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Revision as of 09:37, 18 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 473078550 of page N-Acetylaspartic_acid for the Chem/Drugbox validation project (updated: 'ChemSpiderID', 'ChEMBL', 'KEGG', 'StdInChI', 'StdInChIK...  Latest revision as of 23:35, 26 April 2024 edit Citation bot (talk | contribs)Bots5,429,043 edits Altered pages. Added pmid. Formatted dashes. | Use this bot. Report bugs. | #UCB_CommandLine 
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{{short description|Derivative of aspartic acid found in the brain}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{DISPLAYTITLE:''N''-Acetylaspartic acid}}
{{Chembox
{{chembox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| Name = ''N''-Acetylaspartic acid | Name = ''N''-Acetylaspartic acid
| verifiedrevid = 462256723 | verifiedrevid = 477506883
| ImageFile = Acetylaspartate.png | ImageFile = Acetylaspartate.png
| ImageFile_Ref = {{chemboximage|correct|??}} | ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 160
| ImageName = Stereo, skeletal formula of N-acetylaspartic acid (S) | ImageName = Stereo, skeletal formula of N-acetylaspartic acid (S)
| IUPACName = 2-Acetamidobutanedioic acid<ref>{{Cite web|title=N-acetylaspartate - Compound Summary|url=http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=97508|work=PubChem Compound|publisher=National Center for Biotechnology Information|accessdate=8 January 2012|location=USA|date=26 March 2005|at=Identification and Related Records}}</ref> | IUPACName = 2-Acetamidobutanedioic acid<ref>{{cite web|title=N-acetylaspartate - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=97508|work=PubChem Compound|publisher=National Center for Biotechnology Information|access-date=8 January 2012|location=USA|date=26 March 2005|at=Identification}}</ref>
|Section1={{Chembox Identifiers
| OtherNames = {{Unbulleted list|''N''-Acetylaspartate{{Citation needed|date=January 2012}}|Acetylaspartic acid{{Citation needed|date=January 2012}}
| CASNo = 2545-40-6
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 445Y04YIWR
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo1 = 997-55-7
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1_Comment = <small>''S''</small>
| PubChem = 97508
| PubChem1 = 774916
| PubChem1_Comment = <small>''R''</small>
| PubChem2 = 65065
| PubChem2_Comment = <small>''S''</small>
| ChemSpiderID = 88007
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID1 = 677387
| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID1_Comment = <small>''R''</small>
| EINECS = 219-827-5
| KEGG = C01042
| KEGG_Ref = {{keggcite|changed|kegg}}
| MeSHName = N-acetylaspartate
| ChEBI = 21547
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1162493
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| RTECS = CI9098600
| Beilstein = 1726198 <small>''S''</small>
| 3DMet = B00227
| SMILES = CC(=O)N(CC(=O)O)C(=O)O
| StdInChI = 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)
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = OTCCIMWXFLJLIA-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
}} }}
| Section1 = {{Chembox Identifiers |Section2={{Chembox Properties
| C=6 | H=9 | N=1 | O=5
| Abbreviations = NAA{{Citation needed|date=January 2012}}
| Appearance = Colourless, transparent crystals
| CASNo = 997-55-7
| MeltingPtC = 137 to 140
| CASNo_Ref = {{cascite|changed|??}}
| BoilingPtC = 141 to 144
| CASNo1 = 997-55-7
| LogP = −2.209
| CASNo1_Ref = {{cascite|correct|CAS}}
| pKa = 3.142
| CASNo1_Comment = <small>(''S'')</small>
| PubChem = 97508 | pKb = 10.855
| PubChem_Ref = {{Pubchemcite|correct|Pubchem}}
| PubChem1 = 774916
| PubChem1_Ref = {{Pubchemcite|correct|Pubchem}}
| PubChem1_Comment = <small>(''R'')</small>
| PubChem2 = 65065
| PubChem2_Ref = {{Pubchemcite|correct|Pubchem}}
| PubChem2_Comment = <small>(''S'')</small>
| ChemSpiderID = 58576
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID1 = 677387
| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID1_Comment = <small>(''R'')</small>
| EINECS = 219-827-5
| KEGG = <!-- blanked - oldvalue: C01042 -->
| KEGG_Ref = {{keggcite|changed|kegg}}
| MeSHName = N-acetylaspartate
| ChEBI = 21547
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1162494
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| RTECS = CI9098600
| Beilstein = 1726198 <small>(''S'')</small>
| 3DMet = B00227
| SMILES = CC(=O)NC(CC(O)=O)C(O)=O
| StdInChI = 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)/t4-/m0/s1
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = OTCCIMWXFLJLIA-BYPYZUCNSA-N
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
}} }}
| Section2 = {{Chembox Properties |Section3={{Chembox Hazards
| GHSPictograms = {{GHS07}}
| C=6|H=9|N=1|O=5
| GHSSignalWord = Warning
| ExactMass = 175.048072403 g mol<sup>1−</sup>
| HPhrases = {{H-phrases|315|319|335}}
| Appearance = Colourless, transparent crystals
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
| MeltingPtCL = 137
| MeltingPtCH = 140
| BoilingPtCL = 141
| BoilingPtCH = 144
| LogP = −2.209
| pKa = 3.142
| pKb = 10.855
}} }}
| Section3 = {{Chembox Hazards |Section4={{Chembox Related
| OtherFunction_label = alkanoic acids
| SPhrases = {{S22}}, {{S24/25}}
| OtherFunction = {{unbulleted list|]|]|]|]|]|]}}
}}
| OtherCompounds = {{unbulleted list|]|]}}
| Section4 = {{Chembox Related
| OtherCpds = ]
}} }}
}} }}

'''''N''-Acetylaspartic acid''', or '''''N''-acetylaspartate''' ('''NAA'''), is a derivative of ] with a formula of C<sub>6</sub>H<sub>9</sub>NO<sub>5</sub> and a molecular weight of 175.139.

NAA is the second-most-concentrated ] in the ] after the ] ]. It is detected in the adult brain in ]s,<ref>{{cite journal | vauthors = Simmons ML, Frondoza CG, Coyle JT | title = Immunocytochemical localization of N-acetyl-aspartate with monoclonal antibodies | journal = Neuroscience | volume = 45 | issue = 1 | pages = 37–45 | date = 1991 | pmid = 1754068 | doi = 10.1016/0306-4522(91)90101-s | s2cid = 24071454 }}</ref> ]s and ]<ref name="ReferenceA">{{cite journal | vauthors = Nordengen K, Heuser C, Rinholm JE, Matalon R, Gundersen V | title = Localisation of N-acetylaspartate in oligodendrocytes/myelin | journal = Brain Structure & Function | volume = 220 | issue = 2 | pages = 899–917 | date = March 2015 | pmid = 24379086 | doi = 10.1007/s00429-013-0691-7 | s2cid = 475973 }}</ref> and is synthesized in the ] from the amino acid ] and ].<ref>{{cite journal | vauthors = Patel TB, Clark JB | title = Synthesis of N-acetyl-L-aspartate by rat brain mitochondria and its involvement in mitochondrial/cytosolic carbon transport | journal = The Biochemical Journal | volume = 184 | issue = 3 | pages = 539–46 | date = December 1979 | doi = 10.1042/bj1840539 | pmid = 540047 | pmc = 1161835 }}</ref>

== Function ==
The various functions served by NAA are under investigation, but the primary proposed functions include:

* Neuronal ] that is involved in fluid balance in the brain
* Source of ] for ] and myelin synthesis in oligodendrocytes, the ] cells that myelinate neuronal axons
* Precursor for the synthesis of the neuronal dipeptide ]
* Contributor to energy production from the amino acid ] in neuronal mitochondria

In the brain, NAA was thought to be present predominantly in neuronal cell bodies, where it acts as a neuronal marker,<ref name="PMD11406719">{{cite journal | vauthors = Chatham JC, Blackband SJ | title = Nuclear magnetic resonance spectroscopy and imaging in animal research | journal = ILAR Journal | volume = 42 | issue = 3 | pages = 189–208 | year = 2001 | pmid = 11406719 | doi = 10.1093/ilar.42.3.189 | doi-access = free }}</ref> but it is also free to diffuse throughout neuronal fibers.<ref>{{cite journal | vauthors = Najac C, Branzoli F, Ronen I, Valette J | title = Brain intracellular metabolites are freely diffusing along cell fibers in grey and white matter, as measured by diffusion-weighted MR spectroscopy in the human brain at 7 T | journal = Brain Structure & Function | volume = 221 | issue = 3 | pages = 1245–54 | date = April 2016 | pmid = 25520054 | pmc = 4878649 | doi = 10.1007/s00429-014-0968-5 }}</ref>

== Applications ==
However, the recent discovery of a higher concentration of NAA in myelin and oligodendrocytes than in neurons raises questions about the validity of the use of NAA as a neuronal marker.<ref name="ReferenceA" /> NAA gives off the largest signal in ] of the human brain. The levels measured there are decreased in numerous neuropathological conditions ranging from brain injury to ] to ]. This fact makes NAA a potential diagnostic molecule for doctors treating patients with brain damage or disease.

NAA may be a marker of creativity.<ref>{{cite web|url=https://www.newscientist.com/article/mg20227084.300-creativity-chemical-favours-the-smart.html|title=Creativity chemical favours the smart|first=Linda|last=Geddes}}</ref> High NAA levels in the ] are related to better ] performance in humans.<ref>{{cite journal | vauthors = Kozlovskiy S, Vartanov A, Pyasik M, Polikanova I | year = 2012 | title = Working memory and N-acetylaspartate level in hippocampus, parietal cortex and subventricular zone | journal = International Journal of Psychology | volume = 47 | page = 584 | doi = 10.1080/00207594.2012.709117 | doi-access = free }}</ref> Whole-brain levels of NAA have also been found to be positively correlated with educational attainment in adults.<ref>
{{cite journal
| date = 30 October 2012
| title = The whole-brain N-acetylaspartate correlates with education in normal adults
| url = https://doi.org/10.1016%2Fj.pscychresns.2012.04.013
| vauthors = Glodzik L, Wu WE, Babb JS, Achtnichts L, Amann M, Sollberger M, Monsch AU, Gass A, Gonenb O
| journal = Psychiatry Research: Neuroimaging
| volume = 204
| issue = 1
| pages = 49–54
| doi = 10.1016/j.pscychresns.2012.04.013
| pmid = 23177924
| access-date =
| pmc = 3508436
}}
</ref>

NAA may function as a ] in the brain by acting on ]s.<ref name="pmid12919386">{{cite journal | vauthors = Yan HD, Ishihara K, Serikawa T, Sasa M | title = Activation by N-acetyl-L-aspartate of acutely dissociated hippocampal neurons in rats via metabotropic glutamate receptors | journal = Epilepsia | volume = 44 | issue = 9 | pages = 1153–9 | date = September 2003 | pmid = 12919386 | doi = 10.1046/j.1528-1157.2003.49402.x | s2cid = 39902618 | doi-access = free }}</ref>

== See also ==
* ]
* ]

== References ==
{{reflist|32em}}

== Further reading ==
{{refbegin}}
* {{cite book|editor-first1=John |editor-last1=Moffett|editor-first2=Suzannah B.|editor-last2= Tieman|editor-first3=Daniel R. |editor-last3=Weinberger|editor-first4=Joseph T. |editor-last4=Coyle |editor-first5=Aryan M. A. |editor-last5=Namboodiri | name-list-style = vanc |title=N-Acetylaspartate: A Unique Neuronal Molecule in the Central Nervous System|url={{google books |plainurl=y |id=tR44q6WWRBgC}}|date=21 October 2006|publisher=Springer Science & Business Media|isbn=978-0-387-30172-3}}
*{{cite journal | vauthors = Jung RE, Gasparovic C, Chavez RS, Flores RA, Smith SM, Caprihan A, Yeo RA | title = Biochemical support for the "threshold" theory of creativity: a magnetic resonance spectroscopy study | journal = The Journal of Neuroscience | volume = 29 | issue = 16 | pages = 5319–25 | date = April 2009 | pmid = 19386928 | pmc = 2755552 | doi = 10.1523/JNEUROSCI.0588-09.2009 }}
{{refend}}

== External links ==
*

{{Neurotransmitters}}
{{Glutamatergics}}

{{DEFAULTSORT:Acetylaspartic acid, N-}}
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