Record Information
Version2.0
Creation Date2012-05-31 13:46:17 -0600
Update Date2015-06-03 15:53:47 -0600
Secondary Accession Numbers
  • ECMDB01142
Identification
Name:FMNH
Description:FMNH is a member of the chemical class known as Flavins. These are compounds containing a flavin (7,8-dimethyl-benzo[g]pteridine-2,4-dione) moiety, whose structure is characterized by an isoalloaxzine tricyclic ring. During their use in different catalytic cycles, the reversible interconversion of oxidized (FMN), semiquinone (FMNH
Structure
Thumb
Synonyms:
  • FMNH2
  • Reduced flavin mononucleotide
  • Reduced FMN
Chemical Formula:C17H23N4O9P
Weight:Average: 458.3597
Monoisotopic: 458.120264866
InChI Key:YTNIXZGTHTVJBW-UHFFFAOYSA-N
InChI:InChI=1S/C17H23N4O9P/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/h3-4,11-12,14,18,22-24H,5-6H2,1-2H3,(H2,27,28,29)(H2,19,20,25,26)
CAS number:Not Available
IUPAC Name:[(5-{7,8-dimethyl-2,4-dioxo-1H,2H,3H,4H,5H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl)oxy]phosphonic acid
Traditional IUPAC Name:(5-{7,8-dimethyl-2,4-dioxo-1H,3H,5H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl)oxyphosphonic acid
SMILES:CC1=CC2=C(C=C1C)N(CC(O)C(O)C(O)COP(O)(O)=O)C1=C(N2)C(=O)NC(=O)N1
Chemical 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassFlavin nucleotides
Direct ParentFlavin nucleotides
Alternative Parents
Substituents
  • Flavin nucleotide
  • Flavin
  • Alkyldiarylamine
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Pteridine
  • Pyrimidone
  • Monoalkyl phosphate
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Secondary alcohol
  • Lactam
  • Urea
  • Secondary amine
  • Organoheterocyclic compound
  • Polyol
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Organopnictogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:-0.406PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.64 g/LALOGPS
logP-0.17ALOGPS
logP-1.1ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)1.5ChemAxon
pKa (Strongest Basic)-0.52ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area200.92 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity118.51 m³·mol⁻¹ChemAxon
Polarizability43.23 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Flavin Mononucleotide + Hydrogen ion + NADH > FMNH + NAD
Flavin Mononucleotide + Hydrogen ion + NADPH <> FMNH + NADP
FMNH + Oxygen + Sulfoacetate > Flavin Mononucleotide + Glyoxylic acid + Hydrogen ion + Water + Sulfite
FMNH + Isethionic acid + Oxygen > Flavin Mononucleotide + Glycolaldehyde + Hydrogen ion + Water + Sulfite
FMNH + Methanesulfonate + Oxygen > Formaldehyde + Flavin Mononucleotide + Hydrogen ion + Water + Sulfite
Butanesulfonate + FMNH + Oxygen > Butanal + Flavin Mononucleotide + Hydrogen ion + Water + Sulfite
Ethanesulfonate + FMNH + Oxygen > Acetaldehyde + Flavin Mononucleotide + Hydrogen ion + Water + Sulfite
2 Ferroxamine + FMNH >2 Iron +2 ferroxamine minus Fe(3) + Flavin Mononucleotide +2 Hydrogen ion
FMNH + NAD <> Flavin Mononucleotide + NADH + Hydrogen ion
FMNH + NADP <> Flavin Mononucleotide + NADPH + Hydrogen ion
Uracil + FMNH + Oxygen <> Ureidoacrylate peracid + Flavin Mononucleotide
NAD(P)<sup>+</sup> + FMNH <> NAD(P)H + Flavin Mononucleotide + Hydrogen ion
FMNH + NADP < Flavin Mononucleotide + NADPH + Hydrogen ion
Thymine + Oxygen + FMNH > (<i>Z</i>)-2-methylureidoacrylate peracid + Flavin Mononucleotide + Hydrogen ion
Isethionic acid + FMNH + Oxygen > Glycolaldehyde + Sulfite + Water + Flavin Mononucleotide + Hydrogen ion
an alkanesulfonate + Oxygen + FMNH > an aldehyde + Sulfite + Water + Flavin Mononucleotide + Hydrogen ion
Uracil + Oxygen + FMNH > Hydrogen ion + Ureidoacrylate peracid + Flavin Mononucleotide
Butanesulfonate + Oxygen + FMNH > Butanal + Sulfite + Water + Flavin Mononucleotide + Hydrogen ion
Alkanesulfonate + FMNH + Oxygen <> Aldehyde + Flavin Mononucleotide + Sulfite + Water
Uracil + FMNH + Oxygen + Thymine <> Ureidoacrylate peracid + Flavin Mononucleotide + (Z)-2-Methyl-ureidoacrylate peracid
SMPDB Pathways:
Pyrimidine metabolismPW000942 ThumbThumb?image type=greyscaleThumb?image type=simple
Sulfur metabolismPW000922 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0134900000-c067efd0cfc36a1e948bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2391000000-d074adaacd074db90166View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1290000000-c7e71e5446c90cf0229bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06fr-9686800000-5cbc632057bde5fb7731View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-9130000000-c711ab545300e0d990b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-b1fb1fadd3de6e9ce4bbView in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB01142
Pubchem Compound ID711
Kegg IDC01847
ChemSpider ID691
WikipediaFMNH
BioCyc IDFMNH2
EcoCyc IDFMNH2

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the reduction of soluble flavins by reduced pyridine nucleotides. Seems to reduces the complexed Fe(3+) iron of siderophores to Fe(2+), thus releasing it from the chelator
Gene Name:
fre
Uniprot ID:
P0AEN1
Molecular weight:
26242
Reactions
Reduced riboflavin + NAD(P)(+) = riboflavin + NAD(P)H.
2 cob(II)alamin + NAD(+) = 2 aquacob(III)alamin + NADH.
General function:
Involved in sulfite reductase (NADPH) activity
Specific function:
Component of the sulfite reductase complex that catalyzes the 6-electron reduction of sulfite to sulfide. This is one of several activities required for the biosynthesis of L- cysteine from sulfate
Gene Name:
cysI
Uniprot ID:
P17846
Molecular weight:
63998
Reactions
H(2)S + 3 NADP(+) + 3 H(2)O = sulfite + 3 NADPH.
General function:
Involved in sulfite reductase (NADPH) activity
Specific function:
Component of the sulfite reductase complex that catalyzes the 6-electron reduction of sulfite to sulfide. This is one of several activities required for the biosynthesis of L- cysteine from sulfate. The flavoprotein component catalyzes the electron flow from NADPH -> FAD -> FMN to the hemoprotein component
Gene Name:
cysJ
Uniprot ID:
P38038
Molecular weight:
66269
Reactions
H(2)S + 3 NADP(+) + 3 H(2)O = sulfite + 3 NADPH.
General function:
Involved in 2 iron, 2 sulfur cluster binding
Specific function:
Involved in the reduction of ferric iron in cytoplasmic ferrioxamine B
Gene Name:
fhuF
Uniprot ID:
P39405
Molecular weight:
30113
General function:
Involved in FMN reductase activity
Specific function:
Catalyzes an NAD(P)H-dependent reduction of FMN, but is also able to reduce FAD or riboflavin
Gene Name:
ssuE
Uniprot ID:
P80644
Molecular weight:
21253
Reactions
FMNH(2) + NADP(+) = FMN + NADPH.
General function:
Involved in alkanesulfonate monooxygenase activity
Specific function:
Involved in desulfonation of aliphatic sulfonates. Catalyzes the conversion of pentanesulfonic acid to sulfite and pentaldehyde and is able to desulfonate a wide range of sulfonated substrates including C-2 to C-10 unsubstituted linear alkanesulfonates, substituted ethanesulfonic acids and sulfonated buffers
Gene Name:
ssuD
Uniprot ID:
P80645
Molecular weight:
41736
Reactions
An alkanesufonate (R-CH(2)-SO(3)H) + FMNH(2) + O(2) = an aldehyde (R-CHO) + FMN + sulfite + H(2)O.
General function:
Involved in FMN binding
Specific function:
Makes part of the rut operon, which is required for the utilization of pyrimidines as sole nitrogen source
Gene Name:
rutF
Uniprot ID:
P75893
Molecular weight:
17749
Reactions
FMNH(2) + NAD(+) = FMN + NADH.
General function:
Involved in oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen
Specific function:
Part of the rut operon, which is required for the utilization of pyrimidines as sole nitrogen source
Gene Name:
rutA
Uniprot ID:
P75898
Molecular weight:
42219
Reactions
Uracil + FMNH(2) + O(2) = (Z)-3-ureidoacrylate peracid + FMN + H(2)O.
Thymine + FMNH(2) + O(2) = (Z)-2-methylureidoacrylate peracid + FMN + H(2)O.