CHEBI:28545 - valinomycin

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ChEBI Name valinomycin
ChEBI ID CHEBI:28545
Definition A twelve-membered cyclodepsipeptide composed of three repeating D-α-hydroxyisovaleryl-D-valyl-L-lactoyl-L-valyl units joined in sequence. An antibiotic found in several Streptomyces strains.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:66347, CHEBI:9924, CHEBI:27269
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Formula C54H90N6O18
Net Charge 0
Average Mass 1111.32180
Monoisotopic Mass 1110.631
InChI 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
InChIKey FCFNRCROJUBPLU-DNDCDFAISA-N
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
Metabolite of Species Details
Streptomyces padanus (NCBI:183408) of strain TH 04 See: NAT PROD SCI,2007,13,2,144
Roles Classification
Biological Role(s): potassium ionophore
Any ionophore capable of transportation of potassium ions across membranes.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antiviral agent
A substance that destroys or inhibits replication of viruses.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing valinomycin (CHEBI:28545) has role antimicrobial agent (CHEBI:33281)
valinomycin (CHEBI:28545) has role antiviral agent (CHEBI:22587)
valinomycin (CHEBI:28545) has role bacterial metabolite (CHEBI:76969)
valinomycin (CHEBI:28545) has role potassium ionophore (CHEBI:88227)
valinomycin (CHEBI:28545) is a cyclodepsipeptide (CHEBI:35213)
valinomycin (CHEBI:28545) is a macrocycle (CHEBI:51026)
IUPAC Name
(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
Synonyms Sources
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) ChemIDplus
cyclo[-D-O-Val-D-Val-L-O-Ala-L-Val]3 ChEBI
Valinomycin KEGG COMPOUND
Database Links Databases
C06684 KEGG COMPOUND
Valinomycin Wikipedia
View more database links
Registry Numbers Types Sources
2001-95-8 CAS Registry Number KEGG COMPOUND
2001-95-8 CAS Registry Number ChemIDplus
78657 Reaxys Registry Number Reaxys
78657 Beilstein Registry Number ChemIDplus
78657 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
10603383 PubMed citation Europe PMC
18633285 PubMed citation Europe PMC
19347893 PubMed citation Europe PMC
22683555 PubMed citation Europe PMC
7590182 PubMed citation Europe PMC
Last Modified
15 October 2015
General Comment
2012-07-27 NAT PROD SCI,2007,13,2,144