Compound ID | 2682

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Polypeptin

Class: Antimicrobial peptide

Agent Type: Natural product;
Spectrum of activity: Gram-positive, Gram-negative & Antimycobacterial
Mechanism of action: Unknown
Target Pathogen: Active against Staphylococcus aureus, Streptococcus pneumoniae, Escherichia coli, Salmonella paratyphi, Klebsiella pneumoniae, Salmonella typhimurium, and Clostridium perfringens, also active against Mycobacterium tuberculosis
Description: Natural product from Bacillus circulans (also by Bacillus krzemieniewski); previously described as circulin (1948) but renamed to polypeptin as there is already an existing compound with this name; toxic when administered parenterally
Year first mentioned: 1948
Development status: Experimental
Chemical structure(s):
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Molecular weight: 1057.25
Iso. SMILES: CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N1)CC(C)C)CCN)NC(=O)[C@H](CCN)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC=O)[C@@H](C)O)CCN)CCN
InChI Key: YLHJFOAQDDQFIU-LGGGVIKPSA-N
Can. SMILES: CC[C@H](C)[C@H]1C(=O)N[C@@H](CCN)C(=O)N[C@@H](CCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC[C@@H](C(=O)N[C@@H](CCN)C(=O)N[C@H](CC(C)C)C(=O)N1)NC(=O)[C@H](CCN)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC=O
InChI: InChI=1S/C45H84N16O13/c1-7-23(4)33-44(73)56-28(10-16-48)37(66)54-30(12-18-50)41(70)60-34(24(5)63)43(72)51-19-13-31(40(69)53-27(9-15-47)39(68)58-32(20-22(2)3)42(71)59-33)55-38(67)29(11-17-49)57-45(74)35(25(6)64)61-36(65)26(8-14-46)52-21-62/h21-35,63-64H,7-20,46-50H2,1-6H3,(H,51,72)(H,52,62)(H,53,69)(H,54,66)(H,55,67)(H,56,73)(H,57,74)(H,58,68)(H,59,71)(H,60,70)(H,61,65)/t23-,24+,25+,26-,27-,28-,29-,30-,31-,32+,33-,34-,35-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/3084043
Guide to Pharmacology: polypeptin
Citations:
  • https://pubs.acs.org/doi/epdf/10.1021/jm00232a012
  • https://www.sciencedirect.com/science/article/pii/S0021925818562797
  • https://www.jci.org/articles/view/102135
  • https://pubmed.ncbi.nlm.nih.gov/18101388/
  • https://journals.asm.org/doi/epdf/10.1128/jb.56.6.749-754.1948?src=getftr

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