Riboflavin (Compound)

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ID156
NameRiboflavin
SynonymsVitamin B2; Riboflavine
StructureThumb
DescriptionRiboflavin, also known as vitamin B2, is a vitamin found in food and used as a dietary supplement.
ClassificationCompounds > Diet > Vitamins > Vitamin B > Vitamin B2 (Riboflavin)
CAS number83-88-5
PubChem ID6759
ChEBI ID17015
FooDB IDFDB012160
HMDB IDHMDB00244

Chemical data

MolDBi data

IUPAC Name7,8-dimethyl-10-[(2R,3R,4S)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione
Traditional IUPAC Namevitamin b 2
FormulaC17H20N4O6
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-/m1/s1
InChI KeyAUNGANRZJHBGPY-MBNYWOFBSA-N
Molecular weight376.369
Exact mass376.13828438
SMILESCC1=CC2=C(C=C1C)N(C[C@@H](O)[C@@H](O)[C@@H](O)CO)C1=NC(=O)NC(=O)C1=N2

ClassyFire 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

Publications with Riboflavin

TitleFirst authorYear
Twenty-four hour urinary water-soluble vitamin levels correlate with their intakes in free-living Japanese schoolchildrenTsuji2011
Effect of cooking loss in the assessment of vitamin intake for epidemiological data in JapanKobayashi2011
Twenty-four-hour urinary water-soluble vitamin levels correlate with their intakes in free-living Japanese university studentsTsuji2010
Validity of food frequency questionnaire estimated intakes of folate and other B vitamins in a region without folic acid fortificationJohansson2010
Urinary excretion of vitamin B1, B2, B6, niacin, pantothenic acid, folate, and vitamin C correlates with dietary intakes of free-living elderly, female JapaneseTsuji2010
Intra- and inter-individual variations of blood and urinary water-soluble vitamins in Japanese young adults consuming a semi-purified diet for 7 daysShibata2009
Comparing metabolite profiles of habitual diet in serum and urinePlaydon2016
Nutrimetabolomics fingerprinting to identify biomarkers of bread exposure in a free-living population from the PREDIMED study cohortGarcia-Aloy2015
A prospective study of one-carbon metabolism biomarkers and risk of renal cell carcinomaGibson2010
Prospective study of serum B vitamins levels and oesophageal and gastric cancers in ChinaRen2016
Plasma Riboflavin and Vitamin B-6, but Not Homocysteine, Folate, or Vitamin B-12, Are Inversely Associated with Breast Cancer Risk in the European Prospective Investigation into Cancer and Nutrition-Varese CohortAgnoli2016
Alcohol consumption, one-carbon metabolites, liver cancer and liver disease mortalitySchwartz2013
A U-shaped relationship between plasma folate and pancreatic cancer risk in the European Prospective Investigation into Cancer and NutritionChuang2011
Serum B vitamin levels and risk of lung cancerJohansson2010
Vitamins B2 and B6 and genetic polymorphisms related to one-carbon metabolism as risk factors for gastric adenocarcinoma in the European prospective investigation into cancer and nutritionEussen2010
One-carbon metabolism biomarkers and risk of colon and rectal cancersWeinstein2008
One-carbon metabolism and prostate cancer risk: prospective investigation of seven circulating B vitamins and metabolitesJohansson2009
Untangling the role of one-carbon metabolism in colorectal cancer risk: a comprehensive Bayesian network analysisMyte2017
Plasma vitamins B2, B6, and B12, and related genetic variants as predictors of colorectal cancer riskEussen2010
A prospective study of one-carbon metabolism biomarkers and cancer of the head and neck and esophagusFanidi2015
Low vitamin B12 increases risk of gastric cancer: A prospective study of one-carbon metabolism nutrients and risk of upper gastrointestinal tract cancerMiranti2017
Circulating biomarkers of one-carbon metabolism in relation to renal cell carcinoma incidence and survivalJohansson2014

Biomarker data

Measurements of Riboflavin in biospecimens

Concentration values

IDParent IDDepthSubject groupPopulationCountryCohortBiomarker Time definitionBiospecimenAnalytical methodBiomarkerBiomarker detailMeasurement sizeDetected (nb)Detected (%)Detected only?Arithmethic meanArithmethic SDGeometric meanGeometric SDMinMin (detected)Percentile_05Percentile_10Percentile_25MedianPercentile_75Percentile_90Percentile_95MaxInterquartile rangeMean 95% CI lowerMean 95% CI upperGMean 95% CI lowerGMean 95% CI upperUnitConverted arithmetic meanConverted geometric meanConverted medianConverted unitAdjustment typeAdjusted onRegressed onExpressed asPublication

Reproducibility values

IDExcretion IDSubject groupPopulationCountryCohortBiomarker Time definitionBiospecimenAnalytical methodBiomarkerBiomarker detailArithmetic meanGeometric meanMedianUnitAdjusted onReproducibility sizeICCICC 95% CI lowerICC 95% CI upperCV% WSCV% BSVAR WSVAR BSPublication

Associations of Riboflavin with exposures

Correlation values

IDIntake IDExcretion IDSubject groupPopulationCountryCohortIntake Time definitionIntake Assessment methodIntakeIntake detailSupplement intakes included?Intake Arithmetic meanIntake Geometric meanIntake MedianIntake UnitIntake Adjusted onBiomarker Time definitionBiospecimenAnalytical methodBiomarkerBiomarker detailBiomarker Arithmetic meanBiomarker Geometric meanBiomarker MedianBiomarker UnitBiomarker Adjusted onCorrelation sizeCorrelation typeCorrelation valueCorrelation 95% CI lowerCorrelation 95% CI upperCorrelation p-valueSignificant?Measurement adjustmentDeattenuated?CovariatesPublication

Metabolomic associations

IDIntake IDExcretion IDSubject groupPopulationCountryCohortNo. of subjectsIntake Assessment methodIntakeIntervention doseBiospecimenAnalytical methodBiomarkerStructural identificationFeature selectionArea under curveSensitivitySpecificityPLS-DA VIPBeta coefficientBeta coefficient p-valueANOVA p-valuePublication

Associations of Riboflavin with cancer risk

Cancer associations

IDExcretion IDSubject groupPopulationCountryCohortNo. of subjectsNo. of casesNo. of controlsBiospecimenAnalytical methodBiomarkerBiomarker detailCancerStudy designPublication

Exposure data

Measurements of Riboflavin exposures in populations

Intake values

IDParent IDDepthSubject groupPopulationCountryCohortIntake Time definitionIntake assessment toolIntake food coverageIntake time coverageIntake Assessment methodIntakeIntake detailFood descriptionSupplement intakes included?Measurement sizeDetected (nb)Detected (%)Detected only?Arithmethic meanArithmethic SDGeometric meanGeometric SDMinMin (detected)Percentile_05Percentile_10Percentile_25MedianPercentile_75Percentile_90Percentile_95MaxInterquartile rangeMean 95% CI lowerMean 95% CI upperGMean 95% CI lowerGMean 95% CI upperUnitConverted arithmetic meanConverted geometric meanConverted medianConverted unitAdjustment typeAdjusted onRegressed onExpressed asPublication

Associations of Riboflavin exposures with biomarkers

Correlation values

IDIntake IDExcretion IDSubject groupPopulationCountryCohortIntake Time definitionIntake Assessment methodIntakeIntake detailSupplement intakes included?Intake Arithmetic meanIntake Geometric meanIntake MedianIntake UnitIntake Adjusted onBiomarker Time definitionBiospecimenAnalytical methodBiomarkerBiomarker detailBiomarker Arithmetic meanBiomarker Geometric meanBiomarker MedianBiomarker UnitBiomarker Adjusted onCorrelation sizeCorrelation typeCorrelation valueCorrelation 95% CI lowerCorrelation 95% CI upperCorrelation p-valueSignificant?Measurement adjustmentDeattenuated?CovariatesPublication