Nigericin

HCID 34230CAS 28380-24-7
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Grundinformationen

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
Summenformel
C40H68O11
Durchschnittliche Molmasse
725 g/mol
Monoisotopische Masse
724,476163

Überblick

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.

Namen und Bezeichner

Bevorzugter 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
Englischer Name
NIGERICIN SODIUM SALT
Summenformel
C40H68O11
Molmasse
724.96

Namen und Synonyme

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
Weitere Namen anzeigen
x-464Aids003767Aids-003767NIGERICIN NAPOLYETHERIN AAntibiotic M 2
RefChem:165829DTXCID7021079686-881-8Antibiotic K 178Helix CBSPBio_001599Antibiotic K178;Antibiotic X464C40H68O11

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,5
Polarare Oberfläche (TPSA)
142 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
11
Frei drehbare Bindungen
9
Schwere Atome
51

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Antibiotics
PesticidesBiocide

Physikochemische Eigenschaften

Schmelzpunkt
183.5 · 183.5-185°
Siedepunkt
779.9 · 779.9±60.0 °C(Predicted)
Dichte
1.19 · 1.19±0.1 g/cm3(Predicted)
storage temp.
2 · 2-8°C
Löslichkeit
10 mg/mL, · chloroform: 10 mg/mL, clear, colorless
Aggregatzustand
Solid

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Sicherheitsdaten

F
10
wgk
3
ridadr
UN 3462 6.1/PG 3
hs_code
29419090
RTECS-Nr.
QT6840000
risk_code
25-36/37/38

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 2 Einträge

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.

Anwendungen · 1 Eintrag

VerwendenNigericin 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.

Anbieter50 Anbieter

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]

Ergänzende Hinweise

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

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