N-Methyl-D-aspartic acid (CHEM035431)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:45:48 UTC
Update Date2016-11-09 01:21:18 UTC
Accession NumberCHEM035431
Identification
Common NameN-Methyl-D-aspartic acid
ClassSmall Molecule
DescriptionAn aspartic acid derivative having an N-methyl substituent and D-configuration.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(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
Chemical FormulaC5H9NO4
Average Molecular Mass147.129 g/mol
Monoisotopic Mass147.053 g/mol
CAS Registry Number6384-92-5
IUPAC Name(2R)-2-(methylamino)butanedioic acid
Traditional NameN methyl D aspartate
SMILESCN[C@H](CC(O)=O)C(O)=O
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
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.
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k96-9300000000-416b6ee56e62fb8e5961Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-9410000000-4a49e66d4a20edeb3235Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9600000000-7a4c870f26f91384c5d0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000f-9000000000-5a5c118fa9bc800c8c72Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-b494ed61acdeddeb3be4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0002-1900000000-87587cfe05ee404f1550Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0gba-1900000000-849defcb6a9a98faef16Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0gba-1900000000-9f82f9c552f606136a19Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-9000000000-b6e45215a0b6b9a0960fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0007-9500000000-060344e1da8123dc5c51Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-bbf199eb1c5bbac7de35Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-9300000000-9f1996c5b204a0ee904eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000f-9000000000-18a491a74a3279ec33d1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000l-9000000000-b9b082c40ee1ed6fbb8bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-9300000000-435580f32c2f9263f08fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000f-9000000000-d6cd5876d7888f53004aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-9400000000-6e3a2b4573d59f5f903dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-69cb5c680dcf502b4d39Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000l-9000000000-3b16cb5a635969b81fb4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-6e09556b565532cc28ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-9600000000-f385ad30a0df8435d853Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-eeb3a907ee733c1543e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f80-9600000000-1c3def640e73db97c7e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-9f7de36da4128db64ccbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0900000000-6c4446f90caead6f5b51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufs-3900000000-44106308c45837087fe5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ac3-9100000000-fe891bbc2ab7063b8bacSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002393
FooDB IDFDB022992
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-10705
METLIN ID6662
PDB IDNot Available
Wikipedia LinkN-Methyl-D-aspartic_acid
Chemspider ID21436
ChEBI ID31882
PubChem Compound ID22880
Kegg Compound IDC12269
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10514280
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10893301
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=1967316
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=2170646
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=3351864
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=8568805
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=9572889
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10. Miller RF: D-Serine as a glial modulator of nerve cells. Glia. 2004 Aug 15;47(3):275-83.
11. 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.
12. 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.
13. 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.
14. Hardingham GE, Bading H: The Yin and Yang of NMDA receptor signalling. Trends Neurosci. 2003 Feb;26(2):81-9.
15. 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.
16. 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.
17. 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.
18. 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.
19. 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.
20. 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.
21. 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.
22. 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.
23. 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.
24. Boehning D, Snyder SH: Novel neural modulators. Annu Rev Neurosci. 2003;26:105-31.
25. 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.
26. 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.
27. 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.
28. 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.