VALINOMYCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C54H90N6O18
Molecular Weight	1111.3239
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)[C@]1([H])C(=O)O[C@@]([H])(C)C(=N[C@@]([H])(C(C)C)C(=O)O[C@]([H])(C(C)C)C(=N[C@]([H])(C(C)C)C(=O)O[C@@]([H])(C)C(=N[C@@]([H])(C(C)C)C(=O)O[C@]([H])(C(C)C)C(=N[C@]([H])(C(C)C)C(=O)O[C@@]([H])(C)C(=N[C@@]([H])(C(C)C)C(=O)O[C@]([H])(C(C)C)C(=N1)O)O)O)O)O)O

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	1111.3239
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 2502

PubMed

Title	Date	PubMed
Participation of hyf-encoded hydrogenase 4 in molecular hydrogen release coupled with proton-potassium exchange in Escherichia coli.	2001	11817571
Quantitative distinctions of active site molecular recognition by P-glycoprotein and cytochrome P450 3A4.	2001 Dec	11743742
On-chip integration of sequential ion-sensing system based on intermittent reagent pumping and formation of two-layer flow.	2001 Nov 15	11816587
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
ATP generation during reduced inorganic sulfur compound oxidation by Acidithiobacillus caldus is exclusively due to electron transport phosphorylation.	2002 Apr	12013432
Reconstitution of coupled fumarate respiration in liposomes by incorporating the electron transport enzymes isolated from Wolinella succinogenes.	2002 Apr	11952800
Effects of the ionophores valinomycin, ionomycin and gramicidin A on the element compartmentation in cultured rat hepatocytes.	2002 Apr	11869878
Valinomycin sensitivity proves that light-induced thylakoid voltages result in millisecond phase of chlorophyll fluorescence transients.	2002 Apr 22	12034474
Potassium-selective atomic force microscopy on ion-releasing substrates and living cells.	2002 Aug 15	12199601
Acetylcholine leads to free radical production dependent on K(ATP) channels, G(i) proteins, phosphatidylinositol 3-kinase and tyrosine kinase.	2002 Aug 15	12160951
Photodynamic activation of ion transport through lipid membranes and its correlation with an increased dielectric constant of the membrane.	2002 Aug 19	12101014
Calcium uptake and calcium transporter expression by trophoblast cells from human term placenta.	2002 Aug 31	12175914
Stimulation of voltage-dependent calcium channels during capacitation and by progesterone in human sperm.	2002 Dec 15	12464273
Phosphatidylserine content is a more important contributor than transmembrane potential to interactions of merocyanine 540 with lipid bilayers.	2002 Dec 23	12488051
N-terminal domain of the dual-targeted pea glutathione reductase signal peptide controls organellar targeting efficiency.	2002 Dec 6	12460562
Potassium channel openers protect cardiac mitochondria by attenuating oxidant stress at reoxygenation.	2002 Feb	11788400
Determinants of the phagosomal pH in neutrophils.	2002 Feb 22	11744729
Conditions that may affect the results of susceptibility testing of Mycobacterium tuberculosis to pyrazinamide.	2002 Jan	11800471
Regulation of intracellular pH in Calu-3 human airway cells.	2002 Jan 15	11790817
Anacardic acid-mediated changes in membrane potential and pH gradient across liposomal membranes.	2002 Jan 2	11750264
Mitochondrial sequestration and Ca(2+)-dependent release of cytosolic Zn(2+) loads in cortical neurons.	2002 Jul	12127148
Roles of the Na,K-ATPase alpha4 isoform and the Na+/H+ exchanger in sperm motility.	2002 Jul	12112599
Evaluation of the separate equilibrium processes that dictate the upper detection limit of neutral ionophore-based potentiometric sensors.	2002 Jul 1	12141674
Efflux of chromate by Pseudomonas aeruginosa cells expressing the ChrA protein.	2002 Jul 2	12113942
The fetal and neonatal brain protein neuronatin protects PC12 cells against certain types of toxic insult.	2002 Jun 30	12101027
Evidence for a gamma-hydroxybutyrate (GHB) uptake by rat brain synaptic vesicles.	2002 Mar	11948254
Interference of MI-D, a new mesoionic compound, on artificial and native membranes.	2002 Mar	11835268
Ca(2+) influx through the osteoclastic plasma membrane ryanodine receptor.	2002 May	11934703
Measuring the dielectric properties of herpes simplex virus type 1 virions with dielectrophoresis.	2002 May 10	12031284
Permeability transition-independent release of mitochondrial cytochrome c induced by valinomycin.	2002 Nov	12392554
Artificial cell based on lipid hollow polyelectrolyte microcapsules: channel reconstruction and membrane potential measurement.	2002 Nov 1	12422268
Improved purification for thermophilic F1F0 ATP synthase using n-dodecyl beta-D-maltoside.	2002 Nov 1	12392721
Ferrous-iron-dependent uptake of L-glutamate by a mesophilic, mixotrophic iron-oxidizing bacterium strain OKM-9.	2002 Oct	12450111
Biochemical and biophysical properties of purified phospholipid vesicles containing bovine heart cytochrome c oxidase.	2002 Oct	12356479
Rehydration of high-density sickle erythrocytes in vitro.	2002 Oct 15	12351416
Cyclic hexapeptide of D,L-alpha-aminoxy acids as a selective receptor for chloride ion.	2002 Oct 23	12381172
Opening of ATP-sensitive potassium channels causes generation of free radicals in vascular smooth muscle cells.	2002 Sep	12200636
Measurement of extracellular pH, K(+), and lactate in ischemic heart.	2002 Sep 1	12234463
Vesicle transmembrane potential is required for translocation to the cytosol of externally added FGF-1.	2002 Sep 2	12198150
Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites.	2003 Apr	12739759
Activation of Akt is essential for acetylcholine to trigger generation of oxygen free radicals.	2003 Apr 1	12667962
Purified human MDR 1 modulates membrane potential in reconstituted proteoliposomes.	2003 Apr 1	12653559
Active sulfate secretion by the intestine of winter flounder is through exchange for luminal chloride.	2003 Feb	12388449
Involvement of a Na+/HCO-3 cotransporter in mouse sperm capacitation.	2003 Feb 28	12496293
Evidence for nucleotide-dependent passive H+ transport protein in the plasma membrane of barley roots.	2003 Jan	12552147
Activity of isosteviol lactone on mitochondrial metabolism.	2003 Jun 5	12697384
Application of the empirical force field to macrocyclic ion carriers, siderophores, and biomimetic analogs.	2003 Mar	12601799
Calcium release from Synechocystis cells induced by depolarization of the plasma membrane: MscL as an outward Ca2+ channel.	2003 May	12724376
Transport of L-arginine and nitric oxide formation in human platelets.	2003 May	12709060

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 `Sat Jun 26 13:43:32 UTC 2021` Edited by `admin` on `Sat Jun 26 13:43:32 UTC 2021`
Record UNII	N561YS75MN
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

VALINOMYCIN

Common 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

NSC-122023

Code

English

VALINOMYCIN [HSDB]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1976