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Flavin mononucleotide

Flavin mononucleotide

Other names	FMN
Identifiers
CAS number	146-17-8
PubChem	710
MeSH	Flavin+mononucleotide
SMILES	O=C(N3)C2=NC1=CC(C)=C(C)C=C1N(C[C@H] (O)[C@H](O)[C@@H](COP(O)(O)=O)O)C2=NC3=O
Properties
Molecular formula	C₁₇H₂₁N₄O₉P
Molar mass	456.344 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Flavin mononucleotide (FMN), or riboflavin-5′-phosphate, is derived from riboflavin (vitamin B₂) and functions as prosthetic group of various oxidoreductases including NADH dehydrogenase. During catalytic cycle, the reversible interconversion of oxidized (FMN), semiquinone (FMNH^•) and reduced (FMNH₂) forms occurs. FMN is a stronger oxidizing agent than NAD and is particularly useful because it can take part in both one and two electron transfers.

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It is the principal form in which riboflavin is found in cells and tissues. Energetically, it is more expensive to produce, but is more soluble than riboflavin.

Designated with E number E101a, it is used as a food dye and is likely derived from genetically modified organisms.

E106, a very closely related food dye, is riboflavin-5′-phosphate sodium salt, which consists mainly of the monosodium 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 jams, milk products and sweets and sugar products.

v • d • e Types of enzyme cofactors
Coenzymes	NAD⁺ - NADP⁺ - Coenzyme A - Tetrahydrofolic acid - Menaquinone - Ascorbic acid - Coenzyme F420 - Adenosine triphosphate - S-Adenosyl methionine - 3'-Phosphoadenosine-5'-phosphosulfate - Coenzyme Q - Tetrahydrobiopterin - Cytidine triphosphate - Glutathione - Coenzyme M - Coenzyme B - Methanofuran - Tetrahydromethanopterin
Prosthetic groups: Organic group	Flavin mononucleotide - Flavin adenine dinucleotide - Pyrroloquinoline quinone - Pyridoxal phosphate - Biotin - Methylcobalamin - Cobamamide - Thiamine pyrophosphate - Heme - Molybdopterin - Lipoic acid
Prosthetic groups: Metals	Calcium - Copper - Iron - Magnesium - Manganese - Nickel - Zinc