| Revision as of 08:41, 15 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[WP:CHEMVALID|Chem/Drugbox validation← Previous edit |
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{{chembox |
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{{chembox |
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| verifiedrevid = 448017937 |
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| verifiedrevid = 450609788 |
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| ImageFile = Carbamoylphosphat deprotoniert.svg |
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| ImageFile = Carbamoylphosphat deprotoniert.svg |
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| ImageSize = 150px |
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| ImageSize = 150px |
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| ImageClass = skin-invert |
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| ImageName = Structural formula |
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| ImageName = Structural formula |
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| ImageFile1 = Carbamoyl-phosphate-dianion-3D-balls.png |
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| ImageFile1 = Carbamoyl-phosphate-dianion-3D-balls.png |
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| IUPACName = (Carbamoyloxy)phosphonic acid |
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| IUPACName = (Carbamoyloxy)phosphonic acid |
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| OtherNames = |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 590-55-6 |
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| CASNo = 590-55-6 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = GC5KZW01Q3 |
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| PubChem = 278 |
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| PubChem = 278 |
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| SMILES = C(=O)(N)OP(=O)(O)O |
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| SMILES = C(=O)(N)OP(=O)(O)O |
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| MeSHName = Carbamoyl+phosphate |
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| MeSHName = Carbamoyl+phosphate |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 17672 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 369105 |
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| ChemSpiderID = 272 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = C00169 |
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| InChI = 1S/CH4NO5P/c2-1(3)7-8(4,5)6/h(H2,2,3)(H2,4,5,6) |
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| InChIKey = FFQKYPRQEYGKAF-UHFFFAOYSA-N |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = CH<sub>2</sub>NO<sub>5</sub>P<sup>2-</sup> |
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| Formula = CH<sub>2</sub>NO<sub>5</sub>P<sup>2−</sup> |
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| MolarMass = 141.020 g/mol |
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| MolarMass = 141.020 g/mol |
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| Solubility = |
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'''Carbamoyl phosphate''' is an ] of biochemical significance. In land-dwelling animals it is an intermediary metabolite participating in the ] disposal through in the ] and the synthesis of ]s. |
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'''Carbamoyl phosphate''' is an ] of biochemical significance. In land-dwelling animals, it is an ] in ] disposal through the ] and the synthesis of ]s. Its enzymatic counterpart, carbamoyl phosphate synthetase I (CPS I), interacts with a class of molecules called ]s, NAD dependent protein deacetylases, and ATP to form carbamoyl phosphate. CP then enters the urea cycle in which it reacts with ] (a process catalyzed by the enzyme ]) to form ]. |
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== Classification == |
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It is produced from ], ] (derived from ]), and ] (from ]). The synthesis is catalysed by the enzyme ], as follows: |
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Carbamoyl phosphate is a ] in a ] that involves ] disposal through the ] and the ] of ]s.<ref name="pmid20301396">{{cite book |vauthors=Adam MP, Feldman J, Mirzaa GM, Pagon RA, Wallace SE, Bean LJ, Gripp KW, Amemiya A, Ah Mew N, Simpson KL, Gropman AL, Lanpher BC, Chapman KA, Summar ML |section=Urea Cycle Disorders Overview |veditors=Adam MP, Feldman J, Mirzaa GM, etal |title=Gene Reviews |publisher=University of Washington, Seattle |date=1993 |pmid=20301396}}</ref> |
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==Production== |
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* HCO<sub>3</sub><sup>−</sup> + ATP → ADP + HO–C(O)–OPO<sub>3</sub><sup>2−</sup> (]) |
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It is produced from ], ] (derived from ]), and ] (from ]).<ref name=":0">{{cite book | vauthors = Bhagavan NV, Ha CE |chapter=Protein and Amino Acid Metabolism |date=2015 |title=Essentials of Medical Biochemistry |edition=Second |pages=227–268| veditors = Bhagavan NV, Ha CE|location=San Diego|publisher=Academic Press|language=en|doi=10.1016/b978-0-12-416687-5.00015-4|isbn=978-0-12-416687-5 }}</ref> The synthesis is catalyzed by the enzyme ].<ref name=":0" /> This uses three reactions as follows: |
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* HO–C(O)–OPO<sub>3</sub><sup>2−</sup> + NH<sub>3</sub> + OH<sup>−</sup> → HPO<sub>4</sub><sup>2−</sup> + ] + H<sub>2</sub>O |
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*<sup>−</sup>O–C(O)NH<sub>2</sub> + ATP → ADP + H<sub>2</sub>NC(O)OPO<sub>3</sub><sup>2−</sup> |
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* {{chem|HCO|3|−}} + ATP → ADP + {{chem|HO–C(O)–OPO|3|2−}} (carboxyl phosphate) |
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==See also== |
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* {{chem|HO–C(O)–OPO|3|2−}} + NH<sub>3</sub> + OH<sup>−</sup> → {{chem|HPO|4|2−}} + ] + H<sub>2</sub>O |
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*<sup>−</sup>O–C(O)NH<sub>2</sub> + ATP → ADP + {{chem|H|2|NC(O)OPO|3|2−}} |
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== Clinical significance == |
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A defect in the CPS I enzyme, and a subsequent deficiency in the production of carbamoyl phosphate has been linked to ] in humans.<ref name="pmid19410549">{{cite journal | vauthors = Nakagawa T, Lomb DJ, Haigis MC, Guarente L | title = SIRT5 Deacetylates carbamoyl phosphate synthetase 1 and regulates the urea cycle | journal = Cell | volume = 137 | issue = 3 | pages = 560–570 | date = May 2009 | pmid = 19410549 | pmc = 2698666 | doi = 10.1016/j.cell.2009.02.026 | name-list-style = vanc }}</ref> |
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== See also == |
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* ] |
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==References== |
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== References == |
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{{reflist}} |
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=== Further reading === |
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*{{cite book | author= Nelson, David L. and Michael M. Cox | title= Lehninger Principles of Biochemistry fourth edition | publisher=W. H. Freeman and company New York}} |
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* {{cite book| vauthors = Nelson DL, Cox MM |title= Lehninger Principles of Biochemistry fourth edition |publisher= W. H. Freeman and company |location= New York |isbn= 978-0-7167-4339-2 |year= 2005 |url-access= registration |url= https://archive.org/details/lehningerprincip00lehn_0 }} |
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{{refend}} |
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{{Nucleotide metabolism intermediates}} |
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{{Nucleotide metabolism intermediates}} |
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{{Urea cycle}} |
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{{Urea cycle}} |
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