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FMNH2 (YMDB00686)

Identification
YMDB IDYMDB00686
NameFMNH2
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionFMNH2, also known as FMNH or reduced FMN, 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. FMNH2 exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on FMNH2.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1,5-dihydroriboflavin 5'-(dihydrogen phosphate)
  • flavin mononucleotide (reduced)
  • FMNH2
  • Reduced FMN
  • FMNH
  • 1,5-Dihydroriboflavin 5'-(dihydrogen phosphoric acid)
  • Reduced flavin mononucleotide
  • Flavin mononucleotide hydroquinone
CAS numberNot Available
WeightAverage: 458.3597
Monoisotopic: 458.120264866
InChI KeyYTNIXZGTHTVJBW-SCRDCRAPSA-N
InChIInChI=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)/t11-,12+,14-/m0/s1
IUPAC Name{[(2R,3S,4S)-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 Namefmnh(.)
Chemical FormulaC17H23N4O9P
SMILESCC1=C(C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(O)=O)C3=C(NC2=C1)C(=O)NC(=O)N3
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
  • Alkyldiarylamine
  • Monosaccharide phosphate
  • Pteridine
  • Pyrimidone
  • Monoalkyl phosphate
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Benzenoid
  • Vinylogous amide
  • Heteroaromatic compound
  • Urea
  • Secondary alcohol
  • Lactam
  • Secondary amine
  • Azacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.64 g/LALOGPS
logP-0.17ALOGPS
logP-1.1ChemAxon
logS-2.8ALOGPS
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
Polarizability41.65 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Riboflavin metabolismPW002443 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Riboflavin metabolismec00740 Map00740
SMPDB Reactions
alkylsulfonate + FMNH2 + oxygen → Betaine aldehyde + Sulfite + Flavin Mononucleotide + water + hydron
KEGG Reactions
NADH + Flavin Mononucleotide + hydron → NAD + FMNH2
Flavin Mononucleotide + NADPH + hydron → NADP + FMNH2
Fumaric acid + FMNH2 ↔ Flavin Mononucleotide + Succinic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-8985500000-75b16c96ea0f481a249bJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0a4i-3097008000-4a68372916e7237f45d3JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0134900000-c067efd0cfc36a1e948bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2391000000-d074adaacd074db90166JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1290000000-c7e71e5446c90cf0229bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06fr-9686800000-5cbc632057bde5fb7731JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-9130000000-c711ab545300e0d990b8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-b1fb1fadd3de6e9ce4bbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0003900000-159698f8e2f51a77a650JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01oy-2039100000-3d12d69e3f37a5d16d9dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-1091000000-4227f41a22b0e7dc3bdcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-056r-9000800000-adceeefc6ce022df6b41JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-92fea992d3a941dc7202JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Sharp, R. E., Chapman, S. K., Reid, G. A. (1996). "Modulation of flavocytochrome b2 intraprotein electron transfer via an interdomain hinge region." Biochem J 316 ( Pt 2):507-513.8687394
  • Hazzard, J. T., McDonough, C. A., Tollin, G. (1994). "Intramolecular electron transfer in yeast flavocytochrome b2 upon one-electron photooxidation of the fully reduced enzyme: evidence for redox state control of heme-flavin communication." Biochemistry 33:13445-13454.7947753
  • Liger, D., Graille, M., Zhou, C. Z., Leulliot, N., Quevillon-Cheruel, S., Blondeau, K., Janin, J., van Tilbeurgh, H. (2004). "Crystal structure and functional characterization of yeast YLR011wp, an enzyme with NAD(P)H-FMN and ferric iron reductase activities." J Biol Chem 279:34890-34897.15184374
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID16048
HMDB IDHMDB0001142
Pubchem Compound ID44229161
Kegg IDC01847
ChemSpider ID393046
FOODB IDFDB022449
WikipediaFlavin_mononucleotide
BioCyc IDFMNH2

Enzymes

Protein Details
1. Putative nitronate monooxygenase
General function:
Involved in nitronate monooxygenase activity
Specific function:
Catalyzes the oxidation of alkyl nitronates to produce the corresponding carbonyl compounds and nitrites
Gene Name:
Not Available
Uniprot ID:
P47177
Molecular weight:
45142.60156
Reactions
Ethylnitronate + O(2) + FMNH(2) → acetaldehyde + nitrite + FMN + H(2)O.
Protein Details
2. Pyridoxamine 5'-phosphate oxidase
General function:
Involved in pyridoxamine-phosphate oxidase activity
Specific function:
Catalyzes the oxidation of either pyridoxine 5'- phosphate (PNP) or pyridoxamine 5'-phosphate (PMP) into pyridoxal 5'-phosphate (PLP)
Gene Name:
PDX3
Uniprot ID:
P38075
Molecular weight:
26908.0
Reactions
Pyridoxamine 5'-phosphate + H(2)O + O(2) → pyridoxal 5'-phosphate + NH(3) + H(2)O(2).
Pyridoxine 5'-phosphate + O(2) → pyridoxal 5'-phosphate + H(2)O(2).
Protein Details
3. Fumarate reductase
General function:
Involved in electron carrier activity
Specific function:
Could be a fumarate reductase
Gene Name:
Not Available
Uniprot ID:
P32614
Molecular weight:
50843.69922
Reactions
Succinate + NAD(+) → fumarate + NADH.
Protein Details
4. Osmotic growth protein 1
General function:
Involved in electron carrier activity
Specific function:
Could be a fumarate reductase
Gene Name:
OSM1
Uniprot ID:
P21375
Molecular weight:
55064.80078
Reactions
Protein Details
5. NAD(P)H-dependent FMN reductase LOT6
General function:
Involved in FMN reductase activity
Specific function:
Has several reductase activities that are NAD(P)H- dependent and involve FMN as a cofactor, ferricyanide being the best substrate for reduction. May be involved in ferric iron assimilation
Gene Name:
LOT6
Uniprot ID:
Q07923
Molecular weight:
21280.40039
Reactions
FMNH(2) + NAD(P)(+) → FMN + NAD(P)H.