Showing metabocard for Riboflavin (BMDB0000244)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:27:18 UTC
Update Date2020-06-04 20:46:39 UTC
BMDB IDBMDB0000244
Secondary Accession Numbers
  • BMDB00244
Metabolite Identification
Common NameRiboflavin
DescriptionRiboflavin, also known as vitamin B2 or lactoflavin, 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 a drug which is used for the treatment of ariboflavinosis (vitamin b2 deficiency). Riboflavin exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Riboflavin exists in all living species, ranging from bacteria to humans. Riboflavin is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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
Chemical FormulaC17H20N4O6
Average Molecular Weight376.3639
Monoisotopic Molecular Weight376.138284392
IUPAC Name7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione
Traditional Nameriboflavin
CAS Registry Number83-88-5
SMILES
CC1=C(C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=NC(=O)NC(=O)C3=NC2=C1
InChI Identifier
InChI=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
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
Ontology
StatusDetected and Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point290 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0847 mg/mLNot Available
LogP-1.46HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Erythrocyte
  • Heart
  • Kidney
  • Liver
  • Milk
  • Placenta
  • Prostate Tissue
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
ErythrocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
HeartExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.251 uMNot SpecifiedNot SpecifiedNormal
    • Park, Y. W; Juáre...
 details
MilkDetected and Quantified3.268 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified3.268 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.915 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified3.72 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified2.79 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified5.101 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.597 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.915 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified5.155 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.65 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.836 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.836 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.676 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified5.0483 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.676 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.278 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified5.155 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.597 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified5.155 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.915 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.915 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.517 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.543 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.517 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified18.599 - 63.237 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified4.49 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.49 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.597 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.57 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.57 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified3.720 - 4.384 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified6.0 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified5.8 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified6.3 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified5.8 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000244
DrugBank IDDB00140
Phenol Explorer Compound IDNot Available
FooDB IDFDB012160
KNApSAcK IDC00001552
Chemspider ID431981
KEGG Compound IDC00255
BioCyc IDRIBOFLAVIN
BiGG IDNot Available
Wikipedia LinkRiboflavin
METLIN IDNot Available
PubChem Compound493570
PDB IDNot Available
ChEBI ID17015
References
Synthesis ReferenceTishler, 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.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309. [PubMed:17558655 ]
  2. Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S. [PubMed:22081685 ]
  3. Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W. (2007). Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113 doi: 10.1016/j.smallrumres.2006.09.013. Small Ruminant Research.
  4. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
  5. USDA Food Composition Databases [Link]
  6. Fooddata+, The Technical University of Denmark (DTU) [Link]

Enzymes

Enzyme Details
1. Triokinase/FMN cyclase
General function:
Carbohydrate transport and metabolism
Specific function:
Catalyzes both the phosphorylation of dihydroxyacetone and of glyceraldehyde, and the splitting of ribonucleoside diphosphate-X compounds among which FAD is the best substrate. Represses IFIH1-mediated cellular antiviral response.
Gene Name:
TKFC
Uniprot ID:
Q58DK4
Molecular weight:
59124.0
Enzyme Details
2. Low molecular weight phosphotyrosine protein phosphatase
General function:
Signal transduction mechanisms
Specific function:
Acts on tyrosine phosphorylated proteins, low-MW aryl phosphates and natural and synthetic acyl phosphates.
Gene Name:
ACP1
Uniprot ID:
P11064
Molecular weight:
18055.0
Reactions
Flavin Mononucleotide + Water → Riboflavin + Hydrogen phosphatedetails
Enzyme Details
3. RFK protein
General function:
Not Available
Specific function:
Not Available
Gene Name:
RFK
Uniprot ID:
Q3SZP4
Molecular weight:
25377.0
Reactions
Adenosine triphosphate + Riboflavin → ADP + Flavin Mononucleotidedetails