Record Information
Version2.0
Creation Date2012-05-31 13:53:53 -0600
Update Date2015-09-13 12:56:11 -0600
Secondary Accession Numbers
  • ECMDB01520
Identification
Name:Flavin Mononucleotide
DescriptionFMN is coenzyme for a number of oxidative enzymes including NADH dehydrogenase. It is the principal form in which riboflavin is found in cells.
Structure
Thumb
Synonyms:
  • 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
Weight:Average: 456.3438
Monoisotopic: 456.104614802
InChI Key:FVTCRASFADXXNN-SCRDCRAPSA-N
InChI:InChI=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
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
SMILES:CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(O)=O)C1=NC(=O)NC(=O)C1=N2
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 Parents
Substituents
  • Flavin nucleotide
  • Flavin
  • Isoalloxazine
  • Diazanaphthalene
  • Pteridine
  • Quinoxaline
  • Monoalkyl phosphate
  • Pyrimidone
  • Pyrazine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Benzenoid
  • Alkyl phosphate
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Secondary alcohol
  • Lactam
  • Azacycle
  • Polyol
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-3
Melting point:290 °C
Experimental Properties:
PropertyValueSource
Water Solubility:92 mg/mL [HMP experimental]PhysProp
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:Cytoplasm
Reactions:
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
Flavin Mononucleotide + Water <> Riboflavin + Phosphate
Adenosine triphosphate + Riboflavin <> ADP + Flavin Mononucleotide
FMNH + NAD <> Flavin Mononucleotide + NADH + Hydrogen ion
FMNH + NADP <> Flavin Mononucleotide + NADPH + Hydrogen ion
Uracil + FMNH + Oxygen <> Ureidoacrylate peracid + Flavin Mononucleotide
NAD(P)<sup>+</sup> + FMNH <> NAD(P)H + Flavin Mononucleotide + Hydrogen ion
Riboflavin + Adenosine triphosphate > Hydrogen ion + Flavin Mononucleotide + ADP
FMNH + NADP < Flavin Mononucleotide + NADPH + 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
Butanesulfonate + Oxygen + FMNH > Butanal + Sulfite + Water + Flavin Mononucleotide + Hydrogen ion
Adenosine triphosphate + Riboflavin > ADP + Flavin Mononucleotide
Adenosine triphosphate + Flavin Mononucleotide > Pyrophosphate + FAD
Uracil + FMNH(2) + Oxygen > Ureidoacrylate peracid + Flavin Mononucleotide + Water
Thymine + FMNH(2) + Oxygen > (Z)-2-Methyl-ureidoacrylate peracid + Flavin Mononucleotide + Water
FMNH(2) + NAD > Flavin Mononucleotide + NADH
An alkanesufonate (R-CH(2)-SO(3)H) + FMNH(2) + Oxygen > an aldehyde (R-CHO) + Flavin Mononucleotide + Sulfite + Water
FMNH(2) + NADP > Flavin Mononucleotide + NADPH
Alkanesulfonate + FMNH + Oxygen <> Aldehyde + Flavin Mononucleotide + Sulfite + Water
Uracil + FMNH + Oxygen + Thymine <> Ureidoacrylate peracid + Flavin Mononucleotide + (Z)-2-Methyl-ureidoacrylate peracid
alkylsulfonate + FMNH2 + Oxygen > Betaine aldehyde + Sulfite + Flavin Mononucleotide + Water +2 Hydrogen ion + Sulfite
Butanesulfonate + Oxygen + FMNH2 > Hydrogen ion + Water + Sulfite + Flavin Mononucleotide + Betaine aldehyde + Sulfite
Oxygen + FMNH2 + 3-(N-morpholino)propanesulfonate > Sulfite + Water + Hydrogen ion + Flavin Mononucleotide + Betaine aldehyde + Sulfite
ethanesulfonate + Oxygen + FMNH2 > Hydrogen ion + Water + Flavin Mononucleotide + Sulfite + Betaine aldehyde + Sulfite
isethionate + Oxygen + FMNH2 > Betaine aldehyde + Flavin Mononucleotide + Hydrogen ion + Water + Sulfite + Sulfite
Oxygen + methanesulfonate + FMNH2 + Methanesulfonate > Hydrogen ion + Water + Flavin Mononucleotide + Sulfite + Betaine aldehyde + Sulfite
Riboflavin + Adenosine triphosphate + Riboflavin > Adenosine diphosphate + Hydrogen ion + Flavin Mononucleotide + ADP
Flavin Mononucleotide + Hydrogen ion + Adenosine triphosphate > Pyrophosphate + FAD
Uracil + FMNH2 + Oxygen > Ureidoacrylate peracid + Flavin Mononucleotide + Hydrogen ion + Peroxyaminoacrylate
Alkanesulfonate + FMNH + Oxygen <> Aldehyde + Flavin Mononucleotide + Sulfite + Water
Flavin Mononucleotide + Hydrogen ion + NADH > FMNH + NAD
Adenosine triphosphate + Riboflavin <> ADP + Flavin Mononucleotide + Hydrogen ion
Flavin Mononucleotide + Hydrogen ion + NADH > FMNH + NAD
More...

SMPDB Pathways:
Flavin biosynthesisPW001971 ThumbThumb?image type=greyscaleThumb?image type=simple
Oxidative phosphorylationPW000919 ThumbThumb?image type=greyscaleThumb?image type=simple
Porphyrin metabolismPW000936 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyrimidine metabolismPW000942 ThumbThumb?image type=greyscaleThumb?image type=simple
Sulfur metabolismPW000922 ThumbThumb?image type=greyscaleThumb?image type=simple
Uracil degradation IIIPW002026 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (butanesulfonate)PW000923 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (ethanesulfonate)PW000925 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (isethionate)PW000926 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (methanesulfonate)PW000927 ThumbThumb?image type=greyscaleThumb?image type=simple
sulfur metabolism (propanesulfonate)PW000924 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
53± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
3± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
53± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007d-6931400000-cad44822b1dfefb25732View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0592-6901126000-2ec87848003ebe8e438dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0002-9000200000-bc07cc2b3950f70a9db3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-9000200000-bc07cc2b3950f70a9db3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-0a4i-0000900000-6e5ca4123f461d0e208dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 16V, positivesplash10-0a4i-0000900000-f1a0fdd1328522519b91View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 24V, positivesplash10-0a4r-2028900000-899e2dcd3bfb217b5766View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 32V, positivesplash10-052f-7289200000-ebb8d8c94ce8d3a5fb86View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 41V, positivesplash10-0006-9782000000-786258c7a5f6feda99e2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 53V, positivesplash10-00dj-4910000000-e978502607653ec51659View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 66V, positivesplash10-006t-3900000000-cd1a65145bae541f2919View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 78V, positivesplash10-0002-3900000000-9be5fed1e1eb535085f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 91V, positivesplash10-0fr2-4900000000-d58071130f19cd6bc833View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 107V, positivesplash10-0ktb-7900000000-c3b2300acb88daf0d14fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 124V, positivesplash10-052b-9700000000-e2c1ef96f28d92a23db4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 149V, positivesplash10-0kbb-9300000000-91cbf6b5c1f4e37d016aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, positivesplash10-000i-0000900000-b60cf8984dd78397651eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, positivesplash10-00kf-0096000000-9690dc0d4d8c890d6900View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, positivesplash10-0fka-0960000000-6d860483a67d4bd784abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, positivesplash10-0002-0019000000-60cf80bbeab6e68f82d5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 31V, positivesplash10-004i-0009000000-eea6861c71c50e5ce846View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0134900000-c3ae39f771e510a09ae6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2391100000-1b8212d4ae35c1e1f1f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1090000000-8948e075f379e327a852View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03kc-9251600000-e0759dcc125b6178b7f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9120000000-656647e95148b2404066View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4778caa348b1cda5e72cView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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:
ResourceLink
CHEBI ID17621
HMDB IDHMDB01520
Pubchem Compound ID710
Kegg IDC00061
ChemSpider ID559060
WikipediaFMN
BioCyc IDFMN
EcoCyc IDFMN
Ligand ExpoFMN

Enzymes

General function:
Involved in acid phosphatase activity
Specific function:
A phosphate monoester + H(2)O = an alcohol + phosphate
Gene Name:
appA
Uniprot ID:
P07102
Molecular weight:
47056
Reactions
A phosphate monoester + H(2)O = an alcohol + phosphate.
Myo-inositol hexakisphosphate + H(2)O = 1D-myo-inositol 1,2,3,5,6-pentakisphosphate + phosphate.
General function:
Involved in acid phosphatase activity
Specific function:
Dephosphorylates several organic phosphomonoesters and catalyzes the transfer of low-energy phosphate groups from phosphomonoesters to hydroxyl groups of various organic compounds. Preferentially acts on aryl phosphoesters. Might function as a broad-spectrum dephosphorylating enzyme able to scavenge both 3'- and 5'-nucleotides and also additional organic phosphomonoesters
Gene Name:
aphA
Uniprot ID:
P0AE22
Molecular weight:
26103
Reactions
A phosphate monoester + H(2)O = an alcohol + phosphate.
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the reduction of soluble flavins by reduced pyridine nucleotides. Seems to reduces the complexed Fe(3+) iron of siderophores to Fe(2+), thus releasing it from the chelator
Gene Name:
fre
Uniprot ID:
P0AEN1
Molecular weight:
26242
Reactions
Reduced riboflavin + NAD(P)(+) = riboflavin + NAD(P)H.
2 cob(II)alamin + NAD(+) = 2 aquacob(III)alamin + NADH.
General function:
Involved in FMN adenylyltransferase activity
Specific function:
ATP + riboflavin = ADP + FMN
Gene Name:
ribF
Uniprot ID:
P0AG40
Molecular weight:
34734
Reactions
ATP + riboflavin = ADP + FMN.
ATP + FMN = diphosphate + FAD.
General function:
Involved in sulfite reductase (NADPH) activity
Specific function:
Component of the sulfite reductase complex that catalyzes the 6-electron reduction of sulfite to sulfide. This is one of several activities required for the biosynthesis of L- cysteine from sulfate
Gene Name:
cysI
Uniprot ID:
P17846
Molecular weight:
63998
Reactions
H(2)S + 3 NADP(+) + 3 H(2)O = sulfite + 3 NADPH.
General function:
Involved in sulfite reductase (NADPH) activity
Specific function:
Component of the sulfite reductase complex that catalyzes the 6-electron reduction of sulfite to sulfide. This is one of several activities required for the biosynthesis of L- cysteine from sulfate. The flavoprotein component catalyzes the electron flow from NADPH -> FAD -> FMN to the hemoprotein component
Gene Name:
cysJ
Uniprot ID:
P38038
Molecular weight:
66269
Reactions
H(2)S + 3 NADP(+) + 3 H(2)O = sulfite + 3 NADPH.
General function:
Involved in 2 iron, 2 sulfur cluster binding
Specific function:
Involved in the reduction of ferric iron in cytoplasmic ferrioxamine B
Gene Name:
fhuF
Uniprot ID:
P39405
Molecular weight:
30113
General function:
Involved in catalytic activity
Specific function:
Catalyzes the dephosphorylation of the artificial chromogenic substrate p-nitrophenyl phosphate (pNPP) and of the natural substrates FMN and beta-glucose 1-phosphate
Gene Name:
ybjI
Uniprot ID:
P75809
Molecular weight:
30196
General function:
Involved in FMN reductase activity
Specific function:
Catalyzes an NAD(P)H-dependent reduction of FMN, but is also able to reduce FAD or riboflavin
Gene Name:
ssuE
Uniprot ID:
P80644
Molecular weight:
21253
Reactions
FMNH(2) + NADP(+) = FMN + NADPH.
General function:
Involved in alkanesulfonate monooxygenase activity
Specific function:
Involved in desulfonation of aliphatic sulfonates. Catalyzes the conversion of pentanesulfonic acid to sulfite and pentaldehyde and is able to desulfonate a wide range of sulfonated substrates including C-2 to C-10 unsubstituted linear alkanesulfonates, substituted ethanesulfonic acids and sulfonated buffers
Gene Name:
ssuD
Uniprot ID:
P80645
Molecular weight:
41736
Reactions
An alkanesufonate (R-CH(2)-SO(3)H) + FMNH(2) + O(2) = an aldehyde (R-CHO) + FMN + sulfite + H(2)O.
General function:
Involved in FMN binding
Specific function:
Makes part of the rut operon, which is required for the utilization of pyrimidines as sole nitrogen source
Gene Name:
rutF
Uniprot ID:
P75893
Molecular weight:
17749
Reactions
FMNH(2) + NAD(+) = FMN + NADH.
General function:
Involved in oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen
Specific function:
Part of the rut operon, which is required for the utilization of pyrimidines as sole nitrogen source
Gene Name:
rutA
Uniprot ID:
P75898
Molecular weight:
42219
Reactions
Uracil + FMNH(2) + O(2) = (Z)-3-ureidoacrylate peracid + FMN + H(2)O.
Thymine + FMNH(2) + O(2) = (Z)-2-methylureidoacrylate peracid + FMN + H(2)O.