Compound ID | 1995

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Erythromycin

Synonym(s): Ilotycin

Class: Macrolide

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Protein synthesis inhibitor. Binds to the bacterial 50S ribosomal subunit inhibiting translocation reaction
Target Pathogen: Broad Gram-positive activity
Description: Natural product from Streptomyces erythraeus; systemic and topicalapplication.
Institute where first reported: Lilly Research Laboratories
Year first mentioned: 1952
Highest development stage: Approved by FDA
Development status: Approved
Chemical structure(s):
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Molecular weight: 733.93
Iso. SMILES: CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)C)C)O)(C)O
InChI Key: ULGZDMOVFRHVEP-RWJQBGPGSA-N
Can. SMILES: CC[C@@H]1[C@](C)([C@@H]([C@@H](C)C(=O)[C@H](C)C[C@](C)([C@@H]([C@@H](C)[C@@H]([C@@H](C)C(=O)O1)O[C@H]2C[C@](C)([C@H]([C@H](C)O2)O)OC)O[C@H]3[C@@H]([C@H](C[C@@H](C)O3)N(C)C)O)O)O)O
InChI: InChI=1S/C37H67NO13/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/12560
Guide to Pharmacology: erythromycin
Citations:
  • https://pubs.acs.org/doi/10.1021/ja01618a092
  • https://www.sciencedirect.com/science/article/pii/S0140673652915572
  • https://doi.org/10.1016/S0025-6196(12)60219-5
  • https://doi.org/10.1126/science.143.3613.1445
  • https://www.nejm.org/doi/10.1056/NEJM195208142470710

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