Pyridoxal 5'-phosphate (Compound)

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ID189
NamePyridoxal 5'-phosphate
SynonymsPyridoxal phosphate; PLP
StructureThumb
DescriptionActive form of vitamin B6.
ClassificationCompounds > Diet > Vitamins > Vitamin B > Vitamin B6 (Pyridoxine)
CAS number54-47-7
PubChem ID1051
ChEBI ID18405
FooDB IDFDB021820
HMDB IDHMDB01491

Chemical data

MolDBi data

IUPAC Name[(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid
Traditional IUPAC Namepyridoxal phosphate
FormulaC8H10NO6P
InChIInChI=1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14)
InChI KeyNGVDGCNFYWLIFO-UHFFFAOYSA-N
Molecular weight247.1419
Exact mass247.024573569
SMILESCC1=NC=C(COP(O)(O)=O)C(C=O)=C1O

ClassyFire Taxonomy

Description belongs to the class of organic compounds known as pyridoxals and derivatives. Pyridoxals and derivatives are compounds containing a pyridoxal moiety, which consists of a pyridine ring substituted at positions 2,3,4, and 5 by a methyl group, a hydroxyl group, a carbaldehyde group, and a hydroxymethyl group, respectively.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridine carboxaldehydes
Direct ParentPyridoxals and derivatives
Alternative Parents

Publications with Pyridoxal 5'-phosphate

TitleFirst authorYear
Effect of cooking loss in the assessment of vitamin intake for epidemiological data in JapanKobayashi2011
Validity of food frequency questionnaire estimated intakes of folate and other B vitamins in a region without folic acid fortificationJohansson2010
Reliability and validity of food frequency questionnaire and nutrient biomarkers in elders with and without mild cognitive impairmentBowman2011
Vitamin B6 status assessment in relation to dietary intake in high school students aged 16–18 yearsChang2007
Reliability of selected antioxidants and compounds involved in one-carbon metabolism in two Dutch cohortsLeenders2013
Intra- and inter-individual variations of blood and urinary water-soluble vitamins in Japanese young adults consuming a semi-purified diet for 7 daysShibata2009
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
Prediagnostic levels of serum one-carbon metabolites and risk of hepatocellular carcinomaButler2013
Prediagnostic plasma pyridoxal 5'-phosphate (vitamin b6) levels and invasive breast carcinoma risk: the multiethnic cohortLurie2012
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
Prospective study of plasma vitamin B6 and risk of colorectal cancer in menLee2009
Plasma levels of B vitamins and colorectal cancer risk: the multiethnic cohort studyLe Marchand2009
One-carbon metabolism biomarkers and risk of colon and rectal cancersWeinstein2008
Plasma folate, vitamin B-6, vitamin B-12, and risk of breast cancer in womenLin2008
Plasma vitamin B6 and the risk of colorectal cancer and adenoma in womenWei2005
Plasma folate, vitamin B6, vitamin B12, homocysteine, and risk of breast cancerZhang2003
Null association between prostate cancer and serum folate, vitamin B(6), vitamin B(12), and homocysteineWeinstein2003
Association of the B-vitamins pyridoxal 5'-phosphate (B(6)), B(12), and folate with lung cancer risk in older menHartman2001
Pancreatic cancer risk and nutrition-related methyl-group availability indicators in male smokersStolzenberg-Solomon1999
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
Vitamin B-6 and colorectal cancer risk: a prospective population-based study using 3 distinct plasma markers of vitamin B-6 statusGylling2017
Circulating Folate, Vitamin B6, and Methionine in Relation to Lung Cancer Risk in the Lung Cancer Cohort Consortium (LC3)Fanidi2018
A prospective study on folate, B12, and pyridoxal 5'-phosphate (B6) and breast cancerWu1999
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
Serum B6 vitamers (pyridoxal 5'-phosphate, pyridoxal, and 4-pyridoxic acid) and pancreatic cancer risk: two nested case-control studies in Asian populationsHuang2016
Circulating biomarkers of one-carbon metabolism in relation to renal cell carcinoma incidence and survivalJohansson2014
Plasma folate, vitamin B6, vitamin B12, and homocysteine and pancreatic cancer risk in four large cohortsSchernhammer2007
Plasma folate, vitamin B-6, and vitamin B-12 and breast cancer risk in BRCA1- and BRCA2-mutation carriers: a prospective studyKim2016

Biomarker data

Measurements of Pyridoxal 5'-phosphate 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 Pyridoxal 5'-phosphate 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 Pyridoxal 5'-phosphate with cancer risk

Cancer associations

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

Exposure data

Measurements of Pyridoxal 5'-phosphate 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 Pyridoxal 5'-phosphate 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