931-T16323-02Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0931-T16323-02Size:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
28380-24-7
Target
Sodium Channel, Apoptosis, NOD-like Receptor (NLR), Caspase, Pyroptosis, Potassium Channel, Antibiotic, Wnt/beta-catenin, Antibacterial
Related Pathways
Apoptosis, Stem Cells, Proteases/Proteasome, Cytoskeletal Signaling, Microbiology/Virology, Membrane transporter/Ion channel, Immunology/Inflammation
Purity
0.985
Bioactivity
Nigericin is a polyether antibiotic with potent antimicrobial, antimalarial, anticoronaviral and anticancer activities. It is capable of promoting cellular potassium efflux, inducing Caspase-1/GSDMD and Caspase-3-mediated cellular pyroptosis and apoptosis in triple-negative breast cancer, and inducing apoptosis in PEL (primary exudative lymphoma) cells through mitochondrial dysfunction and Wnt/β-catenin signaling downregulation.
Smiles
C[C@H]1[C@]2(O[C@@](C)(C1)[C@@]3(O[C@@](C)(CC3)[C@@]4(O[C@](C[C@@H]4C)([C@]5(O[C@](CO)(O)[C@H](C)C[C@@H]5C)[H])[H])[H])[H])O[C@H](C[C@@H]6O[C@@]([C@H](C(O)=O)C)([C@@H](C)CC6)[H])C[C@@H](OC)[C@H]2C
Molecular Formula
C40H68O11
Molecular Weight
724.96
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

Nigericin

Nigericin is a polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus. It has a role as an antimicrobial agent, an antibacterial agent, a bacterial metabolite and a potassium ionophore.

CAS Number28380-24-7
PubChem CID34230
IUPAC Name(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]propanoic acid
Molecular FormulaC40H68O11
Molecular Weight725.0
XLogP5.5
Topological Polar Surface Area142
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count11
Rotatable Bond Count9
Heavy Atom Count51
Formal Charge0
Complexity1230
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
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
InChIKey
DANUORFCFTYTSZ-SJSJOXFOSA-N
Chemical Structure
2D Structure
2D structure of Nigericin
CAS: 28380-24-7
CID: 34230
Formula: C40H68O11
MW: 725.0
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight725.0
XLogP35.5
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count11
Rotatable Bond Count9
Exact Mass724.47616298
Monoisotopic Mass724.47616298
Topological Polar Surface Area142 Ų
Heavy Atom Count51
Formal Charge0
Complexity1230
Isotope Atom Count0
Defined Atom Stereocenter Count19
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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