| Revision as of 13:30, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 444095685 of page Saccharopine for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 22:49, 19 October 2022 edit KormiSK (talk | contribs)Extended confirmed users919 edits The image was NOT saccharopine, so I'm replacing it; two -CH2- groups are missing in the Lys part of the structureTag: Visual edit |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 444093785 |
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| Watchedfields = changed |
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|ImageFile=Saccharopine.svg |
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| verifiedrevid = 464385925 |
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|ImageSize=200px |
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| ImageFile = Saccharopine.PNG |
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|IUPACName=2- pentanedioic acid |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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|OtherNames= |
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| ImageName = Stereo, skeletal formula of saccharopine ((2S)-2-<nowiki/>{amino}) |
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|Section1= {{Chembox Identifiers |
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| IUPACName = 2-pentanedioic acid<ref>{{cite web|title=N-(5-AMINO-5-CARBOXYPENTYL)GLUTAMIC ACID - Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=1087&loc=ec_rcs|work=PubChem Compound|publisher=National Center for Biotechnology Information|accessdate=11 July 2012|location=USA|date=23 June 2005|at=Identification}}</ref> |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| Section1 = {{Chembox Identifiers |
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| CASNo = 997-68-2 |
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| CASNo_Ref = {{cascite|changed|??}} |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = WBQ73O8W32 |
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| PubChem = 160556 |
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| ChemSpiderID = 141086 |
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| ChemSpiderID = 141086 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| InChI = 1/C11H20N2O6/c12-7(10(16)17)3-1-2-6-13-8(11(18)19)4-5-9(14)15/h7-8,13H,1-6,12H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1 |
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| InChIKey = ZDGJAHTZVHVLOT-YUMQZZPRBV |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C11H20N2O6/c12-7(10(16)17)3-1-2-6-13-8(11(18)19)4-5-9(14)15/h7-8,13H,1-6,12H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = ZDGJAHTZVHVLOT-YUMQZZPRSA-N |
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| CASNo = <!-- blanked - oldvalue: 997-68-2 --> |
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| PubChem = 160556 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB04207 |
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| DrugBank = DB04207 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| KEGG = C00449 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| MeSHName = saccharopine |
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| ChEBI = 16927 |
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| ChEBI = 16927 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| SMILES = O=C(O)(N)CCCCN(C(=O)O)CCC(=O)O |
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| 3DMet = B01246 |
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| MeSHName=Saccharopine |
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| SMILES = NC(CCCCNC(CCC(=O)O)C(=O)O)C(=O)O |
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}} |
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| StdInChI = 1S/C11H20N2O6/c12-7(10(16)17)3-1-2-6-13-8(11(18)19)4-5-9(14)15/h7-8,13H,1-6,12H2,(H,14,15)(H,16,17)(H,18,19) |
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|Section2= {{Chembox Properties |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| Formula=C<sub>11</sub>H<sub>20</sub>N<sub>2</sub>O<sub>6</sub> |
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| StdInChIKey = ZDGJAHTZVHVLOT-UHFFFAOYSA-N |
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| MolarMass=276.286 |
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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= |
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| C=11 | H=20 | N=2 | O=6 |
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| BoilingPt=257-259°C |
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| Solubility= |
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| Section3 = {{Chembox Related |
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}} |
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| OtherFunction_label = alkanoic acids |
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|Section3= {{Chembox Hazards |
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| OtherFunction = {{unbulleted list|]|]}} |
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| MainHazards= |
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| OtherCompounds = ] |
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| Autoignition= |
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'''Saccharopine''' is an intermediate in the ] of amino acid ]. It is a precursor of lysine in the ] pathway which occurs in ] and ]s. In mammals and higher plants saccharopine is an intermediate in the degradation of lysine, formed by condensation of lysine and ]. |
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==Reaction== |
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The reactions involved, catalysed by ]s, are: |
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:lysine + alpha-ketoglutarate ⇌ saccharopine ⇌ glutamate + ] |
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==Pathology== |
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] (high amounts of saccharopine in the urine) and saccharopinemia (an excess of saccharopine in the blood) are conditions present in some inherited disorders of lysine degradation. |
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==History== |
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Saccharopine was first isolated in 1961 from ] (''Saccharomyces'', hence the name) by Darling and Larsen.<ref>Darling, S., and Larsen, P. O., Saccharopine, a new amino acid in Baker's and Brewer's yeast: I. Isolation and properties. ''Acta Chem. Scand.'', 15, 743 (1961).</ref> |
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==See also== |
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* ] |
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==References== |
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{{reflist}} |
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{{amino acid metabolism intermediates}} |
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] |