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Structure Database (LMSD)

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Common Name

Oleandomycin

Systematic Name

Synonyms

LM ID

LMPK04000007

Formula

C₃₅H₆₁NO₁₂

Exact Mass

Calculate m/z

687.419379

Status

Curated

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Classification

Biological Context

Oleandomycin is a classic macrolide antibiotic produced by strains of Streptomyces that demonstrates antimicrobial activity similar to penicillin and erythromycin.¹ Structurally, it consists of a macrocyclic lactone ring of 14 carbon atoms with one sugar, oleandrose, and one amino sugar, desoxamine, attached to the lactone ring. The mechanism of its biosynthesis and development of resistance to its antibiotic activity have been studied in order to understand the reactive enzymes in these processes.^1,2

This information has been provided by Cayman Chemical

References

1. Quirós, L.M., and Salas, J.A. Biosynthesis of the macrolide oleandomycin by Streptomyces antibioticus. Purification and kinetic characterization of an oleandomycin glucosyltransferase. The Journal of Biological Chemisty 270(31), 18234-18239 (1995).

2. Vilches, C., Méndez, C., Hardisson, C., et al. Biosynthesis of oleandomycin by Streptomyces antibioticus: Influence of nutritional conditions and development of resistance. J. Gen. Microbiol. 136(8), 1447-1454 (1990).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Streptomyces antibioticus (#1890)

Actinomycetes (#1760)

THE STRUCTURE OF OLEANDOMYCIN,
J Am Chem Soc, 1960

DOI: 10.1021/ja01497a066

String Representations

InChiKey (Click to copy)

RZPAKFUAFGMUPI-QESOVKLGSA-N

InChi (Click to copy)

InChI=1S/C35H61NO12/c1-16-14-35(15-43-35)32(40)19(4)27(37)18(3)22(7)46-33(41)21(6)31(47-26-13-25(42-11)28(38)23(8)45-26)20(5)30(16)48-34-29(39)24(36(9)10)12-17(2)44-34/h16-31,34,37-39H,12-15H2,1-11H3/t16-,17+,18-,19+,20+,21+,22+,23-,24-,25-,26-,27-,28-,29+,30-,31-,34-,35+/m0/s1

SMILES (Click to copy)

[C@@]12(C(=O)[C@H](C)[C@@H](O)[C@@H](C)[C@@H](C)OC(=O)[C@H](C)[C@@H](O[C@@H]3O[C@H]([C@H](O)[C@@H](OC)C3)C)[C@H](C)[C@@H](O[C@@H]3O[C@@H](C[C@H](N(C)C)[C@H]3O)C)[C@@H](C)C1)OC2