Compound ID | 2607

Update compound information

Megalomicin A

Synonym(s): Megalomicin

Class: Macrolide

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Antimycobacterial
Mechanism of action: Protein synthesis inhibitor
Target Pathogen: Active against Staphylococcus, Streptococcus, Enterococcus, and Mycobacterium smegmatis
Description: Natural product from Micromonospora megalomicea; erythromycin resistant isolates are cross-resistant to megalomicin
Institute where first reported: Department of Microbiology, Schering Corporation Bloomfield, NJ USA
Year first mentioned: 1969
Development status: Experimental
Chemical structure(s):
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Molecular weight: 877.11
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)O)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O[C@H]4C[C@H]([C@H]([C@@H](O4)C)O)N(C)C)C)C)O)(C)O
InChI Key: LRWRQTMTYVZKQW-WWDNQWNISA-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)O)O[C@H]3[C@@H]([C@H](C[C@@H](C)O3)N(C)C)O)O[C@H]4C[C@H]([C@H]([C@H](C)O4)O)N(C)C)O)O
InChI: InChI=1S/C44H80N2O15/c1-16-30-44(11,54)37(50)23(4)33(47)21(2)19-43(10,61-31-18-29(46(14)15)34(48)26(7)56-31)39(60-41-35(49)28(45(12)13)17-22(3)55-41)24(5)36(25(6)40(52)58-30)59-32-20-42(9,53)38(51)27(8)57-32/h21-32,34-39,41,48-51,53-54H,16-20H2,1-15H3/t21-,22-,23+,24+,25-,26+,27+,28+,29-,30-,31+,32+,34+,35-,36+,37-,38+,39-,41+,42-,43-,44-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/31864
Citations:
  • https://pubs.acs.org/doi/epdf/10.1021/ja01054a047
  • https://www.jstage.jst.go.jp/article/antibiotics1968/22/6/22_6_253/_pdf/-char/en
    • Patent: US3819611A

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