Record Information
Version1.0
Creation date2010-04-08 22:10:01 UTC
Update date2020-09-17 15:38:30 UTC
Primary IDFDB012160
Secondary Accession Numbers
  • FDB031145
Chemical Information
FooDB NameRiboflavine
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. It occurs in the free form only in the retina of the eye, in whey, and in urine; its principal forms in tissues and cells are as flavin mononucleotide and flavin-adenine dinucleotide. Riboflavin is a drug which is used for the treatment of ariboflavinosis (vitamin b2 deficiency). The antioxidant activity of riboflavin is principally derived from its role as a precursor of FAD and the role of this cofactor in the production of the antioxidant reduced glutathione. Riboflavin is an extremely weak basic (essentially neutral) compound (based on its pKa). Riboflavin exists in all living species, ranging from bacteria to humans. Binds to riboflavin hydrogenase, riboflavin kinase, and riboflavin synthase. In humans, riboflavin is involved in the metabolic disorder called the medium chain acyl-coa dehydrogenase deficiency (mcad) pathway. Outside of the human body, Riboflavin is found, on average, in the highest concentration within a few different foods, such as saffrons, saskatoon berries, and leavening agents and in a lower concentration in grape wines, hippoglossus (common halibut), and spiny lobsters. Riboflavin has also been detected, but not quantified in, several different foods, such as bog bilberries, lowbush blueberries, greenthread tea, nanking cherries, and black radish. This could make riboflavin a potential biomarker for the consumption of these foods. Riboflavin is a potentially toxic compound. Nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, and leafy vegetables. The richest natural source is yeast.
CAS Number83-88-5
Structure
Thumb
Synonyms
SynonymSource
1-Deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentitolChEBI
6,7-Dimethyl-9-D-ribitylisoalloxazineChEBI
7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4(3H,10H)-dioneChEBI
7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)isoalloxazineChEBI
7,8-Dimethyl-10-ribitylisoalloxazineChEBI
e101ChEBI
LactoflavinChEBI
RiboflavinaChEBI
RIBOFLAVINEChEBI
RiboflavinumChEBI
Vitamin b2ChEBI
Vitamin gChEBI
BisulaseKegg
(-)-RiboflavinHMDB
1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-D-ribitolHMDB
6,7-Dimethyl-9-ribitylisoalloxazineHMDB
7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-benzo[g]pteridine-2,4(3H,10H)-dioneHMDB
BeflavinHMDB
BeflavineHMDB
Benzo[g]pteridine riboflavin deriv.HMDB
e 101HMDB
FlavaxinHMDB
Flavin BBHMDB
FlaxainHMDB
FOOD Yellow 15HMDB
HyreHMDB
LactobeneHMDB
LactoflavineHMDB
RibipcaHMDB
RibocrisinaHMDB
RibodermHMDB
RibosynHMDB
RibotoneHMDB
RibovelHMDB
Russupteridine yellow IIIHMDB
San yellow bHMDB
VitaflavineHMDB
Vitasan b2HMDB
Vitamin b 2HMDB
1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-D-ribitol, 9CIdb_source
E101db_source
Food Yellow 15biospider
Isoalloxazine, 7,8-dimethyl-10-D-ribityl-biospider
Ovoflavinedb_source
Riboflavinbiospider
Vitamin B2db_source
Vitamin Gdb_source
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H20N4O6
IUPAC name7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione
InChI IdentifierInChI=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
InChI KeyAUNGANRZJHBGPY-SCRDCRAPSA-N
Isomeric SMILESCC1=C(C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=NC(=O)NC(=O)C3=NC2=C1
Average Molecular Weight376.3639
Monoisotopic Molecular Weight376.138284392
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 54.25%; H 5.36%; N 14.89%; O 25.51%DFC
Melting PointMp 280° dec.DFC
Boiling PointNot Available
Experimental Water Solubility0.0847 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-1.46HANSCH,C ET AL. (1995)
Experimental pKapKa2 10.2 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -125 (20N NaOH)DFC
Spectroscopic UV Data455 () (H2O)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSRiboflavine, non-derivatized, GC-MS Spectrumsplash10-006x-4980000000-dd278a577316361d270aSpectrum
GC-MSRiboflavine, non-derivatized, GC-MS Spectrumsplash10-006x-4980000000-dd278a577316361d270aSpectrum
Predicted GC-MSRiboflavine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0btc-9014000000-75f046dc3c6cb008690eSpectrum
Predicted GC-MSRiboflavine, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0zfs-5146149000-f9db57dd1ccd4a014604Spectrum
Predicted GC-MSRiboflavine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRiboflavine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRiboflavine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRiboflavine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRiboflavine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRiboflavine, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRiboflavine, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRiboflavine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRiboflavine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRiboflavine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRiboflavine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRiboflavine, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRiboflavine, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRiboflavine, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRiboflavine, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRiboflavine, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRiboflavine, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRiboflavine, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRiboflavine, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRiboflavine, TMS_3_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSRiboflavine, TMS_3_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-0091000000-a82c54d3153103fcdb1f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0091000000-a82c54d3153103fcdb1f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0090000000-2aff124ee1fc62c138442017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0090000000-f8b29c3e2c601a944a6c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0090000000-4e8c9bd38ea0f5ae9a942017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0090000000-5288e9226616bb75603c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0093000000-5999e10d04a53f4dae9b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0091000000-8f391045e25f26d533842021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-08fv-0290000000-b4d5f66b726c01d08c552021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-4690000000-d195fd5aee22ece7f2ec2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004i-0039000000-549fbc0a59262f64680e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0195000000-58354696aaddaffc0fd82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0f76-9231000000-67715e21d6e9ce2655fe2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-0090000000-838afb0228d293bee0a32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2190000000-b659be001c9aa265c2572021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-0090000000-21473bfb7f4a3eafd0592021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0019000000-86365dedafa031aa77872012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-4390000000-ac1b59ab7cc2209f42412012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00dj-4900000000-72d33eb27b9bd6a13d9e2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-004l-0569000000-874b71fdc78d04853bf02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004i-0239000000-659ca9fae9643f3ce73d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004l-0569000000-874b71fdc78d04853bf02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0006-0092000000-1f1be5508c1d50d8dff72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0006-0092000000-74bf0b86efe72fe371982017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-057i-0069000000-bb0522be4472e049dbc52017-09-14View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID431981
ChEMBL IDCHEMBL1534
KEGG Compound IDC00255
Pubchem Compound ID493570
Pubchem Substance IDNot Available
ChEBI ID17015
Phenol-Explorer IDNot Available
DrugBank IDDB00140
HMDB IDHMDB00244
CRC / DFC (Dictionary of Food Compounds) IDHDV43-H:HDV43-H
EAFUS ID3302
Dr. Duke IDVITAMIN-B-2|VIT-B2|RIBOFLAVIN
BIGG ID34409
KNApSAcK IDNot Available
HET IDRBF
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDRiboflavin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti arabiflavinoticDUKE
anti carpal-tunnelDUKE
anti cataract52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti cephalagic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti cervicaldysplasic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti cheiliticDUKE
anti cheiloticDUKE
anti decubiticDUKE
anti glossiticDUKE
anti keratiticDUKE
anti Lyme33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti migraine52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti pellagric52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti photophobic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
Enzymes
NameGene NameUniProt ID
Lysosomal acid phosphataseACP2P11117
Testicular acid phosphataseACPTQ9BZG2
Prostatic acid phosphataseACPPP15309
Lysophosphatidic acid phosphatase type 6ACP6Q9NPH0
Putative uncharacterized protein ACP1ACP1B5MCC7
Glycogen phosphorylase, liver formPYGLP06737
Solute carrier family 52, riboflavin transporter, member 1SLC52A1Q9NWF4
Pathways
NameSMPDB LinkKEGG Link
Riboflavin MetabolismSMP00070 map00740
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).