AZD5718   Click here for help

GtoPdb Ligand ID: 10352

Synonyms: compound 12 [PMID: 30869888]
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: AZD5718 is an inhibitor of 5-LOX activating protein (FLAP) that was developed by Astra Zeneca [4]. It is orally active and is suitable for once-daily dosing. Initial clinical findings from a first-in-human study confirmed AZD5718 target engagement, and indicated that the compound is safe and well tolerated [2]. It is being advanced for further evaluation in patients with coronary artery disease. The 5-LOX pathway has been targeted for drug development as an intervention in a number of diseases where chronic inflammation drives the pathophysiology (e.g. asthma, chronic obstructive pulmonary disease and atherosclerotic coronary artery disease). Since FLAP is a crucial regulator of 5-LOX activity, it too is being pursued as a druggable anti-inflammatory target. FLAP inhibitors and 5-LOX inhibitors reduce production of the leukotriene precursor LTA4 [1,3].
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 3
Rotatable bonds 6
Topological polar surface area 121.77
Molecular weight 446.21
XLogP 3.32
No. Lipinski's rules broken 0
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 O=C(C1CCCCC1C(=O)c1ccc(cc1)c1n[nH]c(c1)C)Nc1cnn2c1C(=O)NCC2
Isomeric SMILES O=C([C@@H]1CCCC[C@H]1C(=O)c1ccc(cc1)c1n[nH]c(c1)C)Nc1cnn2c1C(=O)NCC2
InChI InChI=1S/C24H26N6O3/c1-14-12-19(29-28-14)15-6-8-16(9-7-15)22(31)17-4-2-3-5-18(17)23(32)27-20-13-26-30-11-10-25-24(33)21(20)30/h6-9,12-13,17-18H,2-5,10-11H2,1H3,(H,25,33)(H,27,32)(H,28,29)/t17-,18-/m1/s1
InChI Key ROTWSDMXHVGAHZ-QZTJIDSGSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(1R,2R)-2-[4-(5-methyl-1H-pyrazol-3-yl)benzoyl]-N-(4-oxo-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-3-yl)cyclohexane-1-carboxamide
Synonyms Click here for help
compound 12 [PMID: 30869888]
Database Links Click here for help
GtoPdb PubChem SID 384403633
PubChem CID 122678117
Search Google for chemical match using the InChIKey ROTWSDMXHVGAHZ-QZTJIDSGSA-N
Search Google for chemicals with the same backbone ROTWSDMXHVGAHZ
UniChem Compound Search for chemical match using the InChIKey ROTWSDMXHVGAHZ-QZTJIDSGSA-N
UniChem Connectivity Search for chemical match using the InChIKey ROTWSDMXHVGAHZ-QZTJIDSGSA-N