Compound ID | 2110

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Pacidamycin

Class: Natural product antibiotic

Spectrum of activity: Gram-negative
Details of activity: Interferes with cell-wall synthesis by inhibiting transfer of the peptidoglycan precursor moiety (MurNAc-pentapeptide) to the membrane lipid carrier, undecaprenyl phosphate. Activity against Pseudomonas aeruginosa; high frequency of mutations
Description: Natural product produced by Streptomyces
Year first mentioned: 1988
Development status: Experimental
Chemical structure(s):
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Molecular weight: 805.83
Iso. SMILES: C[C@@H]([C@@H](C(=O)NC[C@H]1C[C@H]([C@@H](O1)N2C=CC(=O)NC2=O)O)NC(=O)[C@H](C)NC(=O)N[C@@H](CC3=CNC4=CC=CC=C43)C(=O)O)N(C)C(=O)[C@H](CC5=CC=C(C=C5)O)N
InChI Key: HKPRQZOLLXYDJX-KOGPLRHPSA-N
Can. SMILES: C[C@@H](C(=O)N[C@@H]([C@H](C)N(C)C(=O)[C@H](CC1=CC=C(C=C1)O)N)C(=O)NC[C@H]2C[C@H]([C@H](N3C=CC(=O)NC3=O)O2)O)NC(=O)N[C@@H](CC4=CNC5=C4C=CC=C5)C(=O)O
InChI: InChI=1S/C38H47N9O11/c1-19(42-37(56)43-28(36(54)55)15-22-17-40-27-7-5-4-6-25(22)27)32(51)45-31(20(2)46(3)34(53)26(39)14-21-8-10-23(48)11-9-21)33(52)41-18-24-16-29(49)35(58-24)47-13-12-30(50)44-38(47)57/h4-13,17,19-20,24,26,28-29,31,35,40,48-49H,14-16,18,39H2,1-3H3,(H,41,52)(H,45,51)(H,54,55)(H2,42,43,56)(H,44,50,57)/t19-,20-,24+,26-,28-,29+,31-,35+/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/44340968
Guide to Pharmacology: pacidamycin
Citations:
  • https://journals.asm.org/doi/pdf/10.1128/aac.01198-13
  • https://pubmed.ncbi.nlm.nih.gov/20665770/
  • https://www.jstage.jst.go.jp/article/antibiotics1968/42/4/42_4_521/_article
  • https://pubmed.ncbi.nlm.nih.gov/31471595/

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