Compound ID | 251

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Kibdelomycin

Class: DNA synthesis inhibitor

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: DNA synthesis inhibitor. Bacterial topoisomerase inhibitor
Target Pathogen: Active against Staphylococcus aureus, and Clostridium difficile
Propensity to select resistant mutants: Yes
Description: Natural product from Kibdelosporangium sp.
Institute where first reported: Merck Research Laboratories, USA
Year first mentioned: 2011
Development status: Experimental
Chemical structure(s):
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Molecular weight: 939.87
Iso. SMILES: C[C@H]1C=C[C@H]2[C@@H](CCC(=C)[C@@H]2C1/C(=C/3\C(=O)[C@@H](N(C3=O)[C@@H]4[C@H]([C@H]([C@H]([C@H](O4)C)OC(=O)N)OC(=O)C)OC)C(C)C)/O)O[C@H]5C[C@]([C@@H]([C@H](O5)C)O)([C@H](C)NC(=O)C6=C(C(=C(N6)C)Cl)Cl)O
InChI Key: IKNUYGJLHHAVHT-VFBNHSMVSA-N
Can. SMILES: CC(C)[C@H]1C(=O)/C(=C(\C2[C@@H](C)C=C[C@H]3[C@@H](CCC(=C)[C@@H]32)O[C@H]4C[C@@]([C@H](C)NC(=O)C5=C(C(=C(C)N5)Cl)Cl)([C@@H]([C@@H](C)O4)O)O)/O)/C(=O)N1[C@@H]6[C@H]([C@H]([C@H]([C@@H](C)O6)OC(=O)N)OC(=O)C)OC
InChI: InChI=1S/C44H60Cl2N4O14/c1-16(2)33-35(53)29(41(56)50(33)42-38(59-10)37(62-23(9)51)36(20(6)61-42)64-43(47)57)34(52)28-18(4)11-13-24-25(14-12-17(3)27(24)28)63-26-15-44(58,39(54)21(7)60-26)22(8)49-40(55)32-31(46)30(45)19(5)48-32/h11,13,16,18,20-22,24-28,33,36-39,42,48,52,54,58H,3,12,14-15H2,1-2,4-10H3,(H2,47,57)(H,49,55)/b34-29-/t18-,20+,21+,22-,24-,25+,26-,27-,28?,33-,36-,37-,38-,39+,42-,44+/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/71463014
Guide to Pharmacology: kibdelomycin A
Citations:
  • http://aac.asm.org/content/58/4/2387.full
  • https://www.ncbi.nlm.nih.gov/pubmed/25845866
  • https://doi.org/10.1016/j.chembiol.2011.06.011

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