Compound ID | 3641

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Fabimycin

Synonym(s): (2E)-3-[(7S)-7-amino-8-oxo-6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-3-yl]-N-methyl-N-[(3-methyl-1-benzofuran-2-yl)methyl]prop-2-enamide

Class: Small molecule antibacterial agent

Agent Type: Synthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Fatty acid synthesis inhibitor. FabI (Fatty acid biosynthesis: Enoyl-[acyl-carrier-protein] reductase [NADH])
Target Pathogen: Active against Staphylococcus aureus and moderately active against Escherichia coli, Klebsiella pneumoniae, and Acinetobacter baumannii
Propensity to select resistant mutants: Yes, low at 8x~32x MIC
Description: Synthetic compound based on Debio-1452-NH3 which can enter the Gram-negative outer membrane
Institute where first reported: Department of Chemistry and Carl R. Woese Institute for Genomic Biology, University of Illinois at Urbana−Champaign, Urbana, Illinois 61801, United States
Year first mentioned: 2022
Development status: Experimental
Chemical structure(s):
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Molecular weight:
Iso. SMILES: CN(Cc1oc2ccccc2c1C)C(=O)\C=C\c3cnc4NC(=O)[C@@H](N)CCc4c3
InChI Key: ZWQNEFFHBSGFHV-HKMNZKMDSA-N
Can. SMILES: CC1=C(CN(C)C(=O)/C=C/C2=CN=C3C(=C2)CC[C@@H](C(=O)N3)N)OC4=C1C=CC=C4
InChI: InChI=1S/C23H24N4O3/c1-14-17-5-3-4-6-19(17)30-20(14)13-27(2)21(28)10-7-15-11-16-8-9-18(24)23(29)26-22(16)25-12-15/h3-7,10-12,18H,8-9,13,24H2,1-2H3,(H,25,26,29)/b10-7+/t18-/m0/s1
External links:
Citation: https://pubs.acs.org/doi/10.1021/acscentsci.2c00598
Patent: WO2022187329 WO2021123372 WO2022268890

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