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Revision as of 11:52, 23 August 2011 editLuckas-bot (talk | contribs)929,662 editsm r2.7.1) (robot Adding: gl:Uridín monofosfato← Previous edit		Latest revision as of 05:12, 3 March 2024 edit undoMaxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,050 edits Added the cs1 style template to denote Vancouver ("vanc") citation style, because references contain "vauthors" attribute to specify the list of authors. Added doi-access. | Use this tool. Report bugs. | #UCB_Gadget
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			{{cs1 config|name-list-style=vanc}}
	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 417404339
			| Watchedfields = changed
⚫	|ImageFile=Uridinmonophosphat protoniert.svg
		⚫	| verifiedrevid = 446304818
	|ImageSize=
		⚫	| ImageFile =Uridinmonophosphat protoniert.svg
	|IUPACName=
			| ImageAlt = Skeletal formula of UMP
	|OtherNames=
			| ImageFile1 = Uridine monophosphate anion 3D ball.png
⚫	|Section1= {{Chembox Identifiers
			| ImageAlt1 = Ball-and-stick model of the UMP molecule as an anion
⚫	| CASNo=58-97-9
			| IUPACName =methyl dihydrogen phosphate
⚫	| CASNo_Ref = {{cascite|correct|CAS}}
			| OtherNames =Uridylic acid; Uridine 5'-monophosphate; 5'-Uridylic acid; Uridine 5'-phosphate; Uridine phosphate; 5'-UMP; Uridine 5'-phosphoric acid
⚫	| PubChem=1172
		⚫	|Section1={{Chembox Identifiers
⚫	| SMILES=C1=CN(C(=O)NC1=O) C2C(C(C(O2)COP(=O)(O)O)O)O
			| IUPHAR_ligand = 5125
⚫	| MeSHName=Uridine+monophosphate
		⚫	| CASNo =58-97-9
		⚫	| CASNo_Ref = {{cascite|correct|CAS}}
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = E2OU15WN0N
		⚫	| PubChem = 6030
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
			| ChemSpiderID = 5808
		⚫	| SMILES = c1cn(c(=O)c1=O)2(((O2)COP(=O)(O)O)O)O
			| InChI = 1/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
			| InChIKey = DJJCXFVJDGTHFX-XVFCMESIBD
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChI = 1S/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChIKey = DJJCXFVJDGTHFX-XVFCMESISA-N
		⚫	| MeSHName =Uridine+monophosphate
	}}		}}
	|Section2= {{Chembox Properties		|Section2={{Chembox Properties
			| C=9 | H=13 | N=2 | O=9 | P=1
	| Formula=C<sub>9</sub>H<sub>13</sub>N<sub>2</sub>O<sub>9</sub>P
			| Appearance =
	| MolarMass=324.181
		⚫	| pKa = 1.0, 6.4, 9.5
	| Appearance=
			| Density =
⚫	| pKa= 1.0, 6.4, 9.5
			| MeltingPtC = 202
	| Density=
	| MeltingPt= 202 °C (dec.) <ref name=lide>M. Lide, D. R. Lide: ''CRC Handbook of Chemistry and Physics.'' 87. Auflage, S. 3-56, CRC Press, 1998, ISBN 9780849305948</ref>		| MeltingPt_notes = (decomposes)<ref name=lide>{{cite book | vauthors = Lide M, Lide DR | title = CRC Handbook of Chemistry and Physics | edition = 87 | pages = 3–56 | publisher = CRC Press | year = 1998 | isbn = 978-0-8493-0594-8 }}</ref>
	| BoilingPt=		| BoilingPt =
	| Solubility= good, also in methanol <ref name=lide/>		| Solubility = good, also in methanol <ref name=lide/>
⚫	}}
⚫	|Section3= {{Chembox Hazards
	| MainHazards=
	| FlashPt=
	| Autoignition=
	}}		}}
		⚫	|Section3={{Chembox Hazards
			| MainHazards =
			| FlashPt =
			| AutoignitionPt =
		⚫	}}
	}}		}}
	'''Uridine monophosphate''', also known as '''5'-uridylic acid''' and abbreviated '''UMP''', is a ] that is found in ]. It is an ] of ] with the ] ]. UMP consists of the ] ], the ] ] ], and the ] ]; hence, it is a ].
			'''Uridine monophosphate''' ('''UMP'''), also known as '''5′-uridylic acid''' (] '''uridylate'''), is a ] that is used as a ] in ]. It is an ] of ] with the ] ]. UMP consists of the ] ], the ] ] ], and the ] ]; hence, it is a ]. As a ] or ] its name takes the form of the prefix '''uridylyl-'''. The deoxy form is abbreviated ]. Covalent attachment of UMP (e.g., to a protein such as adenylyltransferase) is called '''uridylylation''' (or sometimes uridylation).<ref>{{cite book | vauthors = Voet D, Voet JG, Pratt CW | year = 2008 | title = Fundamentals of Biochemistry | url = https://archive.org/details/fundamentalsofbi0000voet | url-access = registration | edition = 3rd | publisher = John Wiley & Sons }}</ref>
	Another common shorthand for the molecule is '''uridylate''' - the deprotonated form of the molecule, which is predominant in aqueous solution. As a ] it takes the form of the prefix '''uridylyl-'''.
	== Biosynthesis ==		== Biosynthesis ==
	Uridine monophosphate is formed from ] (orotidylic acid) in a decarboxylation reaction catalyzed by the ] ]. Uncatalyzed, the decarboxylation reaction is extremely slow (estimated to occur on average one time per 78 million years). Adequately catalyzed, the reaction takes place once per second, an increase of 10<sup>17</sup>-fold. <ref name=Stryer_2006>{{cite book | author = Berg J, Tymoczko JL, Stryer L | title = Biochemistry | publisher = W. H. Freeman | edition = 6th ed. | location = San Francisco | year = 2006 | isbn = 0716787245 }}</ref>		Uridine monophosphate is formed from ] (orotidylic acid) in a decarboxylation reaction catalyzed by the ] ]. Uncatalyzed, the decarboxylation reaction is extremely slow (estimated to occur on average one time per 78 million years). Adequately catalyzed, the reaction takes place once per second, an increase of 10<sup>17</sup>-fold.<ref name=Stryer_2006>{{cite book | vauthors = Berg J, Tymoczko JL, Stryer L | title = Biochemistry | publisher = W. H. Freeman | edition = 6th | location = San Francisco | year = 2006 | isbn = 0-7167-8724-5 }}</ref>
	In humans, the orotidylate decarboxylase function is carried out by the protein ]. <ref></ref> Defective UMP synthase can result in ], a metabolic disorder.		In humans, the orotidylate decarboxylase function is carried out by the protein ].<ref>{{cite journal | vauthors = Winkler JK, Suttle DP | title = Analysis of UMP synthase gene and mRNA structure in hereditary orotic aciduria fibroblasts | journal = American Journal of Human Genetics | volume = 43 | issue = 1 | pages = 86–94 | date = July 1988 | pmid = 2837086 | pmc = 1715274 }}</ref> Defective UMP synthase can result in ], a metabolic disorder.
	== Effects on Animal Intelligence ==		== Effects on animal intelligence ==
	In a recent study, gerbils fed supplements of uridine monophosphate, choline, and ] (DHA) were found to have significantly improved performance in running mazes over those not fed the supplements, implying an increase in cognitive function.<ref></ref>		In a study, ]s fed a combination of uridine monophosphate, ], and ] (DHA) were found to have significantly improved performance in running mazes over those not fed the supplements, implying an increase in cognitive function.<ref name="Holguin_2008">{{cite journal | vauthors = Holguin S, Martinez J, Chow C, Wurtman R | title = Dietary uridine enhances the improvement in learning and memory produced by administering DHA to gerbils | journal = FASEB Journal | volume = 22 | issue = 11 | pages = 3938–46 | date = November 2008 | pmid = 18606862 | pmc = 2574024 | doi = 10.1096/fj.08-112425| doi-access = free }}
			*{{cite press release |date=July 3, 2008 |title=Get Smart About What You Eat And You Might Actually Improve Your Intelligence |website=ScienceDaily |url=https://www.sciencedaily.com/releases/2008/07/080702150706.htm}}</ref>
			== In foods ==
	== Uridine Monophosphate in Foods ==
			In brain research studies, uridine monophosphate is used as a convenient delivery compound for ].<ref>{{cite journal | vauthors = Wurtman RJ, Cansev M, Sakamoto T, Ulus IH | title = Use of phosphatide precursors to promote synaptogenesis | journal = Annual Review of Nutrition | volume = 29 | pages = 59–87 | date = 2009 | pmid = 19400698 | doi = 10.1146/annurev-nutr-080508-141059 }}</ref> ] is the active component of this compound. Uridine is present in many foods, mainly in the form of RNA. Non-phosphorylated uridine is not bioavailable beyond first-pass metabolism, as it is almost entirely catabolised in the liver and gastrointestinal tract.<ref>{{cite journal | vauthors = Gasser T, Moyer JD, Handschumacher RE | title = Novel single-pass exchange of circulating uridine in rat liver | journal = Science | volume = 213 | issue = 4509 | pages = 777–8 | date = August 1981 | pmid = 7256279 | doi = 10.1126/science.7256279 | bibcode = 1981Sci...213..777G }}</ref>
	In brain research studies such as those mentioned in this article, uridine monophosphate is used as a convenient delivery compound for ]. ] is the active ingredient of the compound. A common misconception is that uridine and its compounds are not available in significant quantities from foods and must be obtained from expensive supplements or prescription drugs. This is not so. Uridine monophosphate is a major component of ]. Any food rich in ], such as Brewer's yeast or some organ meats, will provide significant quantities of it. For more information, consult the article on ].
⚫	== References ==
⚫	{{reflist}}
	== See also ==		== See also ==
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	* ]		* ]
	* ]		* ]
	* ]
		⚫	== References ==
		⚫	{{reflist}}
	{{Nucleobases, nucleosides, and nucleotides}}		{{Nucleobases, nucleosides, and nucleotides}}
	{{Nucleotide metabolism intermediates}}		{{Nucleotide metabolism intermediates}}
			{{Purinergics}}
	]		]
			]
	]		]
	{{biochem-stub}}
	]
	]
	]
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