Compound ID | 3078

Janiemycin

Synonym(s): Chaetoglobosin C

Class: Antimicrobial peptide

Spectrum of activity: Gram-positive
Details of activity: Active against Streptococcus pyogenes, Staphylococcus aureus, Streptococcus pneumoniae, Corynebacterium sp., Listeria sp., Lactobacillus casei, Clostridium tetanomorphum, and Mycobacterium tuberculosis ; likely membrane-active agent but reported as cell wall synthesis inhibitor
Description: Natural product from Streptomyces macrosporeus; protects mice from Streptococcus pyogenes; not effective when administered orally but subcutaneous administration protects mice from Streptococcus pyogenes and Streptococcus pneumoniae infections comparable to penicillin G
Institute where first reported: The Squibb Institute for Medical Research New Brunswick
Year first mentioned: 1970
Development status: Experimental
Chemical structure(s):
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Molecular weight: 528.64
Iso. SMILES: C[C@H]/1C/C=C/[C@H]2[C@H]3[C@](O3)([C@H]([C@@H]4C2(C(=O)CCC(=O)C(=O)/C(=C1)/C)C(=O)N[C@H]4CC5=CNC6=CC=CC=C65)C)C
InChI Key: RIZAHVBYKWUPHQ-JZDGHNCDSA-N
Can. SMILES: C[C@H]/1C/C=C/[C@H]2[C@H]3[C@@](C)([C@@H](C)[C@H]4[C@H](CC5=CNC6=C5C=CC=C6)NC(=O)C24C(=O)CCC(=O)C(=O)/C(=C1)/C)O3
InChI: InChI=1S/C32H36N2O5/c1-17-8-7-10-22-29-31(4,39-29)19(3)27-24(15-20-16-33-23-11-6-5-9-21(20)23)34-30(38)32(22,27)26(36)13-12-25(35)28(37)18(2)14-17/h5-7,9-11,14,16-17,19,22,24,27,29,33H,8,12-13,15H2,1-4H3,(H,34,38)/b10-7+,18-14-/t17-,19-,22-,24-,27-,29-,31+,32?/m0/s1

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