FMN (PAMDB110703)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110703
Identification
Name: FMN
Description:The trianion arising from deprotonation of the diphosphate hydroxy groups and the imide nitrogen of flavin mononucleotide (FMN).
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • flavin mononucleotide
  • riboflavin 5'-phosphate
Chemical Formula: C17H18N4O9P
Average Molecular Weight: 453.32
Monoisotopic Molecular Weight: 456.1046148038
InChI Key: ANKZYBDXHMZBDK-SCRDCRAPSA-K
InChI: 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,(H3,20,25,26,27,28,29)/p-3/t11-,12+,14-/m0/s1
CAS number: 146-17-8
IUPAC Name:1-deoxy-1-(7,8-dimethyl-2,4-dioxo-2H-benzo[g]pteridin-3-id-10(4H)-yl)-5-O-phosphonato-D-ribitol
Traditional IUPAC Name: riboflavin 5'-phosphate
SMILES:CC2(=CC1(N=C3(C(=O)[N-]C(=O)N=C(N(CC(O)C(O)C(O)COP([O-])(=O)[O-])C=1C=C(C)2)3)))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities 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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Nucleosides, nucleotides, and analogues
Sub ClassFlavin nucleotides
Direct Parent Flavin nucleotides
Alternative Parents
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
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-3
Melting point: 290 °C
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 mg/mLALOGPS
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 Area201.58 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity107.14 m3·mol-1ChemAxon
Polarizability42.19 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
3-(N-morpholino)propanesulfonate + FMNH(2) + Oxygen → 3-(N-morpholino)propanal + Sulfite + Water + FMN + Hydrogen ion
3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + Oxygen + FMNH(2) → Hydrogen ion + 3,4-dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione + Water + FMN
Butanesulfonate + Oxygen + FMNH(2) → Butanal + Sulfite + Water + FMN + Hydrogen ion
FMNH(2) + NAD+ → FMN + NADH + Hydrogen ion
isethionate + FMNH(2) + Oxygen → Glycolaldehyde + Sulfite + Water + FMN + Hydrogen ion
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0002-9000200000-bc07cc2b3950f70a9db3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
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. [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. [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. [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. [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. [3592624 ]
  • Ajayi OA: Bioavailability of riboflavin from fortified palm juice. Plant Foods Hum Nutr. 1989 Dec;39(4):375-80. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [10720170 ]
  • Blajchman MA, Goldman M, Baeza F: Improving the bacteriological safety of platelet transfusions. Transfus Med Rev. 2004 Jan;18(1):11-24. [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. [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. [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. [6830748 ]
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)
External Links:
ResourceLink
CAS146-17-8
ChEBI58210
HMDBHMDB01520
IAF126033703
KEGGC00061
MetaboLightsMTBLC58210
PubChem44229199
WikipediaFlavin_mononucleotide