FComEx: N-Acetylaspartylglutamic acid (PC000838)

Record Information

Version

1.0

Creation date

2015-10-09 22:33:01 UTC

Update date

2017-01-19 02:36:38 UTC

FoodComEx ID

PC000838

FoodDB Record

FDB022406

Chemical Information

Name

N-Acetylaspartylglutamic acid

Description

N-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) [HMDB]

CAS Number

3106-85-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
a-Spaglumic acid	hmdb
Acetyl-a-L-aspartylglutamic acid	hmdb
Acetyl-alpha-L-aspartylglutamic acid	hmdb
alpha-Spaglumic acid	hmdb
Isospaglumic acid	hmdb
N-(N-Acetylaspartyl)glutamic acid	hmdb
N-Acetyl-a-aspartylglutamic acid	hmdb
N-Acetyl-a-L-aspartyl-L-glutamic acid	hmdb
N-Acetyl-alpha-aspartylglutamic acid	hmdb
N-Acetyl-alpha-L-aspartyl-L-glutamic acid	hmdb
N-Acetyl-L-aspartyl-L-glutamic acid	hmdb
NAAG	hmdb

Chemical Formula

C11H16N2O8

IUPAC name

2-(3-carboxy-2-acetamidopropanamido)pentanedioic acid

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 Key

OPVPGKGADVGKTG-UHFFFAOYSA-N

Isomeric SMILES

CC(=O)NC(CC(O)=O)C(=O)NC(CCC(O)=O)C(O)=O

Average Molecular Weight

304.2533

Monoisotopic Molecular Weight

304.090665498

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents