Valinomycin
Basic information
- CAS
2001-95-8- Standard 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- Molecular formula
- C54H90N6O18
- Average molar mass
- 1,111.3 g/mol
- Monoisotopic mass
- 1,110.63116004
Overview
Shiny crystalline solid. Used as an insecticide and nematocide. Not registered as a pesticide in the U.S. (EPA, 1998)
Names & identifiers
- Preferred name
- 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
- English name
- VALINOMYCIN
- Molecular formula
- C54H90N6O18
- Molecular weight
- 1111.32
Names & synonyms
valinomycin2001-95-8Potassium ionophore IAntibiotic N-329 BValinomicinvalinoMould ElementN561YS75MNDTXSID9041150CHEBI:28545NSC122023NSC-122023
Show more names
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)-
Database identifiers
Properties
Computed structural properties
- XLogP
- 9.1
- Topological polar surface area
- 332 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 18
- Rotatable bonds
- 9
- Heavy atoms
- 78
- Formal charge
- 0
- Complexity
- 1,910
Experimental & physicochemical properties
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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
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.
Hazard information
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).
Chemistry & industry
Pharmacology
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.
Uses & manufacturing
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
Applications
DescriptionValinomycin (2001-95-8) is a selective K+ ionophore capable of transporting potassium ions through lipid membranes.1 Valinomycin can induce apoptosis in cells by causing a rapid loss of mitochondrial membrane potential via potassium efflux.2,3
Usesantibiotic; LD50 (rat, po) 4 mg/kg
UsesK+-selective ionophoric cyclodepsipeptide; potassium ionophore which uncouples oxidative phosphorylation, induces apoptosis in murine thymocytes, inhibits NGF-induced neuronal differentiation and anta gonizes ET-induced vasoconstriction. Used as insecticide, nematocide.
UsesValinomycin 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.
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Compound notes
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