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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-05-22 14:17:51 UTC

Update Date

2023-02-21 17:16:23 UTC

HMDB ID

HMDB0002393

Secondary Accession Numbers

HMDB02393

Metabolite Identification

Common 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 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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

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 )

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

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	187 - 192 °C	Not Available
Boiling Point	258.24 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.390 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	125.0	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002076
[M+H]+	Not Available	130.2	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002076

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	132.255	31661259
DarkChem	[M-H]-	128.156	31661259
DeepCCS	[M+H]+	125.48	30932474
DeepCCS	[M-H]-	121.613	30932474
DeepCCS	[M-2H]-	159.147	30932474
DeepCCS	[M+Na]+	134.505	30932474
AllCCS	[M+H]+	135.0	32859911
AllCCS	[M+H-H2O]+	131.0	32859911
AllCCS	[M+NH4]+	138.7	32859911
AllCCS	[M+Na]+	139.8	32859911
AllCCS	[M-H]-	127.2	32859911
AllCCS	[M+Na-2H]-	129.4	32859911
AllCCS	[M+HCOO]-	132.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Methyl-D-aspartic acid	CN[C@H](CC(O)=O)C(O)=O	2321.2	Standard polar	33892256
N-Methyl-D-aspartic acid	CN[C@H](CC(O)=O)C(O)=O	1213.4	Standard non polar	33892256
N-Methyl-D-aspartic acid	CN[C@H](CC(O)=O)C(O)=O	1453.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Methyl-D-aspartic acid,1TMS,isomer #1	CN[C@H](CC(=O)O[Si](C)(C)C)C(=O)O	1394.6	Semi standard non polar	33892256
N-Methyl-D-aspartic acid,1TMS,isomer #2	CN[C@H](CC(=O)O)C(=O)O[Si](C)(C)C	1361.2	Semi standard non polar	33892256
N-Methyl-D-aspartic acid,1TMS,isomer #3	CN([C@H](CC(=O)O)C(=O)O)[Si](C)(C)C	1496.2	Semi standard non polar	33892256
N-Methyl-D-aspartic acid,2TMS,isomer #1	CN[C@H](CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1433.5	Semi standard non polar	33892256
N-Methyl-D-aspartic acid,2TMS,isomer #2	CN([C@H](CC(=O)O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	1522.1	Semi standard non polar	33892256
N-Methyl-D-aspartic acid,2TMS,isomer #3	CN([C@H](CC(=O)O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1524.5	Semi standard non polar	33892256
N-Methyl-D-aspartic acid,3TMS,isomer #1	CN([C@H](CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1557.7	Semi standard non polar	33892256
N-Methyl-D-aspartic acid,3TMS,isomer #1	CN([C@H](CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1556.9	Standard non polar	33892256
N-Methyl-D-aspartic acid,3TMS,isomer #1	CN([C@H](CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1666.6	Standard polar	33892256
N-Methyl-D-aspartic acid,1TBDMS,isomer #1	CN[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	1633.4	Semi standard non polar	33892256
N-Methyl-D-aspartic acid,1TBDMS,isomer #2	CN[C@H](CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	1593.6	Semi standard non polar	33892256
N-Methyl-D-aspartic acid,1TBDMS,isomer #3	CN([C@H](CC(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	1743.3	Semi standard non polar	33892256
N-Methyl-D-aspartic acid,2TBDMS,isomer #1	CN[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1865.3	Semi standard non polar	33892256
N-Methyl-D-aspartic acid,2TBDMS,isomer #2	CN([C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	1995.7	Semi standard non polar	33892256
N-Methyl-D-aspartic acid,2TBDMS,isomer #3	CN([C@H](CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1989.5	Semi standard non polar	33892256
N-Methyl-D-aspartic acid,3TBDMS,isomer #1	CN([C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2217.0	Semi standard non polar	33892256
N-Methyl-D-aspartic acid,3TBDMS,isomer #1	CN([C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2202.2	Standard non polar	33892256
N-Methyl-D-aspartic acid,3TBDMS,isomer #1	CN([C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2093.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Methyl-D-aspartic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0k96-9300000000-416b6ee56e62fb8e5961	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Methyl-D-aspartic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00dl-9410000000-4a49e66d4a20edeb3235	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Methyl-D-aspartic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Methyl-D-aspartic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

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

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Brain
Fibroblasts
Kidney
Neuron

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022992

KNApSAcK ID

Not Available

Chemspider ID

21436

KEGG Compound ID

C12269

BioCyc ID

CPD-10705

BiGG ID

Not Available

Wikipedia Link

N-Methyl-D-aspartic_acid

METLIN ID

6662

PubChem Compound

22880

PDB ID

Not Available

ChEBI ID

31882

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1359131

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Baskys A, Fang L, Bayazitov I: Activation of neuroprotective pathways by metabotropic group I glutamate receptors: a potential target for drug discovery? Ann N Y Acad Sci. 2005 Aug;1053:55-73. [PubMed:16179509 ]
Hitchcock IS, Skerry TM, Howard MR, Genever PG: NMDA receptor-mediated regulation of human megakaryocytopoiesis. Blood. 2003 Aug 15;102(4):1254-9. Epub 2003 Mar 20. [PubMed:12649130 ]
Miller RF: D-Serine as a glial modulator of nerve cells. Glia. 2004 Aug 15;47(3):275-83. [PubMed:15252817 ]
Sanelli TR, Sopper MM, Strong MJ: Sequestration of nNOS in neurofilamentous aggregate bearing neurons in vitro leads to enhanced NMDA-mediated calcium influx. Brain Res. 2004 Apr 9;1004(1-2):8-17. [PubMed:15033415 ]
Weyermann J, Lochmann D, Georgens C, Zimmer A: Albumin-protamine-oligonucleotide-nanoparticles as a new antisense delivery system. Part 2: cellular uptake and effect. Eur J Pharm Biopharm. 2005 Apr;59(3):431-8. [PubMed:15760723 ]
Baskys A, Blaabjerg M: Understanding regulation of nerve cell death by mGluRs as a method for development of successful neuroprotective strategies. J Neurol Sci. 2005 Mar 15;229-230:201-9. Epub 2004 Dec 15. [PubMed:15760640 ]
Hardingham GE, Bading H: The Yin and Yang of NMDA receptor signalling. Trends Neurosci. 2003 Feb;26(2):81-9. [PubMed:12536131 ]
Lareo LR, Corredor C: Ionotropic glutamate receptor activated by N-methyl-D-aspartate: a key molecule of conscious life. Med Hypotheses. 2004;63(2):245-9. [PubMed:15236783 ]
Fonnum F, Lock EA: The contributions of excitotoxicity, glutathione depletion and DNA repair in chemically induced injury to neurones: exemplified with toxic effects on cerebellar granule cells. J Neurochem. 2004 Feb;88(3):513-31. [PubMed:14720201 ]
Wang GS, Hong CJ, Yen TY, Huang HY, Ou Y, Huang TN, Jung WG, Kuo TY, Sheng M, Wang TF, Hsueh YP: Transcriptional modification by a CASK-interacting nucleosome assembly protein. Neuron. 2004 Apr 8;42(1):113-28. [PubMed:15066269 ]
Liu D, Cheng T, Guo H, Fernandez JA, Griffin JH, Song X, Zlokovic BV: Tissue plasminogen activator neurovascular toxicity is controlled by activated protein C. Nat Med. 2004 Dec;10(12):1379-83. Epub 2004 Oct 31. [PubMed:15516929 ]
Eugenin EA, D'Aversa TG, Lopez L, Calderon TM, Berman JW: MCP-1 (CCL2) protects human neurons and astrocytes from NMDA or HIV-tat-induced apoptosis. J Neurochem. 2003 Jun;85(5):1299-311. [PubMed:12753088 ]
Okuda H, Ogita K: [Protective effects of N-methyl-D-aspartate against neuronal damages]. Nihon Shinkei Seishin Yakurigaku Zasshi. 2002 Oct;22(5):153-8. [PubMed:12451685 ]
Andre VM, Flores-Hernandez J, Cepeda C, Starling AJ, Nguyen S, Lobo MK, Vinters HV, Levine MS, Mathern GW: NMDA receptor alterations in neurons from pediatric cortical dysplasia tissue. Cereb Cortex. 2004 Jun;14(6):634-46. Epub 2004 Mar 28. [PubMed:15054078 ]
Reyes O, Sosa I, Kuffler DP: Neuroprotection of adult human neurons against ischemia by hypothermia and alkalinization. P R Health Sci J. 2006 Mar;25(1):43-50. [PubMed:16883678 ]
Boehning D, Snyder SH: Novel neural modulators. Annu Rev Neurosci. 2003;26:105-31. [PubMed:14527267 ]
Tuneva EO, Bychkova ON, Boldyrev AA: Effect of NMDA on production of reactive oxygen species by human lymphocytes. Bull Exp Biol Med. 2003 Aug;136(2):159-61. [PubMed:14631498 ]
D'Aniello S, Fisher GH, Topo E, Ferrandino G, Garcia-Fernandez J, D'Aniello A: N-methyl-D-aspartic acid (NMDA) in the nervous system of the amphioxus Branchiostoma lanceolatum. BMC Neurosci. 2007 Dec 20;8:109. doi: 10.1186/1471-2202-8-109. [PubMed:18096065 ]
WATKINS JC: THE SYNTHESIS OF SOME ACIDIC AMINO ACIDS POSSESSING NEUROPHARMACOLOGICAL ACTIVITY. J Med Pharm Chem. 1962 Nov;91:1187-99. doi: 10.1021/jm01241a010. [PubMed:14056452 ]
Aiyer R, Mehta N, Gungor S, Gulati A: A Systematic Review of NMDA Receptor Antagonists for Treatment of Neuropathic Pain in Clinical Practice. Clin J Pain. 2018 May;34(5):450-467. doi: 10.1097/AJP.0000000000000547. [PubMed:28877137 ]

Enzymes

Enzyme Details

1. A-kinase anchor protein 9

General function:: Cell cycle control, cell division, chromosome partitioning
Specific function:: Binds to type II regulatory subunits of protein kinase A. Scaffolding protein that assembles several protein kinases and phosphatases on the centrosome and Golgi apparatus. May be required to maintain the integrity of the Golgi apparatus. Isoform 4 is associated with the N-methyl-D-aspartate receptor and is specifically found in the neuromuscular junction (NMJ) as well as in neuronal synapses, suggesting a role in the organization of postsynaptic specializations
Gene Name:: AKAP9
Uniprot ID:: Q99996
Molecular weight:: 453664.2

Enzyme Details

2. Rho GTPase-activating protein 32

General function:: Involved in protein binding
Specific function:: GTPase-activating protein (GAP) promoting GTP hydrolysis on RHOA, CDC42 and RAC1 small GTPases. May be involved in the differentiation of neuronal cells during the formation of neurite extensions. Involved in NMDA receptor activity-dependent actin reorganization in dendritic spines. May mediate cross-talks between Ras- and Rho-regulated signaling pathways in cell growth regulation. Isoform 2 has higher GAP activity
Gene Name:: ARHGAP32
Uniprot ID:: A7KAX9
Molecular weight:: 230527.1

Showing metabocard for N-Methyl-D-aspartic acid (HMDB0002393)

MOL for HMDB0002393 (N-Methyl-D-aspartic acid)

3D MOL for HMDB0002393 (N-Methyl-D-aspartic acid)

3D SDF for HMDB0002393 (N-Methyl-D-aspartic acid)

3D-SDF for HMDB0002393 (N-Methyl-D-aspartic acid)

PDB for HMDB0002393 (N-Methyl-D-aspartic acid)

3D PDB for HMDB0002393 (N-Methyl-D-aspartic acid)

SMILES for HMDB0002393 (N-Methyl-D-aspartic acid)

INCHI for HMDB0002393 (N-Methyl-D-aspartic acid)

Structure for HMDB0002393 (N-Methyl-D-aspartic acid)

3D Structure for HMDB0002393 (N-Methyl-D-aspartic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes