Record Information
Version1.0
Creation date2011-09-21 00:22:57 UTC
Update date2019-11-26 03:21:07 UTC
Primary IDFDB022992
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN-Methyl-D-aspartic acid
DescriptionN-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 Number6384-92-5
Structure
Thumb
Synonyms
SynonymSource
(R)-2-Methylamino-succinic acidChEBI
2-Methylamino-succinic acidChEBI
Methyl aspartic acidChEBI
N-Methyl aspartic acidChEBI
N-Methyl-D-aspartateChEBI
N-MethylaspartateChEBI
NMDAChEBI
(R)-2-Methylamino-succinateGenerator
2-Methylamino-succinateGenerator
Methyl aspartateGenerator
N-Methyl aspartateGenerator
N-Methylaspartic acidGenerator
Acid, N-methyl-D-asparticMeSH
N Methyl D aspartateMeSH
N Methyl D aspartic acidMeSH
N MethylaspartateMeSH
N-Me-D-asp-OHHMDB
N-Methyl D-aspartateHMDB
N-Methyl D-aspartic acidHMDB
N-Me-D-Asp-OHhmdb
N-methyl D-aspartatehmdb
N-methyl D-aspartic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility40.6 g/LALOGPS
logP-2.6ALOGPS
logP-3.3ChemAxon
logS-0.56ALOGPS
pKa (Strongest Acidic)1.46ChemAxon
pKa (Strongest Basic)10.34ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.31 m³·mol⁻¹ChemAxon
Polarizability13.18 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H9NO4
IUPAC name(2R)-2-(methylamino)butanedioic acid
InChI IdentifierInChI=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 KeyHOKKHZGPKSLGJE-GSVOUGTGSA-N
Isomeric SMILESCN[C@H](CC(O)=O)C(O)=O
Average Molecular Weight147.1293
Monoisotopic Molecular Weight147.053157781
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAspartic 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSN-Methyl-D-aspartic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0k96-9300000000-416b6ee56e62fb8e5961Spectrum
Predicted GC-MSN-Methyl-D-aspartic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-9410000000-4a49e66d4a20edeb3235Spectrum
Predicted GC-MSN-Methyl-D-aspartic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSN-Methyl-D-aspartic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9600000000-7a4c870f26f91384c5d02012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000f-9000000000-5a5c118fa9bc800c8c722012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-b494ed61acdeddeb3be42012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0002-1900000000-87587cfe05ee404f15502021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0gba-1900000000-849defcb6a9a98faef162021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0gba-1900000000-9f82f9c552f606136a192021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-9000000000-b6e45215a0b6b9a0960f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0007-9500000000-060344e1da8123dc5c512021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-bbf199eb1c5bbac7de352021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-9300000000-9f1996c5b204a0ee904e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000f-9000000000-18a491a74a3279ec33d12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000l-9000000000-b9b082c40ee1ed6fbb8b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-9300000000-435580f32c2f9263f08f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000f-9000000000-d6cd5876d7888f53004a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-9400000000-6e3a2b4573d59f5f903d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-69cb5c680dcf502b4d392021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000l-9000000000-3b16cb5a635969b81fb42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-6e09556b565532cc28ce2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-9600000000-f385ad30a0df8435d8532021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-eeb3a907ee733c1543e92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f80-9600000000-1c3def640e73db97c7e42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-9f7de36da4128db64ccb2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0900000000-6c4446f90caead6f5b512017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufs-3900000000-44106308c45837087fe52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ac3-9100000000-fe891bbc2ab7063b8bac2017-09-01View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID21436
ChEMBL IDCHEMBL291278
KEGG Compound IDC12269
Pubchem Compound ID22880
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02393
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDOEM
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNMDA
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
A-kinase anchor protein 9AKAP9Q99996
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference