| 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- Flanin
- Flavine mononucleotide
- Flavol
- FMN
- Riboflavin
- Riboflavin 5'-monophosphate
- Riboflavin 5'-phosphate
- Riboflavin Mononucleotide
- Riboflavin monophosphate
- Riboflavin phosphate
- Riboflavin-5'-phosphate na
- Riboflavin-5-phosphate
- Riboflavine 5'-monophosphate
- Riboflavine 5'-phosphate
- Riboflavine dihydrogen phosphate
- Riboflavine monophosphate
- Riboflavine phosphate
- Riboflavine-5'-phosphate
- 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)
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| 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 |
|
| Biofunction |
- Component of Riboflavin metabolism
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| Application |
Not Available |
| Cellular locations |
- Cytoplasm (predicted from logP)
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| 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 |
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| Predicted Properties |
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| Spectra |
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| Biological Properties |
| Cellular Locations |
- Cytoplasm (predicted from logP)
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| Biofluid Locations |
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| Tissue Location |
- Muscle
- Erythrocyte
- Platelet
- Eye Lens
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| Pathways |
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| Normal Concentrations |
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| Blood |
Detected and Quantified |
|
0.0084 (0.0035-0.013) uM |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
0.016 +/- 0.009 uM |
Adolescent (13-18 years old) |
Female |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
0.0075 (0.004-0.011) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
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| Abnormal Concentrations |
|
| Blood |
Detected and Quantified |
|
0.013 +/- 0.006 uM |
Children (1-13 year old) |
Both |
Severely malnourished children |
Not Available |
| Blood |
Detected and Quantified |
|
0.012 +/- 0.006 uM |
Adolescent (13-18 years old) |
Female |
Anorexia nervosa |
Not Available |
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| 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
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| Associated OMIM IDs |
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| External Links |
| DrugBank ID |
DB03247  |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB001984 |
| KNApSAcK ID |
C00019686  |
| Chemspider ID |
559060  |
| KEGG Compound ID |
C00061  |
| BioCyc ID |
FMN  |
| BiGG ID |
33703  |
| Wikipedia Link |
FMN  |
| NuGOwiki Link |
HMDB01520  |
| Metagene Link |
HMDB01520  |
| METLIN ID |
6295  |
| PubChem Compound |
643976  |
| PDB ID |
FMN  |
| ChEBI ID |
17621  |
| 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 |
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- Ajayi OA: Bioavailability of riboflavin from fortified palm juice. Plant Foods Hum Nutr. 1989 Dec;39(4):375-80.
Pubmed: 2631092
- Blajchman MA, Goldman M, Baeza F: Improving the bacteriological safety of platelet transfusions. Transfus Med Rev. 2004 Jan;18(1):11-24.
Pubmed: 14689374
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
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| Enzymes |
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| Name: |
Lathosterol oxidase
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| 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]
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| Gene Name: |
SC5DL |
| Uniprot ID: |
O75845  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Methionine synthase reductase
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| 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]
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| Gene Name: |
MTRR |
| Uniprot ID: |
Q9UBK8  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Pyridoxine-5'-phosphate oxidase
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| 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]
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| Gene Name: |
PNPO |
| Uniprot ID: |
Q9NVS9  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Flavin reductase
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| Reactions: |
- reduced riboflavin + NADP+ = riboflavin + NADPH + H+ [RN:R05707]
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| Gene Name: |
BLVRB |
| Uniprot ID: |
P30043  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
FAD synthase
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| Reactions: |
- ATP + FMN = diphosphate + FAD [RN:R00161]
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| Gene Name: |
FLAD1 |
| Uniprot ID: |
Q8NFF5  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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