Editing Carbamoyl phosphate

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 450609788
| ImageFile = Carbamoylphosphat deprotoniert.svg
| ImageSize = 150px
| ImageClass = skin-invert
| ImageName = Structural formula
| ImageFile1 = Carbamoyl-phosphate-dianion-3D-balls.png
| ImageSize1 = 160px
| ImageName1 = Ball-and-stick model
| IUPACName = (Carbamoyloxy)phosphonic acid
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 590-55-6
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = GC5KZW01Q3
| PubChem = 278
| SMILES = C(=O)(N)OP(=O)(O)O
| MeSHName = Carbamoyl+phosphate
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 17672
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 369105
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 272
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C00169
| InChI = 1S/CH4NO5P/c2-1(3)7-8(4,5)6/h(H2,2,3)(H2,4,5,6)
| InChIKey = FFQKYPRQEYGKAF-UHFFFAOYSA-N
  }}
|Section2={{Chembox Properties
| Formula = CH<sub>2</sub>NO<sub>5</sub>P<sup>2−</sup>
| MolarMass = 141.020 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
  }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
  }}
}}
'''Carbamoyl phosphate''' is an [[anion]] of biochemical significance. In land-dwelling animals, it is an [[Metabolic intermediate|intermediary metabolite]] in [[nitrogen]] disposal through the [[urea cycle]] and the synthesis of [[pyrimidine]]s. Its enzymatic counterpart, [[carbamoyl phosphate synthetase I]] (CPS I), interacts with a class of molecules called [[sirtuin]]s, NAD dependent protein deacetylases, and ATP to form carbamoyl phosphate. CP then enters the urea cycle in which it reacts with [[ornithine]] (a process catalyzed by the enzyme [[ornithine transcarbamylase]]) to form [[citrulline]].

== Classification ==
Carbamoyl phosphate is a [[metabolic intermediate]] in a [[Metabolic pathway|pathway]] that involves [[nitrogen]] disposal through the [[urea cycle]] and the [[biosynthesis]] of [[pyrimidine]]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>

==Production==
It is produced from [[bicarbonate]], [[ammonia]] (derived from [[amino acids]]), and [[phosphate]] (from [[Adenosine triphosphate|ATP]]).<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 [[carbamoyl phosphate synthetase]].<ref name=":0" /> This uses three reactions as follows:

* {{chem|HCO|3|−}} + ATP → ADP + {{chem|HO–C(O)–OPO|3|2−}} (carboxyl phosphate)
* {{chem|HO–C(O)–OPO|3|2−}}  +  NH<sub>3</sub>  + OH<sup>−</sup>   →  {{chem|HPO|4|2−}}  +  [[Carbamate|<sup>−</sup>O–C(O)NH<sub>2</sub>]]  +  H<sub>2</sub>O
*<sup>−</sup>O–C(O)NH<sub>2</sub>  +  ATP  →  ADP +  {{chem|H|2|NC(O)OPO|3|2−}}

== Clinical significance ==
A defect in the CPS I enzyme, and a subsequent deficiency in the production of carbamoyl phosphate has been linked to [[hyperammonemia]] 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>

== See also ==
* [[Ornithine transcarbamylase]]
*[[Citrulline]]
*[[Urea cycle|Urea Cycle]]

== References ==
{{reflist}}

=== Further reading ===
{{refbegin}}
* {{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 }}
{{refend}}

{{Nucleotide metabolism intermediates}}
{{Urea cycle}}

[[Category:Organophosphates]]
[[Category:Carbamates]]
[[Category:Acid anhydrides]]
[[Category:Urea cycle]]