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platensimycin   Click here for help

GtoPdb Ligand ID: 14539

PDB Ligand
Compound class: Natural product
Comment: Platensimycin is a naturally occurring antibacterial, originally isolated from the soil-dwelling actinomycete Streptomyces platensis [4]. Total chemical synthesis has been reported [3]. Platensimycin has broad-spectrum Gram-positive and antimycobacterial activity, acting as an inhibitor of fatty acid synthesis [1,5].
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 8
Hydrogen bond donors 4
Rotatable bonds 6
Topological polar surface area 133.16
Molecular weight 441.47
XLogP 2.2
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES C[C@@]1(CCC(=O)NC2=C(C(=CC=C2O)C(=O)O)O)C(=O)C=C[C@@]34C[C@H]5C[C@@H]([C@@H]13)O[C@@]5(C)C4
Isomeric SMILES C[C@]12C[C@]34C[C@H]1C[C@@H]([C@H]3[C@](C(=O)C=C4)(C)CCC(=O)NC5=C(C=CC(=C5O)C(=O)O)O)O2
InChI InChI=1S/C24H27NO7/c1-22(7-6-17(28)25-18-14(26)4-3-13(19(18)29)21(30)31)16(27)5-8-24-10-12-9-15(20(22)24)32-23(12,2)11-24/h3-5,8,12,15,20,26,29H,6-7,9-11H2,1-2H3,(H,25,28)(H,30,31)/t12-,15+,20+,22-,23+,24+/m1/s1
InChI Key CSOMAHTTWTVBFL-OFBLZTNGSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Platensimycin was not advanced to clinical evaluation due to its poor pharmacokinetic properties (rapid clearance resulting in decreased systemic exposure) [2].
Mechanism Of Action and Pharmacodynamic Effects Click here for help
In bacteria, platensimycin inhibits 3-oxoacyl-[acyl-carrier-protein] synthase 2 (FabF, KAS II), a key component of the fatty acid synthase II (FAS-II) enzyme system that catalyzes the elongation cycle of fatty acid synthesis [5]. The FAS-II system is also the target in mycobacteria, with inhibition of both 3-oxoacyl-[acyl-carrier-protein] synthase 1 (KasA) and 3-oxoacyl-[acyl-carrier-protein] synthase 2 (KasB) observed [1].