Nigericin

HCID 34230

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Basic information

CAS: 28380-24-7
Standard SMILES: CO[C@@H]1C[C@@H](C[C@H]2CC[C@H](C)[C@H]([C@@H](C)C(=O)O)O2)O[C@]2(O[C@](C)([C@H]3CC[C@@](C)([C@@H]4O[C@@H]([C@H]5O[C@@](O)(CO)[C@H](C)C[C@@H]5C)C[C@@H]4C)O3)C[C@H]2C)[C@@H]1C
InChIKey: DANUORFCFTYTSZ-SJSJOXFOSA-N
Molecular formula: C40H68O11
Average molar mass: 725 g/mol
Monoisotopic mass: 724.476163

Overview

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.

Names & identifiers

Preferred name: Nigericin
IUPAC: (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
English name: NIGERICIN SODIUM SALT
Molecular formula: C40H68O11
Molecular weight: 724.96

Names & synonyms

nigericinAzalomycin M28380-24-7Helixin CAntibiotic X-464RRU6GY95ISCHEBI:7569DTXSID9041079(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

Show more names

x-464Aids003767Aids-003767NIGERICIN NAPOLYETHERIN AAntibiotic M 2

RefChem:165829DTXCID7021079686-881-8Antibiotic K 178Helix CBSPBio_001599Antibiotic K178;Antibiotic X464C40H68O11

Database identifiers

CAS: 28380-24-7
PubChem CID: 34230
DTXSID: DTXSID9041079
ChEMBL: CHEMBL405862
ChEBI: CHEBI:7569
UNII: RRU6GY95IS
EC Number: 686-881-8
Nikkaji: J19.064K

Properties

Computed structural properties

XLogP: 5.5
Topological polar surface area: 142 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 11
Rotatable bonds: 9
Heavy atoms: 51
Formal charge: 0
Complexity: 1,230

Experimental & physicochemical properties

DrugsPharmaceuticals -> Antibiotics

PesticidesBiocide

Physicochemical properties

Melting point: 183.5 · 183.5-185°
alpha: 24 · D24 +36.2° (c = 0.842 in CHCl3)
Boiling point: 779.9 · 779.9±60.0 °C(Predicted)
Density: 1.19 · 1.19±0.1 g/cm3(Predicted)
storage temp.: 2 · 2-8°C
solubility: 10 mg/mL, · chloroform: 10 mg/mL, clear, colorless
form: Solid
pka: 4.39 · 4.39±0.10(Predicted)
color: White to off-white
InChIKey: DANUORFCFTYTSZ-ANZYULKNSA-N
EWG's Food Scores: 1 · 1
FDA UNII: 6 GY95IS · RRU6GY95IS
Symbol(GHS): 6 · GHS06
Signal word: Danger
Hazard statements: 319 · H319-H335-H301-H315
Precautionary statements: 264 · P264-P270-P301+P310-P321-P330-P405-P501-P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P
Hazard Codes: T,Xi
Risk Statements: 25 · 25-36/37/38
Safety Statements: 26 · 26-36/37/39-45-36
RIDADR: 3462 · UN 3462 6.1/PG 3
WGK Germany: 3 · 3
RTECS: 6840000 · QT6840000
F: 10 · 10
HazardClass: 6.1 · 6.1(b)
PackingGroup: III
HS Code: 29419090 · 29419090
Toxicity: 50 in · LD50 in mice (mg/kg): 10-15 i.p. (Shoji); also reported as 2.5 i.p. (Harned)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 146 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Safety data

F: 10
wgk: 3
rtecs: QT6840000
ridadr: UN 3462 6.1/PG 3
hs_code: 29419090
Toxicity: LD50 in mice (mg/kg): 10-15 i.p. (Shoji); also reported as 2.5 i.p. (Harned)
risk_code: 25-36/37/38
Signal word: Danger
Symbol(GHS): GHS06
hazard_code: T,Xi
safety_code: 26-36/37/39-45-36
hazard_class: 6.1(b)
packing_group: III
Hazard statements: H319-H335-H301-H315
Precautionary statements: P264-P270-P301+P310-P321-P330-P405-P501-P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Chemical agents that increase the permeability of biological or artificial lipid membranes to specific ions. Most ionophores are relatively small organic molecules that act as mobile carriers within membranes or coalesce to form ion permeable channels across membranes. Many are antibiotics, and many act as uncoupling agents by short-circuiting the proton gradient across mitochondrial membranes.

Substances that inhibit the growth or reproduction of BACTERIA.

Applications · 1 item

UsesNigericin is a polyether antibiotic produced by Streptomyces, notably S. hygroscopicus, isolated in the 1950s. Its complex structure was finally elucidated in 1968. Nigericin is an ionophore, possessing very high affinity for monovalent cations such as Na+ and K+. Nigericin disrupts membrane potential and Golgi apparatus in mitochondria. Although nigericin can be isolated as the free acid (under acidic conditions), like most ionophores it is extracted into organic solvents and is most conveniently isolated as a salt. In vitro, nigericin has broad biological activity against Gram positive bacteria, fungi, tumour cell lines and some viruses, including HIV. Nigericin is the most common member of the polyether class which are common false positives in in vitro screening bioassays using crude microbial extracts. They are thus important standards for dereplication.

Suppliers83 total

陕西缔都新材料有限公司81124267 17392282731 · [email protected]

湖北万得化工有限公司15377098680 15377098680 · [email protected]

武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]

上海哲研生物科技有限公司021-18017610038 18017610038 · [email protected]

咸宁深蓝生物医药研发有限公司18171815831 · [email protected]

Additional notes

DefinitionChEBI: A polyether antibiotic which affects ion transport and ATPase activity in mitochondria. It is produced by Streptomyces hygroscopicus.

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