NVP-AAM077   Click here for help

GtoPdb Ligand ID: 4276

Synonyms: PEAQX
Compound class: Synthetic organic
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 6
Hydrogen bond donors 5
Rotatable bonds 5
Topological polar surface area 145.09
Molecular weight 453.01
XLogP 2.68
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 Brc1ccc(cc1)C(NC(P(=O)(O)O)c1cccc2c1[nH]c(=O)c(=O)[nH]2)C
Isomeric SMILES Brc1ccc(cc1)[C@@H](N[C@@H](P(=O)(O)O)c1cccc2c1[nH]c(=O)c(=O)[nH]2)C
InChI InChI=1S/C17H17BrN3O5P/c1-9(10-5-7-11(18)8-6-10)19-17(27(24,25)26)12-3-2-4-13-14(12)21-16(23)15(22)20-13/h2-9,17,19H,1H3,(H,20,22)(H,21,23)(H2,24,25,26)/t9-,17-/m0/s1
InChI Key XXZGNAZRWCBSBK-XYZCENFISA-N
References
1. Auberson YP, Allgeier H, Bischoff S, Lingenhoehl K, Moretti R, Schmutz M. (2002)
5-Phosphonomethylquinoxalinediones as competitive NMDA receptor antagonists with a preference for the human 1A/2A, rather than 1A/2B receptor composition.
Bioorg Med Chem Lett, 12 (7): 1099-102. [PMID:11909726]
2. Feng B, Tse HW, Skifter DA, Morley R, Jane DE, Monaghan DT. (2004)
Structure-activity analysis of a novel NR2C/NR2D-preferring NMDA receptor antagonist: 1-(phenanthrene-2-carbonyl) piperazine-2,3-dicarboxylic acid.
Br J Pharmacol, 141 (3): 508-16. [PMID:14718249]
3. Frizelle PA, Chen PE, Wyllie DJ. (2006)
Equilibrium constants for (R)-[(S)-1-(4-bromo-phenyl)-ethylamino]-(2,3-dioxo-1,2,3,4-tetrahydroquinoxalin-5-yl)-methyl]-phosphonic acid (NVP-AAM077) acting at recombinant NR1/NR2A and NR1/NR2B N-methyl-D-aspartate receptors: Implications for studies of synaptic transmission.
Mol Pharmacol, 70 (3): 1022-32. [PMID:16778008]
4. Neyton J, Paoletti P. (2006)
Relating NMDA receptor function to receptor subunit composition: limitations of the pharmacological approach.
J Neurosci, 26 (5): 1331-3. [PMID:16452656]