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Record Information
Version1.0
Creation Date2016-09-30 22:36:58 UTC
Update Date2020-05-21 16:26:52 UTC
BMDB IDBMDB0000812
Secondary Accession Numbers
  • BMDB00812
Metabolite Identification
Common NameN-Acetyl-L-aspartic acid
DescriptionN-Acetyl-L-aspartic acid, also known as acetylaspartate or NAA, 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. N-Acetyl-L-aspartic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-L-aspartic acid exists in all living organisms, ranging from bacteria to humans. N-acetyl-L-aspartic acid can be converted into acetic acid and L-aspartic acid; which is mediated by the enzyme aspartoacylase. In cattle, N-acetyl-L-aspartic acid is involved in the metabolic pathway called the aspartate metabolism pathway. N-Acetyl-L-aspartic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
(S)-2-(Acetylamino)butanedioic acidChEBI
(S)-2-(Acetylamino)succinic acidChEBI
Acetyl-L-aspartic acidChEBI
Acetylaspartic acidChEBI
L-N-Acetylaspartic acidChEBI
N-Acetylaspartic acidChEBI
NAAChEBI
(S)-2-(Acetylamino)butanedioateGenerator
(S)-2-(Acetylamino)succinateGenerator
Acetyl-L-aspartateGenerator
AcetylaspartateGenerator
L-N-AcetylaspartateGenerator
N-AcetylaspartateGenerator
N-Acetyl-L-aspartateGenerator
(2S)-2-AcetamidobutanedioateHMDB
(2S)-2-Acetamidobutanedioic acidHMDB
N-Acetyl-S-aspartateHMDB
N-Acetyl-S-aspartic acidHMDB
N-Acetyl aspartateHMDB
N-Acetylaspartate, monopotassium saltHMDB
Acetyl aspartic acidHMDB
Chemical FormulaC6H9NO5
Average Molecular Weight175.1394
Monoisotopic Molecular Weight175.048072403
IUPAC Name(2S)-2-acetamidobutanedioic acid
Traditional Nameacetyl-L-aspartic acid
CAS Registry Number997-55-7
SMILES
CC(=O)N[C@@H](CC(O)=O)C(O)=O
InChI Identifier
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
InChI KeyOTCCIMWXFLJLIA-BYPYZUCNSA-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
  • 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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
  • Myelin sheath
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point137 - 140 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility675 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
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
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
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Myelin sheath
Biospecimen Locations
  • Basal Ganglia
  • Brain
  • Fibroblasts
  • Neuron
  • Placenta
  • Prostate Tissue
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Basal GangliaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000812
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022260
KNApSAcK IDNot Available
Chemspider ID58576
KEGG Compound IDC01042
BioCyc IDCPD-420
BiGG ID36685
Wikipedia LinkN-acetylaspartic_acid
METLIN ID5776
PubChem Compound65065
PDB IDNot Available
ChEBI ID21547
References
Synthesis ReferenceMontoro, Fernando; Calatayud, Jose; Vilar, Angel. N-Acetyl-L-aspartic acid. Span. (1983), 5 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the deacetylation of N-acetylaspartic acid (NAA) to produce acetate and L-aspartate. NAA occurs in high concentration in brain and its hydrolysis NAA plays a significant part in the maintenance of intact white matter (By similarity).
Gene Name:
ASPA
Uniprot ID:
P46446
Molecular weight:
35738.0
Reactions
N-Acetyl-L-aspartic acid + Water → Acetic acid + L-Aspartic aciddetails