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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 19:03:47 UTC
HMDB IDHMDB0001067
Secondary Accession Numbers
  • HMDB01067
Metabolite Identification
Common NameN-Acetylaspartylglutamic acid
DescriptionN-Acetylaspartylglutamate (NAAG) is a neuropeptide found in millimolar concentrations in brain that is localized to subpopulations of glutamatergic, cholinergic, GABAergic, and noradrenergic neuronal systems. NAAG is released upon depolarization by a Ca(2+)-dependent process and is an agonist at mGluR3 receptors and an antagonist at NMDA receptors. NAAG is catabolized to N-acetylaspartate and glutamate primarily by glutamate carboxypeptidase II, which is expressed on the extracellular surface of astrocytes. The levels of NAAG and the activity of carboxypeptidase II are altered in a regionally specific fashion in several neuropsychiatric disorders. (PMID 9361299 ). N-Acetylaspartylglutamic acid (NAAG) is a purported precursor of N-Acetylaspartic acid (NAA) and is present at about one-tenth of the concentration of NAA in the brain. NAAG has been reported to activate N-methyl- D-aspartic acid (NMDA) receptors in neurons. Previous immunohistochemical studies in the vertebrate central nervous system (CNS) have suggested that NAAG is exclusively localized to neurons. Recent evidence, however, indicates that NAAG might also be localized to nonneuronal cells within the CNS. Only traces of NAA and NAAG are detectable in other tissues. Some compounds can change levels of NAA and NAAG in the brain. For example, methylphenidante increases the levels of NAA and NAAG in the cerebral cortex; amphetamine also increases NAA concentration in a mature brain by 26%, raising the possibility that other neurochemical systems might be involved in the clinical effects of stimulants. (PMID: 10603234 ).
Structure
Thumb
Synonyms
ValueSource
a-Spaglumic acidHMDB
Acetyl-a-L-aspartylglutamic acidHMDB
Acetyl-alpha-L-aspartylglutamic acidHMDB
alpha-Spaglumic acidHMDB
Isospaglumic acidHMDB
N-(N-Acetylaspartyl)glutamic acidHMDB
N-Acetyl-a-aspartylglutamic acidHMDB
N-Acetyl-a-L-aspartyl-L-glutamic acidHMDB
N-Acetyl-alpha-aspartylglutamic acidHMDB
N-Acetyl-alpha-L-aspartyl-L-glutamic acidHMDB
N-Acetyl-L-aspartyl-L-glutamic acidHMDB
NAAGHMDB
Chemical FormulaC11H16N2O8
Average Molecular Weight304.2533
Monoisotopic Molecular Weight304.090665498
IUPAC Name2-(3-carboxy-2-acetamidopropanamido)pentanedioic acid
Traditional Name2-(3-carboxy-2-acetamidopropanamido)pentanedioic acid
CAS Registry Number3106-85-2
SMILES
CC(=O)NC(CC(O)=O)C(=O)NC(CCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C11H16N2O8/c1-5(14)12-7(4-9(17)18)10(19)13-6(11(20)21)2-3-8(15)16/h6-7H,2-4H2,1H3,(H,12,14)(H,13,19)(H,15,16)(H,17,18)(H,20,21)
InChI KeyOPVPGKGADVGKTG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Glutamic acid or derivatives
  • Aspartic acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Tricarboxylic acid or derivatives
  • Fatty amide
  • Fatty acyl
  • N-acyl-amine
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

  Health condition:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Biofluid and excreta:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.29 g/LALOGPS
logP-1.1ALOGPS
logP-2.3ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.13ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area170.1 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity64.06 m³·mol⁻¹ChemAxon
Polarizability27 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0540-9880000000-c7c9c0da9dbe98eab286View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-05fr-9461560000-ce0ada373d3e90e6c80cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0900000000-2f2be5e8f2f3cf8bb047View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001r-9600000000-b3b345b7a22f2cdfac08View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001r-9000000000-20ed6fe2510cf8b50b0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-69dcaac6a427428064b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f8j-3890000000-205f74a5dd8b3075e884View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-9400000000-743ec6872c52fd64b45dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zg3-0193000000-467da8775363ff392ab6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05mx-1490000000-0aeed33e0dd1146b31deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9710000000-4fd638435c8a9ed8fc4bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified4.89 +/- 0.12 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.2 +/- 0.87 umol/mmol creatinineAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified4.55 (0.7-8.4) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.35 +/- 1.08 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified2.7 +/- 0.92 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified18.7 (0.0-37.4) uMAdult (>18 years old)BothCanavan disease details
UrineDetected and Quantified2.1 +/- 0.9 umol/mmol creatinineAdult (>18 years old)BothSchizophrenia details
Associated Disorders and Diseases
Disease References
Canavan disease
  1. Burlina AP, Ferrari V, Divry P, Gradowska W, Jakobs C, Bennett MJ, Sewell AC, Dionisi-Vici C, Burlina AB: N-acetylaspartylglutamate in Canavan disease: an adverse effector? Eur J Pediatr. 1999 May;158(5):406-9. [PubMed:10333125 ]
Schizophrenia
  1. Do KQ, Lauer CJ, Schreiber W, Zollinger M, Gutteck-Amsler U, Cuenod M, Holsboer F: gamma-Glutamylglutamine and taurine concentrations are decreased in the cerebrospinal fluid of drug-naive patients with schizophrenic disorders. J Neurochem. 1995 Dec;65(6):2652-62. [PubMed:7595563 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022406
KNApSAcK IDNot Available
Chemspider ID5065
KEGG Compound IDC12270
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNAAG
METLIN IDNot Available
PubChem Compound5255
PDB IDNot Available
ChEBI ID200472
References
Synthesis ReferenceMarchetti, Enzo; Mattalia, Gabriele; Curatolo, Francesco; Bergesi, Giuseppe. Structure and synthesis of the natural dipeptides N-acetyl-b-L-aspartyl-L-glutamic acid and its isomer N-acetyl-a-L-aspartyl-L-glutamic acid. Annali di Chimica (Rome, Italy) (1967), 57(6), 624-31.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Coyle JT: The nagging question of the function of N-acetylaspartylglutamate. Neurobiol Dis. 1997;4(3-4):231-8. [PubMed:9361299 ]
  2. Ma D, Zhang J, Sugahara K, Ageta T, Nakayama K, Kodama H: Simultaneous determination of N-acetylaspartic acid, N-acetylglutamic acid, and N-acetylaspartylglutamic acid in whole brain of 3-mercaptopropionic acid-treated rats using liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. Anal Biochem. 1999 Dec 15;276(2):124-8. [PubMed:10603234 ]