(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-ヒドロキシ-6-(ヒドロキシメチル)-3,5-ジメチルオキサン-2-イル]-2,3'-ジメチル-[2,2'-ビオキソラン]-5-イル]-9-メトキシ-2,4,10-トリメチル-1,6-ジオキサスピロ[4.5]デカン-7-イル]メチル}-3-メチルオキサン-2-イル]プロパン酸

Nigericin

HCID 34230CAS 28380-24-7

基本情報

標準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
分子式: C40H68O11
平均分子量: 725 g/mol
単同位体質量: 724.476163

概要

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.

名称と識別子

優先名称: 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
現地名: (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-ヒドロキシ-6-(ヒドロキシメチル)-3,5-ジメチルオキサン-2-イル]-2,3'-ジメチル-[2,2'-ビオキソラン]-5-イル]-9-メトキシ-2,4,10-トリメチル-1,6-ジオキサスピロ[4.5]デカン-7-イル]メチル}-3-メチルオキサン-2-イル]プロパン酸
英語名: NIGERICIN SODIUM SALT
分子式: C40H68O11
分子量: 724.96

名称と別名

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

名称をさらに表示

ニゲリシンアザロマイシンMナイジェリシンポリエテリンAヘリキシンC(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-ヒドロキシ-6-(ヒドロキシメチル)-3,5-ジメチルオキサン-2-イル]-2,3'-ジメチル-[2,2'-ビオキソラン]-5-イル]-9-メトキシ-2,4,10-トリメチル-1,6-ジオキサスピロ[4.5]デカン-7-イル]メチル}-3-メチルオキサン-2-イル]プロパン酸x-464Aids003767Aids-003767NIGERICIN NAPOLYETHERIN AAntibiotic M 2

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

データベース識別子

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

物性

構造計算による物性

XLogP: 5.5
極性表面積: 142 Å²
水素結合供与体数: 3
水素結合受容体数: 11
回転可能結合数: 9
重原子数: 51
形式電荷: 0
複雑度: 1,230

実験および物理化学的性質

DrugsPharmaceuticals -> Antibiotics

PesticidesBiocide

物理化学的性質

融点: 183.5 · 183.5-185°
比旋光度: 24 · D24 +36.2° (c = 0.842 in CHCl3)
沸点: 779.9 · 779.9±60.0 °C(Predicted)
比重(密度): 1.19 · 1.19±0.1 g/cm3(Predicted)
貯蔵温度: 2 · 2-8°C
溶解性: 10 mg/mL · クロロホルム：10 mg/mL 無色透明
外見: Solid
酸解離定数(Pka): 4.39 · 4.39±0.10(Predicted)
色: White to off-white
InChIKey: DANUORFCFTYTSZ-ANZYULKNSA-N

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 3 (100%)

安全データ

F: 10
wgk: 3
rtecs: QT6840000
ridadr: UN 3462 6.1/PG 3
毒性: LD50 in mice (mg/kg): 10-15 i.p. (Shoji); also reported as 2.5 i.p. (Harned)
hs_code: 29419090
risk_code: 25-36/37/38
hazard_code: T,Xi
safety_code: 26-36/37/39-45-36
hazard_class: 6.1(b)
packing_group: III

化学と産業

薬理情報

MeSH Pharmacological Classification · 2 件

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.

応用分野 · 1 件

使用Nigericin 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.

サプライヤー50 社

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]

補足説明

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