Record Information
Version2.0
Creation Date2012-10-10 12:21:08 -0600
Update Date2015-06-03 17:26:07 -0600
Secondary Accession Numbers
  • ECMDB23187
Identification
Name:FMNH(2)
DescriptionFMNH2 is the reduced form of flavin mononucleotide. It is a substrate of the enzyme FMN reductase (EC 1.5.1.29), an enzyme that catalyzes the chemical reaction FMNH2 + NAD(P)+ <=> FMN + NAD(P)H + H+. 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. During a catalytic cycle, the reversible interconversion of 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.
Structure
Thumb
Synonyms:
  • (2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-1,5-dihydrobenzogpteridin-10-yl)-2,3,4-trihydroxypentyl phosphate
  • (2R,3S,4S)-5-(7,8-Dimethyl-2,4-dioxo-1,5-dihydrobenzogpteridin-10-yl)-2,3,4-trihydroxypentyl phosphoric acid
  • 1,5-dihydroriboflavin 5'-phosphate
  • 1,5-Dihydroriboflavin 5'-phosphoric acid
  • 1-Deoxy-1-(7,8-dimethyl-2,4-dioxo-1,3,4,5-tetrahydrobenzogpteridin-10(2H)-yl)-5-O-phosphonato-D-ribitol
  • FMNH2
  • FMNH2 dianion
  • Reduced flavin mononucleotide
  • Reduced flavin mononucleotide dianion
  • Reduced FMN
  • Reduced FMN dianion
  • Reduced FMN(2-)
Chemical Formula:C17H21N4O9P
Weight:Average: 456.3438
Monoisotopic: 456.104614802
InChI Key:YTNIXZGTHTVJBW-SCRDCRAPSA-L
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)/p-2/t11-,12+,14-/m0/s1
CAS number:5666-16-0
IUPAC Name:7,8-dimethyl-10-[(2S,3S,4R)-2,3,4-trihydroxy-5-(phosphonooxy)pentyl]-5H,10H-benzo[g]pteridine-2,4-bis(olate)
Traditional IUPAC Name:7,8-dimethyl-10-[(2S,3S,4R)-2,3,4-trihydroxy-5-(phosphonooxy)pentyl]-5H-benzo[g]pteridine-2,4-bis(olate)
SMILES:[H][C@@](O)(COP(O)(O)=O)[C@@]([H])(O)[C@@]([H])(O)CN1C2=C(NC3=C1N=C([O-])N=C3[O-])C=C(C)C(C)=C2
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
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Urea
  • Secondary alcohol
  • Lactam
  • Azacycle
  • Secondary amine
  • Organoheterocyclic compound
  • Polyol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organic anion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility3.51 g/LALOGPS
logP0.17ALOGPS
logP0.76ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.49ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area214.62 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity129.3 m³·mol⁻¹ChemAxon
Polarizability42.14 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000900000-e455e3948eae153eec05View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-4501900000-27f922a0e5002ebf5ed9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6w-9581100000-a918c84784030cbb62daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-4200900000-ee59b527071c2c3ae265View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9100000000-53f2bfcd8bdcb9a5cfb0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-6cc277e65a4b3ea534bcView in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16048
HMDB IDHMDB01142
Pubchem Compound ID445395
Kegg IDC01847
ChemSpider IDNot Available
WikipediaFMNH
BioCyc IDFMNH2
EcoCyc IDFMNH2

Enzymes

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.