Plusbacin A3

Class: Cyclic-lipodepsipeptide

Spectrum of activity:	Gram-negative
Details of activity:	Transglycosylase inhibitor; Inhibits VanA type VRE and MRSA
Description:	Maki H, Miura K, Yamano Y, et al. Katanosin B and plusbacin A3: inhibitors of cell wall synthesis in methicillin-resistant Staphylococcus aureus. 39th-ICAAC 1999;329.
Institute where first reported:	Shionogi; St. Marianna University School of Medicine; Toho University School of Medicine
Year first mentioned:	1999
Highest developmental phase:	Preclinical
Development status:	Inactive
Reason Dropped:	This is likely to have been due to poor pharmokinetics (LS)

Chemical structure(s):
Canonical SMILES:	CCCCCCCCCCCC1CC(=O)N(C(=O)CC(CCCCCCCCCCC(C)C)O)[C@H]([C@@H](C)O)C(=O)N[C@H](C)C(=O)N2CC[C@@H]([C@H]2C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@H]([C@H](C(=O)O)O)C(=O)N[C@H](CO)C(=O)N3CC[C@@H]([C@H]3C(=O)N[C@@H]([C@@H](C(=O)O)O)C(=O)O1)O)O
Isomeric SMILES:	CCCCCCCCCCCC1CC(=O)N([C@@H](C(=O)N[C@@H](C(=O)N2CC[C@@H]([C@H]2C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)N3CC[C@@H]([C@H]3C(=O)N[C@H](C(=O)O1)[C@@H](C(=O)O)O)O)CO)[C@H](C(=O)O)O)CCCN=C(N)N)O)C)[C@@H](C)O)C(=O)CC(CCCCCCCCCCC(C)C)O
InChI:	InChI=1S/C64H109N11O22/c1-6-7-8-9-10-11-16-19-22-26-40-34-46(82)75(45(81)33-39(78)25-21-18-15-13-12-14-17-20-24-36(2)3)49(38(5)77)56(87)68-37(4)59(90)73-31-28-43(79)50(73)57(88)69-41(27-23-30-67-64(65)66)54(85)71-47(52(83)61(92)93)55(86)70-42(35-76)60(91)74-32-29-44(80)51(74)58(89)72-48(63(96)97-40)53(84)62(94)95/h36-44,47-53,76-80,83-84H,6-35H2,1-5H3,(H,68,87)(H,69,88)(H,70,86)(H,71,85)(H,72,89)(H,92,93)(H,94,95)(H4,65,66,67)/t37-,38-,39?,40?,41+,42-,43+,44+,47-,48+,49-,50+,51+,52-,53+/m1/s1
InChI Key:	RRAOZJHXDSMGMH-LOKPQUDHSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/122404412

External links:
Guide to Pharmacology:	plusbacin A3
Main Source:	https://journals.asm.org/doi/10.1128/aac.45.6.1823-1827.2001?url_ver=Z39.88-2003&rfr_id=ori%3Arid%3Acrossref.org&rfr_dat=cr_pub++0pubmed