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Revision as of 13:04, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 472724591 of page Inosinic_acid for the Chem/Drugbox validation project (updated: '').		Latest revision as of 22:40, 16 November 2024 edit Beland (talk | contribs)Autopatrolled, Administrators236,908 edits fix dark mode problem, replace PNG with SVG
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			{{Redirect|E630|the locomotive E.630|ČSD Class E 499.3#E.630}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
			{{refimprove|date=November 2014}}
	{{Chembox		{{Chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 446427605
			| Watchedfields = changed
	| ImageFile = Inosinic acid structure.svg|thumb
		⚫	| verifiedrevid = 476998270
⚫	| ImageSize =
	| IUPACName = 5'-inosinic acid		| ImageFile = Inosinic acid structure.svg
			| ImageClass = skin-invert-image
⚫	| OtherNames = IMP,<br>hypoxanthine ribotide
		⚫	| ImageSize = 220
⚫	| Section1 = {{Chembox Identifiers
			| ImageFile1 = Inosine monophosphate 3D ball.png
⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ImageSize1 = 220
			| ImageAlt1 = Ball-and-stick model of the inosinic acid molecule
			| IUPACName = 5'-Inosinic acid
		⚫	| OtherNames = {{Unbulleted list|IMP|Hypoxanthine ribotide}}
		⚫	|Section1={{Chembox Identifiers
			| IUPHAR_ligand = 5124
		⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 8264		| ChemSpiderID = 8264
	| InChI = 1/C10H13N4O8P/c15-6-4(1-21-23(18,19)20)22-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)17/h2-4,6-7,10,15-16H,1H2,(H,11,12,17)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1		| InChI = 1/C10H13N4O8P/c15-6-4(1-21-23(18,19)20)22-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)17/h2-4,6-7,10,15-16H,1H2,(H,11,12,17)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
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	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 131-99-7		| CASNo = 131-99-7
		⚫	| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| PubChem = 8582
			| UNII = TAO7US05G5
⚫	| ChEBI_Ref = {{ebicite|correct|EBI}}
		⚫	| PubChem = 8582
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
			| ChEMBL = 1233478
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 17202		| ChEBI = 17202
	| SMILES = O=C3/N=C\Nc1c3ncn12O((O)2O)COP(=O)(O)O		| SMILES = O=C3/N=C\Nc1c3ncn12O((O)2O)COP(=O)(O)O
	| MeSHName = Inosine+monophosphate		| MeSHName = Inosine+monophosphate
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
			| C=10|H=13|N=4|O=8|P=1
	| Formula = C<sub>10</sub>H<sub>13</sub>N<sub>4</sub>O<sub>8</sub>P
			| Appearance =
	| MolarMass = 348.206 g/mol
	| Appearance =		| Density =
	| Density =		| MeltingPt =
	| MeltingPt =		| BoilingPt =
	| BoilingPt =
	}}		}}
	| Section3 = {{Chembox Hazards		|Section3={{Chembox Hazards
	| Solubility =		| MainHazards =
	| MainHazards =		| FlashPt =
	| FlashPt =		| AutoignitionPt =
	| Autoignition =
	}}		}}
	}}		}}
			'''Inosinic acid''' or '''inosine monophosphate''' ('''IMP''') is a ] (that is, a ] monophosphate). Widely used as a flavor enhancer, it is typically obtained from chicken byproducts or other ] waste. Inosinic acid is important in ]. It is the ] of ] and the first nucleotide formed during the synthesis of ] nucleotides. It can also be formed by the ] of ] by ]. It can be ] to ].
			The enzyme deoxyribonucleoside triphosphate pyrophosphohydrolase, encoded by YJR069C in '']'' and containing (d)ITPase and (d)XTPase activities, hydrolyzes ] (ITP) releasing ] and IMP.<ref name="pmid 22531138">{{cite journal |vauthors=Davies O, Mendes P, Smallbone K, Malys N | title = Characterisation of multiple substrate-specific (d)ITP/(d)XTPase and modelling of deaminated purine nucleotide metabolism | journal = BMB Reports | volume = 45 | issue = 4 | pages = 259–64 | year = 2012 | pmid = 22531138| doi = 10.5483/BMBRep.2012.45.4.259| doi-access = free }}</ref>
			Important derivatives of inosinic acid include the purine nucleotides found in ]s and ], which is used to store ] in ] and other tissues.
			In the food industry, inosinic acid and its ] such as ] are used as ]s. It is known as ] reference '''E630'''.
			==Inosinate synthesis==
			{{Main|Purine metabolism#Biosynthesis}}
			The inosinate synthesis is complex, beginning with a ] (PRPP). ] taking part in IMP synthesis constitute a multienzyme complex in the cell. Evidence demonstrates that there are multifunctional enzymes, and some of them catalyze non-sequential steps in the pathway.{{Citation needed|date=July 2020}}
			]
			==Synthesis of other purine nucleotides==
			Within a few steps inosinate becomes ] or ].<ref name=":0">{{Citation|last=Mader|first=M. M.|title=7.03 - Antimetabolites|date=2007-01-01|url=http://www.sciencedirect.com/science/article/pii/B008045044X002042|work=Comprehensive Medicinal Chemistry II|pages=55–79|editor-last=Taylor|editor-first=John B.|place=Oxford|publisher=Elsevier|language=en|doi=10.1016/b0-08-045044-x/00204-2|isbn=978-0-08-045044-5|access-date=2020-12-17|last2=Henry|first2=J. R.|editor2-last=Triggle|editor2-first=David J.}}</ref> Both compounds are ] ].<ref name=":0" /> AMP differs from inosinate by the replacement of IMP's carbon-6 carbonyl with an amino group. The interconversion of AMP and IMP occurs as part of the ].<ref>Voet, D, Voet, J. G., Biochemistry (3rd Edition), John Wiley & Sons, Inc., 2004, pg 1095</ref> GMP is formed by the inosinate oxidation to ] (XMP), and afterwards adds an amino group on carbon 2. Hydrogen acceptor on inosinate oxidation is ]. Finally, carbon 2 gains the amino group by spending an ATP molecule (which becomes AMP+2Pi). While AMP synthesis requires GTP, GMP synthesis uses ATP. That difference offers an important regulation possibility.
			]
			==Regulation of purine nucleotide biosynthesis==
			Inosinate and many other molecules inhibit the synthesis of 5-] from 5-phosphoribosyl-1-pyrophosphate (PRPP), disabling the enzyme that catalyzes the reaction: glutamine-5-phosphoribosyl-1-pyrophosphate-amidotransferase. In other words, when levels of inosinate are high, glutamine-5-phosphoribosyl-1-pyrophosphate-amidotransferase is inhibited, and, as a consequence, inosinate levels decrease. Also, as a result, adenylate and guanylate are not produced, which means that RNA synthesis cannot be completed because of the lack of these two important RNA nucleotides.
			==Applications==
			Inosinic acid can be converted into various ] including ] (E631), ] (E632), and ] (E633). These three compounds are used as ]s for the basic taste ] or savoriness with a comparatively high effectiveness. They are mostly used in soups, sauces, and seasonings for the intensification and balance of the flavor of meat.
			==See also==
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			==References==
			{{reflist}}
			==Further reading==
			* Berg, Jeremy M.; ''Bioquímica''; Editorial Reverté; 6ena edició; Barcelona 2007.
			* Nelson, David L.; ''Principles of biochemistry''; Editorial W.H Freeman and Company; 4th edition; New York 2005.
			{{Nucleobases, nucleosides, and nucleotides}}
			{{Nucleotide metabolism intermediates}}
			{{Purinergics}}
			{{DEFAULTSORT:Inosinic Acid}}
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			]
			]
			]
			]
			]