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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:48 UTC
HMDB IDHMDB01067
Secondary Accession NumbersNone
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 KeyInChIKey=OPVPGKGADVGKTG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Amino fatty acid
  • Fatty acyl
  • N-acyl-amine
  • Fatty amide
  • Acetamide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity64.06 m3·mol-1ChemAxon
Polarizability27 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationNot Available
PathwaysNot Available
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. [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. [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
NuGOwiki LinkHMDB01067
Metagene LinkHMDB01067
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. [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. [10603234 ]