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Record Information
Version	2.0
Creation Date	2012-10-10 12:21:08 -0600
Update Date	2015-06-03 17:26:07 -0600
Secondary Accession Numbers	ECMDB23187
Identification
Name:	FMNH(2)
Description	FMNH2 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	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xaf84cee8> Close
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.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Flavin nucleotides
Sub Class	Not Available
Direct Parent	Flavin nucleotides
Alternative Parents	Flavins Alkyldiarylamines Monosaccharide phosphates Pyrimidones Alkyl phosphates Benzenoids Heteroaromatic compounds Vinylogous amides Lactams Ureas Secondary alcohols Polyols Secondary amines Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Organic anions
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 Framework	Aromatic heteropolycyclic compounds
External Descriptors	organophosphate oxoanion (CHEBI:57618 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 3.51 g/L ALOGPS logP 0.17 ALOGPS logP 0.76 ChemAxon logS -2.1 ALOGPS pKa (Strongest Acidic) 1.49 ChemAxon pKa (Strongest Basic) -1.1 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 12 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 214.62 Ų ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 129.3 m³·mol⁻¹ ChemAxon Polarizability 42.14 ų ChemAxon Number of Rings 3 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Uracil + FMNH(2) + Oxygen > Ureidoacrylate peracid + Flavin Mononucleotide + Water Thymine + FMNH(2) + Oxygen > (Z)-2-Methyl-ureidoacrylate peracid + Flavin Mononucleotide + Water FMNH(2) + NAD > Flavin Mononucleotide + NADH An alkanesufonate (R-CH(2)-SO(3)H) + FMNH(2) + Oxygen > an aldehyde (R-CHO) + Flavin Mononucleotide + Sulfite + Water FMNH(2) + NADP > Flavin Mononucleotide + NADPH
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0a4i-0000900000-e455e3948eae153eec05 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0a4j-4501900000-27f922a0e5002ebf5ed9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0f6w-9581100000-a918c84784030cbb62da View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0a4i-4200900000-ee59b527071c2c3ae265 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004j-9100000000-53f2bfcd8bdcb9a5cfb0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-6cc277e65a4b3ea534bc View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Not Available
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 16048 HMDB ID HMDB01142 Pubchem Compound ID 445395 Kegg ID C01847 ChemSpider ID Not Available Wikipedia FMNH BioCyc ID FMNH2 EcoCyc ID FMNH2

Enzymes