PKUMDL_MH_1001   Click here for help

GtoPdb Ligand ID: 9141

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Computational approaches discovered a previously unknown allosteric site on 15-lipoxygenase (15-LOX). PKUMDL_MH_1001 is reported as a positive allosteric modulator acting at this novel site [1]. PKUMDL_MH_1001 increases levels of 15-LOX products and reduces production of pro-inflammatory mediators in human whole blood assays. The structure specified in 'supplementary data' [1] has 2 unresolved stereo centres and there are 9 same connectivity records in PubChem.
This compound has potential to drive inflammation resolution by shifting the arachidonic acid metabolic pathway to the production of 15-LOX products such as lipoxins, and inhibiting production of pro-inflammatory mediators such as leukotrienes and prostaglandins.
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Ligand Activity Visualisation Charts

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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 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.

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Hydrogen bond acceptors 5
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 39.15
Molecular weight 428.26
XLogP 3.82
No. Lipinski's rules broken 0
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.

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Canonical SMILES CN1CCN(CC1)CC(=O)N1N=C2C(C1c1ccccc1)CCCC2=Cc1ccccc1
Isomeric SMILES CN1CCN(CC1)CC(=O)N1N=C2C(C1c1ccccc1)CCC/C/2=C\c1ccccc1
InChI InChI=1S/C27H32N4O/c1-29-15-17-30(18-16-29)20-25(32)31-27(22-11-6-3-7-12-22)24-14-8-13-23(26(24)28-31)19-21-9-4-2-5-10-21/h2-7,9-12,19,24,27H,8,13-18,20H2,1H3/b23-19+
InChI Key GEMFAWUXUVGGTE-FCDQGJHFSA-N
References
1. Meng H, McClendon CL, Dai Z, Li K, Zhang X, He S, Shang E, Liu Y, Lai L. (2016)
Discovery of Novel 15-Lipoxygenase Activators To Shift the Human Arachidonic Acid Metabolic Network toward Inflammation Resolution.
J Med Chem, 59 (9): 4202-9. [PMID:26290290]