25-Hydroxycholecalciferol (Compound)

Go to Compound classification
ID578
Name25-Hydroxycholecalciferol
SynonymsCalcidiol; Calcifediol; 25-OH-Vitamin D; Vitamin D (in blood)
StructureThumb
DescriptionMetabolite of vitamin D3 (cholecalciferol). Major circulating form of vitamin D, prehormone. Laboratory test for vitamin D status.
ClassificationCompounds > Diet > Vitamins > Vitamin D > Vitamin D3 (Cholecalciferol)
CAS number19356-17-3
PubChem ID5283731
ChEBI ID17933
FooDB IDFDB021782
HMDB IDHMDB03550

Chemical data

MolDBi data

IUPAC Name(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
Traditional IUPAC Name25-hydroxyvitamin D3
FormulaC27H44O2
InChIInChI=1S/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11+,22-12-/t20-,23+,24-,25+,27-/m1/s1
InChI KeyJWUBBDSIWDLEOM-DTOXIADCSA-N
Molecular weight400.6371
Exact mass400.334130652
SMILESC[C@H](CCCC(C)(C)O)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C

ClassyFire Taxonomy

Description belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassVitamin D and derivatives
Direct ParentVitamin D and derivatives
Alternative Parents

Publications with 25-Hydroxycholecalciferol

TitleFirst authorYear
Reliability and validity of food frequency questionnaire and nutrient biomarkers in elders with and without mild cognitive impairmentBowman2011
Relationships between dietary intakes and fasting plasma concentrations of fat-soluble vitamins in humansBooth1997
Contributions of vitamin D intake and seasonal sunlight exposure to plasma 25-hydroxyvitamin D concentration in elderly womenSalamone1994
Comparison of micronutrient intake measured by a dietary questionnaire and biochemical indicators of micronutrient statusJacques1993
Intraindividual variation in plasma 25-hydroxyvitamin D measures 5 years apart among postmenopausal womenMeng2012
Reproducibility of plasma, red blood cell, and urine biomarkers among premenopausal and postmenopausal women from the Nurses' Health StudiesKotsopoulos2010
Reproducibility of serum 25-hydroxyvitamin d and vitamin D-binding protein levels over time in a prospective cohort study of black and white adultsSonderman2012
Long-term variation in serum 25-hydroxyvitamin D concentration among participants in the Prostate, Lung, Colorectal, and Ovarian Cancer Screening TrialHofmann2010
Serum 25-hydroxyvitamin D concentrations and lung cancer risk in never-smoking postmenopausal womenCheng2017
Serum Vitamin D and Risk of Breast Cancer within Five YearsO'Brien2017
Plasma vitamin D and prostate cancer risk: results from the Selenium and Vitamin E Cancer Prevention TrialKristal2014
Serum 25-OH vitamin D levels and risk of developing prostate cancer in older menBarnett2010
Prospective study of serum 25(OH)-vitamin D concentration and risk of oesophageal and gastric cancersChen2007
Vitamin D status and skin cancer risk independent of time outdoors: 11-year prospective study in an Australian communityvan der Pols2013
Serum 25-hydroxyvitamin d and cancer risk in older adults: results from a large German prospective cohort studyOrdonez-Mena2013
Plasma 25-hydroxyvitamin D and risk of non-melanoma and melanoma skin cancer: a prospective cohort studyAfzal2013
Vitamin D status and the risk of lung cancer: a cohort study in FinlandKilkkinen2008
Plasma 25-hydroxy vitamin D and subsequent prostate cancer risk in a nested Case-Control study in Japan: The JPHC studySawada2017
Serum 25-hydroxyvitamin D, vitamin D binding protein, and prostate cancer risk in black menLayne2017
Total and Free Circulating Vitamin D and Vitamin D-Binding Protein in Relation to Colorectal Cancer Risk in a Prospective Study of African AmericansAndersen2017
Plasma 25-Hydroxyvitamin D, Vitamin D Binding Protein, and Risk of Colorectal Cancer in the Nurses' Health StudySong2016
Serum vitamin D (25OHD3) levels and the risk of different subtypes of breast cancer: A nested case-control studyShirazi2016
Circulating vitamin D in relation to cancer incidence and survival of the head and neck and oesophagus in the EPIC cohortFanidi2016
Plasma 25-Hydroxyvitamin D and Risk of Breast Cancer in Women Followed over 20 YearsEliassen2016
A prospective study of plasma 25-hydroxyvitamin D concentration and prostate cancer riskDeschasaux2016
Serum 25-hydroxyvitamin D, vitamin D binding protein and risk of colorectal cancer in the Prostate, Lung, Colorectal and Ovarian Cancer Screening TrialWeinstein2015
Vitamin D-binding protein and pancreatic cancer: a nested case-control studyPiper2015
Circulating Vitamin D Levels and Risk of Colorectal Cancer in WomenChandler2015
Serum 25-hydroxyvitamin D concentrations and risk of prostate cancer: results from the Prostate Cancer Prevention TrialSchenk2014
Circulating 25-hydroxyvitamin D3 in relation to renal cell carcinoma incidence and survival in the EPIC cohortMuller2014
Vitamin D-binding protein, circulating vitamin D and risk of renal cell carcinomaMondul2014
Plasma 25-hydroxyvitamin D3 is associated with decreased risk of postmenopausal breast cancer in whites: a nested case-control study in the multiethnic cohort studyKim2014
Prediagnostic circulating vitamin D levels and risk of hepatocellular carcinoma in European populations: a nested case-control studyFedirko2014
Serum vitamin D, vitamin D binding protein, and risk of colorectal cancerAnic2014
Circulating 25-hydroxyvitamin D, vitamin D-binding protein and risk of prostate cancerWeinstein2013
Association between serum 25(OH) vitamin D, incident liver cancer and chronic liver disease mortality in the Linxian Nutrition Intervention Trials: a nested case-control studyWang2013
Vitamin D, season, and risk of prostate cancer: a nested case-control study within Norwegian health studiesMeyer2013
Plasma 25-hydroxyvitamin D concentration and lymphoma risk: results of the European Prospective Investigation into Cancer and NutritionLuczynska2013
Plasma 25-hydroxyvitamin D and the risk of breast cancer in the European prospective investigation into cancer and nutrition: a nested case-control studyKuhn2013
The influence of health and lifestyle characteristics on the relation of serum 25-hydroxyvitamin D with risk of colorectal and breast cancer in postmenopausal womenNeuhouser2012
Influence of vitamin D binding protein on the association between circulating vitamin D and risk of bladder cancerMondul2012
Serum vitamin D and risk of bladder cancer in the Prostate, Lung, Colorectal, and Ovarian (PLCO) Cancer Screening trialMondul2012
Pre-diagnostic circulating vitamin D and risk of melanoma in menMajor2012
Vitamin D, PTH, and calcium and the risk of prostate cancer: a prospective nested case-control studyBrandstedt2012
Serum 25-hydroxyvitamin D and risk of lung cancer in male smokers: a nested case-control studyWeinstein2011
Serum 25-hydroxyvitamin D and risks of colon and rectal cancer in Finnish menWeinstein2011
Circulating levels of vitamin D and colon and rectal cancer: the Physicians' Health Study and a meta-analysis of prospective studiesLee2011
Plasma 25-hydroxyvitamin D and risk of breast cancer in the Nurses' Health Study IIEliassen2011
Serum 25-hydroxyvitamin D and risk of oropharynx and larynx cancers in Finnish menArem2011
Plasma 25-hydroxyvitamin D levels and the risk of colorectal cancer: the multiethnic cohort studyWoolcott2010
Independent and joint effects of serum 25-hydroxyvitamin D and calcium on ovarian cancer risk: a prospective nested case-control studyToriola2010
Serum 25-hydroxyvitamin D and the risk of ovarian cancerToriola2010
Inverse association between serum 25(OH) vitamin D levels and non-melanoma skin cancer in elderly menTang2010
Plasma 25-hydroxyvitamin D and prostate cancer risk: the multiethnic cohortPark2010
Serum vitamin D and risk of bladder cancerMondul2010
Association between pre-diagnostic circulating vitamin D concentration and risk of colorectal cancer in European populations:a nested case-control studyJenab2010
Serum 25(OH) vitamin D and risk of breast cancer: a nested case-control study from the French E3N cohortEngel2010
Association of prediagnostic serum vitamin D levels with the development of basal cell carcinomaAsgari2010
Serum levels of vitamin D, PTH and calcium and breast cancer risk-a prospective nested case-control studyAlmquist2010
Serum 25-hydroxyvitamin D at pregnancy and risk of breast cancer in a prospective studyAgborsangaya2010
Serum vitamin D and risk of prostate cancer in a case-control analysis nested within the European Prospective Investigation into Cancer and Nutrition (EPIC)Travis2009
Serum vitamin D and risk of pancreatic cancer in the prostate, lung, colorectal, and ovarian screening trialStolzenberg-Solomon2009
Reduced prediagnostic 25-hydroxyvitamin D levels in women with breast cancer: a nested case-control studyRejnmark2009
Serum 25-hydroxyvitamin D concentrations and postmenopausal breast cancer risk: a nested case control study in the Cancer Prevention Study-II Nutrition CohortMcCullough2009
A prospective investigation of serum 25-hydroxyvitamin D and risk of lymphoid cancersLim2009
Serum levels of vitamin D metabolites and breast cancer risk in the prostate, lung, colorectal, and ovarian cancer screening trialFreedman2008
Serum vitamin D concentration and prostate cancer risk: a nested case-control studyAhn2008
Plasma vitamin D and risk of colorectal cancer: the Japan Public Health Center-Based Prospective StudyOtani2007
Lack of association between serum levels of 25-hydroxyvitamin D and the subsequent risk of prostate cancer in Finnish menFaupel-Badger2007
A prospective nested case-control study of vitamin D status and pancreatic cancer risk in male smokersStolzenberg-Solomon2006
Plasma 25-hydroxyvitamin D and 1,25-dihydroxyvitamin D and risk of breast cancerBertone-Johnson2005
Plasma 1,25-dihydroxy- and 25-hydroxyvitamin D and subsequent risk of prostate cancerPlatz2004
Plasma levels of 25-hydroxyvitamin D, 1,25-dihydroxyvitamin D and the risk of prostate cancerJacobs2004
Plasma vitamin D metabolites and risk of colorectal cancer in womenFeskanich2004
Prostate cancer risk and prediagnostic serum 25-hydroxyvitamin D levels (Finland)Ahonen2000
Serum vitamin D metabolite levels and the subsequent development of prostate cancer (Hawaii, United States)Nomura1998
Serum levels of vitamin D metabolites and the subsequent risk of colon and rectal cancer in Finnish menTangrea1997
Colon cancer and serum vitamin D metabolite levels 10-17 years prior to diagnosisBraun1995
Circulating 25-hydroxyvitamin D and risk of epithelial ovarian cancer: Cohort Consortium Vitamin D Pooling Project of Rarer CancersZheng2010
Circulating 25-hydroxyvitamin D and risk of endometrial cancer: Cohort Consortium Vitamin D Pooling Project of Rarer CancersZeleniuch-Jacquotte2010
Circulating 25-hydroxyvitamin D and risk of pancreatic cancer: Cohort Consortium Vitamin D Pooling Project of Rarer CancersStolzenberg-Solomon2010
Circulating 25-hydroxyvitamin D and risk of non-hodgkin lymphoma: Cohort Consortium Vitamin D Pooling Project of Rarer CancersPurdue2010
Circulating 25-hydroxyvitamin D and risk of kidney cancer: Cohort Consortium Vitamin D Pooling Project of Rarer CancersGallicchio2010
Circulating 25-hydroxyvitamin D and risk of esophageal and gastric cancer: Cohort Consortium Vitamin D Pooling Project of Rarer CancersAbnet2010
Interactions between plasma levels of 25-hydroxyvitamin D, insulin-like growth factor (IGF)-1 and C-peptide with risk of colorectal cancerWu2011
Low plasma 25-hydroxyvitamin D and risk of tobacco-related cancerAfzal2013
In older men, lower plasma 25-hydroxyvitamin D is associated with reduced incidence of prostate, but not colorectal or lung cancerWong2014
Pre-diagnostic plasma 25-hydroxyvitamin D levels and risk of non-melanoma skin cancer in womenLiang2012
Circulating levels of 25-hydroxyvitamin D and risk of breast cancer: a nested case-control studyScarmo2013
Prospective population-based study of the association between serum 25-hydroxyvitamin-D levels and the incidence of specific types of cancerSkaaby2014
Plasma 25-hydroxyvitamin D and risk of colorectal cancer after adjusting for inflammatory markersSong2014
Both high and low levels of blood vitamin D are associated with a higher prostate cancer risk: a longitudinal, nested case-control study in the Nordic countriesTuohimaa2004
Plasma 25-hydroxyvitamin D and 1,25-dihydroxyvitamin D and risk of incident ovarian cancerTworoger2007
Plasma 25-hydroxyvitamin D and risk of pancreatic cancerWolpin2012
A nested case control study of plasma 25-hydroxyvitamin D concentrations and risk of colorectal cancerWu2007
Plasma 25-hydroxyvitamin D and colorectal cancer risk according to tumour immunity statusSong2016
Weight Status and Alcohol Intake Modify the Association between Vitamin D and Breast Cancer RiskDeschasaux2016
Vitamin D, PTH, and calcium and tumor aggressiveness in prostate cancer: a prospective nested case-control studyBrandstedt2016
Association Between Prediagnostic Serum 25-Hydroxyvitamin D Concentration and GliomaZigmont2015
Longitudinal biobanks-based study on the joint effects of infections, nutrition and hormones on risk of prostate cancerLumme2016
Serum 25-hydroxyvitamin D and breast cancer in the military: a case-control study utilizing pre-diagnostic serumMohr2013
Pre-diagnostic vitamin D concentrations and cancer risks in older individuals: an analysis of cohorts participating in the CHANCES consortiumOrdonez-Mena2016
Serum 25-hydroxy vitamin D and prostate cancer risk in a large nested case-control studyAlbanes2011
Association of 25-Hydroxyvitamin D with Liver Cancer Incidence and Chronic Liver Disease Mortality in Finnish Male Smokers of the ATBC StudyLai2018
Plasma 25-hydroxyvitamin D concentration and subsequent risk of total and site specific cancers in Japanese population: large case-cohort study within Japan Public Health Center-based Prospective Study cohortBudhathoki2018
Circulating Vitamin D and Colorectal Cancer Risk: An International Pooling Project of 17 CohortsMcCullough2018
No association between circulating concentrations of vitamin D and risk of lung cancer: an analysis in 20 prospective studies in the Lung Cancer Cohort Consortium (LC3)Muller2018
Associations of serum 25-hydroxyvitamin D level with incidence of lung cancer and histologic types in Norwegian adults: a case-cohort analysis of the HUNT studySun2018
Circulating concentrations of vitamin D in relation to pancreatic cancer risk in European populationsvan Duijnhoven2018
High plasma 25-hydroxyvitamin D and high risk of nonmelanoma skin cancer: a Mendelian randomization study of 97 849 individualsWinslow2018
Circulating vitamin d and risk of epithelial ovarian cancerArslan2009
Plasma free 25-hydroxyvitamin D, vitamin D binding protein, and risk of breast cancer in the Nurses' Health Study IIWang2014

Biomarker data

Measurements of 25-Hydroxycholecalciferol 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 25-Hydroxycholecalciferol 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 25-Hydroxycholecalciferol with cancer risk

Cancer associations

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

Exposure data

Measurements of 25-Hydroxycholecalciferol 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 25-Hydroxycholecalciferol 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