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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 of VALINOMYCIN

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

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.

Originator

Sources: DOI: 10.1002/cber.19550880111

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Participation of hyf-encoded hydrogenase 4 in molecular hydrogen release coupled with proton-potassium exchange in Escherichia coli.
2001
Quantitative distinctions of active site molecular recognition by P-glycoprotein and cytochrome P450 3A4.
2001 Dec
On-chip integration of sequential ion-sensing system based on intermittent reagent pumping and formation of two-layer flow.
2001 Nov 15
BCL-2 does not control programmed cell death in the IPLB-LdFB cell line from the insect Lymantria dispar.
2002
Profiling of drugs for membrane activity using liposomes as an in vitro model system.
2002
ATP generation during reduced inorganic sulfur compound oxidation by Acidithiobacillus caldus is exclusively due to electron transport phosphorylation.
2002 Apr
Reconstitution of coupled fumarate respiration in liposomes by incorporating the electron transport enzymes isolated from Wolinella succinogenes.
2002 Apr
Effects of the ionophores valinomycin, ionomycin and gramicidin A on the element compartmentation in cultured rat hepatocytes.
2002 Apr
Valinomycin sensitivity proves that light-induced thylakoid voltages result in millisecond phase of chlorophyll fluorescence transients.
2002 Apr 22
Potassium-selective atomic force microscopy on ion-releasing substrates and living cells.
2002 Aug 15
Acetylcholine leads to free radical production dependent on K(ATP) channels, G(i) proteins, phosphatidylinositol 3-kinase and tyrosine kinase.
2002 Aug 15
Photodynamic activation of ion transport through lipid membranes and its correlation with an increased dielectric constant of the membrane.
2002 Aug 19
Calcium uptake and calcium transporter expression by trophoblast cells from human term placenta.
2002 Aug 31
Stimulation of voltage-dependent calcium channels during capacitation and by progesterone in human sperm.
2002 Dec 15
Phosphatidylserine content is a more important contributor than transmembrane potential to interactions of merocyanine 540 with lipid bilayers.
2002 Dec 23
N-terminal domain of the dual-targeted pea glutathione reductase signal peptide controls organellar targeting efficiency.
2002 Dec 6
Potassium channel openers protect cardiac mitochondria by attenuating oxidant stress at reoxygenation.
2002 Feb
Determinants of the phagosomal pH in neutrophils.
2002 Feb 22
Conditions that may affect the results of susceptibility testing of Mycobacterium tuberculosis to pyrazinamide.
2002 Jan
Regulation of intracellular pH in Calu-3 human airway cells.
2002 Jan 15
Anacardic acid-mediated changes in membrane potential and pH gradient across liposomal membranes.
2002 Jan 2
Mitochondrial sequestration and Ca(2+)-dependent release of cytosolic Zn(2+) loads in cortical neurons.
2002 Jul
Roles of the Na,K-ATPase alpha4 isoform and the Na+/H+ exchanger in sperm motility.
2002 Jul
Evaluation of the separate equilibrium processes that dictate the upper detection limit of neutral ionophore-based potentiometric sensors.
2002 Jul 1
Efflux of chromate by Pseudomonas aeruginosa cells expressing the ChrA protein.
2002 Jul 2
The fetal and neonatal brain protein neuronatin protects PC12 cells against certain types of toxic insult.
2002 Jun 30
Evidence for a gamma-hydroxybutyrate (GHB) uptake by rat brain synaptic vesicles.
2002 Mar
Interference of MI-D, a new mesoionic compound, on artificial and native membranes.
2002 Mar
Ca(2+) influx through the osteoclastic plasma membrane ryanodine receptor.
2002 May
Measuring the dielectric properties of herpes simplex virus type 1 virions with dielectrophoresis.
2002 May 10
Permeability transition-independent release of mitochondrial cytochrome c induced by valinomycin.
2002 Nov
Artificial cell based on lipid hollow polyelectrolyte microcapsules: channel reconstruction and membrane potential measurement.
2002 Nov 1
Improved purification for thermophilic F1F0 ATP synthase using n-dodecyl beta-D-maltoside.
2002 Nov 1
Ferrous-iron-dependent uptake of L-glutamate by a mesophilic, mixotrophic iron-oxidizing bacterium strain OKM-9.
2002 Oct
Biochemical and biophysical properties of purified phospholipid vesicles containing bovine heart cytochrome c oxidase.
2002 Oct
Rehydration of high-density sickle erythrocytes in vitro.
2002 Oct 15
Cyclic hexapeptide of D,L-alpha-aminoxy acids as a selective receptor for chloride ion.
2002 Oct 23
Opening of ATP-sensitive potassium channels causes generation of free radicals in vascular smooth muscle cells.
2002 Sep
Measurement of extracellular pH, K(+), and lactate in ischemic heart.
2002 Sep 1
Vesicle transmembrane potential is required for translocation to the cytosol of externally added FGF-1.
2002 Sep 2
Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites.
2003 Apr
Activation of Akt is essential for acetylcholine to trigger generation of oxygen free radicals.
2003 Apr 1
Purified human MDR 1 modulates membrane potential in reconstituted proteoliposomes.
2003 Apr 1
Active sulfate secretion by the intestine of winter flounder is through exchange for luminal chloride.
2003 Feb
Involvement of a Na+/HCO-3 cotransporter in mouse sperm capacitation.
2003 Feb 28
Evidence for nucleotide-dependent passive H+ transport protein in the plasma membrane of barley roots.
2003 Jan
Activity of isosteviol lactone on mitochondrial metabolism.
2003 Jun 5
Application of the empirical force field to macrocyclic ion carriers, siderophores, and biomimetic analogs.
2003 Mar
Calcium release from Synechocystis cells induced by depolarization of the plasma membrane: MscL as an outward Ca2+ channel.
2003 May
Transport of L-arginine and nitric oxide formation in human platelets.
2003 May
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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
HSDB   MI  
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
Created by admin on Sat Jun 26 13:43:32 UTC 2021 , Edited by admin on Sat Jun 26 13:43:32 UTC 2021
Code System Code Type Description
HSDB
6423
Created by admin on Sat Jun 26 13:43:32 UTC 2021 , Edited by admin on Sat Jun 26 13:43:32 UTC 2021
PRIMARY
MESH
D014634
Created by admin on Sat Jun 26 13:43:32 UTC 2021 , Edited by admin on Sat Jun 26 13:43:32 UTC 2021
PRIMARY
PUBCHEM
3000706
Created by admin on Sat Jun 26 13:43:32 UTC 2021 , Edited by admin on Sat Jun 26 13:43:32 UTC 2021
PRIMARY
EPA CompTox
2001-95-8
Created by admin on Sat Jun 26 13:43:32 UTC 2021 , Edited by admin on Sat Jun 26 13:43:32 UTC 2021
PRIMARY
ECHA (EC/EINECS)
217-896-6
Created by admin on Sat Jun 26 13:43:32 UTC 2021 , Edited by admin on Sat Jun 26 13:43:32 UTC 2021
PRIMARY
DRUG BANK
DB14057
Created by admin on Sat Jun 26 13:43:32 UTC 2021 , Edited by admin on Sat Jun 26 13:43:32 UTC 2021
PRIMARY
MERCK INDEX
M11366
Created by admin on Sat Jun 26 13:43:32 UTC 2021 , Edited by admin on Sat Jun 26 13:43:32 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C924
Created by admin on Sat Jun 26 13:43:32 UTC 2021 , Edited by admin on Sat Jun 26 13:43:32 UTC 2021
PRIMARY
FDA UNII
N561YS75MN
Created by admin on Sat Jun 26 13:43:32 UTC 2021 , Edited by admin on Sat Jun 26 13:43:32 UTC 2021
PRIMARY
CAS
2001-95-8
Created by admin on Sat Jun 26 13:43:32 UTC 2021 , Edited by admin on Sat Jun 26 13:43:32 UTC 2021
PRIMARY
WIKIPEDIA
VALINOMYCIN
Created by admin on Sat Jun 26 13:43:32 UTC 2021 , Edited by admin on Sat Jun 26 13:43:32 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY