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lefamulin   Click here for help

GtoPdb Ligand ID: 10824

Synonyms: BC-3781 | BC3781 | compound 7 [PMID: 24874438] | Xenleta®
Approved drug PDB Ligand
lefamulin is an approved drug (FDA (2019), EMA (2020))
Compound class: Synthetic organic
Comment: Lefamulin (BC-3781) is a pleuromutilin class antibacterial [1,3]. It is active against pathogens that commonly cause community-acquired bacterial pneumonia (CABP) and acute bacterial skin and skin structure infection (ABSSSI) [2].
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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Click here for structure editor
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 6
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 135.15
Molecular weight 507.3
XLogP 3.51
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[C@]1(C)C[C@@H](OC(=O)CS[C@@H]2CC[C@H](C[C@H]2O)N)[C@]2(C)[C@H](C)CC[C@]3([C@H]([C@@H]1O)C)[C@H]2C(=O)CC3
Isomeric SMILES C=C[C@]1(C)C[C@@H](OC(=O)CS[C@@H]2CC[C@H](C[C@H]2O)N)[C@]2(C)[C@H](C)CC[C@]3([C@H]([C@@H]1O)C)[C@H]2C(=O)CC3
InChI InChI=1S/C28H45NO5S/c1-6-26(4)14-22(34-23(32)15-35-21-8-7-18(29)13-20(21)31)27(5)16(2)9-11-28(17(3)25(26)33)12-10-19(30)24(27)28/h6,16-18,20-22,24-25,31,33H,1,7-15,29H2,2-5H3/t16-,17+,18-,20-,21-,22-,24+,25+,26-,27+,28+/m1/s1
InChI Key KPVIXBKIJXZQJX-FCEONZPQSA-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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. EU EMA (2020)  |  US FDA (2019)
International Nonproprietary Names Click here for help
INN number INN
9849 lefamulin
Synonyms Click here for help
BC-3781 | BC3781 | compound 7 [PMID: 24874438] | Xenleta®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Lefamulin (BC-3781)
Other databases
BindingDB Ligand 50019649
CAS Registry No. 1061337-51-6 (source: WHO INN record)
ChEMBL Ligand CHEMBL3291398
DrugCentral Ligand 5348
GtoPdb PubChem SID 405560265
PubChem CID 25185057
RCSB PDB Ligand 62B
Search Google for chemical match using the InChIKey KPVIXBKIJXZQJX-FCEONZPQSA-N
Search Google for chemicals with the same backbone KPVIXBKIJXZQJX
Search PubMed clinical trials lefamulin
Search PubMed titles lefamulin
Search PubMed titles/abstracts lefamulin
UniChem Compound Search for chemical match using the InChIKey KPVIXBKIJXZQJX-FCEONZPQSA-N
UniChem Connectivity Search for chemical match using the InChIKey KPVIXBKIJXZQJX-FCEONZPQSA-N