fudapirine   Click here for help

GtoPdb Ligand ID: 13002

Synonyms: sudapyridine | WX-081
Compound class: Synthetic organic
Comment: Fudapirine (sudapyridine and formerly WX-081) is the lead from a novel diarylpyridine series with antimycobacterial activity and an analogue of bedaquiline [1,3]. Fudapirine has advanced to clinical evaluation for the treatment of tuberculosis.
The chemical structure of sudapyridine is identical to that which was submitted to the WHO for the INN fudapirine (proposed INN list 132, Feb 2025).
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 4
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 45.06
Molecular weight 537.09
XLogP 4.33
No. Lipinski's rules broken 1

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 CN(C)CC[C@@](C1=CC=CC2=C1C=CC=C2)([C@H](C3=CC=CC=C3)C4=CC(=CN=C4OC)C5=CC=C(C=C5)Cl)O
Isomeric SMILES CN(C)CC[C@@](C1=CC=CC2=CC=CC=C21)([C@H](C3=CC=CC=C3)C4=C(N=CC(=C4)C5=CC=C(C=C5)Cl)OC)O
InChI InChI=1S/C34H33ClN2O2/c1-37(2)21-20-34(38,31-15-9-13-25-10-7-8-14-29(25)31)32(26-11-5-4-6-12-26)30-22-27(23-36-33(30)39-3)24-16-18-28(35)19-17-24/h4-19,22-23,32,38H,20-21H2,1-3H3/t32-,34-/m1/s1
InChI Key MMUCHWPQRGEHDV-ZFEZZJPFSA-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
(1R,2S)-1-[5-(4-chlorophenyl)-2-methoxypyridin-3-yl]-4-(dimethylamino)-2-naphthalen-1-yl-1-phenylbutan-2-ol
International Nonproprietary Names Click here for help
INN number INN
13334 fudapirine
Synonyms Click here for help
sudapyridine | WX-081
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Sudapyridine
Other databases
CAS Registry No. 1859978-72-5 (source: WHO INN record)
GtoPdb PubChem SID 485206123
PubChem CID 156777270
Search Google for chemical match using the InChIKey MMUCHWPQRGEHDV-ZFEZZJPFSA-N
Search Google for chemicals with the same backbone MMUCHWPQRGEHDV
Search PubMed clinical trials fudapirine
Search PubMed titles fudapirine
Search PubMed titles/abstracts fudapirine
UniChem Compound Search for chemical match using the InChIKey MMUCHWPQRGEHDV-ZFEZZJPFSA-N
UniChem Connectivity Search for chemical match using the InChIKey MMUCHWPQRGEHDV-ZFEZZJPFSA-N