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Identification
YMDB IDYMDB00534
NameRiboflavin
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionRiboflavin, also known as lactoflavin or vitamin B2, belongs to the class of organic compounds known as flavins. Flavins are compounds containing a flavin (7,8-dimethyl-benzo[g]pteridine-2,4-dione) moiety, with a structure characterized by an isoalloaxzine tricyclic ring. Riboflavin is an extremely weak basic (essentially neutral) compound (based on its pKa). Riboflavin exists in all living species, ranging from bacteria to humans. Riboflavin is a potentially toxic compound.
Structure
Thumb
Synonyms
  • (-)-Riboflavin
  • 1-deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentitol
  • 6,7-Dimethyl-9-D-ribitylisoalloxazine
  • 6,7-Dimethyl-9-ribitylisoalloxazine
  • 7,8-Dimethyl-10-(1' d-ribityl)isoalloxazine
  • 7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4(3H,10H)-dione
  • 7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)isoalloxazine
  • 7,8-dimethyl-10-ribitylisoalloxazine
  • Aqua-Flave
  • Beflavin
  • Beflavine
  • Benzo[g]pteridine riboflavin deriv.
  • Dermadram
  • Fiboflavin
  • Flavaxin
  • Flavin
  • Flavin BB
  • Flaxain
  • Hyflavin
  • Hyre
  • Isoalloxazine, 7,8-dimethyl-10-D-ribityl-
  • Lactobene
  • lactoflavin
  • Lactoflavine
  • Lactoflavine, zinvit-g
  • Ovoflavin
  • Ribipca
  • Ribocrisina
  • Riboderm
  • Riboflavine
  • Riboflavinequinone
  • Ribosyn
  • Ribotone
  • Ribovel
  • Vitaflavine
  • vitamin b2
  • Vitamin Bi
  • Vitamin G
  • Vitasan B2
  • e101
  • Riboflavina
  • Riboflavinum
  • Bisulase
  • 1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-D-ribitol
  • 7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-benzo[g]pteridine-2,4(3H,10H)-dione
  • e 101
  • FOOD Yellow 15
  • Russupteridine yellow III
  • San yellow b
  • Vitamin b 2
  • Riboflavin
CAS number83-88-5
WeightAverage: 376.3639
Monoisotopic: 376.138284392
InChI KeyAUNGANRZJHBGPY-SCRDCRAPSA-N
InChIInChI=1S/C17H20N4O6/c1-7-3-9-10(4-8(7)2)21(5-11(23)14(25)12(24)6-22)15-13(18-9)16(26)20-17(27)19-15/h3-4,11-12,14,22-25H,5-6H2,1-2H3,(H,20,26,27)/t11-,12+,14-/m0/s1
IUPAC Name7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione
Traditional IUPAC Nameriboflavin
Chemical FormulaC17H20N4O6
SMILESCC1=C(C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=NC(=O)NC(=O)C3=NC2=C1
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavins. Flavins are compounds containing a flavin (7,8-dimethyl-benzo[g]pteridine-2,4-dione) moiety, with a structure characterized by an isoalloaxzine tricyclic ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassAlloxazines and isoalloxazines
Direct ParentFlavins
Alternative Parents
Substituents
  • Flavin
  • 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 Descriptors
Physical Properties
StateSolid
Charge0
Melting point290 °C
Experimental Properties
PropertyValueReference
Water Solubility0.0847 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-1.46 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.66 g/LALOGPS
logP-1ALOGPS
logP-0.92ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)5.97ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.05 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity96.27 m³·mol⁻¹ChemAxon
Polarizability37.51 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • extracellular
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Riboflavin metabolismPW002443 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Riboflavin metabolismec00740 Map00740
SMPDB Reactions
6,7-Dimethyl-8-(1-D-ribityl)lumazineRiboflavin + 5-Amino-6-ribitylamino uracil
Adenosine triphosphate + RiboflavinADP + Flavin Mononucleotide
KEGG Reactions
Flavin Mononucleotide + water Riboflavin + phosphate
Riboflavin + Adenosine triphosphateFlavin Mononucleotide + hydron + ADP
6,7-Dimethyl-8-(1-D-ribityl)lumazineRiboflavin + 5-Amino-6-ribitylamino uracil
Concentrations
Intracellular ConcentrationsNot Available
Extracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
1 ± 0 µM hops, malted barleyanaerobicBaker's yeastAlcoholic beverage, beer, regular, all - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
1 ± 0 µM grape juiceanaerobicBaker's yeastAlcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
Conversion Details Here
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-4980000000-dd278a577316361d270aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-4980000000-dd278a577316361d270aJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0btc-9014000000-75f046dc3c6cb008690eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0zfs-5146149000-f9db57dd1ccd4a014604JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0019000000-86365dedafa031aa7787JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-4390000000-ac1b59ab7cc2209f4241JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00dj-4900000000-72d33eb27b9bd6a13d9eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-004l-0569000000-874b71fdc78d04853bf0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-0091000000-a82c54d3153103fcdb1fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004i-0239000000-659ca9fae9643f3ce73dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0091000000-a82c54d3153103fcdb1fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0090000000-2aff124ee1fc62c13844JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0090000000-f8b29c3e2c601a944a6cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0090000000-4e8c9bd38ea0f5ae9a94JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004l-0569000000-874b71fdc78d04853bf0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0006-0092000000-1f1be5508c1d50d8dff7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0006-0092000000-74bf0b86efe72fe37198JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-057i-0069000000-bb0522be4472e049dbc5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-057i-0069000000-208440cf501d0b9050d7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-006x-0029000000-8c3d72bf2a06d79bbd31JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-006x-0039000000-7d8dc991995cfc262ad1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0006-0092000000-4f524f1e6c8131751c92JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0560-0069000000-edc332be3fcbf6d0c14bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-1029000000-cb7561783d706b360970JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-4092000000-a884c2c509c2da1c9005JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-1190000000-1d77df8220a965f08454JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-007o-9068000000-99f78bac6ce18b370145JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9141000000-70e4d57c08631d27b93dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9220000000-ddd6caad2f26c593ced0JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Wu, M., Repetto, B., Glerum, D. M., Tzagoloff, A. (1995). "Cloning and characterization of FAD1, the structural gene for flavin adenine dinucleotide synthetase of Saccharomyces cerevisiae." Mol Cell Biol 15:264-271.7799934
  • Alcoholic beverage, beer, regular, all - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
  • Alcoholic beverage, wine, table, red - U.S. Department of Agriculture, Agricultural Research Service. 2010. USDA National Nutrient Database for Standard Reference, Release 23. Nutrient Data Laboratory Home Page
  • Nookaew, I., Jewett, M. C., Meechai, A., Thammarongtham, C., Laoteng, K., Cheevadhanarak, S., Nielsen, J., Bhumiratana, S. (2008). "The genome-scale metabolic model iIN800 of Saccharomyces cerevisiae and its validation: a scaffold to query lipid metabolism." BMC Syst Biol 2:71.18687109
  • TSUBOI, K. K., WIENER, G., HUDSON, P. B. (1957). "Acid phosphatase. VII. Yeast phosphomonoesterase; isolation procedure and stability characteristics." J Biol Chem 224:621-635.13405892
Synthesis Reference:Tishler, Max; Pfister, Karl, III; Babson, R. D.; Ladenburg, Kurt; Fleming, Ann J. Reaction between o-aminoazo compounds and barbituric acid. A new synthesis of riboflavin. Journal of the American Chemical Society (1947), 69 1487-92.
External Links:
ResourceLink
CHEBI ID17015
HMDB IDHMDB00244
Pubchem Compound ID6759
Kegg IDC00255
ChemSpider ID23975973
FOODB IDFDB012160
WikipediaRiboflavin
BioCyc IDRIBOFLAVIN

Enzymes

General function:
Involved in acid phosphatase activity
Specific function:
A phosphate monoester + H(2)O = an alcohol + phosphate
Gene Name:
PHO11
Uniprot ID:
P35842
Molecular weight:
52757.39844
Reactions
A phosphate monoester + H(2)O → an alcohol + phosphate.
General function:
Involved in riboflavin kinase activity
Specific function:
Catalyzes the phosphorylation of riboflavin (vitamin B2) to form flavin mononucleotide (FMN) coenzyme
Gene Name:
FMN1
Uniprot ID:
Q03778
Molecular weight:
24536.90039
Reactions
ATP + riboflavin → ADP + FMN.
General function:
Involved in acid phosphatase activity
Specific function:
Partially mediates extracellular nucleotide derived phosphate hydrolysis along with NPP1 and NPP2
Gene Name:
PHO5
Uniprot ID:
P00635
Molecular weight:
52858.10156
Reactions
A phosphate monoester + H(2)O → an alcohol + phosphate.
General function:
Involved in riboflavin biosynthetic process
Specific function:
Condensation of 5-amino-6-(1'-D)-ribityl-amino- 2,4(1H,3H)-pyrimidinedione with L-3,4-dihydroxy-2-butanone 4- phosphate to produce 6,7-dimethyl-8-(1-D-ribityl)lumazine
Gene Name:
RIB4
Uniprot ID:
P50861
Molecular weight:
18555.40039
Reactions
2 6,7-dimethyl-8-(1-D-ribityl)lumazine → riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine.
General function:
Involved in riboflavin synthase activity
Specific function:
2 6,7-dimethyl-8-(1-D-ribityl)lumazine = riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine
Gene Name:
RIB5
Uniprot ID:
P38145
Molecular weight:
26195.59961
Reactions
2 6,7-dimethyl-8-(1-D-ribityl)lumazine → riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine.