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Record Information
Version1.0
Creation Date2016-09-30 22:47:07 UTC
Update Date2020-05-21 16:28:35 UTC
BMDB IDBMDB0001520
Secondary Accession Numbers
  • BMDB01520
Metabolite Identification
Common NameFlavin Mononucleotide
DescriptionFlavin mononucleotide, also known as riboflavin 5'-phosphate or flanin, 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. Flavin mononucleotide is an extremely weak basic (essentially neutral) compound (based on its pKa). Flavin mononucleotide exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
ValueSource
Riboflavin 5'-(dihydrogen phosphate)ChEBI
Riboflavin 5'-monophosphateChEBI
Riboflavin 5'-phosphateChEBI
Riboflavin monophosphateChEBI
Riboflavin-5-phosphateChEBI
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
FlaninHMDB
Flavine mononucleotideHMDB
FlavolHMDB
FMNHMDB
RiboflavinHMDB
Riboflavin mononucleotideHMDB
Riboflavin phosphateHMDB
Riboflavin-5'-phosphate naHMDB
Riboflavine 5'-monophosphateHMDB
Riboflavine 5'-phosphateHMDB
Riboflavine monophosphateHMDB
Riboflavine phosphateHMDB
Riboflavine-5'-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
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 KeyFVTCRASFADXXNN-SCRDCRAPSA-N
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
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point290 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility92 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.78ALOGPS
logP-1ChemAxon
logS-2.8ALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007d-6931400000-cad44822b1dfefb25732View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0592-6901126000-2ec87848003ebe8e438dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0002-9000200000-bc07cc2b3950f70a9db3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-9000200000-bc07cc2b3950f70a9db3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0134900000-c3ae39f771e510a09ae6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2391100000-1b8212d4ae35c1e1f1f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1090000000-8948e075f379e327a852View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03kc-9251600000-e0759dcc125b6178b7f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9120000000-656647e95148b2404066View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4778caa348b1cda5e72cView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Erythrocyte
  • Eye Lens
  • Liver
  • Placenta
  • Platelet
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
ErythrocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Eye LensExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001520
DrugBank IDDB03247
Phenol Explorer Compound IDNot Available
FooDB IDFDB030862
KNApSAcK IDC00019686
Chemspider ID559060
KEGG Compound IDC00061
BioCyc IDFMN
BiGG ID33703
Wikipedia LinkFlavin_mononucleotide
METLIN ID6295
PubChem Compound643976
PDB IDNot Available
ChEBI ID17621
References
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)Not Available
General ReferencesNot Available

Enzymes

General function:
Carbohydrate transport and metabolism
Specific function:
Catalyzes both the phosphorylation of dihydroxyacetone and of glyceraldehyde, and the splitting of ribonucleoside diphosphate-X compounds among which FAD is the best substrate. Represses IFIH1-mediated cellular antiviral response.
Gene Name:
TKFC
Uniprot ID:
Q58DK4
Molecular weight:
59124.0
General function:
Signal transduction mechanisms
Specific function:
Acts on tyrosine phosphorylated proteins, low-MW aryl phosphates and natural and synthetic acyl phosphates.
Gene Name:
ACP1
Uniprot ID:
P11064
Molecular weight:
18055.0
Reactions
Flavin Mononucleotide + Water → Riboflavin + Hydrogen phosphatedetails
General function:
Not Available
Specific function:
Catalyzes the adenylation of flavin mononucleotide (FMN) to form flavin adenine dinucleotide (FAD) coenzyme.
Gene Name:
FLAD1
Uniprot ID:
F6R6Q1
Molecular weight:
54273.0
Reactions
Adenosine triphosphate + Flavin Mononucleotide → FAD + Pyrophosphatedetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
RFK
Uniprot ID:
Q3SZP4
Molecular weight:
25377.0
Reactions
Adenosine triphosphate + Riboflavin → ADP + Flavin Mononucleotidedetails
General function:
Not Available
Specific function:
Hydrolase that metabolizes extracellular nucleotides, including ATP, GTP, UTP and CTP (By similarity). Limits mast cell and basophil responses during inflammation and during the chronic phases of allergic responses by eliminating the extracellular ATP that functions as signaling molecule and activates basophils and mast cells and induces the release of inflammatory cytokines. Metabolizes extracellular ATP in the lumen of the small intestine, and thereby prevents ATP-induced apoptosis of intestinal plasmacytoid dendritic cells (By similarity). Has also alkaline phosphodiesterase activity (By similarity).
Gene Name:
ENPP3
Uniprot ID:
P15396
Molecular weight:
99523.0
Reactions
FAD + Water → Adenosine monophosphate + Flavin Mononucleotidedetails