Compound ID | 2133

Update compound information

Paenibacterin and analogues

Class: Lipopeptide

Spectrum of activity: Gram-negative
Details of activity: Disrupts the integrity of the outer membrane through binding to lipopolysaccarides and possibly additional modes of action. Its mode of action is similar to polymyxin. Active against enterobacterales and non-fermenters.
Description: Natural product produced by Paenibacillus; cationic nonribosomal peptide, cyclic depsipeptides
Year first mentioned: 2012
Development status: Experimental
Chemical structure(s):
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Molecular weight: 1605.1
Iso. SMILES: CCCCCCCCCCCCCCC(=O)N[C@@H](CCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@H]1[C@H](OC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]2CCCN2C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)CCCN)CO)C(C)C)CCCCN)CO)[C@@H](C)CC)C(C)C)CCCCN)[C@@H](C)CC)C
InChI Key: GZPVAWHDCVFCAB-APSGCZIASA-N
Can. SMILES: CCCCCCCCCCCCCCC(=O)N[C@@H](CCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@H]1[C@@H](C)OC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]2CCCN2C(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCCN)NC1=O
InChI: InChI=1S/C79H145N17O17/c1-13-16-17-18-19-20-21-22-23-24-25-26-39-60(99)84-53(36-31-42-82)69(102)90-63(49(8)9)76(109)95-66-52(12)113-79(112)65(51(11)15-3)94-70(103)55(35-28-30-41-81)86-75(108)62(48(6)7)92-73(106)59-38-33-44-96(59)78(111)64(50(10)14-2)93-72(105)58(46-98)89-67(100)54(34-27-29-40-80)85-74(107)61(47(4)5)91-71(104)57(45-97)88-68(101)56(37-32-43-83)87-77(66)110/h47-59,61-66,97-98H,13-46,80-83H2,1-12H3,(H,84,99)(H,85,107)(H,86,108)(H,87,110)(H,88,101)(H,89,100)(H,90,102)(H,91,104)(H,92,106)(H,93,105)(H,94,103)(H,95,109)/t50-,51-,52+,53-,54-,55-,56-,57-,58-,59-,61-,62-,63-,64-,65-,66-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/78319277
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/24866700/
  • https://academic.oup.com/femsle/article/364/8/fnx049/3052911?login=false

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