Structure via PubChem · Public domain (PubChem)
plantazolicin
Sign in to saveAlso known as PZN, plantazolicin A
Plantazolicin (PZN) is a natural antibiotic produced by the gram-positive soil bacterium Bacillus velezensis FZB42 (previously Bacillus amyloliquefaciens FZB42). PZN has specifically been identified as a selective bactericidal agent active against Bacillus anthracis, the causative agent of anthrax. This natural product is a ribosomally synthesized and post-translationally modified peptide (RiPP); it can be classified further as a thiazole/oxazole-modified microcin (TOMM) or a linear azole-containing peptide (LAP).
Chemical data
- Formula
- C63H69N17O13S2
- Molecular weight
- 1336.5 g/mol
- IUPAC name
- (2S)-2-[[2-[2-[2-[2-[2-[(1S,2S)-1-[[(2S,3S)-2-[[2-[2-[2-[2-[2-[4-(diaminomethylideneamino)-1-(dimethylamino)butyl]-1,3-thiazol-4-yl]-5-methyl-1,3-oxazol-4-yl]-1,3-thiazol-4-yl]-5-methyl-1,3-oxazol-4-yl]-5-methyl-1,3-oxazole-4-carbonyl]amino]-3-methylpentanoyl]amino]-2-methylbutyl]-1,3-oxazol-4-yl]-1,3-oxazol-4-yl]-1,3-oxazol-4-yl]-1,3-oxazol-4-yl]-5-methyl-4,5-dihydro-1,3-oxazole-4-carbonyl]amino]-3-phenylpropanoic acid
- SMILES
- CC[C@H](C)[C@@H](C1=NC(=CO1)C2=NC(=CO2)C3=NC(=CO3)C4=NC(=CO4)C5=NC(C(O5)C)C(=O)N[C@@H](CC6=CC=CC=C6)C(=O)O)NC(=O)[C@H]([C@@H](C)CC)NC(=O)C7=C(OC(=N7)C8=C(OC(=N8)C9=CSC(=N9)C1=C(OC(=N1)C1=CSC(=N1)C(CCCN=C(N)N)N(C)C)C)C)C
- InChIKey
- SKALCVOFYPVXLA-DUJKJIRYSA-N
- XLogP
- 4.1
- Polar surface area
- 478 Ų
- H-bond donors
- 6
- H-bond acceptors
- 27
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 1335.470217268
Show 5 more facts
- canonical SMILES
- CCC(C)C(C1=NC(=CO1)C2=NC(=CO2)C3=NC(=CO3)C4=NC(=CO4)C5=NC(C(O5)C)C(=O)NC(CC6=CC=CC=C6)C(=O)O)NC(=O)C(C(C)CC)NC(=O)C7=C(OC(=N7)C8=C(OC(=N8)C9=CSC(=N9)C1=C(OC(=N1)C1=CSC(=N1)C(CCCN=C(N)N)N(C)C)C)C)C
- chemical formula
- C₆₃H₆₉N₁₇O₁₃S₂
- Commons category
- Plantazolicin
- isomeric SMILES
- CC[C@H](C)[C@@H](C1=NC(=CO1)C2=NC(=CO2)C3=NC(=CO3)C4=NC(=CO4)C5=NC(C(O5)C)C(=O)N[C@@H](CC6=CC=CC=C6)C(=O)O)NC(=O)[C@H]([C@@H](C)CC)NC(=O)C7=C(OC(=N7)C8=C(OC(=N8)C9=CSC(=N9)C1=C(OC(=N1)C1=CSC(=N1)C(CCCN=C(N)N)N(C)C)C)C)C
- found in taxon
- Bacillus amyloliquefaciens
Sources (1)
via Wikidata · CC0
~3 min read
Encyclopedic overview
3 sectionsContents
- History
- Biosynthesis
- References
Plantazolicin (PZN) is a natural antibiotic produced by the gram-positive soil bacterium Bacillus velezensis FZB42 (previously Bacillus amyloliquefaciens FZB42). PZN has specifically been identified as a selective bactericidal agent active against Bacillus anthracis, the causative agent of anthrax. This natural product is a ribosomally synthesized and post-translationally modified peptide (RiPP); it can be classified further as a thiazole/oxazole-modified microcin (TOMM) or a linear azole-containing peptide (LAP).
The significance of PZN stems from its narrow-spectrum antibiotic activity. Most antibiotics in clinical use are broad-spectrum, acting against a wide variety of bacteria, and antibiotic resistance to these drugs is common. In contrast, PZN is antibacterial against only a small number of species, including Bacillus anthracis.
Excerpted from Wikipedia’s “plantazolicin” article, available under the CC BY-SA 4.0 licence.