ChemFOnt: Showing chemical card for N-Methyl-D-aspartic acid (CFc000001615)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:17 UTC

Chemfont ID

CFc000001615

Molecule Identification

Common Name

N-Methyl-D-aspartic acid

Definition

N-Methyl-D-aspartic acid is an amino acid derivative acting as a specific agonist at the NMDA receptor, and therefore mimics the action of the neurotransmitter glutamate on that receptor. In contrast to glutamate, NMDA binds to and regulates the above receptor only, but not other glutamate receptors. NMDA is a water-soluble endogenous metabolite that plays an important role in the neuroendocrine system of species across Animalia (PMID:18096065 ). It was first synthesized in the 1960s (PMID:14056452 ). NMDA is an excitotoxin; this trait has applications in behavioural neuroscience research. The body of work utilizing this technique falls under the term "lesion studies." Researchers apply NMDA to specific regions of an (animal) subject's brain or spinal cord and subsequently test for the behaviour of interest, such as operant behaviour. If the behaviour is compromised, it suggests that the destroyed tissue was part of a brain region that made an important contribution to the normal expression of that behaviour. Examples of antagonists of the NMDA receptor are ketamine, amantadine, dextromethorphan (DXM), riluzole, and memantine. They are commonly referred to as NMDA receptor antagonists (PMID:28877137 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(R)-2-Methylamino-succinic acid	ChEBI
2-Methylamino-succinic acid	ChEBI
Methyl aspartic acid	ChEBI
N-Methyl aspartic acid	ChEBI
N-Methyl-D-aspartate	ChEBI
N-Methylaspartate	ChEBI
NMDA	ChEBI
(R)-2-Methylamino-succinate	Generator
2-Methylamino-succinate	Generator
Methyl aspartate	Generator
N-Methyl aspartate	Generator
N-Methylaspartic acid	Generator
Acid, N-methyl-D-aspartic	MeSH
N Methyl D aspartate	MeSH
N Methyl D aspartic acid	MeSH
N Methylaspartate	MeSH
N-Me-D-asp-OH	HMDB
N-Methyl D-aspartate	HMDB
N-Methyl D-aspartic acid	HMDB

Chemical Formula

C₅H₉NO₄

Average Molecular Weight

147.1293

Monoisotopic Molecular Weight

147.053157781

IUPAC Name

(2R)-2-(methylamino)butanedioic acid

Traditional Name

N methyl D aspartate

CAS Registry Number

6384-92-5

SMILES

CN[C@H](CC(O)=O)C(O)=O

InChI Identifier

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

InChI Key

HOKKHZGPKSLGJE-GSVOUGTGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Aspartic acid and derivatives

Alternative Parents

Substituents

Aspartic acid or derivatives
Alpha-amino acid
D-alpha-amino acid
Dicarboxylic acid or derivatives
Fatty acid
Amino acid
Carboxylic acid
Secondary aliphatic amine
Secondary amine
Amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

secondary amino compound (CHEBI:31882 )
amino dicarboxylic acid (CHEBI:31882 )
D-alpha-amino acid (CHEBI:31882 )
D-aspartic acid derivative (CHEBI:31882 )

Functional Ontology

Not Available

Fibroblast (HMDB: HMDB0002393)

Organ

Brain (HMDB: HMDB0002393)
Kidney (HMDB: HMDB0002393)

Cellular substructure

Cytoplasm (HMDB: HMDB0002393)

Source

Exogenous

Exogenous (HMDB: HMDB0002393)

Food

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	40.6 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-3.3	ChemAxon
logS	-0.56	ALOGPS
pKa (Strongest Acidic)	1.46	ChemAxon
pKa (Strongest Basic)	10.34	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	31.31 m³·mol⁻¹	ChemAxon
Polarizability	13.18 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon