Hmp_logo

Human Metabolome Database Version 3.5

HMDB has recently undergone some major changes, if you are experiencing problems please click here to provide us with feedback.

Showing metabocard for Flavin Mononucleotide (HMDB01520)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-03-25 14:36:55 -0600
HMDB ID HMDB01520
Secondary Accession Numbers None
Metabolite Identification
Common Name Flavin Mononucleotide
Description Flavin 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C17H21N4O9P
Average Molecular Weight 456.3438
Monoisotopic Molecular Weight 456.104614802
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 Number 146-17-8
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 Key FVTCRASFADXXNN-SCRDCRAPSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Pteridines and Derivatives
Sub Class Alloxazines 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 Parent Flavins
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Riboflavin metabolism
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 290 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 92 mg/mL Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.67 g/L ALOGPS
LogP -0.78 ALOGPS
LogP -1 ChemAxon
LogS -2.83 ALOGPS
pKa (strongest acidic) 1.57 ChemAxon
pKa (strongest basic) 0.68 ChemAxon
Hydrogen Acceptor Count 11 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 201.58 A2 ChemAxon
Rotatable Bond Count 7 ChemAxon
Refractivity 107.14 ChemAxon
Polarizability 42.19 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -3 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Muscle
  • Erythrocyte
  • Platelet
  • Eye Lens
Pathways
Name SMPDB Link KEGG Link
Riboflavin Metabolism SMP00070 map00740 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.0084 (0.0035-0.013) uM Adult (>18 years old) Female Normal Not Available
Blood Detected and Quantified
Article_icon
0.016 +/- 0.009 uM Adolescent (13-18 years old) Female Normal Not Available
Blood Detected and Quantified
Article_icon
0.0075 (0.004-0.011) uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.013 +/- 0.006 uM Children (1-13 year old) Both Severely malnourished children Not Available
Blood Detected and Quantified
Article_icon
0.012 +/- 0.006 uM Adolescent (13-18 years old) Female Anorexia nervosa Not Available
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 Link_out
    Associated OMIM IDs
    DrugBank ID DB03247 Link_out
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB001984
    KNApSAcK ID C00019686 Link_out
    Chemspider ID 559060 Link_out
    KEGG Compound ID C00061 Link_out
    BioCyc ID FMN Link_out
    BiGG ID 33703 Link_out
    Wikipedia Link FMN Link_out
    NuGOwiki Link HMDB01520 Link_out
    Metagene Link HMDB01520 Link_out
    METLIN ID 6295 Link_out
    PubChem Compound 643976 Link_out
    PDB ID FMN Link_out
    ChEBI ID 17621 Link_out
    References
    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)
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    11. Ajayi OA: Bioavailability of riboflavin from fortified palm juice. Plant Foods Hum Nutr. 1989 Dec;39(4):375-80. Pubmed: 2631092 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    Enzymes
    Name: Tartrate-resistant acid phosphatase type 5
    Reactions:
    • a phosphate monoester + H2O = an alcohol + phosphate [RN:R00626]
    Gene Name: ACP5
    Uniprot ID: P13686 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Prostatic acid phosphatase
    Reactions:
    • a phosphate monoester + H2O = an alcohol + phosphate [RN:R00626]
    Gene Name: ACPP
    Uniprot ID: P15309 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 1
    Reactions:
    • a dinucleotide + H2O = 2 mononucleotides [RN:R00056]
    Gene Name: ENPP1
    Uniprot ID: P22413 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Lathosterol oxidase
    Reactions:
    • 5alpha-cholest-7-en-3beta-ol + NAD(P)H + H+ + O2 = cholesta-5,7-dien-3beta-ol + NAD(P)+ + 2 H2O [RN:R03310 R07215]
    Gene Name: SC5DL
    Uniprot ID: O75845 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: NADPH--cytochrome P450 reductase
    Reactions:
    • NADPH + H+ + n oxidized hemoprotein = NADP+ + n reduced hemoprotein
    Gene Name: POR
    Uniprot ID: P16435 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Dihydroorotate dehydrogenase, mitochondrial
    Reactions:
    • (S)-dihydroorotate + a quinone = orotate + a quinol [RN:R01868]
    Gene Name: DHODH
    Uniprot ID: Q02127 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: NADH dehydrogenase [ubiquinone] flavoprotein 1, mitochondrial
    Reactions:
    • NADH + H+ + acceptor = NAD+ + reduced acceptor [RN:R00281]
    Gene Name: NDUFV1
    Uniprot ID: P49821 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 3
    Reactions:
    • a dinucleotide + H2O = 2 mononucleotides [RN:R00056]
    Gene Name: ENPP3
    Uniprot ID: O14638 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Methionine synthase reductase
    Reactions:
    • 2 [methionine synthase]-methylcob(I)alamin + 2 S-adenosylhomocysteine + NADP+ = 2 [methionine synthase]-cob(II)alamin + NADPH + H+ + 2 S-adenosyl-L-methionine [RN:R05182]
    Gene Name: MTRR
    Uniprot ID: Q9UBK8 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Pyridoxine-5'-phosphate oxidase
    Reactions:
    • (1) pyridoxamine 5'-phosphate + H2O + O2 = pyridoxal 5'-phosphate + NH3 + H2O2 [RN:R00277]
    • (2) pyridoxine 5'-phosphate + O2 = pyridoxal 5'-phosphate + H2O2 [RN:R00278]
    Gene Name: PNPO
    Uniprot ID: Q9NVS9 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Flavin reductase
    Reactions:
    • reduced riboflavin + NADP+ = riboflavin + NADPH + H+ [RN:R05707]
    Gene Name: BLVRB
    Uniprot ID: P30043 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Dihydropyrimidine dehydrogenase [NADP+]
    Reactions:
    • 5,6-dihydrouracil + NADP+ = uracil + NADPH + H+ [RN:R00978]
    Gene Name: DPYD
    Uniprot ID: Q12882 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Hydroxyacid oxidase 1
    Reactions:
    • an (S)-2-hydroxy acid + O2 = a 2-oxo acid + H2O2 [RN:R01341]
    Gene Name: HAO1
    Uniprot ID: Q9UJM8 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Hydroxyacid oxidase 2
    Reactions:
    • an (S)-2-hydroxy acid + O2 = a 2-oxo acid + H2O2 [RN:R01341]
    Gene Name: HAO2
    Uniprot ID: Q9NYQ3 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Sarcosine dehydrogenase, mitochondrial
    Reactions:
    • sarcosine + acceptor + H2O = glycine + formaldehyde + reduced acceptor [RN:R00611]
    Gene Name: SARDH
    Uniprot ID: Q9UL12 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Nitric oxide synthase, inducible
    Reactions:
    • L-arginine + n NADPH + n H+ + m O2 = citrulline + nitric oxide + n NADP+ [RN:R00557]
    Gene Name: NOS2
    Uniprot ID: P35228 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Nitric oxide synthase, brain
    Reactions:
    • L-arginine + n NADPH + n H+ + m O2 = citrulline + nitric oxide + n NADP+ [RN:R00557]
    Gene Name: NOS1
    Uniprot ID: P29475 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Nitric oxide synthase, endothelial
    Reactions:
    • L-arginine + n NADPH + n H+ + m O2 = citrulline + nitric oxide + n NADP+ [RN:R00557]
    Gene Name: NOS3
    Uniprot ID: P29474 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Riboflavin kinase
    Reactions:
    • ATP + riboflavin = ADP + FMN [RN:R00549]
    Gene Name: RFK
    Uniprot ID: Q969G6 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Ribosomal protein S6 kinase alpha-4
    Reactions:
    • ATP + a protein = ADP + a phosphoprotein [RN:R00162]
    Gene Name: RPS6KA4
    Uniprot ID: O75676 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Serine/threonine-protein kinase Sgk1
    Reactions:
    • ATP + a protein = ADP + a phosphoprotein [RN:R00162]
    Gene Name: SGK1
    Uniprot ID: O00141 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Phosphopantothenoylcysteine decarboxylase
    Reactions:
    • N-[(R)-4'-phosphopantothenoyl]-L-cysteine = pantotheine 4'-phosphate + CO2 [RN:R03269]
    Gene Name: PPCDC
    Uniprot ID: Q96CD2 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Lysophosphatidic acid phosphatase type 6
    Reactions:
    • a phosphate monoester + H2O = an alcohol + phosphate [RN:R00626]
    Gene Name: ACP6
    Uniprot ID: Q9NPH0 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: FAD synthase
    Reactions:
    • ATP + FMN = diphosphate + FAD [RN:R00161]
    Gene Name: FLAD1
    Uniprot ID: Q8NFF5 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: NADPH-dependent diflavin oxidoreductase 1
    Reactions:
      Gene Name: NDOR1
      Uniprot ID: Q9UHB4 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Iodotyrosine dehalogenase 1
      Reactions:
        Gene Name: IYD
        Uniprot ID: Q6PHW0 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: tRNA wybutosine-synthesizing protein 1 homolog
        Reactions:
          Gene Name: TYW1
          Uniprot ID: Q9NV66 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: tRNA wybutosine-synthesizing protein 1 homolog B
          Reactions:
            Gene Name: TYW1B
            Uniprot ID: Q6NUM6 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Testicular acid phosphatase
            Reactions:
            • a phosphate monoester + H2O = an alcohol + phosphate [RN:R00626]
            Gene Name: ACPT
            Uniprot ID: Q9BZG2 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Putative uncharacterized protein ACP1
            Reactions:
              Gene Name: ACP1
              Uniprot ID: B5MCC7 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA