| Flavin mononucleotide (FMN), or riboflavin-5′-phosphate, is a biomolecule produced from riboflavin (vitamin B2) by the enzyme riboflavin kinase and functions as the prosthetic group of various oxidoreductases, including NADH dehydrogenase, as well as a cofactor in biological blue-light photo receptors. During the catalytic cycle, various oxidoreductases induce reversible interconversions between the oxidized (FMN), semiquinone (FMNH•), and reduced (FMNH2) forms of the isoalloxazine core. FMN is a stronger oxidizing agent than 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 cells and tissues. It requires more energy to produce, but is more soluble than riboflavin. In cells, FMN occurs freely circulating but also in several 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. |
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| InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15) |
| QIVBCDIJIAJPQS-UHFFFAOYSA-N |
| NC(Cc1c[nH]c2ccccc12)C(O)=O |
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Daphnia magna
(NCBI:txid35525)
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See:
Mixtures of similarly acting compounds in Daphnia magna: From gene to metabolite and beyondTine Vandenbrouck, Oliver A.H. Jones, Nathalie Dom, Julian L. Griffin, Wim De CoenEnvironment International 36 (2010) 254-268
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Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
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View more via ChEBI Ontology
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2-amino-3-(1H-indol-3-yl)propanoic acid
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IUPAC
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alpha-Amino-beta-(3-indolyl)-propionic acid
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KEGG COMPOUND
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α-amino-β-3-indolepropionic acid
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ChEBI
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β-3-indolylalanine
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ChEBI
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Htrp
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IUPAC
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triptófano
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ChEBI
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Trp
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ChEBI
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Tryptophan
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KEGG COMPOUND
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tryptophane
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ChEBI
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W
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ChEBI
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4532
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Gmelin Registry Number
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Gmelin
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54-12-6
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CAS Registry Number
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NIST Chemistry WebBook
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54-12-6
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CAS Registry Number
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ChemIDplus
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86196
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Reaxys Registry Number
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Reaxys
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17439666
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PubMed citation
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Europe PMC
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22264337
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PubMed citation
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Europe PMC
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