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Identification
YMDB IDYMDB00085
NameFlavin Mononucleotide
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionFlavin Mononucleotide, also known as riboflavin 5'-phosphate or flanin, belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions. Flavin Mononucleotide is an extremely weak basic (essentially neutral) compound (based on its pKa). Flavin Mononucleotide exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • Flanin
  • Flavine mononucleotide
  • Flavol
  • FMN
  • Riboflavin
  • Riboflavin 5'-monophosphate
  • Riboflavin 5'-phosphate
  • Riboflavin Mononucleotide
  • Riboflavin monophosphate
  • Riboflavin phosphate
  • Riboflavin-5-phosphate
  • Riboflavin-5'-phosphate na
  • Riboflavine 5'-monophosphate
  • Riboflavine 5'-phosphate
  • Riboflavine dihydrogen phosphate
  • Riboflavine monophosphate
  • Riboflavine phosphate
  • Riboflavine-5'-phosphate
  • Vitamin B2 phosphate
  • Riboflavin 5'-(dihydrogen phosphate)
  • Riboflavin 5'-(dihydrogen phosphoric acid)
  • Riboflavin 5'-monophosphoric acid
  • Riboflavin 5'-phosphoric acid
  • Riboflavin monophosphoric acid
  • Riboflavin-5-phosphoric acid
  • Riboflavine dihydrogen phosphoric acid
  • 5'-monoPhosphate, riboflavin
  • 5'-Phosphate, riboflavin
  • Flavin mononucleotide sodium salt
  • Mononucleotide, riboflavin
  • Flavin mononucleotide monosodium salt
  • Flavin mononucleotide monosodium salt, dihydrate
  • Phosphate, sodium riboflavin
  • Riboflavin 5' phosphate
  • Riboflavin phosphate, sodium
  • Mononucleotide, flavin
  • Riboflavin 5' monophosphate
  • Flavin mononucleotide disodium salt
  • Sodium riboflavin phosphate
CAS number146-17-8
WeightAverage: 456.3438
Monoisotopic: 456.104614802
InChI KeyFVTCRASFADXXNN-SCRDCRAPSA-N
InChIInChI=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
IUPAC Name{[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}phosphonic acid
Traditional IUPAC Nameriboflavin 5'-phosphate
Chemical FormulaC17H21N4O9P
SMILES[H]O[C@]([H])(C([H])([H])OP(=O)(O[H])O[H])[C@@]([H])(O[H])[C@@]([H])(O[H])C([H])([H])N1C2=NC(=O)N([H])C(=O)C2=NC2=C1C([H])=C(C(=C2[H])C([H])([H])[H])C([H])([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassFlavin nucleotides
Sub ClassNot Available
Direct ParentFlavin nucleotides
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting point290 °C
Experimental Properties
PropertyValueReference
Water Solubility92 mg/mL [HMP experimental]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.67 g/LALOGPS
logP-0.78ALOGPS
logP-1ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)1.49ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area201.58 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity107.14 m³·mol⁻¹ChemAxon
Polarizability42.19 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • extracellular
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Oxidative phosphorylationPW002461 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyrimidine metabolismPW002469 ThumbThumb?image type=greyscaleThumb?image type=simple
Riboflavin metabolismPW002443 ThumbThumb?image type=greyscaleThumb?image type=simple
Sulfur metabolismPW002483 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Oxidative phosphorylationec00190 Map00190
Pyrimidine metabolismec00240 Map00240
Riboflavin metabolismec00740 Map00740
Sulfur metabolismec00920 Map00920
SMPDB Reactions
Adenosine triphosphate + RiboflavinADP + Flavin Mononucleotide
Adenosine triphosphate + Flavin MononucleotidePyrophosphate + FAD
alkylsulfonate + FMNH2 + oxygen → Betaine aldehyde + Sulfite + Flavin Mononucleotide + water + hydron
KEGG Reactions
Flavin Mononucleotide + water Riboflavin + phosphate
Flavin Mononucleotide + Adenosine triphosphate + hydronPyrophosphate + FAD
NADH + Flavin Mononucleotide + hydronNAD + FMNH2
Flavin Mononucleotide + NADPH + hydronNADP + FMNH2
Fumaric acid + FMNH2Flavin Mononucleotide + Succinic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Wu, M., Repetto, B., Glerum, D. M., Tzagoloff, A. (1995). "Cloning and characterization of FAD1, the structural gene for flavin adenine dinucleotide synthetase of Saccharomyces cerevisiae." Mol Cell Biol 15:264-271.7799934
  • KEARNEY, E. B., ENGLARD, S. (1951). "The enzymatic phosphorylation of riboflavin." J Biol Chem 193:821-834.14907770
  • TSUBOI, K. K., WIENER, G., HUDSON, P. B. (1957). "Acid phosphatase. VII. Yeast phosphomonoesterase; isolation procedure and stability characteristics." J Biol Chem 224:621-635.13405892
  • Liger, D., Graille, M., Zhou, C. Z., Leulliot, N., Quevillon-Cheruel, S., Blondeau, K., Janin, J., van Tilbeurgh, H. (2004). "Crystal structure and functional characterization of yeast YLR011wp, an enzyme with NAD(P)H-FMN and ferric iron reductase activities." J Biol Chem 279:34890-34897.15184374
Synthesis Reference:Ono, Shigeru; Hirano, Hiroko; Sato, Yoshiyuki. Formation of flavin adenine dinucleotide and flavin mononucleotide by lens homogenate. Experimental Eye Research (1982), 34(2), 297-301.
External Links:
ResourceLink
CHEBI ID17621
HMDB IDHMDB01520
Pubchem Compound ID710
Kegg IDC00061
ChemSpider ID24608082
FOODB IDFDB001984
WikipediaFlavin_mononucleotide
BioCyc IDFMN

Enzymes

General function:
Involved in nitronate monooxygenase activity
Specific function:
Catalyzes the oxidation of alkyl nitronates to produce the corresponding carbonyl compounds and nitrites
Gene Name:
Not Available
Uniprot ID:
P47177
Molecular weight:
45142.60156
Reactions
Ethylnitronate + O(2) + FMNH(2) → acetaldehyde + nitrite + FMN + H(2)O.
General function:
Involved in pyridoxamine-phosphate oxidase activity
Specific function:
Catalyzes the oxidation of either pyridoxine 5'- phosphate (PNP) or pyridoxamine 5'-phosphate (PMP) into pyridoxal 5'-phosphate (PLP)
Gene Name:
PDX3
Uniprot ID:
P38075
Molecular weight:
26908.0
Reactions
Pyridoxamine 5'-phosphate + H(2)O + O(2) → pyridoxal 5'-phosphate + NH(3) + H(2)O(2).
Pyridoxine 5'-phosphate + O(2) → pyridoxal 5'-phosphate + H(2)O(2).
General function:
Involved in electron carrier activity
Specific function:
Could be a fumarate reductase
Gene Name:
Not Available
Uniprot ID:
P32614
Molecular weight:
50843.69922
Reactions
Succinate + NAD(+) → fumarate + NADH.
General function:
Involved in electron carrier activity
Specific function:
Could be a fumarate reductase
Gene Name:
OSM1
Uniprot ID:
P21375
Molecular weight:
55064.80078
Reactions
General function:
Involved in acid phosphatase activity
Specific function:
A phosphate monoester + H(2)O = an alcohol + phosphate
Gene Name:
PHO11
Uniprot ID:
P35842
Molecular weight:
52757.39844
Reactions
A phosphate monoester + H(2)O → an alcohol + phosphate.
General function:
Involved in riboflavin kinase activity
Specific function:
Catalyzes the phosphorylation of riboflavin (vitamin B2) to form flavin mononucleotide (FMN) coenzyme
Gene Name:
FMN1
Uniprot ID:
Q03778
Molecular weight:
24536.90039
Reactions
ATP + riboflavin → ADP + FMN.
General function:
Involved in acid phosphatase activity
Specific function:
Partially mediates extracellular nucleotide derived phosphate hydrolysis along with NPP1 and NPP2
Gene Name:
PHO5
Uniprot ID:
P00635
Molecular weight:
52858.10156
Reactions
A phosphate monoester + H(2)O → an alcohol + phosphate.
General function:
Involved in FMN reductase activity
Specific function:
Has several reductase activities that are NAD(P)H- dependent and involve FMN as a cofactor, ferricyanide being the best substrate for reduction. May be involved in ferric iron assimilation
Gene Name:
LOT6
Uniprot ID:
Q07923
Molecular weight:
21280.40039
Reactions
FMNH(2) + NAD(P)(+) → FMN + NAD(P)H.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the adenylation of flavin mononucleotide (FMN) to form flavin adenine dinucleotide (FAD) coenzyme
Gene Name:
FAD1
Uniprot ID:
P38913
Molecular weight:
35545.80078
Reactions
ATP + FMN → diphosphate + FAD.

Transporters

General function:
Involved in binding
Specific function:
Transport of FAD from the cytosol to the mitochondrial matrix
Gene Name:
FLX1
Uniprot ID:
P40464
Molecular weight:
34408.89844