ChemFOnt: Showing chemical card for N-Acetyl-1-aspartylglutamic acid (CFc000234939)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 02:06:13 UTC

Chemfont ID

CFc000234939

Molecule Identification

Common Name

N-Acetyl-1-aspartylglutamic acid

Definition

N-Acetylaspartylglutamic acid, also known as a-spaglumic acid or NAAG, 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. N-Acetylaspartylglutamic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). The levels of N-Acetylaspartylglutamic acid and the activity of carboxypeptidase II are altered in a regionally specific fashion in several neuropsychiatric disorders. For example, methylphenidante increases the levels of NAA and N-Acetylaspartylglutamic acid 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. N-Acetylaspartylglutamic acid has been reported to activate N-methyl- D-aspartic acid (NMDA) receptors in neurons.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-Acetylaspartylglutamate	Generator
2-({3-carboxy-1-hydroxy-2-[(1-hydroxyethylidene)amino]propylidene}amino)pentanedioate	HMDB
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

Average Molecular Weight

304.2533

Monoisotopic Molecular Weight

304.090665498

IUPAC Name

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

Traditional Name

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

CAS Registry Number

3106-85-2

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 Key

OPVPGKGADVGKTG-UHFFFAOYSA-N

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

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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.29 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-2.3	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.13	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	170.1 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	64.06 m³·mol⁻¹	ChemAxon
Polarizability	27 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon