Wollamide B

Class: Antimicrobial peptide (cyclic hexapeptide)

Spectrum of activity:	Gram-positive
Details of activity:	Active against Staphylococcus aureus, Mycobacterium bovis, and multidrug- and extensively-drug-resistant Mycobacterium tuberculosis
Description:	Natural product from Streptomyces sp., MST-11508; shows cytotoxicity to Hep2G cells at IC50 56 uM vs antimycobacterial effect at IC50 0.6-3.1 uM ; an optimised synthetic wollamide B1 with lower mammalian cytotoxicity compared to natural product had been reported; shows synergistic effect with pretomanid, delamanid, ethambutol, and para-aminosalicylic acid
Institute where first reported:	Frazer Institute, The University of Queensland, Brisbane, Queensland, Australia; Institute for Molecular Bioscience, The University of Queensland, St. Lucia, QLD 4072, Australia
Year first mentioned:	2014
Development status:	Experimental

Chemical structure(s):
Canonical SMILES:	CC(C)C[C@H]1C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(=O)N)C(=O)N[C@H](CCCN)C(=O)N[C@@H](CC2=CNC3=C2C=CC=C3)C(=O)N1
Isomeric SMILES:	CC(C)C[C@H]1C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N1)CC2=CNC3=CC=CC=C32)CCCN)CC(=O)N)C(C)C)CC(C)C
InChI:	InChI=1S/C37H57N9O7/c1-19(2)14-26-33(49)43-27(15-20(3)4)36(52)46-31(21(5)6)37(53)45-29(17-30(39)47)35(51)41-25(12-9-13-38)32(48)44-28(34(50)42-26)16-22-18-40-24-11-8-7-10-23(22)24/h7-8,10-11,18-21,25-29,31,40H,9,12-17,38H2,1-6H3,(H2,39,47)(H,41,51)(H,42,50)(H,43,49)(H,44,48)(H,45,53)(H,46,52)/t25-,26+,27-,28+,29+,31+/m1/s1
InChI Key:	OXJJMHSZSDGXNW-SCJLKASNSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/102341742

External links:
Guide to Pharmacology:	wollamide B
Main Source:	https://journals.asm.org/doi/10.1128/spectrum.00465-23
Citations:	https://journals.asm.org/doi/10.1128/aac.01773-18 https://journals.plos.org/plosone/article?id=10.1371/journal.pone.0176088 https://pubs.acs.org/doi/10.1021/ol502472c