Compound ID | 2995

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Signermycin B

Class: Antivirulence agent

Spectrum of activity: Gram-positive
Details of activity: Active against methicillin-resistant and -susceptible Staphylococcus aureus, vancomycin-resistant and -susceptible Enterococcus faecalis, and Streptococcus mutans; inhibits phosphorylation activity of WalK by binding to the dimerization domain of WalK blocking WalK/WalR signal transduction necessary for cell growth and division (WalK inhibitor)
Description: Natural product from Streptomyces sp. strain MK851-mF8 extract; a tetramic acid moiety and a decalin ring
Institute where first reported: Department of Bioscience, Graduate School of Agriculture, Kinki University, Nara, Japan
Year first mentioned: 2012
Development status: Experimental
Chemical structure(s):
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Molecular weight: 389.53
Iso. SMILES: CCC[C@@H]1[C@H]([C@H]2[C@H](C[C@@H](C)[C@H](O)[C@H]2CC)C=C1C)C(=C3C(=O)N[C@@H](C)C3=O)O
InChI Key: UBDIMKJQYWYXIM-SWQDJHHFSA-N
Can. SMILES: CCC[C@H]1C(=C[C@H]2C[C@@H](C)[C@@H]([C@@H](CC)[C@H]2[C@@H]1C(=C3C(=O)[C@H](C)NC3=O)O)O)C
InChI: InChI=1S/C23H35NO4/c1-6-8-16-11(3)9-14-10-12(4)20(25)15(7-2)17(14)18(16)22(27)19-21(26)13(5)24-23(19)28/h9,12-18,20,25,27H,6-8,10H2,1-5H3,(H,24,28)/t12-,13+,14+,15+,16+,17+,18-,20+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/substance/273978175
Citation: https://journals.asm.org/doi/10.1128/aac.06467-11

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