Showing Compound N-Methyl-D-aspartic acid (FDB022992)

Record Information

Version

1.0

Creation date

2011-09-21 00:22:57 UTC

Update date

2019-11-26 03:21:07 UTC

Primary ID

FDB022992

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

N-Methyl-D-aspartic acid

Description

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 synthetic substance that is not normally found in biological tissue. It was first synthesized in the 1960's. NMDA is an excitotoxin; this trait has applications in behavioral 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 behavior of interest, such as operant behavior. If the behavior is compromised, it suggests the destroyed tissue was part of a brain region that made an important contribution to the normal expression of that behavior. Examples of antagonists of the NMDA receptor are APV, dextromethorphan, ketamine, phencyclidine (PCP), riluzole, and memantine. They are commonly referred to as NMDA receptor antagonists. [HMDB]

CAS Number

6384-92-5

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	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
N-Me-D-Asp-OH	hmdb
N-methyl D-aspartate	hmdb
N-methyl D-aspartic acid	hmdb

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

Chemical Formula

C5H9NO4

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

147.1293

Monoisotopic Molecular Weight

147.053157781

Classification

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 )

Ontology

Disposition

Biological location:

Organ and components:

Cell and elements:

Cell:

Subcellular:

Cytoplasm

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	N-Methyl-D-aspartic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0k96-9300000000-416b6ee56e62fb8e5961	Spectrum
Predicted GC-MS	N-Methyl-D-aspartic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dl-9410000000-4a49e66d4a20edeb3235	Spectrum
Predicted GC-MS	N-Methyl-D-aspartic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	N-Methyl-D-aspartic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9600000000-7a4c870f26f91384c5d0	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000f-9000000000-5a5c118fa9bc800c8c72	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-b494ed61acdeddeb3be4	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-0002-1900000000-87587cfe05ee404f1550	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0gba-1900000000-849defcb6a9a98faef16	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0gba-1900000000-9f82f9c552f606136a19	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0006-9000000000-b6e45215a0b6b9a0960f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-0007-9500000000-060344e1da8123dc5c51	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-bbf199eb1c5bbac7de35	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9300000000-9f1996c5b204a0ee904e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000f-9000000000-18a491a74a3279ec33d1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000l-9000000000-b9b082c40ee1ed6fbb8b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9300000000-435580f32c2f9263f08f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000f-9000000000-d6cd5876d7888f53004a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9400000000-6e3a2b4573d59f5f903d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-69cb5c680dcf502b4d39	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000l-9000000000-3b16cb5a635969b81fb4	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-6e09556b565532cc28ce	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-000i-9600000000-f385ad30a0df8435d853	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-eeb3a907ee733c1543e9	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f80-9600000000-1c3def640e73db97c7e4	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-9f7de36da4128db64ccb	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f6t-0900000000-6c4446f90caead6f5b51	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ufs-3900000000-44106308c45837087fe5	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ac3-9100000000-fe891bbc2ab7063b8bac	2017-09-01	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum