Record Information
Version2.0
Creation Date2012-08-03 14:57:54 -0600
Update Date2015-09-13 12:56:16 -0600
Secondary Accession Numbers
  • ECMDB21401
Identification
Name:N-Acetyl-L-aspartic acid
DescriptionN-Acetyl-L-aspartic acid is a derivative of aspartic acid. (Wikipedia)
Structure
Thumb
Synonyms:
  • (2S)-2-acetamidobutanedioate
  • (2S)-2-acetamidobutanedioic acid
  • (S)-2-(acetylamino)butanedioate
  • (S)-2-(acetylamino)butanedioic acid
  • (S)-2-(acetylamino)Succinate
  • (S)-2-(acetylamino)succinic acid
  • Acetyl-l-aspartate
  • Acetyl-l-aspartic acid
  • Acetylaspartate
  • Acetylaspartic acid
  • L-n-acetylaspartate
  • L-n-acetylaspartic acid
  • N-Acetyl-L-aspartate
  • N-acetyl-s-aspartate
  • N-acetyl-s-aspartic acid
  • N-acetylaspartate
  • N-acetylaspartic acid
  • NAA
Chemical Formula:C6H9NO5
Weight:Average: 175.1394
Monoisotopic: 175.048072403
InChI Key:OTCCIMWXFLJLIA-BYPYZUCNSA-N
InChI:InChI=1S/C6H9NO5/c1-3(8)7-4(6(11)12)2-5(9)10/h4H,2H2,1H3,(H,7,8)(H,9,10)(H,11,12)/t4-/m0/s1
CAS number:997-55-7
IUPAC Name:(2S)-2-acetamidobutanedioic acid
Traditional IUPAC Name:acetyl-L-aspartic acid
SMILES:CC(=O)N[C@@H](CC(O)=O)C(O)=O
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
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:137-140 °C
Experimental Properties:
PropertyValueSource
Water Solubility:675 mg/mL [HMP experimental]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility21.1 g/LALOGPS
logP-0.79ALOGPS
logP-1.4ChemAxon
logS-0.92ALOGPS
pKa (Strongest Acidic)3.41ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area103.7 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity35.98 m³·mol⁻¹ChemAxon
Polarizability15.29 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
141± 0 uMBW2511348 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L GlucoStationary Phase, glucose limitedBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h37 oCPMID: 17379776
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0cdi-0910000000-80f173aa655a9e8604b5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-008a-0930000000-63ecd768773360e39272View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-001i-0950000000-beff64b09b14e79c535cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0cdi-0910000000-80f173aa655a9e8604b5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-008a-0930000000-63ecd768773360e39272View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-0950000000-beff64b09b14e79c535cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0pvj-0910000000-8952da198dfa2ecb7e21View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01x1-0930000000-ac192f128bc253b6c299View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-9400000000-e45e6641c1b4fdac03e7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-9541000000-1ca7edd5f216e4355383View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-2900000000-73b8786c25f0b59927c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00dr-9000000000-f7f7d5d562cbcf3f69faView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-006x-9000000000-01988ea29217a99519e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-0900000000-e8fc0d2735d5a8ce1818View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9800000000-10648516e9c8e71f36ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-5a1edaf86830da3de4a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4r-9000000000-be6d8862f50bbbceda29View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4l-9000000000-d8e588abce3e75dbb9e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-e8fc0d2735d5a8ce1818View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9800000000-10648516e9c8e71f36ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-7d599142d42610746077View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4r-9000000000-be6d8862f50bbbceda29View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9000000000-d8e588abce3e75dbb9e6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-9600000000-f176de6becb0016bc74dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00or-1900000000-26dc8573491416b97a27View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-9600000000-0cb75d9cdfce88068fbeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-052r-9400000000-327e451ed714e29b3e49View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-004i-0900000000-7f8ca1d0dd5f77ffad96View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4r-9000000000-a67943ff273546b3c435View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-7208631bdea4f3ac52f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06ei-7900000000-10e9adf8706f97c39bedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02h3-9200000000-fb40f9d409269d43e36cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05gi-0900000000-86f974a42eb88002ebd7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06si-3900000000-06245050379b733be566View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9100000000-e47b08fe049f17160867View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Bal D, Gryff-Keller A, Gradowska W: Absolute configuration of N-acetylaspartate in urine from patients with Canavan disease. J Inherit Metab Dis. 2005;28(4):607-9. Pubmed: 15902566
  • Clementi V, Tonon C, Lodi R, Malucelli E, Barbiroli B, Iotti S: Assessment of glutamate and glutamine contribution to in vivo N-acetylaspartate quantification in human brain by (1)H-magnetic resonance spectroscopy. Magn Reson Med. 2005 Dec;54(6):1333-9. Pubmed: 16265633
  • Gideon P, Henriksen O, Sperling B, Christiansen P, Olsen TS, Jorgensen HS, Arlien-Soborg P: Early time course of N-acetylaspartate, creatine and phosphocreatine, and compounds containing choline in the brain after acute stroke. A proton magnetic resonance spectroscopy study. Stroke. 1992 Nov;23(11):1566-72. Pubmed: 1440704
  • Gordon N: Canavan disease: a review of recent developments. Eur J Paediatr Neurol. 2001;5(2):65-9. Pubmed: 11589315
  • Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. Pubmed: 8087979
  • Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
  • Izumiyama H, Abe T, Tanioka D, Fukuda A, Kunii N: Clinicopathological examination of glioma by proton magnetic resonance spectroscopy background. Brain Tumor Pathol. 2004;21(1):39-46. Pubmed: 15696968
  • Kaul R, Gao GP, Balamurugan K, Matalon R: Cloning of the human aspartoacylase cDNA and a common missense mutation in Canavan disease. Nat Genet. 1993 Oct;5(2):118-23. Pubmed: 8252036
  • Kvittingen EA, Guldal G, Borsting S, Skalpe IO, Stokke O, Jellum E: N-acetylaspartic aciduria in a child with a progressive cerebral atrophy. Clin Chim Acta. 1986 Aug 15;158(3):217-27. Pubmed: 3769199
  • Lam WW, Wang ZJ, Zhao H, Berry GT, Kaplan P, Gibson J, Kaplan BS, Bilaniuk LT, Hunter JV, Haselgrove JC, Zimmermann RA: 1H MR spectroscopy of the basal ganglia in childhood: a semiquantitative analysis. Neuroradiology. 1998 May;40(5):315-23. Pubmed: 9638674
  • Manji HK, Moore GJ, Chen G: Clinical and preclinical evidence for the neurotrophic effects of mood stabilizers: implications for the pathophysiology and treatment of manic-depressive illness. Biol Psychiatry. 2000 Oct 15;48(8):740-54. Pubmed: 11063971
  • Martin RC, Sawrie S, Hugg J, Gilliam F, Faught E, Kuzniecky R: Cognitive correlates of 1H MRSI-detected hippocampal abnormalities in temporal lobe epilepsy. Neurology. 1999 Dec 10;53(9):2052-8. Pubmed: 10599780
  • Rocca MA, Mezzapesa DM, Falini A, Ghezzi A, Martinelli V, Scotti G, Comi G, Filippi M: Evidence for axonal pathology and adaptive cortical reorganization in patients at presentation with clinically isolated syndromes suggestive of multiple sclerosis. Neuroimage. 2003 Apr;18(4):847-55. Pubmed: 12725761
  • Rothstein JD, Tsai G, Kuncl RW, Clawson L, Cornblath DR, Drachman DB, Pestronk A, Stauch BL, Coyle JT: Abnormal excitatory amino acid metabolism in amyotrophic lateral sclerosis. Ann Neurol. 1990 Jul;28(1):18-25. Pubmed: 2375630
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • Surendran S, Matalon KM, Szucs S, Tyring SK, Matalon R: Metabolic changes in the knockout mouse for Canavan's disease: implications for patients with Canavan's disease. J Child Neurol. 2003 Sep;18(9):611-5. Pubmed: 14572139
  • Tacke U, Olbrich H, Sass JO, Fekete A, Horvath J, Ziyeh S, Kleijer WJ, Rolland MO, Fisher S, Payne S, Vargiami E, Zafeiriou DI, Omran H: Possible genotype-phenotype correlations in children with mild clinical course of Canavan disease. Neuropediatrics. 2005 Aug;36(4):252-5. Pubmed: 16138249
  • Tedeschi G, Bonavita S, Banerjee TK, Virta A, Schiffmann R: Diffuse central neuronal involvement in Fabry disease: a proton MRS imaging study. Neurology. 1999 May 12;52(8):1663-7. Pubmed: 10331696
  • Trope I, Lopez-Villegas D, Lenkinski RE: Magnetic resonance imaging and spectroscopy of regional brain structure in a 10-year-old boy with elevated blood lead levels. Pediatrics. 1998 Jun;101(6):E7. Pubmed: 9606249
  • Vermathen P, Laxer KD, Matson GB, Weiner MW: Hippocampal structures: anteroposterior N-acetylaspartate differences in patients with epilepsy and control subjects as shown with proton MR spectroscopic imaging. Radiology. 2000 Feb;214(2):403-10. Pubmed: 10671587
  • Wevers RA, Engelke U, Wendel U, de Jong JG, Gabreels FJ, Heerschap A: Standardized method for high-resolution 1H-NMR of cerebrospinal fluid. Clin Chem. 1995 May;41(5):744-51. Pubmed: 7729054
  • Zhu XH, Chen W: Observed BOLD effects on cerebral metabolite resonances in human visual cortex during visual stimulation: a functional (1)H MRS study at 4 T. Magn Reson Med. 2001 Nov;46(5):841-7. Pubmed: 11675633
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID21547
HMDB IDHMDB00812
Pubchem Compound ID65065
Kegg IDC01042
ChemSpider ID58576
WikipediaN-acetylaspartate
BioCyc IDNot Available