View source for Flavin mononucleotide/en

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{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 461100522
| ImageFile = Flavin mononucleotide v2.svg
| ImageSize = 180
| ImageAlt = Skeletal formula of flavin mononucleotide
| ImageFile1 = Flavin mononucleotide 3D ball.png
| ImageSize1 = 180
| ImageAlt1 = Ball-and-stick model of the flavin mononucleotide molecule
| 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)
| 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
| OtherNames = {{Unbulleted list|FMN}}
|Section1={{Chembox Identifiers
| IUPHAR_ligand = 5185
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 559060
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7N464URE7E
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FVTCRASFADXXNN-SCRDCRAPSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 146-17-8
| CASNo2_Ref = {{cascite|correct|CAS}}
| CASNo2 = 130-40-5
| CASNo2_Comment = (sodium salt)
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1201794
| PubChem = 643976
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17621
| 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
| MeSHName = Flavin+mononucleotide
  }}
|Section2={{Chembox Properties
| Formula = C<sub>17</sub>H<sub>21</sub>N<sub>4</sub>O<sub>9</sub>P
| MolarMass = 456.344 g/mol
| Appearance = 
| Density = 
| MeltingPt = 195 °C
| BoilingPt = 
  }}
|Section3={{Chembox Hazards
| MainHazards = 
| FlashPt = 
| AutoignitionPt = 
  }}
}}
'''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.

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.

==Food additive==
Flavin mononucleotide is also used as an orange-red food colour additive, designated in Europe as [[E number]] E101a.

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.

==See also==
* [[Flavin adenine dinucleotide]]


==External links==
*[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]

{{Enzyme cofactors}}

{{二次利用|date=19 March 2024}}
[[Category:Flavins]]
[[Category:Food colorings]]
[[Category:Organophosphates]]
[[Category:Oxidoreductases]]
[[Category:Cofactors]]