eglumegad   Click here for help

GtoPdb Ligand ID: 1393

Synonyms: LY354740
PDB Ligand
Compound class: Synthetic organic
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species

eglumegad is commercially available from our sponsors

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 5
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 100.62
Molecular weight 185.07
XLogP -3.39
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 OC(=O)C1C2C1C(CC2)(N)C(=O)O
Isomeric SMILES OC(=O)[C@H]1[C@H]2[C@@H]1[C@](CC2)(N)C(=O)O
InChI InChI=1S/C8H11NO4/c9-8(7(12)13)2-1-3-4(5(3)8)6(10)11/h3-5H,1-2,9H2,(H,10,11)(H,12,13)/t3-,4-,5-,8-/m0/s1
InChI Key VTAARTQTOOYTES-RGDLXGNYSA-N
References
1. Bond A, Monn JA, Lodge D. (1997)
A novel orally active group 2 metabotropic glutamate receptor agonist: LY354740.
Neuroreport, 8 (6): 1463-6. [PMID:9172154]
2. Cartmell J, Adam G, Chaboz S, Henningsen R, Kemp JA, Klingelschmidt A, Metzler V, Monsma F, Schaffhauser H, Wichmann J et al.. (1998)
Characterization of [3H]-(2S,2'R,3'R)-2-(2',3'-dicarboxy-cyclopropyl)glycine ([3H]-DCG IV) binding to metabotropic mGlu2 receptor-transfected cell membranes.
Br J Pharmacol, 123 (3): 497-504. [PMID:9504391]
3. Dunayevich E, Erickson J, Levine L, Landbloom R, Schoepp DD, Tollefson GD. (2008)
Efficacy and tolerability of an mGlu2/3 agonist in the treatment of generalized anxiety disorder.
Neuropsychopharmacology, 33 (7): 1603-10. [PMID:17712352]
4. Johnson BG, Wright RA, Arnold MB, Wheeler WJ, Ornstein PL, Schoepp DD. (1999)
[3H]-LY341495 as a novel antagonist radioligand for group II metabotropic glutamate (mGlu) receptors: characterization of binding to membranes of mGlu receptor subtype expressing cells.
Neuropharmacology, 38 (10): 1519-29. [PMID:10530814]
5. Kłodzińska A, Chojnacka-Wójcik E, Pałucha A, Brański P, Popik P, Pilc A. (1999)
Potential anti-anxiety, anti-addictive effects of LY 354740, a selective group II glutamate metabotropic receptors agonist in animal models.
Neuropharmacology, 38 (12): 1831-9. [PMID:10608278]
6. Malherbe P, Kratzeisen C, Lundstrom K, Richards JG, Faull RL, Mutel V. (1999)
Cloning and functional expression of alternative spliced variants of the human metabotropic glutamate receptor 8.
Brain Res Mol Brain Res, 67 (2): 201-10. [PMID:10216218]
7. Monn JA, Valli MJ, Massey SM, Hansen MM, Kress TJ, Wepsiec JP, Harkness AR, Grutsch Jr JL, Wright RA, Johnson BG et al.. (1999)
Synthesis, pharmacological characterization, and molecular modeling of heterobicyclic amino acids related to (+)-2-aminobicyclo[3.1.0] hexane-2,6-dicarboxylic acid (LY354740): identification of two new potent, selective, and systemically active agonists for group II metabotropic glutamate receptors.
J Med Chem, 42 (6): 1027-40. [PMID:10090786]
8. Pilc A. (2003)
LY-354740 (Eli Lilly).
IDrugs, 6 (1): 66-71. [PMID:12789623]
9. Schoepp DD, Johnson BG, Wright RA, Salhoff CR, Mayne NG, Wu S, Cockerman SL, Burnett JP, Belegaje R, Bleakman D et al.. (1997)
LY354740 is a potent and highly selective group II metabotropic glutamate receptor agonist in cells expressing human glutamate receptors.
Neuropharmacology, 36 (1): 1-11. [PMID:9144636]
10. Schweitzer C, Kratzeisen C, Adam G, Lundstrom K, Malherbe P, Ohresser S, Stadler H, Wichmann J, Woltering T, Mutel V. (2000)
Characterization of [(3)H]-LY354740 binding to rat mGlu2 and mGlu3 receptors expressed in CHO cells using semliki forest virus vectors.
Neuropharmacology, 39 (10): 1700-6. [PMID:10884552]