https://wiki.tiffa.net/w/index.php?action=history&feed=atom&title=Flavin_mononucleotide%2FenFlavin mononucleotide/en - Revision history2026-06-28T23:47:34ZRevision history for this page on the wikiMediaWiki 1.43.0https://wiki.tiffa.net/w/index.php?title=Flavin_mononucleotide/en&diff=136759&oldid=prevFuzzyBot: Updating to match new version of source page2024-04-10T06:20:10Z<p>Updating to match new version of source page</p>
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{{chembox<br />
| Verifiedfields = changed<br />
| Watchedfields = changed<br />
| verifiedrevid = 461100522<br />
| ImageFile = Flavin mononucleotide v2.svg<br />
| ImageSize = 180<br />
| ImageAlt = Skeletal formula of flavin mononucleotide<br />
| ImageFile1 = Flavin mononucleotide 3D ball.png<br />
| ImageSize1 = 180<br />
| ImageAlt1 = Ball-and-stick model of the flavin mononucleotide molecule<br />
| IUPACName = 1-Deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[''g'']pteridin-10(2''H'')-yl)-<small>D</small>-ribitol 5-(dihydrogen phosphate)<br />
| SystematicName = (2''R'',3''S'',4''S'')-5-(7,8-Dimethyl-2,4-dioxo-3,4-dihydrobenzo[''g'']pteridin-10(2''H'')-yl)-2,3,4-trihydroxypentyl dihydrogen phosphate<br />
| OtherNames = {{Unbulleted list|FMN}}<br />
|Section1={{Chembox Identifiers<br />
| IUPHAR_ligand = 5185<br />
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}<br />
| ChemSpiderID = 559060<br />
| UNII_Ref = {{fdacite|correct|FDA}}<br />
| UNII = 7N464URE7E<br />
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}<br />
| StdInChI = 1S/C17H21N4O9P/c1-7-3-9-10(4-8(7)2)21(15-13(18-9)16(25)20-17(26)19-15)5-11(22)14(24)12(23)6-30-31(27,28)29/h3-4,11-12,14,22-24H,5-6H2,1-2H3,(H,20,25,26)(H2,27,28,29)/t11-,12+,14-/m0/s1<br />
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}<br />
| StdInChIKey = FVTCRASFADXXNN-SCRDCRAPSA-N<br />
| CASNo_Ref = {{cascite|correct|CAS}}<br />
| CASNo = 146-17-8<br />
| CASNo2_Ref = {{cascite|correct|CAS}}<br />
| CASNo2 = 130-40-5<br />
| CASNo2_Comment = (sodium salt)<br />
| ChEMBL_Ref = {{ebicite|changed|EBI}}<br />
| ChEMBL = 1201794<br />
| PubChem = 643976<br />
| ChEBI_Ref = {{ebicite|correct|EBI}}<br />
| ChEBI = 17621<br />
| SMILES = Cc1cc2c(cc1C)n(c-3nc(=O)[nH]c(=O)c3n2)C[C@@H]([C@@H]([C@@H](COP(=O)(O)O)O)O)O<br />
| MeSHName = Flavin+mononucleotide<br />
}}<br />
|Section2={{Chembox Properties<br />
| Formula = C<sub>17</sub>H<sub>21</sub>N<sub>4</sub>O<sub>9</sub>P<br />
| MolarMass = 456.344 g/mol<br />
| Appearance = <br />
| Density = <br />
| MeltingPt = 195 °C<br />
| BoilingPt = <br />
}}<br />
|Section3={{Chembox Hazards<br />
| MainHazards = <br />
| FlashPt = <br />
| AutoignitionPt = <br />
}}<br />
}}<br />
'''Flavin mononucleotide''' ('''FMN'''), or '''riboflavin-5′-phosphate''', is a [[biomolecule]] produced from [[riboflavin]] (vitamin B<sub>2</sub>) by the enzyme [[riboflavin kinase]] and functions as the [[prosthetic group]] of various [[oxidoreductase]]s, including [[NADH dehydrogenase]], as well as cofactor in biological blue-light photo receptors. During the catalytic cycle, a reversible interconversion of the oxidized (FMN), semiquinone (FMNH<sup>•</sup>), and reduced (FMNH<sub>2</sub>) forms occurs in the various oxidoreductases. FMN is a stronger oxidizing agent than [[Nicotinamide adenine dinucleotide|NAD]] and is particularly useful because it can take part in both one- and two-electron transfers. In its role as blue-light photo receptor, (oxidized) FMN stands out from the 'conventional' photo receptors as the signaling state and not an E/Z isomerization.<br />
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It is the principal form in which riboflavin is found in [[cell (biology)|cell]]s and [[biological tissue|tissues]]. It requires more energy to produce, but is more [[soluble]] than riboflavin. In cells, FMN occurs freely circulating but also in several [[covalent|covalently bound]] forms. Covalently or non-covalently bound FMN is a cofactor of many enzymes playing an important pathophysiological role in cellular metabolism. For example dissociation of flavin mononucleotide from mitochondrial complex I has been shown to occur during ischemia/reperfusion brain injury during stroke.<br />
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==Food additive==<br />
Flavin mononucleotide is also used as an orange-red food colour additive, designated in Europe as [[E number]] E101a.<br />
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E106, a very closely related food dye, is riboflavin-5′-phosphate sodium salt, which consists mainly of the [[monosodium]] [[salt (chemistry)|salt]] of the 5′-monophosphate [[ester]] of riboflavin. It is rapidly turned to free riboflavin after [[ingestion]]. It is found in many foods for babies and young children as well as [[jam]]s, [[milk]] products, and sweets and [[sugar]] products.<br />
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==See also==<br />
* [[Flavin adenine dinucleotide]]<br />
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==External links==<br />
*[http://www.ebi.ac.uk/msd-srv/chempdb/cgi-bin/cgi.pl?FUNCTION=getByCode&CODE=FMN FMN] in the [http://www.ebi.ac.uk/msd/ EBI Macromolecular Structure Database]<br />
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{{Enzyme cofactors}}<br />
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{{二次利用|date=19 March 2024}}<br />
[[Category:Flavins]]<br />
[[Category:Food colorings]]<br />
[[Category:Organophosphates]]<br />
[[Category:Oxidoreductases]]<br />
[[Category:Cofactors]]</div>FuzzyBot