pleuromulin   Click here for help

GtoPdb Ligand ID: 12935

Synonyms: drosophilin B | pleuromutilin
Compound class: Natural product or derivative
Comment: Pleuromulin (also known as pleuromutilin) was initially isolated from fungal species of the genus Pleurotus and was the first pleuromutilin class antibacterial to be discovered [1]. Further optimization of pleuromulin led to the development of the clinically approved medicines lefamulin and retapamulin.
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 5
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 83.83
Molecular weight 378.5
XLogP 2.7
No. Lipinski's rules broken 0
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 C=C[C@]1(C)C[C@H]([C@]2(C)[C@H](C)CC[C@]3(CCC(=O)[C@@H]23)[C@@H](C)[C@@H]1O)OC(=O)CO
Isomeric SMILES C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@@]1([C@@H](C[C@@]([C@H]([C@@H]3C)O)(C)C=C)OC(=O)CO)C
InChI InChI=1S/C22H34O5/c1-6-20(4)11-16(27-17(25)12-23)21(5)13(2)7-9-22(14(3)19(20)26)10-8-15(24)18(21)22/h6,13-14,16,18-19,23,26H,1,7-12H2,2-5H3/t13-,14+,16-,18+,19+,20-,21+,22+/m1/s1
InChI Key ZRZNJUXESFHSIO-BKUNHTPHSA-N
References
1. Kavanagh F, Hervey A, Robbins WJ. (1951)
Antibiotic Substances From Basidiomycetes: VIII. Pleurotus Multilus (Fr.) Sacc. and Pleurotus Passeckerianus Pilat.
Proc Natl Acad Sci USA, 37 (9): 570-4. DOI: 10.1073/pnas.37.9.570 [PMID:16589015]
2. Paukner S, Riedl R. (2017)
Pleuromutilins: Potent Drugs for Resistant Bugs-Mode of Action and Resistance.
Cold Spring Harb Perspect Med, 7 (1). [PMID:27742734]