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Showing Compound FMNH (FDB022449)

Record Information
Version1.0
Creation date2011-09-21 00:14:12 UTC
Update date2020-09-17 15:40:48 UTC
Primary IDFDB022449
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameFMNH
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 is an extremely weak basic (essentially neutral) compound (based on its pKa). FMNH2 exists in all living species, ranging from bacteria to humans. Within humans, FMNH2 participates in a number of enzymatic reactions. In particular, 24,25-dihydrolanosterol and FMNH2 can be converted into formic acid, flavin mononucleotide, and 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8-en-3β-ol through its interaction with the enzyme lanosterol 14-alpha demethylase. In addition, 4,4-dimethyl-14α-hydroxymethyl-5α-cholesta-8-en-3β-ol and FMNH2 can be converted into 4,4-dimethyl-14α-formyl-5α-cholest-8-en-3β-ol, flavin mononucleotide, and formic acid through its interaction with the enzyme lanosterol 14-alpha demethylase. The reduced 1,5-dihydro form of flavin mononucleotide. In humans, FMNH2 is involved in kandutsch-russell pathway (cholesterol biosynthesis).
CAS Number5666-16-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1,5-Dihydroriboflavin 5'-(dihydrogen phosphate)ChEBI
Flavin mononucleotide (reduced)ChEBI
FMNHChEBI
Reduced FMNChEBI
1,5-Dihydroriboflavin 5'-(dihydrogen phosphoric acid)Generator
Reduced flavin mononucleotideHMDB
Flavin mononucleotide hydroquinoneMeSH, HMDB
1,5-Dihydroriboflavin 5'-(dihydrogen ate)ChEBI
1,5-Dihydroriboflavin 5'-(dihydrogen ic acid)Generator
FMNH2hmdb
reduced flavin mononucleotidehmdb
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC17H23N4O9P
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
InChI IdentifierInChI=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
InChI KeyYTNIXZGTHTVJBW-SCRDCRAPSA-N
Isomeric SMILESCC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(O)=O)C1=C(N2)C(=O)NC(=O)N1
Average Molecular Weight458.3597
Monoisotopic Molecular Weight458.120264866
Classification
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
Ontology
Disposition

Biological location:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSFMNH, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0007-8985500000-75b16c96ea0f481a249bSpectrum
Predicted GC-MSFMNH, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-3097008000-4a68372916e7237f45d3Spectrum
Predicted GC-MSFMNH, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0134900000-c067efd0cfc36a1e948b2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2391000000-d074adaacd074db901662015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1290000000-c7e71e5446c90cf0229b2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06fr-9686800000-5cbc632057bde5fb77312015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-9130000000-c711ab545300e0d990b82015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-b1fb1fadd3de6e9ce4bb2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0003900000-159698f8e2f51a77a6502021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01oy-2039100000-3d12d69e3f37a5d16d9d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-1091000000-4227f41a22b0e7dc3bdc2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-056r-9000800000-adceeefc6ce022df6b412021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-92fea992d3a941dc72022021-09-24View Spectrum
NMRNot Available
ChemSpider ID393046
ChEMBL IDNot Available
KEGG Compound IDC01847
Pubchem Compound ID445395
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01142
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDFNR
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDFMNH
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference