Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000408
Name: Flavin Mononucleotide
Description:FMN is coenzyme for a number of oxidative enzymes including NADH dehydrogenase. It is the principal form in which riboflavin is found in cells.
  • Flanin
  • Flavin mononucleotide
  • Flavine mononucleotide
  • Flavol
  • FMN
  • Riboflavin
  • Riboflavin 5'-monophosphate
  • Riboflavin 5'-monophosphoric acid
  • Riboflavin 5'-phosphate
  • Riboflavin 5'-phosphoric acid
  • Riboflavin Mononucleotide
  • Riboflavin monophosphate
  • Riboflavin monophosphoric acid
  • Riboflavin phosphate
  • Riboflavin phosphoric acid
  • Riboflavin-5'-phosphate
  • Riboflavin-5'-phosphate na
  • Riboflavin-5'-phosphoric acid
  • Riboflavin-5'-phosphoric acid na
  • Riboflavin-5-phosphate
  • Riboflavin-5-phosphoric acid
  • Riboflavine 5'-monophosphate
  • Riboflavine 5'-monophosphoric acid
  • Riboflavine 5'-phosphate
  • Riboflavine 5'-phosphoric acid
  • Riboflavine dihydrogen phosphate
  • Riboflavine dihydrogen phosphoric acid
  • Riboflavine monophosphate
  • Riboflavine monophosphoric acid
  • Riboflavine phosphate
  • Riboflavine phosphoric acid
  • Riboflavine-5'-phosphate
  • Riboflavine-5'-phosphoric acid
  • Vitamin B2 phosphate
  • Vitamin b2 phosphoric acid
Chemical Formula: C17H21N4O9P
Average Molecular Weight: 456.3438
Monoisotopic Molecular Weight: 456.104614802
CAS number: 146-17-8
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 Name: riboflavin 5'-phosphate
Chemical Taxonomy
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Flavin nucleotides
Sub ClassNot Available
Direct Parent Flavin nucleotides
Alternative Parents
  • Flavin nucleotide
  • Flavin
  • Isoalloxazine
  • Quinoxaline
  • Pteridine
  • Monoalkyl phosphate
  • Pyrimidone
  • Benzenoid
  • Alkyl phosphate
  • Pyrimidine
  • Pyrazine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Heteroaromatic compound
  • Vinylogous amide
  • Secondary alcohol
  • Polyol
  • Lactam
  • 1,2-diol
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Melting point: 290 °C
Experimental Properties:
Water Solubility:92 mg/mL [HMP experimental]PhysProp
Predicted Properties
Water Solubility0.668 mg/mLALOGPS
pKa (Strongest Acidic)1.57ChemAxon
pKa (Strongest Basic)0.68ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area201.58 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity107.14 m3·mol-1ChemAxon
Polarizability42.19 Å3ChemAxon
Number of Rings3ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Flavin Mononucleotide + Hydrogen ion + NADH > FMNH + NAD
Flavin Mononucleotide + Hydrogen ion + NADPH <> FMNH + NADP
Adenosine triphosphate + Riboflavin <> ADP + Flavin Mononucleotide + Hydrogen ion
Adenosine triphosphate + Flavin Mononucleotide + Hydrogen ion > FAD + Pyrophosphate
FMNH + Oxygen + Sulfoacetate > Flavin Mononucleotide + Glyoxylic acid + Hydrogen ion + Water + Sulfite
FMNH + Isethionic acid + Oxygen > Flavin Mononucleotide + Glycolaldehyde + Hydrogen ion + Water + Sulfite
FMNH + Methanesulfonate + Oxygen > Formaldehyde + Flavin Mononucleotide + Hydrogen ion + Water + Sulfite
Butanesulfonate + FMNH + Oxygen > Butanal + Flavin Mononucleotide + Hydrogen ion + Water + Sulfite
Ethanesulfonate + FMNH + Oxygen > Acetaldehyde + Flavin Mononucleotide + Hydrogen ion + Water + Sulfite
2 Ferroxamine + FMNH >2 Iron +2 ferroxamine minus Fe(3) + Flavin Mononucleotide +2 Hydrogen ion
Adenosine triphosphate + Flavin Mononucleotide <> Pyrophosphate + FAD
Adenosine triphosphate + Riboflavin <> ADP + Flavin Mononucleotide
Uracil + FMNH + Oxygen <> Ureidoacrylate peracid + Flavin Mononucleotide
NAD(P)<sup>+</sup> + FMNH <> NAD(P)H + Flavin Mononucleotide + Hydrogen ion
Thymine + Oxygen + FMNH > (<i>Z</i>)-2-methylureidoacrylate peracid + Flavin Mononucleotide + Hydrogen ion
an alkanesulfonate + Oxygen + FMNH > an aldehyde + Sulfite + Water + Flavin Mononucleotide + Hydrogen ion
Flavin Mononucleotide + Water > Riboflavin + Phosphate
Uracil + Oxygen + FMNH > Hydrogen ion + Ureidoacrylate peracid + Flavin Mononucleotide

Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0002-9000200000-bc07cc2b3950f70a9db3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
  • Ahmed F, Khan MR, Akhtaruzzaman M, Karim R, Marks GC, Banu CP, Nahar B, Williams G: Efficacy of twice-weekly multiple micronutrient supplementation for improving the hemoglobin and micronutrient status of anemic adolescent schoolgirls in Bangladesh. Am J Clin Nutr. 2005 Oct;82(4):829-35. Pubmed: 16210713
  • Ajayi OA: Bioavailability of riboflavin from fortified palm juice. Plant Foods Hum Nutr. 1989 Dec;39(4):375-80. Pubmed: 2631092
  • Baeckert PA, Greene HL, Fritz I, Oelberg DG, Adcock EW: Vitamin concentrations in very low birth weight infants given vitamins intravenously in a lipid emulsion: measurement of vitamins A, D, and E and riboflavin. J Pediatr. 1988 Dec;113(6):1057-65. Pubmed: 3142982
  • Bamji MS, Bhaskaram P, Jacob CM: Urinary riboflavin excretion and erythrocyte glutathione reductase activity in preschool children suffering from upper respiratory infections and measles. Ann Nutr Metab. 1987;31(3):191-6. Pubmed: 3592624
  • Bates CJ, Prentice AM, Paul AA, Prentice A, Sutcliffe BA, Whitehead RG: Riboflavin status in infants born in rural Gambia, and the effect of a weaning food supplement. Trans R Soc Trop Med Hyg. 1982;76(2):253-8. Pubmed: 7101408
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Blajchman MA, Goldman M, Baeza F: Improving the bacteriological safety of platelet transfusions. Transfus Med Rev. 2004 Jan;18(1):11-24. Pubmed: 14689374
  • Booth CK, Clark T, Fenn A: Folic acid, riboflavin, thiamine, and vitamin B-6 status of a group of first-time blood donors. Am J Clin Nutr. 1998 Nov;68(5):1075-80. Pubmed: 9808225
  • Brun TA, Chen J, Campbell TC, Boreham J, Feng Z, Parpia B, Shen TF, Li M: Urinary riboflavin excretion after a load test in rural China as a measure of possible riboflavin deficiency. Eur J Clin Nutr. 1990 Mar;44(3):195-206. Pubmed: 2369885
  • Buzina R, Grgic Z, Jusic M, Sapunar J, Milanovic N, Brubacher G: Nutritional status and physical working capacity. Hum Nutr Clin Nutr. 1982;36(6):429-38. Pubmed: 7161138
  • Cikot RJ, Steegers-Theunissen RP, Thomas CM, de Boo TM, Merkus HM, Steegers EA: Longitudinal vitamin and homocysteine levels in normal pregnancy. Br J Nutr. 2001 Jan;85(1):49-58. Pubmed: 11227033
  • Edelbroek PM, Linssen AC, Zitman FG, Rooymans HG, de Wolff FA: Analgesic and antidepressive effects of low-dose amitriptyline in relation to its metabolism in patients with chronic pain. Clin Pharmacol Ther. 1986 Feb;39(2):156-62. Pubmed: 3510800
  • Hardwick CC, Herivel TR, Hernandez SC, Ruane PH, Goodrich RP: Separation, identification and quantification of riboflavin and its photoproducts in blood products using high-performance liquid chromatography with fluorescence detection: a method to support pathogen reduction technology. Photochem Photobiol. 2004 Nov-Dec;80(3):609-15. Pubmed: 15382964
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Lartey A, Manu A, Brown KH, Dewey KG: Predictors of micronutrient status among six- to twelve-month-old breast-fed Ghanaian infants. J Nutr. 2000 Feb;130(2):199-207. Pubmed: 10720170
  • Mathew JL, Kabi BC, Rath B: Anti-oxidant vitamins and steroid responsive nephrotic syndrome in Indian children. J Paediatr Child Health. 2002 Oct;38(5):450-37. Pubmed: 12354259
  • Mikalunas V, Fitzgerald K, Rubin H, McCarthy R, Craig RM: Abnormal vitamin levels in patients receiving home total parenteral nutrition. J Clin Gastroenterol. 2001 Nov-Dec;33(5):393-6. Pubmed: 11606856
  • Ortega RM, Quintas ME, Martinez RM, Andres P, Lopez-Sobaler AM, Requejo AM: Riboflavin levels in maternal milk: the influence of vitamin B2 status during the third trimester of pregnancy. J Am Coll Nutr. 1999 Aug;18(4):324-9. Pubmed: 12038475
  • Rao PN, Levine E, Myers MO, Prakash V, Watson J, Stolier A, Kopicko JJ, Kissinger P, Raj SG, Raj MH: Elevation of serum riboflavin carrier protein in breast cancer. Cancer Epidemiol Biomarkers Prev. 1999 Nov;8(11):985-90. Pubmed: 10566553
  • Schorah CJ, Wild J, Hartley R, Sheppard S, Smithells RW: The effect of periconceptional supplementation on blood vitamin concentrations in women at recurrence risk for neural tube defect. Br J Nutr. 1983 Mar;49(2):203-11. Pubmed: 6830748
  • Thurnham DI, Zheng SF, Munoz N, Crespi M, Grassi A, Hambidge KM, Chai TF: Comparison of riboflavin, vitamin A, and zinc status of Chinese populations at high and low risk for esophageal cancer. Nutr Cancer. 1985;7(3):131-43. Pubmed: 3878498
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Zhou X, Huang C, Hong J, Yao S: [Nested case-control study on riboflavin levels in blood and urine and the risk of lung cancer] Wei Sheng Yan Jiu. 2003 Nov;32(6):597-8, 601. Pubmed: 14963913
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.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
Pubchem Compound ID710
Kegg IDC00061
ChemSpider ID559060
Ligand ExpoFMN