Compound ID | 263

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Vancomyquine (PA1409)

Class: Glycopeptide

Agent Type: Semisynthetic; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Membrane-active agent
Target Pathogen: Active against Enterococcus faecalis, Staphylococci, and Streptococci
Description: A vancomycin covalently bonded to a 4-aminoquinoline; Meunier B. Vancomyquine PA1409: A New Hybrid Antibacterial Molecule. F1-2031 49th-ICAAC 2009
Institute where first reported: PALUMED, France
Year first mentioned: 2009
Highest development stage: Preclinical
Development status: Experimental
Reason dropped: Specific toxicity issues resulted in the closure of the antibioquines program in 2010
Chemical structure(s):
Click here for structure editor
Molecular weight: 1749.96
Iso. SMILES: CN[C@H](CC(C)C)C(=O)N[C@H]1C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H]2C(=O)N[C@H]3C(=O)N[C@H](C(=O)N[C@@H](C(=O)O)C4=CC(O)=CC(O)=C4C5=CC3=CC=C5O)[C@H](O)C6=CC=C(C(Cl)=C6)OC7=CC2=CC(=C7O[C@@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O[C@H]9C[C@](C)(NCCCCNC%10=CC(C(F)(F)F)=NC%11=CC(Cl)=CC=C%10%11)[C@H](O)[C@H](C)O9)OC%12=CC=C(C=C%12Cl)[C@H]1O
InChI Key: BYSOSBDCGPPLKL-CIRXNKTDSA-N
Can. SMILES: CC(C)C[C@H](C(=O)N[C@@H]1[C@@H](C2=CC=C(C(=C2)Cl)OC3=CC4=CC(=C3O[C@H]5[C@@H]([C@H]([C@@H]([C@@H](CO)O5)O)O)O[C@H]6C[C@@](C)([C@@H]([C@H](C)O6)O)NCCCCNC7=CC(=NC8=CC(=CC=C78)Cl)C(F)(F)F)OC9=CC=C(C=C9Cl)[C@H]([C@H]%10C(=O)N[C@H](C%11=CC(=CC(=C%11C%12=CC(=CC=C%12O)[C@H](C(=O)N%10)NC(=O)[C@@H]4NC(=O)[C@H](CC(=O)N)NC1=O)O)O)C(=O)O)O)O)NC
InChI: InChI=1S/C80H87Cl3F3N11O24/c1-31(2)18-46(88-5)71(108)96-62-64(103)34-9-14-50(42(82)20-34)117-52-22-36-23-53(68(52)121-78-69(67(106)66(105)54(30-98)119-78)120-57-29-79(4,70(107)32(3)116-57)90-17-7-6-16-89-44-27-55(80(84,85)86)91-45-24-37(81)11-12-39(44)45)118-51-15-10-35(21-43(51)83)65(104)63-76(113)95-61(77(114)115)41-25-38(99)26-49(101)58(41)40-19-33(8-13-48(40)100)59(73(110)97-63)94-74(111)60(36)93-72(109)47(28-56(87)102)92-75(62)112/h8-15,19-27,31-32,46-47,54,57,59-67,69-70,78,88,90,98-101,103-107H,6-7,16-18,28-30H2,1-5H3,(H2,87,102)(H,89,91)(H,92,112)(H,93,109)(H,94,111)(H,95,113)(H,96,108)(H,97,110)(H,114,115)/t32-,46+,47-,54+,57-,59+,60+,61+,62+,63-,64+,65+,66+,67-,69+,70+,78-,79-/m0/s1
External links:
Citations:
  • https://patents.google.com/patent/WO2010089341A1/en
  • http://aac.asm.org/content/55/1/395.full
    • Patent: WO2010089341A1

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