Compound ID | 2000

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Midecamycin

Synonym(s): Rubimycin  |  espinomycin A  |  platenomycin B1  |  turimycin P3

Class: Macrolide (16-membered macrolide)

Spectrum of activity: Gram-positive
Details of activity: Binds to the peptidyl transferase component of the 50S subunit of ribosomes, thus inhibiting peptide bond formation and bacterial protein synthesis. It is active against Gram-positive bacteria.
Description: Natural product produced by Streptomyces
Year first mentioned: 1975
Development status: Approved,off-patent, not available in many countries
Chemical structure(s):
Click here for structure editor
Molecular weight: 813.97
Iso. SMILES: CCC(=O)O[C@@H]1CC(=O)O[C@@H](C/C=C/C=C/[C@@H]([C@@H](C[C@@H]([C@@H]([C@H]1OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)OC(=O)CC)(C)O)N(C)C)O)CC=O)C)O)C
InChI Key: DMUAPQTXSSNEDD-QALJCMCCSA-N
Can. SMILES: CCC(=O)O[C@@H]1CC(=O)O[C@H](C)C/C=C/C=C/[C@@H]([C@H](C)C[C@H](CC=O)[C@@H]([C@H]1OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](C)O2)O[C@H]3C[C@](C)([C@H]([C@H](C)O3)OC(=O)CC)O)N(C)C)O)O
InChI: InChI=1S/C41H67NO15/c1-11-30(45)54-29-21-32(47)51-24(4)16-14-13-15-17-28(44)23(3)20-27(18-19-43)37(38(29)50-10)57-40-35(48)34(42(8)9)36(25(5)53-40)56-33-22-41(7,49)39(26(6)52-33)55-31(46)12-2/h13-15,17,19,23-29,33-40,44,48-49H,11-12,16,18,20-22H2,1-10H3/b14-13+,17-15+/t23-,24-,25-,26+,27+,28+,29-,33+,34-,35-,36-,37+,38+,39+,40+,41-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5282169
Guide to Pharmacology: midecamycin
Citations:
  • https://academic.oup.com/jac/article/31/suppl_C/1/691484?login=true
  • https://www.clinicalmicrobiologyandinfection.com/article/S1198-743X(14)63931-8/fulltext

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