N-Acetylaspartic acid

N-Acetylaspartic acid
IUPAC name 2-Acetamidobutanedioic acid[1]
Other names N-Acetylaspartate[citation needed] Acetylaspartic acid[citation needed]
Identifiers
Abbreviations	NAA[citation needed]
CAS number	2545-40-6 N, 997-55-7 (S) Y
PubChem	97508, 774916 (R), 65065 (S)
ChemSpider	88007 N, 677387 (R) Y
EC number	219-827-5
KEGG	C01042 N
MeSH	N-acetylaspartate
ChEBI	CHEBI:21547 Y
ChEMBL	CHEMBL1162493 N
RTECS number	CI9098600
Beilstein Reference	1726198 (S)
3DMet	B00227
Jmol-3D images	Image 1
SMILES CC(=O)NC(CC(O)=O)C(O)=O
InChI 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) N Key: OTCCIMWXFLJLIA-UHFFFAOYSA-N N
Properties
Molecular formula	C6H9NO5
Molar mass	175.14 g mol−1
Exact mass	175.048072403 g mol1−
Appearance	Colourless, transparent crystals
Melting point	137-140 °C, 410-413 K, 279-284 °F
Boiling point	141-144 °C, 414-417 K, 286-291 °F
log P	−2.209
Acidity (pKa)	3.142
Basicity (pKb)	10.855
Hazards
S-phrases	S22, S24/25
Related compounds
Related compounds	N-Acetylglutamic acid
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

N-Acetylaspartic acid, or N-acetylaspartate (NAA), is a derivative of aspartic acid with a formula of C₆H₉NO₅ and a molecular weight of 175.139.

NAA is the second-most-concentrated molecule in the brain after the amino acid glutamate. It is detected in the adult brains only in neurons ^[2]synthesized in the mitochondria^[3] of neurons from the amino acid aspartic acid and acetyl-coenzyme A. The various functions served by NAA are still under investigation, but the primary proposed functions include its being:

1. A neuronal osmolyte that is involved in fluid balance in the brain
2. A source of acetate for lipid and myelin synthesis in oligodendrocytes, the glial cells that myelinate neuronal axons
3. A precursor for the synthesis of the important neuronal dipeptide N-Acetylaspartylglutamate
4. A contributor to energy production from the amino acid glutamate in neuronal mitochondria.

In the brain, NAA is thought to be present predominantly in neuronal cell bodies, where it acts as a neuronal marker ^[4]. NAA gives off the largest signal in magnetic resonance spectroscopy of the human brain, and the levels measured there are decreased in numerous neuropathological conditions ranging from brain injury to stroke to Alzheimer's disease. This fact makes NAA a reliable diagnostic molecule for doctors treating patients with brain damage or disease.

NAA may also be a marker of creativity.^[5]

See also

• Aspartoacylase
• Canavan disease

References

This article includes a list of references, related reading or external links, but its sources remain unclear because it lacks inline citations. Please improve this article by introducing more precise citations. (May 2009)

• N-Acetylaspartate: A Unique Neuronal Molecule in the Central Nervous System, eds., J.R.Moffett, S.B.Tieman, D.R.Weinberger, J.T.Coyle, and M.A.Namboodiri, pp. 7–26. New York, NY: Springer Science + Business Media, 2006.

http://www.n-acetylaspartate.com

Finds correlations between measure of creativity and fMRIs of NAA levels in areas of brain: Biochemical Support for the "Threshold" Theory of Creativity: A Magnetic Resonance Spectroscopy Study, Rex E. Jung et al., April 22, 2009, 29(16):5319-5325; doi:10.1523/JNEUROSCI.0588-09.2009

External links

• GeneReviews/NCBI/UW/NIH entry on Canavan disease