Basic information
- CAS
28643-80-3- Standard SMILES
COC1CC(CC2CCC(C)C(C(C)C(=O)O)O2)OC2(OC(C)(C3CCC(C)(C4OC(C5OC(O)(CO)C(C)CC5C)CC4C)O3)CC2C)C1C- InChIKey
DANUORFCFTYTSZ-UHFFFAOYSA-N- Molecular formula
- C40H68O11
- Average molar mass
- 725 g/mol
- Monoisotopic mass
- 724.47616298
Overview
See also: Nigericin (annotation moved to).
Names & identifiers
- Preferred name
- Nigericin sodium salt (from Streptomyces hygroscopicus)
- IUPAC
- 2-[6-[[2-[5-[5-[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
- English name
- Nigericin sodium salt
- Molecular formula
- C40H69NaO11
- Molecular weight
- 748.97
Names & synonyms
NSC292567C40H68O11Neuro_000147SCHEMBL8254774CHEMBL2005417DTXSID70860416AKOS037645262AN34907AS-59318Nigericin sodium salt (from Streptomyces hygroscopicus)2-[6-[[2-[5-[5-[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 acid2-[6-[[2-[5-[5-[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
Show more names
Helexin CNigerian SodiumSodium NigericinNigericin sodiuM saNigericin sodium saltNigericin, monosodium saltNigericin, sodium salt(1:1)SODIUM NIGERICINNSC-292567Nigericin sodium salt USP/EP/BP
Properties
Computed structural properties
- XLogP
- 5.5
- Topological polar surface area
- 142 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 9
- Heavy atoms
- 51
- Formal charge
- 0
- Complexity
- 1,230
Physicochemical properties
- Melting point
- 255 ℃ · approximate 255℃
- Flash point
- 26 °C · 26 °C
- storage temp.
- 2 · 2-8°C
- solubility
- Soluble in chloroform, methanol or ethanol
- form
- lyophilized
- color
- White
- biological source
- Streptomyces hygroscopicus
- Merck
- 13 · 13,6569
- BRN
- 3892398 · 3892398
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 months.
- InChIKey
- MOYOTUKECQMGHE-NTQCAYBPSA-M
- SMILES
- [Na+].[O-]C(=O)C(C1O[C@H](CC[C@@H]1C)C[C@H]2O[C@]3(OC(CC3C)(C4OC(CC4)(C5O[C@H](C[C@@H]5C)[C@H]6O[C@@]([C@@H](C[C@@H]6C)C)(O)CO)C)C)[C@@H]([C@@H](C2)OC)C)C
- LogP
- 4.817 · 4.817 (est)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 38 HI976 · DGN38HI976
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- rtecs
- QT6840000
- ridadr
- UN 3462 6.1/PG 3
- hs_code
- 29419090
- risk_code
- 25-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T
- safety_code
- 26-36/37/39-45
- hazard_class
- 6.1
- Storage Class
- 3 - Flammable liquids
- Hazard statements
- H301-H319
- Hazard Classifications
- Flam. Liq. 3
- Precautionary statements
- P264-P270-P280-P301+P310-P305+P351+P338-P337+P313
Chemistry & industry
Applications
DescriptionNigericin Na (28643-80-3) is a polyether ionophore which disrupts membrane potential and stimulates ATPase activity in mitochondria. Induces apoptosis resulting from intracellular acidification. Ion selectivity for nigericin Na is K+> Rb+> Cs+>>Na+. Cell permeable.
UsesNigericin sodium is the atypical salt of nigericin. Since nigericin is an ionophore, its very high affinity for monovalent cations such as Na+ and K+ means that formation of a salt is a facile possess occurring during purification under any but highly acidic conditions. Typically, the salts of polyether ionophores like the free acid, are readily extracted into organic solvents. The sodium ion is stabilised within a polar pocket of the structure, effectively making the salt and free acid different chemical moieties with the potential for differing pharmacology, a fact not readily appreciated in the literature.
UsesNigericin sodium is a salt of the atypical polyether antibiotic, nigericin. Since nigericin is an ionophore, its very high affinity for monovalent cations such as Na+ and K+ means that formation of a salt is a facile possess occurring during purification under any but highly acidic conditions. Typically, the salts of polyether ionophores like the free acid, are readily extracted into organic solvents. The sodium ion is stabilised within a polar pocket of the structure, effectively making the salt and free acid different chemical moieties with the potential for differing pharmacology, a fact not readily appreciated in the literature.
UsesNigericin sodium salt is a polyether ionophore which catalyzes the electroneutral exchange of alkali metal (K+) for H+ (antiport). It disrupts membrane potential and stimulates ATPase activity in mitochondria. It transports monovalent cations across membranes with the following specificity: K+ >Rb+ >Cs+ >>Na. It kills bacteria by facilitating the diffusion of ions across membranes. It is widely used in studies of the consequences of changes in membrane potential in variable systems.
General DescriptionA monocarboxylate that catalyzes the electroneutral exchange of an alkali metal for H+ (antiport). Transports monovalent cations across membranes with the following specificities: K+>Rb+>Cs+>>Na+. An antibiotic that kills bacteria by facilitating the diffusion of ions across membranes. Disrupts the membrane potential and stimulates mitochondrial ATPase activity.
Related reactions
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Compound notes
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