Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-03-25 20:36:55 UTC
HMDB IDHMDB01520
Secondary Accession NumbersNone
Metabolite Identification
Common NameFlavin Mononucleotide
DescriptionFlavin mononucleotide (FMN), or riboflavin-5′-phosphate, is a biomolecule produced from riboflavin (vitamin B2) by the enzyme riboflavin kinase and functions as prosthetic group of various oxidoreductases including NADH dehydrogenase as well as cofactor in biological blue-light photo receptors. During the catalytic cycle, the reversible interconversion of 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. Flavin mononucleotide is also used as an orange-red food colour additive. It is the principal form in which riboflavin is found in cells and tissues.
Structure
Thumb
Synonyms
  1. Flanin
  2. Flavine mononucleotide
  3. Flavol
  4. FMN
  5. Riboflavin
  6. Riboflavin 5'-monophosphate
  7. Riboflavin 5'-phosphate
  8. Riboflavin Mononucleotide
  9. Riboflavin monophosphate
  10. Riboflavin phosphate
  11. Riboflavin-5'-phosphate na
  12. Riboflavin-5-phosphate
  13. Riboflavine 5'-monophosphate
  14. Riboflavine 5'-phosphate
  15. Riboflavine dihydrogen phosphate
  16. Riboflavine monophosphate
  17. Riboflavine phosphate
  18. Riboflavine-5'-phosphate
  19. Vitamin B2 phosphate
Chemical FormulaC17H21N4O9P
Average Molecular Weight456.3438
Monoisotopic Molecular Weight456.104614802
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[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-3H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxyphosphonic acid
CAS Registry Number146-17-8
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
InChI Identifier
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
InChI KeyFVTCRASFADXXNN-SCRDCRAPSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassPteridines and Derivatives
Sub ClassAlloxazines and Isoalloxazines
Other Descriptors
  • Organic Compounds
  • Pteridines and Derivatives
  • flavin mononucleotide(ChEBI)
Substituents
  • 1,2 Diol
  • Monosaccharide Phosphate
  • Organic Hypophosphite
  • Organic Phosphite
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Pyrazine
  • Pyrimidine
  • Pyrimidone
  • Quinoxaline
  • Saccharide
  • Secondary Alcohol
  • Toluene
Direct ParentFlavins
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Riboflavin metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point290 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility92 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility0.67 g/LALOGPS
logP-0.78ALOGPS
logP-1ChemAxon
logS-2.8ALOGPS
pKa (strongest acidic)1.57ChemAxon
pKa (strongest basic)0.68ChemAxon
physiological charge-3ChemAxon
hydrogen acceptor count11ChemAxon
hydrogen donor count6ChemAxon
polar surface area201.58ChemAxon
rotatable bond count7ChemAxon
refractivity107.14ChemAxon
polarizability42.19ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Erythrocyte
  • Eye Lens
  • Muscle
  • Platelet
Pathways
NameSMPDB LinkKEGG Link
Riboflavin MetabolismSMP00070map00740
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.0084 (0.0035-0.013) uMAdult (>18 years old)FemaleNormal
BloodDetected and Quantified0.016 +/- 0.009 uMAdolescent (13-18 years old)FemaleNormal
BloodDetected and Quantified0.0075 (0.004-0.011) uMAdult (>18 years old)BothNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.013 +/- 0.006 uMChildren (1-13 year old)BothSeverely malnourished children
BloodDetected and Quantified0.012 +/- 0.006 uMAdolescent (13-18 years old)FemaleAnorexia nervosa
Associated Disorders and Diseases
Disease References
Anorexia nervosa
  • Capo-chichi CD, Gueant JL, Lefebvre E, Bennani N, Lorentz E, Vidailhet C, Vidailhet M: Riboflavin and riboflavin-derived cofactors in adolescent girls with anorexia nervosa. Am J Clin Nutr. 1999 Apr;69(4):672-8. Pubmed: 10197568
Associated OMIM IDs
DrugBank IDDB03247
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001984
KNApSAcK IDC00019686
Chemspider ID559060
KEGG Compound IDC00061
BioCyc IDFMN
BiGG ID33703
Wikipedia LinkFMN
NuGOwiki LinkHMDB01520
Metagene LinkHMDB01520
METLIN ID6295
PubChem Compound643976
PDB IDFMN
ChEBI ID17621
References
Synthesis ReferenceOno, 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)Not Available
General References
  1. 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
  2. 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
  3. 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
  4. 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
  5. 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
  6. Ajayi OA: Bioavailability of riboflavin from fortified palm juice. Plant Foods Hum Nutr. 1989 Dec;39(4):375-80. Pubmed: 2631092
  7. 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
  8. 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
  9. 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
  10. 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
  11. 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
  12. 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
  13. 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
  14. 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
  15. 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
  16. 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
  17. Blajchman MA, Goldman M, Baeza F: Improving the bacteriological safety of platelet transfusions. Transfus Med Rev. 2004 Jan;18(1):11-24. Pubmed: 14689374
  18. 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
  19. 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
  20. 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

Enzymes

Gene Name:
ACP2
Uniprot ID:
P11117
Reactions
Flavin Mononucleotide + Water unknown Riboflavin + Phosphoric aciddetails
Gene Name:
ACP1
Uniprot ID:
P24666
Reactions
Flavin Mononucleotide + Water unknown Riboflavin + Phosphoric aciddetails
Gene Name:
ACP5
Uniprot ID:
P13686
Reactions
Flavin Mononucleotide + Water unknown Riboflavin + Phosphoric aciddetails
Gene Name:
ACPP
Uniprot ID:
P15309
Reactions
Flavin Mononucleotide + Water unknown Riboflavin + Phosphoric aciddetails
Gene Name:
ENPP1
Uniprot ID:
P22413
Reactions
FAD + Water unknown Adenosine monophosphate + Flavin Mononucleotidedetails
Gene Name:
SC5DL
Uniprot ID:
O75845
Gene Name:
POR
Uniprot ID:
P16435
Gene Name:
ENPP3
Uniprot ID:
O14638
Reactions
FAD + Water unknown Adenosine monophosphate + Flavin Mononucleotidedetails
Gene Name:
MTRR
Uniprot ID:
Q9UBK8
Gene Name:
PNPO
Uniprot ID:
Q9NVS9
Gene Name:
BLVRB
Uniprot ID:
P30043
Gene Name:
HAO1
Uniprot ID:
Q9UJM8
Gene Name:
HAO2
Uniprot ID:
Q9NYQ3
Gene Name:
SARDH
Uniprot ID:
Q9UL12
Gene Name:
NOS2
Uniprot ID:
P35228
Gene Name:
NOS1
Uniprot ID:
P29475
Gene Name:
NOS3
Uniprot ID:
P29474
Gene Name:
RFK
Uniprot ID:
Q969G6
Reactions
Adenosine triphosphate + Riboflavin unknown ADP + Flavin Mononucleotidedetails
Gene Name:
RPS6KA4
Uniprot ID:
O75676
Gene Name:
SGK1
Uniprot ID:
O00141
Gene Name:
ACP6
Uniprot ID:
Q9NPH0
Reactions
Flavin Mononucleotide + Water unknown Riboflavin + Phosphoric aciddetails
Gene Name:
FLAD1
Uniprot ID:
Q8NFF5
Reactions
Adenosine triphosphate + Flavin Mononucleotide unknown Pyrophosphate + FADdetails
Gene Name:
IYD
Uniprot ID:
Q6PHW0
Gene Name:
ACPT
Uniprot ID:
Q9BZG2
Reactions
Flavin Mononucleotide + Water unknown Riboflavin + Phosphoric aciddetails