VALINOMYCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C54H90N6O18
Molecular Weight	1111.3218
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=FCFNRCROJUBPLU-DNDCDFAISA-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

HIDE SMILES / InChI

Molecular Formula	C54H90N6O18
Molecular Weight	1111.3218
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	12 / 12
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20568524 | DOI: 10.1007/BF01569429 | https://www.ncbi.nlm.nih.gov/pubmed/4784762

Valinomycin is an ionophore and acts by creating an influx of K+ ions in bacterial cells. It is an antibiotic substance with wide range of activity against different bacteria, fungies and virus-infected cells. Also it demonstrates insecticide and nematocide properties. Because of its toxicity to eukaryotic cells, valinomycin cannot be used in human therapy.

CNS Activity

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Activity of isosteviol lactone on mitochondrial metabolism.	2003-06-05	12697384
Calcium release from Synechocystis cells induced by depolarization of the plasma membrane: MscL as an outward Ca2+ channel.	2003-05	12724376
Transport of L-arginine and nitric oxide formation in human platelets.	2003-05	12709060
Activation of Akt is essential for acetylcholine to trigger generation of oxygen free radicals.	2003-04-01	12667962
Purified human MDR 1 modulates membrane potential in reconstituted proteoliposomes.	2003-04-01	12653559
Light-induced increase in free Mg2+ concentration in spinach chloroplasts: measurement of free Mg2+ by using a fluorescent probe and necessity of stromal alkalinization.	2003-04-01	12646275
Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites.	2003-04	12739759
Matrix volume measurements challenge the existence of diazoxide/glibencamide-sensitive KATP channels in rat mitochondria.	2003-03-15	12562892
Application of the empirical force field to macrocyclic ion carriers, siderophores, and biomimetic analogs.	2003-03	12601799
Involvement of a Na+/HCO-3 cotransporter in mouse sperm capacitation.	2003-02-28	12496293
Active sulfate secretion by the intestine of winter flounder is through exchange for luminal chloride.	2003-02	12388449
Evidence for nucleotide-dependent passive H+ transport protein in the plasma membrane of barley roots.	2003-01	12552147
Phosphatidylserine content is a more important contributor than transmembrane potential to interactions of merocyanine 540 with lipid bilayers.	2002-12-23	12488051
Stimulation of voltage-dependent calcium channels during capacitation and by progesterone in human sperm.	2002-12-15	12464273
N-terminal domain of the dual-targeted pea glutathione reductase signal peptide controls organellar targeting efficiency.	2002-12-06	12460562
Artificial cell based on lipid hollow polyelectrolyte microcapsules: channel reconstruction and membrane potential measurement.	2002-11-01	12422268
Improved purification for thermophilic F1F0 ATP synthase using n-dodecyl beta-D-maltoside.	2002-11-01	12392721
Permeability transition-independent release of mitochondrial cytochrome c induced by valinomycin.	2002-11	12392554
Cyclic hexapeptide of D,L-alpha-aminoxy acids as a selective receptor for chloride ion.	2002-10-23	12381172
Rehydration of high-density sickle erythrocytes in vitro.	2002-10-15	12351416
Ferrous-iron-dependent uptake of L-glutamate by a mesophilic, mixotrophic iron-oxidizing bacterium strain OKM-9.	2002-10	12450111
Biochemical and biophysical properties of purified phospholipid vesicles containing bovine heart cytochrome c oxidase.	2002-10	12356479
Vesicle transmembrane potential is required for translocation to the cytosol of externally added FGF-1.	2002-09-02	12198150
Measurement of extracellular pH, K(+), and lactate in ischemic heart.	2002-09-01	12234463
Opening of ATP-sensitive potassium channels causes generation of free radicals in vascular smooth muscle cells.	2002-09	12200636
Calcium uptake and calcium transporter expression by trophoblast cells from human term placenta.	2002-08-31	12175914
Photodynamic activation of ion transport through lipid membranes and its correlation with an increased dielectric constant of the membrane.	2002-08-19	12101014
Potassium-selective atomic force microscopy on ion-releasing substrates and living cells.	2002-08-15	12199601
Acetylcholine leads to free radical production dependent on K(ATP) channels, G(i) proteins, phosphatidylinositol 3-kinase and tyrosine kinase.	2002-08-15	12160951
Efflux of chromate by Pseudomonas aeruginosa cells expressing the ChrA protein.	2002-07-02	12113942
Evaluation of the separate equilibrium processes that dictate the upper detection limit of neutral ionophore-based potentiometric sensors.	2002-07-01	12141674
Mitochondrial sequestration and Ca(2+)-dependent release of cytosolic Zn(2+) loads in cortical neurons.	2002-07	12127148
Roles of the Na,K-ATPase alpha4 isoform and the Na+/H+ exchanger in sperm motility.	2002-07	12112599
The fetal and neonatal brain protein neuronatin protects PC12 cells against certain types of toxic insult.	2002-06-30	12101027
Measuring the dielectric properties of herpes simplex virus type 1 virions with dielectrophoresis.	2002-05-10	12031284
Ca(2+) influx through the osteoclastic plasma membrane ryanodine receptor.	2002-05	11934703
Valinomycin sensitivity proves that light-induced thylakoid voltages result in millisecond phase of chlorophyll fluorescence transients.	2002-04-22	12034474
ATP generation during reduced inorganic sulfur compound oxidation by Acidithiobacillus caldus is exclusively due to electron transport phosphorylation.	2002-04	12013432
Reconstitution of coupled fumarate respiration in liposomes by incorporating the electron transport enzymes isolated from Wolinella succinogenes.	2002-04	11952800
Effects of the ionophores valinomycin, ionomycin and gramicidin A on the element compartmentation in cultured rat hepatocytes.	2002-04	11869878
Evidence for a gamma-hydroxybutyrate (GHB) uptake by rat brain synaptic vesicles.	2002-03	11948254
Ferrous ion transport across chloroplast inner envelope membranes.	2002-03	11891257
Interference of MI-D, a new mesoionic compound, on artificial and native membranes.	2002-03	11835268
Sodium transport in triads isolated from rabbit skeletal muscle.	2002-02-01	11891583
Potentiometric estimation of the stability constants of ion-lonophore complexes in ion-selective membranes by the sandwich membrane method: theory, advantages, and limitations.	2002-02-01	11838668
Functional characterization of CitM, the Mg2+-citrate transporter.	2002-01-01	11891560
BCL-2 does not control programmed cell death in the IPLB-LdFB cell line from the insect Lymantria dispar.	2002	12171034
Profiling of drugs for membrane activity using liposomes as an in vitro model system.	2002	11926363
On-chip integration of sequential ion-sensing system based on intermittent reagent pumping and formation of two-layer flow.	2001-11-15	11816587
Participation of hyf-encoded hydrogenase 4 in molecular hydrogen release coupled with proton-potassium exchange in Escherichia coli.	2001	11817571

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Valinomycin is a potent replication inhibitor of severe acute respiratory syndrome (SARS) (or similar) coronavirus (CoV) infections in Vero cells with an EC50 = 0.85 uM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:06:16 GMT 2025` Edited by `admin` on `Mon Mar 31 22:06:16 GMT 2025`
Record UNII	N561YS75MN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VALINOMYCIN

Common Name

English

NSC-122023

Preferred Name

English

ANTIBIOTIC N-329 B

Common Name

English

IONOPHORE ANTIBIOTIC PRODUCED BY STREPTOMYCES FULVISSIMUS

Common Name

English

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)

Systematic Name

English

VALINOMYCIN [MI]

Common Name

English

VALINOMYCIN [HSDB]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1976