Compound ID | 3663

Update compound information

N-Pentylpantothenamide

Synonym(s): N5-Pan  |  Pentyl-pantothenamide  |  N-pentyl-D-pantothenamide

Class: Small molecule antibacterial agent

Agent Type: Synthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: PanK-targeting CoA biosynthesis antimetabolite
Target Pathogen: Escherichia coli; Staphylococcus aureus
Propensity to select resistant mutants: Yes, ~100 fold MIC increase (pantothenate-dependent resistant vs susceptible E. coli strains)
Institute where first reported: North Texas State University
Year first mentioned: 1970
Highest development stage: Preclinical
Development status: Unknown
Chemical structure(s):
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Molecular weight: 288.38
Iso. SMILES: CCCCCNC(=O)CCNC(=O)[C@@H](C(C)(C)CO)O
InChI Key: HWNKKPMQPCHGBA-LBPRGKRZSA-N
Can. SMILES: CCCCCNC(=O)CCNC(=O)[C@@H](C(C)(C)CO)O
InChI: InChI=1S/C14H28N2O4/c1-4-5-6-8-15-11(18)7-9-16-13(20)12(19)14(2,3)10-17/h12,17,19H,4-10H2,1-3H3,(H,15,18)(H,16,20)/t12-/m0/s1
External links:
Structure link: https://pubchem.ncbi.nlm.nih.gov/compound/10424213
Citations:
  • https://doi.org/10.1016/0003-9861(70)90470-4
  • https://doi.org/10.1021/acs.biochem.7b00509
    • Patents:
  • WO2011152720
  • WO2020141155
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