基本情報
- CAS
2001-95-8- 標準SMILES
CC(C)[C@@H]1NC(=O)[C@H](C)OC(=O)[C@@H](C(C)C)NC(=O)[C@@H](C(C)C)OC(=O)[C@H](C(C)C)NC(=O)[C@H](C)OC(=O)[C@@H](C(C)C)NC(=O)[C@@H](C(C)C)OC(=O)[C@H](C(C)C)NC(=O)[C@H](C)OC(=O)[C@@H](C(C)C)NC(=O)[C@@H](C(C)C)OC1=O- InChIKey
FCFNRCROJUBPLU-DNDCDFAISA-N- 分子式
- C54H90N6O18
- 平均分子量
- 1,111.3 g/mol
- 単同位体質量
- 1,110.63116004
概要
Shiny crystalline solid. Used as an insecticide and nematocide. Not registered as a pesticide in the U.S. (EPA, 1998)
名称と識別子
- 優先名称
- Valinomycin
- IUPAC
- (3S,6S,9R,12R,15S,18S,21R,24R,27S,30S,33R,36R)-6,18,30-trimethyl-3,9,12,15,21,24,27,33,36-nona(propan-2-yl)-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexazacyclohexatriacontane-2,5,8,11,14,17,20,23,26,29,32,35-dodecone
- 現地名
- バリノマイシン
- 英語名
- VALINOMYCIN
- 分子式
- C54H90N6O18
- 分子量
- 1111.32
名称と別名
valinomycin2001-95-8Potassium ionophore IAntibiotic N-329 BValinomicinvalinoMould ElementN561YS75MNDTXSID9041150CHEBI:28545NSC122023NSC-122023
名称をさらに表示
バリノマイシンカリウムイオノフォアI(2R,5R,8S,11S,14R,17R,20S,23S,26R,29R,32S,35S)-2,5,11,14,17,23,26,29,35-ノナイソプロピル-8,20,32-トリメチル-1,7,13,19,25,31-ヘキサオキサ-4,10,16,22,28,34-ヘキサアザシクロヘキサトリアコンタン-3,6,9,12,15,18,21,24,27,30,33,36-ドデカオン(3S,6S,9R,12R,15S,18S,21R,24R,27S,30S,33R,36R)-6,18,30-トリメチル-3,9,12,15,21,24,27,33,36-ノナキス(プロパン-2-イル)-1,7,13,19,25,31-ヘキサオキサ-4,10,16,22,28,34-ヘキサアザシクロヘキサトリアコンタン-2,5,8,11,14,17,20,23,26,29,32,35-ドデカオンシクロ(D-Hyiv-D-Val-L-Lac-L-Val-D-Hyiv-D-Val-L-Lac-L-Val-D-Hyiv-D-Val-L-Lac-L-Val-)valamycin-valyl)[qr]nsc122023[qr]valinomicin[qr]VALINOMYCIN 99%Valinomycin,90%Valinomycin,96%
Cyclic(D-alpha-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl-D-alpha-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl-D-alpha-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl)Cyclododecadepespipeptide Neutral IonophoreNSC 122023(3R,6R,9S,12S,15R,18R,21S,24S,27R,30R,33S,36S)-3,6,9,15,18,21,27,30,33-nonaisopropyl-12,24,36-trimethyl-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriacontane-2,5,8,11,14,17,20,23,26,29,32,35-dodecone(3S,6S,9R,12R,15S,18S,21R,24R,27S,30S,33R,36R)-6,18,30-trimethyl-3,9,12,15,21,24,27,33,36-nona(propan-2-yl)-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexazacyclohexatriacontane-2,5,8,11,14,17,20,23,26,29,32,35-dodeconeRefChem:193589DTXCID4017757591,7,13,19,25,31-Hexaoxa-4,10,16,22,28,34-hexaazacyclohexatriacontane-2,5,8,11,14,17,20,23,26,29,32,35-dodecone, 12,24,36-trimetyl-3,6,9,15,18,21,27,30,33-nonakis(1-methylethyl)-
物性
構造計算による物性
- XLogP
- 9.1
- 極性表面積
- 332 Ų
- 水素結合供与体数
- 6
- 水素結合受容体数
- 18
- 回転可能結合数
- 9
- 重原子数
- 78
- 形式電荷
- 0
- 複雑度
- 1,910
実験および物理化学的性質
DrugsPharmaceuticals -> Antibiotics
PesticidesPesticides -> Other Insecticides
Color/FormShiny rectangular plates
Solubility
Insoluble in water
Soluble in petroleum ether
Melting Point
374 °F (EPA, 1998)
190 °C
187 °C
Vapor Pressure0.00001 [mm Hg] @25 °C
Physical Description
Shiny crystalline solid. Used as an insecticide and nematocide. Not registered as a pesticide in the U.S. (EPA, 1998)
Shiny solid; [Merck Index] Faintly beige powder; [MSDSonline]
Collision Cross Section327.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Other Experimental Properties
ELEMENTAL COMPOSITION: C 58.36%, H 8.16%, N 7.56%, O 25.92%
Composed of 3 moles each of L-valine, D-alpha-hydroxyisovaleric acid, D-valine, and L-lactic acid linked alternately to form 36 membered ring.
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
Danger
H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
P262, P264, P270, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory Information
Valinomycin: HSNO Approval: HSR004759 Approved with controls
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
DOT LabelPoison
Fire HazardsWhen heated to decomposition, it emits toxic fumes of nitrogen oxides. (EPA, 1998)
Health HazardsThis material is highly toxic orally. (EPA, 1998)
Hazards SummaryA mild skin irritant; Corrosive to eyes; [eChemPortal: ERMA] Causes tremor and convulsions in lethal dose animal studies; [RTECS]
Reactive GroupAmides and Imides
Reactivity Profile
VALINOMYCIN is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).
化学と産業
薬理情報
MeSH Pharmacological Classification
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.
用途と製造
Uses
Antibiotic made by Streptomyces fulvissimus; Used as insecticide and nematocide; [Merck Index] Not currently registered with the EPA for use as a pesticide in the US; [CAMEO]
Farming (Pesticides) [Category: Industry]
Insecticide & nematocide
Active against Mycobacterium tuberculosis
General Manufacturing InformationValinomycin: ACTIVE
応用分野
解説バリノマイシン，放線菌から得られる抗生物質の一種で，[ (D-バリン)－(L-乳酸)－(L-バリン)－(D-α-ヒドロキシイソ吉草酸) ]3 という 12個の単位が環状につながっている。抗生物質としてはグラム陽性菌に有効である。高等生物に作用させると細胞膜やミトコンドリア膜のカリウム透過性を選択的に高めるので，イオン輸送などにおける研究手段としてしばしば用いられる。バリノマイシンの輪が膜に入り込んでチャンネルを形成し，そこを，大きさの合致するカリウムイオンが通り抜けるものと考えられる。
用途生体膜研究用、生理作用研究用。
使用Valinomycin is a hydrophobic cyclodepsipeptide with potent antitumour activity. Valinomycin is a highly selective potassium ionophore and this action leads to a diverse range of profound cell membrane effects. More recently, valinomycin has found application as a biosensor to detect to detect potassium efflux.
一般的な説明Shiny crystalline solid. Used as an insecticide and nematocide. Not registered as a pesticide in the U.S.
調製方法
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