Compound ID | 238

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Teixobactin

Class: Antimicrobial peptide

Agent Type: Natural product; Direct acting;
Spectrum of activity: Gram-positive & Antimycobacterial
Mechanism of action: Cell wall synthesis inhibitor. Lipid II inhibitor
Target Pathogen: Active against Staphylococcus aureus, enterococci, Mycobacterium tuberculosis, Clostridium difficile, and Bacillus anthracis
Description: Natural product from Eleftheria terrae; shows efficacy in mouse septicaemia model; a depsipeptide composed of enduracididine, methylphenylalanine, and D-amino acids
Institute where first reported: Novobiotic pharmaceuticals, USA (northeastern)
Year first mentioned: 2015
Highest development stage: Preclinical
Development status: Experimental
Chemical structure(s):
Click here for structure editor
Molecular weight: 1242.47
Iso. SMILES: CC[C@H](C)[C@H]1C(=O)O[C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)C[C@H]2CN=C(N2)N)C)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]([C@@H](C)CC)NC(=O)[C@@H](CCC(=O)N)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H](CC3=CC=CC=C3)NC)C
InChI Key: LMBFAGIMSUYTBN-MPZNNTNKSA-N
Can. SMILES: CC[C@H](C)[C@@H](C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(=O)N)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@@H]1[C@H](C)OC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](C[C@H]2CN=C(N)N2)NC(=O)[C@H](C)NC1=O)NC(=O)[C@@H](CC3=CC=CC=C3)NC
InChI: InChI=1S/C58H95N15O15/c1-12-28(5)42(70-49(79)37(61-11)23-34-19-17-16-18-20-34)53(83)67-39(26-74)51(81)65-36(21-22-41(59)76)48(78)69-44(30(7)14-3)55(85)71-43(29(6)13-2)54(84)68-40(27-75)52(82)73-46-33(10)88-57(87)45(31(8)15-4)72-50(80)38(24-35-25-62-58(60)64-35)66-47(77)32(9)63-56(46)86/h16-20,28-33,35-40,42-46,61,74-75H,12-15,21-27H2,1-11H3,(H2,59,76)(H,63,86)(H,65,81)(H,66,77)(H,67,83)(H,68,84)(H,69,78)(H,70,79)(H,71,85)(H,72,80)(H,73,82)(H3,60,62,64)/t28-,29-,30-,31-,32-,33-,35-,36+,37+,38-,39-,40-,42-,43-,44+,45-,46+/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/86341926
Guide to Pharmacology: teixobactin
Citations:
  • https://msystems.asm.org/content/5/3/e00077-20
  • https://www.nature.com/articles/nature14098

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