Record Information
Version1.0
Creation date2010-04-08 22:10:01 UTC
Update date2018-05-29 00:56:23 UTC
Primary IDFDB012160
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameRiboflavine
DescriptionColour additive in food, nutrient supplement. Vitamin cofactor. Riboflavin, also known as vitamin B2 or additive E101, is an easily absorbed micronutrient with a key role in maintaining health in humans and animals. It 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. Riboflavine is found in many foods, some of which are chinese cabbage, peppermint, cuttlefish, and unclassified food or beverage.
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
(-)-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 2MeSH
1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-D-ribitol, 9CIdb_source
Benzo[g]pteridine riboflavin deriv.HMDB
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-1.1ALOGPS
logP-0.92ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)6.97ChemAxon
pKa (Strongest Basic)0.76ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.05 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity96.27 m³·mol⁻¹ChemAxon
Polarizability37.5 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
DescriptionThis compound belongs to the class of organic compounds known as flavins. These 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
Physico-Chemical Properties - Experimental
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-4980000000-dd278a577316361d270aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006x-4980000000-dd278a577316361d270aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0btc-9014000000-75f046dc3c6cb008690eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0zfs-5146149000-f9db57dd1ccd4a014604View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0019000000-86365dedafa031aa7787View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-4390000000-ac1b59ab7cc2209f4241View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00dj-4900000000-72d33eb27b9bd6a13d9eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-004l-0569000000-874b71fdc78d04853bf0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-0091000000-a82c54d3153103fcdb1fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004i-0239000000-659ca9fae9643f3ce73dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0091000000-a82c54d3153103fcdb1fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0090000000-2aff124ee1fc62c13844View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0090000000-f8b29c3e2c601a944a6cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a4i-0090000000-4e8c9bd38ea0f5ae9a94View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004l-0569000000-874b71fdc78d04853bf0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0006-0092000000-1f1be5508c1d50d8dff7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0006-0092000000-74bf0b86efe72fe37198View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-057i-0069000000-bb0522be4472e049dbc5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-057i-0069000000-208440cf501d0b9050d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-006x-0029000000-8c3d72bf2a06d79bbd31View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-006x-0039000000-7d8dc991995cfc262ad1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0006-0092000000-4f524f1e6c8131751c92View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0560-0069000000-edc332be3fcbf6d0c14bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-1029000000-cb7561783d706b360970View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-4092000000-a884c2c509c2da1c9005View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-1190000000-1d77df8220a965f08454View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-007o-9068000000-99f78bac6ce18b370145View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9141000000-70e4d57c08631d27b93dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9220000000-ddd6caad2f26c593ced0View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
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).