indolmycin   Click here for help

GtoPdb Ligand ID: 11021

Synonyms: PA 155 A | PA-155-A | PA-155A | TAK-083
PDB Ligand Antimalarial Ligand
Compound class: Synthetic organic
Comment: Indolmycin competitively inhibits bacterial tryptophanyl-tRNA synthetases. It has antibacterial activity against MSSA (methicillin-susceptible Staphylococcus aureus), MRSA (methicillin-resistant S. aureus) and VISA (vancomycin-intermediate S. aureus) [2]. The compound also has antimalarial activity [3].

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 66.48
Molecular weight 257.12
XLogP 1.96
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CN=C1NC(=O)[C@@H](O1)[C@@H](c1c[nH]c2c1cccc2)C
Isomeric SMILES CN=C1NC(=O)[C@@H](O1)[C@@H](c1c[nH]c2c1cccc2)C
InChI InChI=1S/C14H15N3O2/c1-8(12-13(18)17-14(15-2)19-12)10-7-16-11-6-4-3-5-9(10)11/h3-8,12,16H,1-2H3,(H,15,17,18)/t8-,12+/m1/s1
InChI Key GNTVWGDQPXCYBV-PELKAZGASA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
IUPAC Name Click here for help
(5S)-5-[(1R)-1-(1H-indol-3-yl)ethyl]-2-methylimino-1,3-oxazolidin-4-one
Synonyms Click here for help
PA 155 A | PA-155-A | PA-155A | TAK-083
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 1319
Other databases
CAS Registry No. 21200-24-8 (source: ChemIDplus)
ChEBI CHEBI:79394
ChEMBL Ligand CHEMBL417852
GtoPdb PubChem SID 405560462
PubChem CID 135417159
RCSB PDB Ligand 5BX
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