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Merck
CN

94675

Valinomycin

≥99.0% (TLC), K+ ionophore, powder

Synonym(s):

Cyclo(L-Val-D-HyIva-D-Val-L-Lac-)3: HyIva = α-Hydroxyisovaleric acid, Lac = Lactic acid

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About This Item

Empirical Formula (Hill Notation):
C54H90N6O18
CAS Number:
2001-95-8
Molecular Weight:
1111.32
NACRES:
NA.32
PubChem Substance ID:
329770374
UNSPSC Code:
12352200
EC Number:
217-896-6
MDL number:
MFCD00005114
Beilstein/REAXYS Number:
78657

Key Documents

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Product Name

Valinomycin, ≥99.0% (TLC)

InChI key

FCFNRCROJUBPLU-RPUZOQEISA-N

InChI

1S/C54H90N6O18/c1-22(2)34-49(67)73-31(19)43(61)55-38(26(9)10)53(71)77-41(29(15)16)47(65)59-36(24(5)6)51(69)75-33(21)45(63)57-39(27(11)12)54(72)78-42(30(17)18)48(66)60-35(23(3)4)50(68)74-32(20)44(62)56-37(25(7)8)52(70)76-40(28(13)14)46(64)58-34/h22-42H,1-21H3,(H,55,61)(H,56,62)(H,57,63)(H,58,64)(H,59,65)(H,60,66)/t31-,32-,33-,34-,35+,36+,37-,38-,39-,40+,41+,42+/m0/s1

SMILES string

CC(C)[C@@H]1NC(=O)[C@H](C)OC(=O)[C@@H](NC(=O)[C@H](OC(=O)[C@@H](NC(=O)[C@H](C)OC(=O)[C@H](NC(=O)[C@H](OC(=O)[C@@H](NC(=O)[C@H](C)OC(=O)[C@H](NC(=O)[C@H](OC1=O)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C

assay

≥99.0% (TLC)

form

powder

mp

187-190 °C

antibiotic activity spectrum

mycobacteria

mode of action

cell membrane | interferes

storage temp.

2-8°C

Quality Level

200

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Application

Valinomycin has been used as an internal standard in the cytotoxicity assay for the detection of cereulide produced by emetic Bacillus cereus. It has also been used in the measurement of the electrogenicity of bile salt/H+ antiport in Escherichia coli.

Biochem/physiol Actions

K+-selective ionophore which uncouples oxidative phosphorylation.
K+-selective ionophoric cyclodepsipeptide; potassium ionophore which uncouples oxidative phosphorylation, induces apoptosis in murine thymocytes, inhibits NGF-induced neuronal differentiation and antagonizes ET-induced vasoconstriction.
Valinomycin affects the ion transport behavior of mitochondrial systems.

General description

Chemical structure: peptide
Valinomycin is a neutral cyclic dodecadepsi-peptide antibiotic, that has a 36-member ring.Valinomycin consists of twelve stereogenic centers that are made of three repeating sequences of a tetramer of D-α-hydroxyisovalericacid-D-valine-L-lactate-L-valine. It shows antibacterial, antitumor, antifungal, antiviral, and insecticidal properties. Valinomycin exerts its antiviral activity against human coronavirus OC43 (HCoV-OC43), severe acute respiratory syndrome coronavirus (SARS-CoV), and middle-east respiratory syndrome coronavirus (MERS-CoV).

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 1 Oral

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
0000490217
0000490217
0000490218
0000490218
0000497034

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Topics in Current Chemistry, 128, 175-175 (1985)
Transmembrane voltage sensor
Membrane Science and Technology, 7, 847-886 (2003)
Dong Zhang et al.
Biomedical journal, 43(5), 414-423 (2020-10-06)
Human coronaviruses (HCoVs), including severe acute respiratory syndrome coronavirus (SARS-CoV), Middle East respiratory syndrome coronavirus (MERS-CoV), and severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), have been resulting in global epidemics with heavy morbidity and mortality. Unfortunately, there are currently no
Measurement of the Electrogenicity of Bile Salt/H+ Antiport in Escherichia coli
Holdsworth S R and Law C J
Molecular Microbiology (2014)
Cytotoxicity assay for detection of cereulide produced by emetic Bacillus cereus
Frenzel E and Ehling-Schulz M
Molecular Microbiology (2012)
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