delamanid   Click here for help

GtoPdb Ligand ID: 12876

Synonyms: Deltyba® | OPC-67683
Approved drug
delamanid is an approved drug (EMA (2014))
Compound class: Synthetic organic
Comment: Delamanid is a nitro-dihydro-imidazooxazole derivative with potent antibacterial activity against mycobacteria [1-2]. This drug is used in the treatment of multidrug-resistant tuberculosis (MDR-TB).
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 7
Hydrogen bond donors 0
Rotatable bonds 9
Topological polar surface area 98.9
Molecular weight 534.49
XLogP 5.67
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES C[C@@]1(CN2C=C(N=C2O1)[N+](=O)[O-])COC3=CC=C(C=C3)N4CCC(CC4)OC5=CC=C(C=C5)OC(F)(F)F
Isomeric SMILES C[C@@]1(CN2C=C(N=C2O1)[N+](=O)[O-])COC3=CC=C(C=C3)N4CCC(CC4)OC5=CC=C(C=C5)OC(F)(F)F
InChI InChI=1S/C25H25F3N4O6/c1-24(15-31-14-22(32(33)34)29-23(31)38-24)16-35-18-4-2-17(3-5-18)30-12-10-20(11-13-30)36-19-6-8-21(9-7-19)37-25(26,27)28/h2-9,14,20H,10-13,15-16H2,1H3/t24-/m1/s1
InChI Key XDAOLTSRNUSPPH-XMMPIXPASA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (EMA (2014))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(2R)-2-methyl-6-nitro-2-[[4-[4-[4-(trifluoromethoxy)phenoxy]piperidin-1-yl]phenoxy]methyl]-3H-imidazo[2,1-b][1,3]oxazole
International Nonproprietary Names Click here for help
INN number INN
9401 delamanid
Synonyms Click here for help
Deltyba® | OPC-67683
Database Links Click here for help
BindingDB Ligand 50592580
CAS Registry No. 681492-22-8 (source: Scifinder)
ChEBI CHEBI:134742
ChEMBL Ligand CHEMBL218650
DrugBank Ligand DB11637
DrugCentral Ligand 4819
GtoPdb PubChem SID 485205997
PubChem CID 6480466
Search Google for chemical match using the InChIKey XDAOLTSRNUSPPH-XMMPIXPASA-N
Search Google for chemicals with the same backbone XDAOLTSRNUSPPH
Search PubMed clinical trials delamanid
Search PubMed titles delamanid
Search PubMed titles/abstracts delamanid
UniChem Compound Search for chemical match using the InChIKey XDAOLTSRNUSPPH-XMMPIXPASA-N
UniChem Connectivity Search for chemical match using the InChIKey XDAOLTSRNUSPPH-XMMPIXPASA-N
Wikipedia Delamanid