Compound ID | 190

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NAB739

Class: Antimicrobial peptide

Agent Type: Semisynthetic; Direct acting;
Spectrum of activity: Gram-negative
Mechanism of action: Membrane-active agent. Disrupts the outer membrane by direct interaction with the lipid A component of the LPS and disrupts the physical integrity of the phospholipid bilayer of the inner membrane
Description: Semisynthetic compound derived from polymyxin B; exhibits less nephrotoxicity vs polymyxin B; potentiates and expands the activity to Gram-negative activity
Institute where first reported: Northen Antibiotics, Finland
Year first mentioned: 2008
Highest development stage: Preclinical
Development status: Active
Chemical structure(s):
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Molecular weight: 1076.29
Iso. SMILES: CCCCCCCC(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)NC1CCNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C(NC(=O)[C@H](NC(=O)[C@@H](NC1=O)CCN)CC2=CC=CC=C2)CC(C)C)CCN)CCN)[C@@H](C)O
InChI Key: MDZVFKKBSGQKQR-XNUGQAHBSA-N
Can. SMILES: CCCCCCCC(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)NC1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)C(CC(C)C)NC(=O)[C@@H](CC2=CC=CC=C2)NC(=O)[C@H](CCN)NC1=O
InChI: InChI=1S/C50H85N13O13/c1-6-7-8-9-13-16-39(67)62-41(30(5)66)50(76)61-38(27-64)48(74)58-35-20-24-54-49(75)40(29(4)65)63-45(71)34(19-23-53)56-42(68)32(17-21-51)57-46(72)36(25-28(2)3)59-47(73)37(26-31-14-11-10-12-15-31)60-43(69)33(18-22-52)55-44(35)70/h10-12,14-15,28-30,32-38,40-41,64-66H,6-9,13,16-27,51-53H2,1-5H3,(H,54,75)(H,55,70)(H,56,68)(H,57,72)(H,58,74)(H,59,73)(H,60,69)(H,61,76)(H,62,67)(H,63,71)/t29-,30-,32+,33+,34+,35?,36?,37-,38+,40+,41+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/77282695
Guide to Pharmacology: NAB739
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/29149329/
  • https://www.nature.com/articles/ja2016146

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