FMNH(2) (PAMDB003577)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB003577
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
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
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
Average Molecular Weight: 456.3438
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as alkyldiarylamines. These are tertiary alkylarylamines having two aryl and one alkyl groups attached to the amino group.
Kingdom Organic compounds
Super ClassOrganonitrogen compounds
Class Amines
Sub ClassTertiary amines
Direct Parent Alkyldiarylamines
Alternative Parents
Substituents
  • Alkyldiarylamine
  • Pteridine
  • Monoalkyl phosphate
  • Imidolactam
  • Benzenoid
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Organic anion
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility3.51 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity129.3 m3·mol-1ChemAxon
Polarizability42.14 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Pathways: 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 ID26330853
WikipediaFMNH
BioCyc IDFMNH2
EcoCyc IDFMNH2