N-Acetylaspartic acid

N-Acetylaspartic acid
Stereo, skeletal formula of N-acetylaspartic acid (S)
Names
IUPAC name
2-Acetamidobutanedioic acid[1]
Identifiers
3D model (JSmol)
3DMet
1726198 S
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.012.403 Edit this at Wikidata
EC Number
  • 219-827-5
KEGG
MeSH N-acetylaspartate
RTECS number
  • CI9098600
UNII
  • 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
  • CC(=O)N[C@@H](CC(=O)O)C(=O)O
Properties
C6H9NO5
Molar mass 175.140 g·mol−1
Appearance Colourless, transparent crystals
Melting point 137 to 140 °C (279 to 284 °F; 410 to 413 K)
Boiling point 141 to 144 °C (286 to 291 °F; 414 to 417 K)
log P −2.209
Acidity (pKa) 3.142
Basicity (pKb) 10.855
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Related compounds
Related alkanoic acids
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 brain in neurons,[2] oligodendrocytes and myelin[3] and is synthesized in the mitochondria from the amino acid aspartic acid and acetyl-coenzyme A.[4]

  1. ^ "N-acetylaspartate - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 8 January 2012.
  2. ^ Simmons ML, Frondoza CG, Coyle JT (1991). "Immunocytochemical localization of N-acetyl-aspartate with monoclonal antibodies". Neuroscience. 45 (1): 37–45. doi:10.1016/0306-4522(91)90101-s. PMID 1754068. S2CID 24071454.
  3. ^ Nordengen K, Heuser C, Rinholm JE, Matalon R, Gundersen V (March 2015). "Localisation of N-acetylaspartate in oligodendrocytes/myelin". Brain Structure & Function. 220 (2): 899–917. doi:10.1007/s00429-013-0691-7. PMID 24379086. S2CID 475973.
  4. ^ Patel TB, Clark JB (December 1979). "Synthesis of N-acetyl-L-aspartate by rat brain mitochondria and its involvement in mitochondrial/cytosolic carbon transport". The Biochemical Journal. 184 (3): 539–46. doi:10.1042/bj1840539. PMC 1161835. PMID 540047.