Compound: nigericin
SMILES: O=C(O)[C@@H]([C@@H]1O[C@H](CC[C@@H]1C)C[C@H]2O[C@]3(O[C@@]([C@@H]4O[C@@]([C@@H]5O[C@@H]([C@H]6O[C@](O)([C@H](C)C[C@@H]6C)CO)C[C@@H]5C)(C)CC4)(C)C[C@H]3C)[C@H](C)[C@@H](C2)OC)C
InChIKey: DANUORFCFTYTSZ-SJSJOXFOSA-N
Synonyms: nigericin, Azalomycin M, 28380-24-7, Helixin C, Antibiotic X-464, RRU6GY95IS, CHEBI:7569, DTXSID9041079, (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, (2R)-2-[(2R,3S,6R)-6-{[(2S,4R,5R,7R,9R,10R)-2-{(2S,2'R,3'S,5R,5'R)-5'-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl]-2,3'-dimethyloctahydro-2,2'-bifuran-5-yl}-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]dec-7-yl]methyl}-3-methyltetrahydro-2H-pyran-2-yl]propanoic acid, (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, (2R)-2-((2R,3S,6R)-6-(((2S,4R,5R,7R,9R,10R)-2-((2S,2'R,3'S,5R,5'R)-5'-((2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl)-2,3'-dimethyloctahydro-2,2'-bifuran-5-yl)-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro(4.5)dec-7-yl)methyl)-3-methyltetrahydro-2H-pyran-2-yl)propanoic acid, RefChem:165829, DTXCID7021079, 686-881-8, Antibiotic K 178, C40H68O11, Helix C, UNII-RRU6GY95IS, BRN 1696755, NSC292567, X-464, NIGERICIN [MI], GlyTouCan:G54753PV, BSPBio_001599, SCHEMBL149611, CHEMBL405862, orb1706910, HMS1791P21, HMS1989P21, HMS3402P21, Antibiotic K178;Antibiotic X464, DBA38024, G54753PV, CA-421, AKOS040742303, DB14056, NCGC00163412-02, HY-127019, CS-0091495, NS00010273, H65178, SR-05000002332, Q7033077, SR-05000002332-2, (2R)-2-((3S)-6-{[2-((5S)-5-{(3S)-5-[(3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethylperhydro-2H-pyran-2-yl]-3-methyloxolan-2-yl}-5-methyloxolan-2-yl)(2S,4R,9R,10R)-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]dec-7-yl]methyl}-3-methylperhydro-2H-pyran-2-yl)propanoic acid, (2R)-2-[(2R,3S,6R)-6-[[(1R,3S,5R,6R,7R,9R)-3-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-tetrahydropyran-2-yl]-3-methyl-tetrahydrofuran-2-yl]-5-methyl-tetrahydrofuran-2-yl]-7-methoxy-1,3,6-trimethyl-4,10-dioxaspiro[4.5]decan-9-yl]methyl]-3-methyl-tetrahydropyran-2-yl]propanoic acid, (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-dimethyl-tetrahydropyran-2-yl]-3-methyl-tetrahydrofuran-2-yl]-5-methyl-tetrahydrofuran-2-yl]-7-methoxy-2,4,6-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]methyl]-3-methyl-tetrahydropyran-2-yl]propanoic acid, (2R)-2-[(2R,3S,6R)-6-{[(2S,4R,5R,7R,9R,10R)-2-{(2S,2'R,3'S,5R,5'R)-5'-[(2S,3S,5R,6R)-6-Hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-2,3'-dimethyl[2,2'-bioxolan]-5-yl}-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]decan-7-yl]methyl}-3-methyloxan-2-yl]propanoic acid, 2H-Pyran-2-acetic acid, tetrahydro-6-[[(2S,4R,5R,7R,9R,10R)-9-methoxy-2,4,10-trimethyl-2-[(2S,2'R,3'S,5R,5'R)-octahydro-2,3'-dimethyl-5'-[(2S,3S,5R,6R)-tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2H-pyran-2-yl][2,2'-bifuran]-5-yl]-1,6-dioxaspiro[4.5]dec-7-yl]methyl]-.alpha.,3-dimethyl-, (.alpha.R,2R,3S,6R)-
Theoretical properties:
molecular_formula: C40H68O11
molecular_weight: 725.0 g/mol
exact_mass: 724.47616298 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 11
rotatable_bond_count: 9
heavy_atom_count: 51
topological_polar_surface_area: 142 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: 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.
chebi: A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by <em>Streptomyces hygroscopicus</em>.
chembl: NIGERICIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Nigericin is an antibiotic derived from Streptomyces hygroscopicus. Its isolation from soil from Nigeria was described in the 1950s, by R.L Harned (et. al), 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, and 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. Its ability to induce K+ efflux also makes it a potent activator of the NLRP3 inflammasome