1,25-Dihydroxycholecalciferol (Compound)

Go to Compound classification
ID1443
Name1,25-Dihydroxycholecalciferol
SynonymsCalcitriol; 1,25-Dihydroxyvitamin D
StructureThumb
DescriptionMetabolite of vitamin D3 (cholecalciferol). Biologically active form of vitamin D (hormone).
ClassificationCompounds > Diet > Vitamins > Vitamin D > Vitamin D3 (Cholecalciferol)
CAS number32222-06-3
PubChem ID5280453
ChEBI ID17823
FooDB IDFDB021822
HMDB IDHMDB01903

Chemical data

MolDBi data

IUPAC Name(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
Traditional IUPAC Namecalcitriol
FormulaC27H44O3
InChIInChI=1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24+,25+,27-/m1/s1
InChI KeyGMRQFYUYWCNGIN-NKMMMXOESA-N
Molecular weight416.6365
Exact mass416.329045274
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)C[C@H](O)C1=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 1,25-Dihydroxycholecalciferol

TitleFirst authorYear
Reproducibility of plasma, red blood cell, and urine biomarkers among premenopausal and postmenopausal women from the Nurses' Health StudiesKotsopoulos2010
Circulating levels of vitamin D and colon and rectal cancer: the Physicians' Health Study and a meta-analysis of prospective studiesLee2011
Serum levels of vitamin D metabolites and breast cancer risk in the prostate, lung, colorectal, and ovarian cancer screening trialFreedman2008
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
Serum vitamin D metabolite levels and the subsequent development of prostate cancer (Hawaii, United States)Nomura1998
Prediagnostic serum vitamin D and breast cancerHiatt1998
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
Plasma 25-hydroxyvitamin D and 1,25-dihydroxyvitamin D and risk of incident ovarian cancerTworoger2007

Biomarker data

Measurements of 1,25-Dihydroxycholecalciferol 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 1,25-Dihydroxycholecalciferol 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 1,25-Dihydroxycholecalciferol with cancer risk

Cancer associations

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

Exposure data

Measurements of 1,25-Dihydroxycholecalciferol 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 1,25-Dihydroxycholecalciferol 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