CHEBI:92181 - lasalocid

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ChEBI Name lasalocid
ChEBI ID CHEBI:92181
Definition A polyether antibiotic used for prevention and treatment of coccidiosis in poultry.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C34H54O8
Net Charge 0
Average Mass 590.798
Monoisotopic Mass 590.38187
InChI InChI=1S/C34H54O8/c1-9-25(31-21(6)18-34(11-3,42-31)26-16-17-33(40,10-2)23(8)41-26)30(37)22(7)28(35)19(4)12-14-24-15-13-20(5)29(36)27(24)32(38)39/h13,15,19,21-23,25-26,28,31,35-36,40H,9-12,14,16-18H2,1-8H3,(H,38,39)/t19-,21+,22+,23+,25+,26-,28+,31+,33-,34+/m1/s1
InChIKey BBMULGJBVDDDNI-OWKLGTHSSA-N
SMILES [H][C@@]1(O[C@@](CC)(C[C@@H]1C)[C@@]1([H])CC[C@](O)(CC)[C@H](C)O1)[C@@H](CC)C(=O)[C@@H](C)[C@@H](O)[C@H](C)CCC1=C(C(O)=O)C(O)=C(C)C=C1
Metabolite of Species Details
Streptomyces lasalocidi (NCBI:txid324833) of strain ATCC 31180T See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): coccidiostat
An agent useful in the treatment or prevention of coccidiosis in man or animals.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
ionophore
A compound which can carry specific ions through membranes of cells or organelles.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
Application(s): coccidiostat
An agent useful in the treatment or prevention of coccidiosis in man or animals.
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ChEBI Ontology
Outgoing lasalocid (CHEBI:92181) has role bacterial metabolite (CHEBI:76969)
lasalocid (CHEBI:92181) has role coccidiostat (CHEBI:35818)
lasalocid (CHEBI:92181) has role ionophore (CHEBI:24869)
lasalocid (CHEBI:92181) is a β-hydroxy ketone (CHEBI:55380)
lasalocid (CHEBI:92181) is a monocarboxylic acid (CHEBI:25384)
lasalocid (CHEBI:92181) is a monohydroxybenzoic acid (CHEBI:25389)
lasalocid (CHEBI:92181) is a oxanes (CHEBI:46942)
lasalocid (CHEBI:92181) is a oxolanes (CHEBI:26912)
lasalocid (CHEBI:92181) is a polyether antibiotic (CHEBI:26179)
lasalocid (CHEBI:92181) is a secondary alcohol (CHEBI:35681)
lasalocid (CHEBI:92181) is a tertiary alcohol (CHEBI:26878)
lasalocid (CHEBI:92181) is conjugate acid of lasalocid(1−) (CHEBI:156364)
Incoming lasalocid(1−) (CHEBI:156364) is conjugate base of lasalocid (CHEBI:92181)
IUPAC Name
(1S,9S)-1,5:6,9-dianhydro-9-[(3R,5S,6S,7R)-9-(2-carboxy-3-hydroxy-4-methylphenyl)-6-hydroxy-5,7-dimethyl-4-oxononan-3-yl]-3,4,7,8-tetradeoxy-6-ethyl-2-C-ethyl-1,8-dimethyl-D-galacto-nonitol
INNs Sources
lasalocid WHO MedNet
lasalocide WHO MedNet
lasalócido WHO MedNet
lasalocidum WHO MedNet
Synonyms Sources
6-[(3R,4S,5S,7R)-7-{(2S,3S,5S)-5-ethyl-5-[(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]-3-methyltetrahydrofuran-2-yl}-4-hydroxy-3,5-dimethyl-6-oxononyl]-2-hydroxy-3-methylbenzoic acid IUPAC
antibiotic X 537A ChemIDplus
ionophore X 537A ChemIDplus
lasalocid A ChemIDplus
Ro 2-2985 ChemIDplus
X 537A ChemIDplus
X-537A ChEBI
Manual Xrefs Databases
D04671 KEGG DRUG
DB11423 DrugBank
Lasalocid Wikipedia
LMPK09000002 LIPID MAPS
LSD PDBeChem
LSM-2214 LINCS
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Registry Number Type Source
25999-31-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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PMC6663702 PubMed Central citation Europe PMC
Last Modified
19 August 2020