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{{short description|Derivative of aspartic acid found in the brain}} |
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{{DISPLAYTITLE:''N''-Acetylaspartic acid}} |
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{{DISPLAYTITLE:''N''-Acetylaspartic acid}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| Name=''N''-Acetylaspartic acid |
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| Watchedfields = changed |
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| verifiedrevid = 453515752 |
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| Name = ''N''-Acetylaspartic acid |
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| verifiedrevid = 477506883 |
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| ImageFile = Acetylaspartate.png |
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| ImageFile = Acetylaspartate.png |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageSize = |
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| ImageSize = 160 |
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| IUPACName = (2''S'')-2-Acetamidobutanedioic acid |
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| ImageName = Stereo, skeletal formula of N-acetylaspartic acid (S) |
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| SystematicdName = |
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| 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> |
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| OtherNames = Acetylaspartic acid<br>''N''-Acetylaspartic acid<br>''N''-Acetyl-<small>L</small>-aspartate<br>Acetyl-<small>L</small>-aspartic acid<br>''N''-Acetyl-<small>L</small>-aspartic acid |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = 2545-40-6 |
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| Abbreviations = NAA |
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| CASNo_Ref = {{cascite}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| CASNo = 997-55-7 |
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| UNII = 445Y04YIWR |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| EINECS = 213-643-9 |
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| PubChem = 65065 |
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| CASNo1 = 997-55-7 |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| SMILES = CC(=O)N(CC(=O)O)C(=O)O |
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| CASNo1_Comment = <small>''S''</small> |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 58576 |
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| PubChem = 97508 |
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| PubChem1 = 774916 |
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| InChI = 1/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 |
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| PubChem1_Comment = <small>''R''</small> |
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| InChIKey = OTCCIMWXFLJLIA-BYPYZUCNBM |
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| PubChem2 = 65065 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| PubChem2_Comment = <small>''S''</small> |
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| 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 |
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| ChemSpiderID = 88007 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| StdInChIKey = OTCCIMWXFLJLIA-BYPYZUCNSA-N |
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| ChemSpiderID1 = 677387 |
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| RTECS = CI9098600 |
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| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID1_Comment = <small>''R''</small> |
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| EINECS = 219-827-5 |
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| KEGG = C01042 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| MeSHName = N-acetylaspartate |
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| MeSHName = N-acetylaspartate |
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| ChEBI = 21547 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = |
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| ChEMBL = 1162493 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| KEGG = |
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| RTECS = CI9098600 |
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| Beilstein = 1726198 <small>''S''</small> |
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| ATCCode_prefix = |
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| 3DMet = B00227 |
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| ATCCode_suffix = |
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| SMILES = CC(=O)N(CC(=O)O)C(=O)O |
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| ATC_Supplemental =}} |
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| 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) |
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| Section2 = {{Chembox Properties |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| Formula = C<sub>6</sub>H<sub>9</sub>NO<sub>5</sub> |
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| StdInChIKey = OTCCIMWXFLJLIA-UHFFFAOYSA-N |
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| MolarMass =175.139 g/mol |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| Appearance = |
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}} |
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| Density = |
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|Section2={{Chembox Properties |
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| MeltingPt = 137-140 °C |
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| C=6 | H=9 | N=1 | O=5 |
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| Melting_notes = |
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| Appearance = Colourless, transparent crystals |
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| BoilingPt = |
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| MeltingPtC = 137 to 140 |
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| Boiling_notes = |
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| BoilingPtC = 141 to 144 |
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| Solubility = |
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| LogP = −2.209 |
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| SolubleOther = |
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| Solvent = |
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| pKa = 3.142 |
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| pKa = |
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| pKb = 10.855 |
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}} |
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| pKb = }} |
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| Section3 = {{Chembox Structure |
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|Section3={{Chembox Hazards |
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| GHSPictograms = {{GHS07}} |
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| CrystalStruct = |
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| GHSSignalWord = Warning |
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| Coordination = |
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| HPhrases = {{H-phrases|315|319|335}} |
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| MolShape = }} |
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| 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}} |
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| Section4 = {{Chembox Thermochemistry |
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}} |
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| DeltaHf = |
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|Section4={{Chembox Related |
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| DeltaHc = |
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| OtherFunction_label = alkanoic acids |
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| Entropy = |
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| OtherFunction = {{unbulleted list|]|]|]|]|]|]}} |
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| HeatCapacity = }} |
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| OtherCompounds = {{unbulleted list|]|]}} |
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| Section5 = {{Chembox Pharmacology |
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}} |
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| AdminRoutes = |
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| Bioavail = |
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| Metabolism = |
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| PregCat_US = }} |
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| Section6 = {{Chembox Explosive |
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| ShockSens = |
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| FrictionSens = |
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| ExplosiveV = |
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| REFactor = }} |
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| Section7 = {{Chembox Hazards |
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| EUClass = |
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| EUIndex = |
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| MainHazards = |
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| NFPA-H = |
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| NFPA-F = |
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| NFPA-R = |
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| NFPA-O = |
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| RPhrases = |
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| SPhrases = {{S22}} {{S24/25}} |
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| RSPhrases = |
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| FlashPt = |
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| Autoignition = |
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| ExploLimits = |
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| PEL = }} |
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| Section8 = {{Chembox Related |
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| OtherAnions = |
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| OtherCations = |
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| OtherFunctn = |
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| Function = |
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| OtherCpds = }} |
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}} |
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}} |
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'''''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. |
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'''''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. |
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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> |
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NAA is the second-most-concentrated molecule in the brain after the amino acid ]. It is synthesized in neurons from the amino acid ] and ]. The various functions served by NAA are still under investigation, but the primary proposed functions include its being: |
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== Function == |
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# A neuronal ] that is involved in fluid balance in the brain |
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The various functions served by NAA are under investigation, but the primary proposed functions include: |
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# A source of acetate for lipid and myelin synthesis in ]s, the glial cells that myelinate neuronal axons |
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# A precursor for the synthesis of the important neuronal dipeptide ] |
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# A contributor to energy production from the amino acid glutamate in neuronal mitochondria. |
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* Neuronal ] that is involved in fluid balance in the brain |
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In the brain, NAA is thought to be present predominantly in neuronal cell bodies, where it acts as a neuronal marker <ref name="PMID:11406719">{{cite journal |author=Chatham JC, Blackband SJ. |title=Nuclear magnetic resonance spectroscopy and imaging in animal research. |journal=ILAR J |volume=42 |issue=3 |pages=189–208 |year=2001 |pmid=11406719 |url=}}</ref>. NAA gives off the largest signal in ] of the human brain, and the levels measured there are decreased in numerous neuropathological conditions ranging from brain injury to ] to ]. This fact makes NAA a reliable diagnostic molecule for doctors treating patients with brain damage or disease. |
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* Source of ] for ] and myelin synthesis in oligodendrocytes, the ] cells that myelinate neuronal axons |
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* Precursor for the synthesis of the neuronal dipeptide ] |
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* Contributor to energy production from the amino acid ] in neuronal mitochondria |
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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> |
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NAA may also be a marker of creativity.<ref>http://www.newscientist.com/article/mg20227084.300-creativity-chemical-favours-the-smart.html</ref> |
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==See also== |
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== Applications == |
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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. |
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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> |
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{{cite journal |
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| date = 30 October 2012 |
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| title = The whole-brain N-acetylaspartate correlates with education in normal adults |
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| url = https://doi.org/10.1016%2Fj.pscychresns.2012.04.013 |
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| vauthors = Glodzik L, Wu WE, Babb JS, Achtnichts L, Amann M, Sollberger M, Monsch AU, Gass A, Gonenb O |
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| journal = Psychiatry Research: Neuroimaging |
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| volume = 204 |
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| issue = 1 |
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| pages = 49–54 |
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| doi = 10.1016/j.pscychresns.2012.04.013 |
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| pmid = 23177924 |
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| access-date = |
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| pmc = 3508436 |
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}} |
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</ref> |
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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> |
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== See also == |
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* ] |
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* ] |
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==References== |
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== References == |
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{{reflist|32em}} |
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{{No footnotes|date=May 2009}} |
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* 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. |
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== Further reading == |
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http://www.n-acetylaspartate.com |
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{{refbegin}} |
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* {{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}} |
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*{{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 }} |
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{{refend}} |
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== External links == |
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Finds correlations between measure of creativity and fMRIs of NAA levels in areas of brain: |
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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 |
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{{Neurotransmitters}} |
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{{reflist}} |
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{{Glutamatergics}} |
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==External links== |
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{{DEFAULTSORT:Acetylaspartic acid, N-}} |
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{{DEFAULTSORT:Acetylaspartic acid, N-}} |
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The various functions served by NAA are under investigation, but the primary proposed functions include:
In the brain, NAA was thought to be present predominantly in neuronal cell bodies, where it acts as a neuronal marker, but it is also free to diffuse throughout neuronal fibers.
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. NAA gives off the largest signal in magnetic resonance spectroscopy of the human brain. 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 potential diagnostic molecule for doctors treating patients with brain damage or disease.
N verify (what is ?)
Infobox references