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lanopepden   Click here for help

GtoPdb Ligand ID: 14318

Synonyms: GSK1322322
Compound class: Synthetic organic
Comment: Lanopepden is a first-in-class antibacterial that targets peptide deformylase (PDF), a bacterial enzyme essential for protein maturation [3-4].
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 9
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 122.1
Molecular weight 479.55
XLogP 1.1
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 CC1=NC(=C(C(=N1)NNC(=O)[C@H](CC2CCCC2)CN(C=O)O)F)N3CCN4CCOC[C@@H]4C3
Isomeric SMILES CC1=NC(=C(C(=N1)N2CCN3CCOC[C@@H]3C2)F)NNC(=O)[C@H](CC4CCCC4)CN(C=O)O
InChI InChI=1S/C22H34FN7O4/c1-15-24-20(19(23)21(25-15)29-7-6-28-8-9-34-13-18(28)12-29)26-27-22(32)17(11-30(33)14-31)10-16-4-2-3-5-16/h14,16-18,33H,2-13H2,1H3,(H,27,32)(H,24,25,26)/t17-,18+/m1/s1
InChI Key SWHNZGMQMGFQGW-MSOLQXFVSA-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
IUPAC Name Click here for help
N-[(2R)-3-[2-[6-[(9aS)-3,4,6,7,9,9a-hexahydro-1H-pyrazino[2,1-c][1,4]oxazin-8-yl]-5-fluoro-2-methylpyrimidin-4-yl]hydrazinyl]-2-(cyclopentylmethyl)-3-oxopropyl]-N-hydroxyformamide
International Nonproprietary Names Click here for help
INN number INN
10045 lanopepden
Synonyms Click here for help
GSK1322322
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Lanopepden
Other databases
BindingDB Ligand 50535502
CAS Registry No. 1152107-25-9 (source: Scifinder)
ChEMBL Ligand CHEMBL3301608
DrugBank Ligand DB11912
GtoPdb PubChem SID 523352110
PubChem CID 52918384
Search Google for chemical match using the InChIKey SWHNZGMQMGFQGW-MSOLQXFVSA-N
Search Google for chemicals with the same backbone SWHNZGMQMGFQGW
Search PubMed clinical trials lanopepden
Search PubMed titles lanopepden
Search PubMed titles/abstracts lanopepden
UniChem Compound Search for chemical match using the InChIKey SWHNZGMQMGFQGW-MSOLQXFVSA-N
UniChem Connectivity Search for chemical match using the InChIKey SWHNZGMQMGFQGW-MSOLQXFVSA-N