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ADEP 4

Synonym(s): Acyldepsipeptide 4  |  ADEP-4  |  ADEP4

Class: Small molecule antibacterial agent

Agent Type: Semisynthetic; Small molecule; Direct acting; Antibiofilm;
Spectrum of activity: Gram-positive
Mechanism of action: Activates ClpP protease inducing bacterial cells to self-digest
Target Pathogen: Active against Staphylococcus aureus, including biofilms and/or persisters when combined with rifampicin
Combined with other compounds: Yes
Propensity to select resistant mutants: Yes, at ~10^-6
Description: Semisynthetic compound based on the natural product acyldepsipeptide from Streptococcus hawaiiensis
Institute where first reported: Eli Lilly and Company; Bayer HealthCare AG, Pharma Research Germany
Year first mentioned: 1985
Development status: Experimental
Chemical structure(s):
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Molecular weight: 770.86
Iso. SMILES: CCCC/C=C/C(=O)N[C@@H](CC1=CC(=CC(=C1)F)F)C(=O)N[C@H]2COC(=O)[C@@H]3C[C@H](CN3C(=O)[C@@H](NC(=O)[C@@H]4CCCCN4C(=O)[C@@H]5CCCN5C2=O)C)C
InChI Key: BAEUBYUDIYWBPI-HQKUAFLWSA-N
Can. SMILES: CCCC/C=C/C(=O)N[C@@H](CC1=CC(=CC(=C1)F)F)C(=O)N[C@H]2COC(=O)[C@@H]3C[C@@H](C)CN3C(=O)[C@H](C)NC(=O)[C@@H]4CCCCN4C(=O)[C@@H]5CCCN5C2=O
InChI: InChI=1S/C39H52F2N6O8/c1-4-5-6-7-13-33(48)43-28(19-25-17-26(40)20-27(41)18-25)34(49)44-29-22-55-39(54)32-16-23(2)21-47(32)36(51)24(3)42-35(50)30-11-8-9-14-45(30)38(53)31-12-10-15-46(31)37(29)52/h7,13,17-18,20,23-24,28-32H,4-6,8-12,14-16,19,21-22H2,1-3H3,(H,42,50)(H,43,48)(H,44,49)/b13-7+/t23-,24+,28+,29+,30+,31+,32+/m1/s1
External links:
Structure link: https://pubchem.ncbi.nlm.nih.gov/compound/11679386
Citation: https://www.nature.com/articles/nm1306
Patent: https://patents.google.com/patent/US4492650A/en

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