feldamycin   Click here for help

GtoPdb Ligand ID: 10979

Synonyms: BMY-28565 | BMY28565 | U-48266
Compound class: Natural product or derivative
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
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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)
InChI Key LUOBEJSTJAVJPL-UHFFFAOYSA-N
References
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]