feldamycin   Click here for help

GtoPdb Ligand ID: 10979

Synonyms: BMY-28565 | BMY28565 | U-48266
Comment: Feldamycin is a naturally occurring antibacterial agent produced by Streptomyces ficellus [1-2,4]. Its in vitro antibacterial activity was not reproduced in rodent infection models. Feldamycin can be made using synthetic chemistry [3].
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 10
Hydrogen bond donors 7
Rotatable bonds 13
Topological polar surface area 185.12
Molecular weight 407.19
XLogP -2.22
No. Lipinski's rules broken 2
Click here for help
Canonical SMILES CNC(C(=O)NC(C(NC(C(=O)O)Cc1cnc[nH]1)C)C(=O)O)Cc1cnc[nH]1
Isomeric SMILES CNC(C(=O)NC(C(NC(C(=O)O)Cc1cnc[nH]1)C)C(=O)O)Cc1cnc[nH]1
InChI InChI=1S/C17H25N7O5/c1-9(23-13(16(26)27)4-11-6-20-8-22-11)14(17(28)29)24-15(25)12(18-2)3-10-5-19-7-21-10/h5-9,12-14,18,23H,3-4H2,1-2H3,(H,19,21)(H,20,22)(H,24,25)(H,26,27)(H,28,29)
1. Argoudelis AD, Mizsak SA, Baczynskyj L, Wnuk RJ. (1976)
The structure of feldamycin.
J Antibiot, 29 (10): 1117-9. [PMID:994330]
2. Argoudelis AD, Reusser F, Mizsak SA, Baczynskyj L. (1976)
Antibiotics produced by Streptomyces ficellus II. Feldamycin and nojirimycin.
J Antibiot, 29 (10): 1007-14. [PMID:994320]
3. Imae K, Kamachi H, Yamashita H, Okita T, Okuyama S, Tsuno T, Yamasaki T, Sawada Y, Ohbayashi M, Naito T et al.. (1991)
Synthesis, stereochemistry, and biological properties of the depigmenting agents, melanostatin, feldamycin and analogs.
J Antibiot, 44 (1): 76-85. [PMID:1672126]
4. Reusser F. (1977)
Ficellomycin and feldamycin; inhibitors of bacterial semiconservative DNA replication.
Biochemistry, 16 (15): 3406-12. [PMID:329871]