LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

Lasalocid A

Systematic Name

Synonyms

X-537 A

LM ID

LMPK09000002

Formula

C₃₄H₅₄O₈

Exact Mass

Calculate m/z

590.381871

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

Lasalocid is a polyketide-synthase derived ionophore antibiotic originally isolated from S. lasaliensis.^1,2 It binds to monovalent and divalent cations, including potassium, sodium, calcium, and magnesium cations.³ Lasalocid (0.01 and 0.1 µg/ml) is active against E. tenella.⁴ In vivo, lasalocid (125 ppm in the feed) reduces the severity of gastrointestinal lesions in chicks experimentally infected with E. tenella, E. maxima, E. necatrix, E. brunetti, or E. acervulina. It has been found in groundwater.⁵ Formulations containing lasalocid have been used in the treatment of coccidiosis in poultry.

This information has been provided by Cayman Chemical

References

1. Migita, A., Watanabe, M., Hirose, Y., et al. Identification of a gene cluster of polyether antibiotic lasalocid from Streptomyces lasaliensis. Biosci. Biotechnol. Biochem. 73(1), 169-176 (2009).

2. Mitrovic, M., and Schildknecht, E.G. Anticoccidial activity of lasalocid (X-537A) in chicks. Poult. Sci. 53(4), 1448-1455 (1974).

3. Antonenko, Y.N., and Yaguzhinsky, L.S. The ion selectivity of nonelectrogenic ionophores measured on a bilayer lipid membrane: nigericin, monensin, A23187 and lasalocid A. Biochim. Biophys. Acta 938(2), 125-130 (1988).

4. Folz, S.D., Lee, B.L., Nowakowski, L.H., et al. Anticoccidial evaluation of halofuginone, lasalocid, maduramicin, monensin and salinomycin. Vet. Parasitol. 28(1-2), 1-9 (1988).

5. Mooney, D., Richards, K.G., Danaher, M., et al. An investigation of anticoccidial veterinary drugs as emerging organic contaminants in groundwater. Sci. Total Environ. 746, 141116 (2020).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Streptomyces lasalocidi (#324833)

Actinomycetes (#1760)

BIOSYNTHESIS OF LASALOCID. I,
J Antibiot, 1974

DOI: 10.7164/antibiotics.27.288

String Representations

InChiKey (Click to copy)

BBMULGJBVDDDNI-OWKLGTHSSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C1(C(C(O)=O)=C(O)C(C)=CC=1)CC[C@@H](C)[C@H](O)[C@H](C)C(=O)[C@@H]([C@]1([H])[C@@H](C)C[C@@](CC)([C@@]2([H])CC[C@](O)(CC)[C@H](C)O2)O1)CC