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Showing Compound FMN (FDB030862)

Record Information
Version1.0
Creation date2015-05-07 20:19:11 UTC
Update date2019-11-26 03:21:55 UTC
Primary IDFDB030862
Secondary Accession Numbers
  • FDB001984
Chemical Information
FooDB NameFMN
DescriptionFlavin mononucleotide, also known as riboflavin 5'-monophosphate or riboflavine dihydrogen phosphate, is a member of the class of compounds known as flavin nucleotides. Flavin nucleotides 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 practically insoluble (in water) and a moderately acidic compound (based on its pKa). Flavin mononucleotide can be found in a number of food items such as spinach, elliott's blueberry, tea leaf willow, and black mulberry, which makes flavin mononucleotide a potential biomarker for the consumption of these food products. Flavin mononucleotide can be found primarily in blood, as well as throughout most human tissues. Flavin mononucleotide exists in all living species, ranging from bacteria to humans. In humans, flavin mononucleotide is involved in several metabolic pathways, some of which include riboflavin metabolism, pyrimidine metabolism, beta-alanine metabolism, and doxorubicin metabolism pathway. Flavin mononucleotide is also involved in several metabolic disorders, some of which include beta ureidopropionase deficiency, UMP synthase deficiency (orotic aciduria), carnosinuria, carnosinemia, and hypophosphatasia. Moreover, flavin mononucleotide is found to be associated with anorexia nervosa. 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, a reversible interconversion of the 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. In its role as blue-light photo receptor, (oxidized) FMN stands out from the 'conventional' photo receptors as the signaling state and not an E/Z isomerization .
CAS Number146-17-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
Predicted Properties
PropertyValueSource
Water Solubility0.67 g/LALOGPS
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
Chemical FormulaC17H21N4O9P
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
InChI IdentifierInChI=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
Isomeric SMILESCC1=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
Average Molecular Weight456.3438
Monoisotopic Molecular Weight456.104614802
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSRiboflavine 5'-(dihydrogen phosphate), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-007d-6931400000-cad44822b1dfefb25732Spectrum
Predicted GC-MSRiboflavine 5'-(dihydrogen phosphate), 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0592-6901126000-2ec87848003ebe8e438dSpectrum
Predicted GC-MSRiboflavine 5'-(dihydrogen phosphate), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRiboflavine 5'-(dihydrogen phosphate), non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0002-9000200000-bc07cc2b3950f70a9db32012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-9000200000-bc07cc2b3950f70a9db32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-0a4i-0000900000-6e5ca4123f461d0e208d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 16V, positivesplash10-0a4i-0000900000-f1a0fdd1328522519b912020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 24V, positivesplash10-0a4r-2028900000-899e2dcd3bfb217b57662020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 32V, positivesplash10-052f-7289200000-ebb8d8c94ce8d3a5fb862020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 41V, positivesplash10-0006-9782000000-786258c7a5f6feda99e22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 53V, positivesplash10-00dj-4910000000-e978502607653ec516592020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 66V, positivesplash10-006t-3900000000-cd1a65145bae541f29192020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 78V, positivesplash10-0002-3900000000-9be5fed1e1eb535085f62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 91V, positivesplash10-0fr2-4900000000-d58071130f19cd6bc8332020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 107V, positivesplash10-0ktb-7900000000-c3b2300acb88daf0d14f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 124V, positivesplash10-052b-9700000000-e2c1ef96f28d92a23db42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 149V, positivesplash10-0kbb-9300000000-91cbf6b5c1f4e37d016a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 31V, positivesplash10-000i-0000900000-b60cf8984dd78397651e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 31V, positivesplash10-00kf-0096000000-9690dc0d4d8c890d69002020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 31V, positivesplash10-0fka-0960000000-6d860483a67d4bd784ab2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 31V, positivesplash10-0002-0019000000-60cf80bbeab6e68f82d52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 31V, positivesplash10-004i-0009000000-eea6861c71c50e5ce8462020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0134900000-c3ae39f771e510a09ae62016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2391100000-1b8212d4ae35c1e1f1f22016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1090000000-8948e075f379e327a8522016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03kc-9251600000-e0759dcc125b6178b7f22016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9120000000-656647e95148b24040662016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4778caa348b1cda5e72c2016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference