Compound ID | 2093

Update compound information

Friulimicin

Class: Lipopeptide

Spectrum of activity: Gram-positive
Details of activity: Inhibits multiple pathways that are essential for a functional Gram-positive cell envelope, especially the membrane-associated biosynthesis steps
Description: Natural compound produced by Actinoplanes; structurally related to amphomycin and daptomycin
Year first mentioned: 2000
Highest developmental phase: Phase 1
Development status: Terminated
Reason Dropped: Unfavorable pharmacokinetics
Chemical structure(s):
Click here for structure editor
Molecular weight: 1289.44
Iso. SMILES: C[C@@H]1[C@@H](C(=O)N2CCCC[C@@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)NCC(=O)N[C@@H](C(=O)N[C@@H](C(=O)N3CCC[C@H]3C(=O)N1)C(C)C)[C@@H](C)N)CC(=O)O)CC(=O)O)[C@H](C)C(=O)O)NC(=O)[C@H](CC(=O)N)NC(=O)C/C=C\CCCCCCC(C)C
InChI Key: SLJYYRCUSIXQEQ-AJAGNRCHSA-N
Can. SMILES: CC(C)CCCCCC/C=C\CC(=O)N[C@@H](CC(=O)N)C(=O)N[C@H]1[C@@H](C)NC(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@@H]([C@@H](C)N)NC(=O)CNC(=O)[C@H](CC(=O)O)NC(=O)CNC(=O)[C@H](CC(=O)O)NC(=O)[C@H]([C@H](C)C(=O)O)NC(=O)[C@H]3CCCCN3C1=O
InChI: InChI=1S/C58H92N14O19/c1-29(2)18-13-11-9-8-10-12-14-21-40(74)64-34(24-39(60)73)51(83)70-48-33(7)63-52(84)38-20-17-23-72(38)56(88)45(30(3)4)68-55(87)47(32(6)59)67-42(76)28-62-49(81)35(25-43(77)78)65-41(75)27-61-50(82)36(26-44(79)80)66-54(86)46(31(5)58(90)91)69-53(85)37-19-15-16-22-71(37)57(48)89/h12,14,29-38,45-48H,8-11,13,15-28,59H2,1-7H3,(H2,60,73)(H,61,82)(H,62,81)(H,63,84)(H,64,74)(H,65,75)(H,66,86)(H,67,76)(H,68,87)(H,69,85)(H,70,83)(H,77,78)(H,79,80)(H,90,91)/b14-12-/t31-,32+,33+,34-,35-,36-,37+,38-,45+,46-,47+,48-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/102237795
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1803135/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2663061/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1803135/

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