Record Information
Version2.0
Creation Date2012-07-30 14:55:12 -0600
Update Date2015-10-15 16:13:56 -0600
Secondary Accession Numbers
  • ECMDB21279
Identification
Name:Reduced riboflavin
Description:Reduced riboflavin is a member of the chemical class known as Quinoxalines. These are compounds containing a quinoxaline moiety, a bicyclic heterocycle made up of a benzene ring fused to a pyrazine ring. Compared to riboflavin, reduced riboflavin has one extra hydrogen attached to an oxygen on its ring structure. Riboflavin, also known as vitamin B2, is the central component of the cofactors FAD and FMN, and is therefore required by all flavoproteins. As such, vitamin B2 is required for a wide variety of cellular processes. It plays a key role in energy metabolism, and for the metabolism of fats, ketone bodies, carbohydrates, and proteins. The reduced form, which occurs in metabolism along with the oxidized form, is colorless. (Wikipedia)
Structure
Thumb
Synonyms:
  • 1-Deoxy-1-(7,8-dimethyl-2,4-dioxo-1,3,4,5-tetrahydrobenzo[g]pteridin-10(2H)-yl)-D-ribitol
  • 4a,5-Dihydroriboflavine
  • 7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-4a,5-dihydroisoalloxazine
  • 7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-5,10-dihydrobenzo[g]pteridine-2,4(3H,4aH)-dione
  • Reduced riboflavin
Chemical Formula:C15H16N4O6
Weight:Average: 348.3107
Monoisotopic: 348.106984264
InChI Key:ATANIONNQLTUND-CKYFFXLPSA-N
InChI:InChI=1S/C15H16N4O6/c20-6-10(22)12(23)9(21)5-19-8-4-2-1-3-7(8)16-11-13(19)17-15(25)18-14(11)24/h1-4,9-10,12,20-23H,5-6H2,(H,18,24,25)/t9-,10-,12-/m1/s1
CAS number:Not Available
IUPAC Name:7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-1H,2H,3H,4H,5H,10H-benzo[g]pteridine-2,4-dione
Traditional IUPAC Name:reduced riboflavin
SMILES:OC[C@@H](O)[C@H](O)[C@H](O)CN1C2=CC=CC=C2N=C2C(=O)NC(=O)N=C12
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alloxazines and isoalloxazines. These are organic compounds comprising the (iso)alloxazine structure (Benzo[g]pteridine-2,4-dione).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassAlloxazines and isoalloxazines
Direct ParentAlloxazines and isoalloxazines
Alternative Parents
Substituents
  • Isoalloxazine
  • Diazanaphthalene
  • Quinoxaline
  • Pyrimidone
  • Pyrazine
  • Pyrimidine
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Secondary alcohol
  • Lactam
  • Polyol
  • Azacycle
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility4.57 g/LALOGPS
logP-0.23ALOGPS
logP-0.99ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)8.49ChemAxon
pKa (Strongest Basic)-0.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area154.39 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity107.64 m³·mol⁻¹ChemAxon
Polarizability38.51 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bwi-8094000000-f43f7112ee283826153bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00di-3042269000-7f5ae8c8ce0af8c53f55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0029000000-bc104c9d050e033b69d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-4091000000-afc0f707ee1ce75b867cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-2190000000-570c6cbcf04a46a68c76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udl-4097000000-b676ae8b47eab2fb18c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-f5254591b51a0d846765View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9010000000-0abc9b0d47dd58c290bdView in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17607
HMDB IDHMDB0001557
Pubchem Compound ID11245895
Kegg IDC01007
ChemSpider ID26330553
WikipediaRiboflavin
BioCyc IDCPD-316
EcoCyc IDCPD-316

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the reduction of soluble flavins by reduced pyridine nucleotides. Seems to reduces the complexed Fe(3+) iron of siderophores to Fe(2+), thus releasing it from the chelator
Gene Name:
fre
Uniprot ID:
P0AEN1
Molecular weight:
26242
Reactions
Reduced riboflavin + NAD(P)(+) = riboflavin + NAD(P)H.
2 cob(II)alamin + NAD(+) = 2 aquacob(III)alamin + NADH.
General function:
Involved in sulfite reductase (NADPH) activity
Specific function:
Component of the sulfite reductase complex that catalyzes the 6-electron reduction of sulfite to sulfide. This is one of several activities required for the biosynthesis of L- cysteine from sulfate
Gene Name:
cysI
Uniprot ID:
P17846
Molecular weight:
63998
Reactions
H(2)S + 3 NADP(+) + 3 H(2)O = sulfite + 3 NADPH.
General function:
Involved in sulfite reductase (NADPH) activity
Specific function:
Component of the sulfite reductase complex that catalyzes the 6-electron reduction of sulfite to sulfide. This is one of several activities required for the biosynthesis of L- cysteine from sulfate. The flavoprotein component catalyzes the electron flow from NADPH -> FAD -> FMN to the hemoprotein component
Gene Name:
cysJ
Uniprot ID:
P38038
Molecular weight:
66269
Reactions
H(2)S + 3 NADP(+) + 3 H(2)O = sulfite + 3 NADPH.
General function:
Involved in 2 iron, 2 sulfur cluster binding
Specific function:
Involved in the reduction of ferric iron in cytoplasmic ferrioxamine B
Gene Name:
fhuF
Uniprot ID:
P39405
Molecular weight:
30113