CHEBI:31882 - N-methyl-D-aspartic acid

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ChEBI Name N-methyl-D-aspartic acid
ChEBI ID CHEBI:31882
ChEBI ASCII Name N-methyl-D-aspartic acid
Definition An aspartic acid derivative having an N-methyl substituent and D-configuration.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:164776
Supplier Information ChemicalBook:CB8854056, eMolecules:528016, Selleckchem:nmda-n-methyl-d-aspartic-acid, ZINC000000901012
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N-methyl-D-aspartic acid or N-methyl-D-aspartate (NMDA) is an amino acid derivative that acts as a specific agonist at the NMDA receptor mimicking the action of glutamate, the neurotransmitter which normally acts at that receptor. Unlike glutamate, NMDA only binds to and regulates the NMDA receptor and has no effect on other glutamate receptors (such as those for AMPA and kainate). NMDA receptors are particularly important when they become overactive during, for example, withdrawal from alcohol as this causes symptoms such as agitation and, sometimes, epileptiform seizures.
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Formula C5H9NO4
Net Charge 0
Average Mass 147.12930
Monoisotopic Mass 147.05316
InChI InChI=1S/C5H9NO4/c1-6-3(5(9)10)2-4(7)8/h3,6H,2H2,1H3,(H,7,8)(H,9,10)/t3-/m1/s1
InChIKey HOKKHZGPKSLGJE-GSVOUGTGSA-N
SMILES CN[C@H](CC(O)=O)C(O)=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): neurotransmitter agent
A substance used for its pharmacological action on any aspect of neurotransmitter systems. Neurotransmitter agents include agonists, antagonists, degradation inhibitors, uptake inhibitors, depleters, precursors, and modulators of receptor function.
Application(s): neurotransmitter agent
A substance used for its pharmacological action on any aspect of neurotransmitter systems. Neurotransmitter agents include agonists, antagonists, degradation inhibitors, uptake inhibitors, depleters, precursors, and modulators of receptor function.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing N-methyl-D-aspartic acid (CHEBI:31882) has role neurotransmitter agent (CHEBI:35942)
N-methyl-D-aspartic acid (CHEBI:31882) is a D-α-amino acid (CHEBI:16733)
N-methyl-D-aspartic acid (CHEBI:31882) is a D-aspartic acid derivative (CHEBI:83979)
N-methyl-D-aspartic acid (CHEBI:31882) is a amino dicarboxylic acid (CHEBI:36164)
N-methyl-D-aspartic acid (CHEBI:31882) is a secondary amino compound (CHEBI:50995)
IUPAC Name
N-methyl-D-aspartic acid
Synonyms Sources
(R)-2-Methylamino-succinic acid ChEMBL
2-Methylamino-succinic acid ChEMBL
Methyl aspartic acid ChemIDplus
N-Methyl aspartic acid ChemIDplus
N-Methyl-D-aspartate KEGG COMPOUND
N-Methyl-D-aspartic acid KEGG COMPOUND
N-Methylaspartate ChemIDplus
NMDA KEGG COMPOUND
Manual Xrefs Databases
C12269 KEGG COMPOUND
CPD-10705 MetaCyc
HMDB0002393 HMDB
N-Methyl-D-aspartic_acid Wikipedia
OEM PDBeChem
View more database links
Registry Numbers Types Sources
1724431 Reaxys Registry Number Reaxys
6384-92-5 CAS Registry Number ChemIDplus
Citations
Bräuner-Osborne H, Egebjerg J, Nielsen EO, Madsen U, Krogsgaard-Larsen P (2000)
Ligands for glutamate receptors: design and therapeutic prospects.
Journal of medicinal chemistry 43, 2609-2645 (Source: ChEMBL) [PubMed:10893301]
Conti P, De Amici M, De Sarro G, Rizzo M, Stensbøl TB, Bräuner-Osborne H, Madsen U, Toma L, De Micheli C (1999)
Synthesis and enantiopharmacology of new AMPA-kainate receptor agonists.
Journal of medicinal chemistry 42, 4099-4107 (Source: ChEMBL) [PubMed:10514280]
[show Abstract]
Kozikowski AP, Steensma D, Araldi GL, Tückmantel W, Wang S, Pshenichkin S, Surina E, Wroblewski JT (1998)
Synthesis and biology of the conformationally restricted ACPD analogue, 2-aminobicyclo[2.1.1]hexane-2,5-dicarboxylic acid-I, a potent mGluR agonist.
Journal of medicinal chemistry 41, 1641-1650 (Source: ChEMBL) [PubMed:9572889]
[show Abstract]
Madsen U, Frydenvang K, Ebert B, Johansen TN, Brehm L, Krogsgaard-Larsen P (1996)
N-methyl-D-aspartic acid receptor agonists: resolution, absolute stereochemistry, and pharmacology of the enantiomers of 2-amino-2-(3-hydroxy-5-methyl-4-isoxazolyl)acetic acid.
Journal of medicinal chemistry 39, 183-190 (Source: ChEMBL) [PubMed:8568805]
[show Abstract]
Madsen U, Brehm L, Schaumburg K, Jørgensen FS, Krogsgaard-Larsen P (1990)
Relationship between structure, conformational flexibility, and biological activity of agonists and antagonists at the N-methyl-D-aspartic acid subtype of excitatory amino acid receptors.
Journal of medicinal chemistry 33, 374-380 (Source: ChEMBL) [PubMed:1967316]
[show Abstract]
Kane JM, Baron BM, Dudley MW, Sorensen SM, Staeger MA, Miller FP (1990)
2,4-Dihydro-3H-1,2,4-triazol-3-ones as anticonvulsant agents.
Journal of medicinal chemistry 33, 2772-2777 (Source: ChEMBL) [PubMed:2170646]
[show Abstract]
Curry K, Peet MJ, Magnuson DS, McLennan H (1988)
Synthesis, resolution, and absolute configuration of the isomers of the neuronal excitant 1-amino-1,3-cyclopentanedicarboxylic acid.
Journal of medicinal chemistry 31, 864-867 (Source: ChEMBL) [PubMed:3351864]
[show Abstract]
Last Modified
02 December 2014