Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2019-01-11 19:16:07 UTC |
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HMDB ID | HMDB0001520 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Flavin Mononucleotide |
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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. |
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Structure | |
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Synonyms | Value | Source |
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Riboflavin 5'-(dihydrogen phosphate) | ChEBI | Riboflavin 5'-monophosphate | ChEBI | Riboflavin 5'-phosphate | ChEBI | Riboflavin monophosphate | ChEBI | Riboflavin-5-phosphate | ChEBI | Riboflavine dihydrogen phosphate | ChEBI | Riboflavin 5'-(dihydrogen phosphoric acid) | Generator | Riboflavin 5'-monophosphoric acid | Generator | Riboflavin 5'-phosphoric acid | Generator | Riboflavin monophosphoric acid | Generator | Riboflavin-5-phosphoric acid | Generator | Riboflavine dihydrogen phosphoric acid | Generator | Flanin | HMDB | Flavine mononucleotide | HMDB | Flavol | HMDB | FMN | HMDB | Riboflavin | HMDB | Riboflavin mononucleotide | HMDB | Riboflavin phosphate | HMDB | Riboflavin-5'-phosphate na | HMDB | Riboflavine 5'-monophosphate | HMDB | Riboflavine 5'-phosphate | HMDB | Riboflavine monophosphate | HMDB | Riboflavine phosphate | HMDB | Riboflavine-5'-phosphate | HMDB | Vitamin b2 phosphate | HMDB | 5'-Monophosphate, riboflavin | MeSH | 5'-Phosphate, riboflavin | MeSH | Flavin mononucleotide sodium salt | MeSH | Mononucleotide, riboflavin | MeSH | Flavin mononucleotide monosodium salt | MeSH | Flavin mononucleotide monosodium salt, dihydrate | MeSH | Phosphate, sodium riboflavin | MeSH | Riboflavin 5' phosphate | MeSH | Riboflavin phosphate, sodium | MeSH | Mononucleotide, flavin | MeSH | Riboflavin 5' monophosphate | MeSH | Flavin mononucleotide disodium salt | MeSH | Sodium riboflavin phosphate | MeSH |
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Chemical Formula | C17H21N4O9P |
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Average Molecular Weight | 456.3438 |
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Monoisotopic Molecular Weight | 456.104614802 |
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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 |
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Traditional Name | riboflavin 5'-phosphate |
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CAS Registry Number | 146-17-8 |
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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 |
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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 |
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InChI Key | FVTCRASFADXXNN-SCRDCRAPSA-N |
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Chemical Taxonomy |
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Description | This compound 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. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Flavin nucleotides |
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Sub Class | Not Available |
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Direct Parent | Flavin nucleotides |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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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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Disease References | Anorexia nervosa |
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- 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 |
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- 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 |
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- 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 ]
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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 ]
- 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 ]
- 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 ]
- 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 ]
- Ajayi OA: Bioavailability of riboflavin from fortified palm juice. Plant Foods Hum Nutr. 1989 Dec;39(4):375-80. [PubMed:2631092 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Blajchman MA, Goldman M, Baeza F: Improving the bacteriological safety of platelet transfusions. Transfus Med Rev. 2004 Jan;18(1):11-24. [PubMed:14689374 ]
- 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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