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, a reversible interconversion of the oxidized (FMN), semiquinone (FMNH•), and reduced (FMNH2) forms occurs in the various oxidoreductases. 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/C9H15N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,12,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,4+,6-/m0/s1 |
FNKQXYHWGSIFBK-RPDRRWSUSA-N |
[H][C@@]1(CNc2nc(N)[nH]c(=O)c2N1)[C@@H](O)[C@H](C)O |
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human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via 5,6,7,8-tetrahydrobiopterin )
cofactor
An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group).
coenzyme
A low-molecular-weight, non-protein organic compound participating in enzymatic reactions as dissociable acceptor or donor of chemical groups or electrons.
(via 5,6,7,8-tetrahydrobiopterin )
prosthetic group
A tightly bound, specific nonpolypeptide unit in a protein determining and involved in its biological activity.
(via 5,6,7,8-tetrahydrobiopterin )
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diagnostic agent
A substance administered to aid diagnosis of a disease.
nutraceutical
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
(via 5,6,7,8-tetrahydrobiopterin )
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View more via ChEBI Ontology
(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydropteridin-4(3H)-one
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sapropterin
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ChemIDplus
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sapropterina
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ChemIDplus
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sapropterinum
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ChemIDplus
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(−)-(6R)-2-amino-6-((1R,2S)-1,2-dihydroxypropyl)-5,6,7,8-tetrahydro-4(3H)-pteridinone
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ChemIDplus
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(6R)-L-erythro-5,6,7,8-tetrahydrobiopterin
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UniProt
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(6R)-L-erythro-tetrahydrobiopterin
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ChEBI
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2-Amino-6-(1,2-dihydroxypropyl)-5,6,7,8-tetrahydoro-4(1H)-pteridinone
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KEGG COMPOUND
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5,6,7,8-Tetrahydrobiopterin
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KEGG COMPOUND
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6R-5,6,7,8-tetrahydrobiopterin
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ChemIDplus
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6R-BH4
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ChEBI
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6R-L-5,6,7,8-tetrahydrobiopterin
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ChemIDplus
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R-THBP
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ChEBI
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tetrahydrobiopterin
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DrugBank
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2612
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DrugCentral
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C00018229
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KNApSAcK
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C00272
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KEGG COMPOUND
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CPD-14053
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MetaCyc
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D08505
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KEGG DRUG
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DB00360
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DrugBank
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EP191335
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Patent
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H4B
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PDBeChem
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HMDB0000787
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HMDB
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Sapropterin
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Wikipedia
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US4713454
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Patent
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View more database links |
17528-72-2
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CAS Registry Number
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KEGG COMPOUND
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27070-47-9
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CAS Registry Number
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ChemIDplus
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4699705
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Reaxys Registry Number
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Reaxys
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10333495
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SUBMITTER
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1297822
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Europe PMC
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16510994
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