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Record Information
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-04-22 23:29:28 UTC
Secondary Accession Numbers
  • HMDB01520
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.
Riboflavin 5'-(dihydrogen phosphate)ChEBI
Riboflavin 5'-monophosphateChEBI
Riboflavin 5'-phosphateChEBI
Riboflavin monophosphateChEBI
Riboflavine dihydrogen phosphateChEBI
Riboflavin 5'-(dihydrogen phosphoric acid)Generator
Riboflavin 5'-monophosphoric acidGenerator
Riboflavin 5'-phosphoric acidGenerator
Riboflavin monophosphoric acidGenerator
Riboflavin-5-phosphoric acidGenerator
Riboflavine dihydrogen phosphoric acidGenerator
Flavine mononucleotideHMDB
Riboflavin mononucleotideHMDB
Riboflavin phosphateHMDB
Riboflavin-5'-phosphate naHMDB
Riboflavine 5'-monophosphateHMDB
Riboflavine 5'-phosphateHMDB
Riboflavine monophosphateHMDB
Riboflavine phosphateHMDB
Vitamin b2 phosphateHMDB
5'-monoPhosphate, riboflavinHMDB
5'-Phosphate, riboflavinHMDB
Flavin mononucleotide sodium saltHMDB
Mononucleotide, riboflavinHMDB
Flavin mononucleotide monosodium saltHMDB
Flavin mononucleotide monosodium salt, dihydrateHMDB
Phosphate, sodium riboflavinHMDB
Riboflavin 5' phosphateHMDB
Riboflavin phosphate, sodiumHMDB
Mononucleotide, flavinHMDB
Riboflavin 5' monophosphateHMDB
Flavin mononucleotide disodium saltHMDB
Sodium riboflavin phosphateHMDB
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 Nameriboflavin 5'-phosphate
CAS Registry Number146-17-8
InChI Identifier
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
  • 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
Physiological effect

Health effect:


Route of exposure:


Biological location:


Naturally occurring process:


Industrial application:

Physical Properties
Experimental Properties
Melting Point290 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility92 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.67 g/LALOGPS
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
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007d-6931400000-cad44822b1dfefb25732Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0592-6901126000-2ec87848003ebe8e438dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0002-9000200000-bc07cc2b3950f70a9db3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-9000200000-bc07cc2b3950f70a9db3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0134900000-c3ae39f771e510a09ae6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2391100000-1b8212d4ae35c1e1f1f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1090000000-8948e075f379e327a852Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03kc-9251600000-e0759dcc125b6178b7f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9120000000-656647e95148b2404066Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4778caa348b1cda5e72cSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Erythrocyte
  • Eye Lens
  • Placenta
  • Platelet
  • Skeletal Muscle
Normal Concentrations
BloodDetected and Quantified0.0084 (0.0035-0.013) uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.016 +/- 0.009 uMAdolescent (13-18 years old)FemaleNormal details
BloodDetected and Quantified0.0075 (0.004-0.011) uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
FecesDetected but not Quantified Adult (>18 years old)Both
FecesDetected but not Quantified Adult (>18 years old)Both
Abnormal Concentrations
BloodDetected and Quantified0.013 +/- 0.006 uMChildren (1-13 years old)BothMalnutrition (type kwashiorkor and marasmus) details
BloodDetected and Quantified0.012 +/- 0.006 uMAdolescent (13-18 years old)FemaleAnorexia nervosa details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
FecesDetected but not Quantified Adult (>18 years old)Both
Metastatic melanoma
Associated Disorders and Diseases
Disease References
Anorexia nervosa
  1. 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 ]
Metastatic melanoma
  1. Frankel AE, Coughlin LA, Kim J, Froehlich TW, Xie Y, Frenkel EP, Koh AY: Metagenomic Shotgun Sequencing and Unbiased Metabolomic Profiling Identify Specific Human Gut Microbiota and Metabolites Associated with Immune Checkpoint Therapy Efficacy in Melanoma Patients. Neoplasia. 2017 Oct;19(10):848-855. doi: 10.1016/j.neo.2017.08.004. Epub 2017 Sep 15. [PubMed:28923537 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB03247
Phenol Explorer Compound IDNot Available
FooDB IDFDB030862
KNApSAcK IDC00019686
Chemspider ID559060
KEGG Compound IDC00061
BiGG ID33703
Wikipedia LinkFlavin_mononucleotide
PubChem Compound643976
PDB IDNot Available
ChEBI ID17621
Food Biomarker OntologyNot Available
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)Download (PDF)
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. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. Ajayi OA: Bioavailability of riboflavin from fortified palm juice. Plant Foods Hum Nutr. 1989 Dec;39(4):375-80. [PubMed:2631092 ]
  12. Blajchman MA, Goldman M, Baeza F: Improving the bacteriological safety of platelet transfusions. Transfus Med Rev. 2004 Jan;18(1):11-24. [PubMed:14689374 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]
  17. 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 ]
  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 ]
  21. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 32 proteins in total.


General function:
Involved in acid phosphatase activity
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight:
Flavin mononucleotide + Water → Riboflavin + Phosphatedetails
General function:
Involved in acid phosphatase activity
Specific function:
Acts on tyrosine phosphorylated proteins, low-MW aryl phosphates and natural and synthetic acyl phosphates. Isoform 3 does not possess phosphatase activity.
Gene Name:
Uniprot ID:
Molecular weight:
Flavin mononucleotide + Water → Riboflavin + Phosphatedetails
General function:
Involved in hydrolase activity
Specific function:
Involved in osteopontin/bone sialoprotein dephosphorylation. Its expression seems to increase in certain pathological states such as Gaucher and Hodgkin diseases, the hairy cell, the B-cell, and the T-cell leukemias.
Gene Name:
Uniprot ID:
Molecular weight:
Flavin mononucleotide + Water → Riboflavin + Phosphatedetails
General function:
Involved in acid phosphatase activity
Specific function:
A non-specific tyrosine phosphatase that dephosphorylates a diverse number of substrates under acidic conditions (pH 4-6) including alkyl, aryl, and acyl orthophosphate monoesters and phosphorylated proteins. Has lipid phosphatase activity and inactivates lysophosphatidic acid in seminal plasma. Isoform 2: the cellular form also has ecto-5'-nucleotidase activity in dorsal root ganglion (DRG) neurons. Generates adenosine from AMP which acts as a pain suppressor. Acts as a tumor suppressor of prostate cancer through dephosphorylation of ERBB2 and deactivation of MAPK-mediated signaling.
Gene Name:
Uniprot ID:
Molecular weight:
Flavin mononucleotide + Water → Riboflavin + Phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Involved primarily in ATP hydrolysis at the plasma membrane. Plays a role in regulating pyrophosphate levels, and functions in bone mineralization and soft tissue calcification. In vitro, has a broad specificity, hydrolyzing other nucleoside 5' triphosphates such as GTP, CTP, TTP and UTP to their corresponding monophosphates with release of pyrophosphate and diadenosine polyphosphates, and also 3',5'-cAMP to AMP. May also be involved in the regulation of the availability of nucleotide sugars in the endoplasmic reticulum and Golgi, and the regulation of purinergic signaling. Appears to modulate insulin sensitivity.
Gene Name:
Uniprot ID:
Molecular weight:
FAD + Water → Adenosine monophosphate + Flavin mononucleotidedetails
General function:
Involved in iron ion binding
Specific function:
Catalyzes a dehydrogenation to introduce C5-6 double bond into lathosterol.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in oxidoreductase activity
Specific function:
This enzyme is required for electron transfer from NADP to cytochrome P450 in microsomes. It can also provide electron transfer to heme oxygenase and cytochrome B5.
Gene Name:
Uniprot ID:
Molecular weight:
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of dihydroorotate to orotate with quinone as electron acceptor.
Gene Name:
Uniprot ID:
Molecular weight:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in catalytic activity
Specific function:
Cleaves a variety of phosphodiester and phosphosulfate bonds including deoxynucleotides, nucleotide sugars, and NAD (By similarity).
Gene Name:
Uniprot ID:
Molecular weight:
FAD + Water → Adenosine monophosphate + Flavin mononucleotidedetails

Only showing the first 10 proteins. There are 32 proteins in total.