Compound ID | 2809

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Amidochelocardin, 2-carboxamido-2-deacetyl-chelocardin

Synonym(s): CDCHD

Class: Tetracycline

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Active against Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, and Escherichia coli
Description: Natural product from a genetically engineered strain of Amycolatopsis sulphurea containing combined genes from chelocardin and oxytetracycline biosynthetic gene clusters; atypical tetracycline; demonstrates efficacy in ascending urinary tract infection model (10-fold lower doses compared to gentamicin); overcomes tetracycline resistance
Institute where first reported: Department of Microbial Natural Products, Helmholtz Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI) and Department of Pharmacy, Saarland University Campus, Saarbrücken, Germany; German Centre for Infection Research (DZIF), Partner Site Braunschweig-Hannover, Braunschweig, Germany
Year first mentioned: 2015
Development status: Experimental
Chemical structure(s):
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Molecular weight: 412.39
Iso. SMILES: CC1=C(C2=C(C3=C(C[C@@H]4[C@@H](C(=O)C(=C([C@@]4(C3=O)O)O)C(=O)N)N)C(=C2C=C1)C)O)O
InChI Key: QTEHNDKGFJMMIK-JTWCOAEXSA-N
Can. SMILES: CC1=CC=C2C(=C3C[C@@H]4[C@@H](C(=O)C(=C([C@@]4(C(=O)C3=C(C2=C1O)O)O)O)C(=O)N)N)C
InChI: InChI=1S/C21H20N2O7/c1-6-3-4-8-7(2)9-5-10-14(22)17(26)13(20(23)29)19(28)21(10,30)18(27)12(9)16(25)11(8)15(6)24/h3-4,10,14,24-25,28,30H,5,22H2,1-2H3,(H2,23,29)/t10-,14+,21-/m1/s1
External links:
Citations:
  • https://microbialcellfactories.biomedcentral.com/articles/10.1186/s12934-020-01495-x
  • https://onlinelibrary.wiley.com/doi/10.1002/anie.201411028
  • https://pubs.acs.org/doi/10.1021/acschembio.8b01125
  • https://journals.asm.org/doi/10.1128/spectrum.01289-23

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