Structure via PubChem · Public domain (PubChem)
calcifediol
Sign in to saveAlso known as 25-hydroxyvitamin D3, calcidiol, Calderol, U-32070E, (3beta,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol, (3S,5Z,7E)-9,10-secocholesta-5,7,10-triene-3,25-diol, (5Z,7E)-(3S)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol, 25-hydroxycholecalciferol
Calcifediol, also known as calcidiol, 25-hydroxycholecalciferol, or 25-hydroxyvitamin D3 (abbreviated 25(OH)D3), is a form of vitamin D produced in the liver by hydroxylation of vitamin D3 (cholecalciferol) by the enzyme vitamin D 25-hydroxylase. Calcifediol can be further hydroxylated by the enzyme 25(OH)D-1α-hydroxylase, primarily in the kidney, to form calcitriol (1,25-(OH)2D3), which is the active hormonal form of vitamin D.
Chemical data
- Formula
- C27H44O2
- Molecular weight
- 400.6 g/mol
- IUPAC name
- (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol
- SMILES
- C[C@H](CCCC(C)(C)O)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](CCC3=C)O)C
- InChIKey
- JWUBBDSIWDLEOM-DTOXIADCSA-N
- XLogP
- 6.2
- Polar surface area
- 40.5 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
5,097 papers- Calcifediol: Mechanisms of Action.Nutrients · 2023
- Calcifediol for Use in Treatment of Respiratory Disease.Nutrients · 2022
- Calcifediol: a review of its pharmacological characteristics and clinical use in correcting vitamin D deficiency.European journal of nutrition · 2023
- Calcifediol (25OHD) Deficiency and Its Treatment in Women's Health and Fertility.Nutrients · 2022
- [Biosynthesis of calcifediol and calcitriol: a review].Sheng wu gong cheng xue bao = Chinese journal of biotechnology · 2024
via PubMed
Wikidata facts
- Mass
- 400.334
Show 6 more facts
- chemical formula
- C₂₇H₄₄O₂
- canonical SMILES
- CC(CCCC(C)(C)O)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C
- World Health Organisation international non-proprietary name
- calcifediol
- isomeric SMILES
- C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2\C(CCC[C@]12C)=C\C=C3\C[C@@H](O)CCC3=C
- NCI Thesaurus ID
- C77155
- Commons category
- Calcifediol
Sources (8)
via Wikidata · CC0
~8 min read
Article
9 sectionsContents
- Biology
- Blood test for vitamin D deficiency
- Supplementation
- Interactive pathway map
- History
- Research
- Other Organisms
- Teleost Fish
- References
{{chembox | Verifiedfields = changed | verifiedrevid = 480474501 | ImageFile = Calcidiol2.svg | ImageClass = skin-invert-image | ImageAlt = Skeletal formula of calcifediol | ImageFile1 = Calcifediol 3D ball.png | ImageClass1 = bg-transparent | ImageAlt1 = Ball-and-stick model of the calcifediol molecule | PIN = (1S,3Z)-3-[(2E)-2-{(1R,3aS,7aR)-1-[(2R)-6-Hydroxy-6-methylheptan-2-yl]-7a-methyloctahydro-4H-inden-4-ylidene}ethylidene]-4-methylidenecyclohexan-1-ol | OtherNames = 25-Hydroxyvitamin D325-HydroxycholecalciferolCalcidiol |Section1= |Section2= | Section6 = |Section7= }} Calcifediol, also known as calcidiol, 25-hydroxycholecalciferol, or 25-hydroxyvitamin D3 (abbreviated 25(OH)D3), is a form of vitamin D produced in the liver by hydroxylation of vitamin D3 (cholecalciferol) by the enzyme vitamin D 25-hydroxylase. Calcifediol can be further hydroxylated by the enzyme 25(OH)D-1α-hydroxylase, primarily in the kidney, to form calcitriol (1,25-(OH)2D3), which is the active hormonal form of vitamin D.
Calcifediol is strongly bound in blood by the vitamin D-binding protein. Measurement of serum calcifediol is the usual test performed to determine a person's vitamin D status, to show vitamin D deficiency or sufficiency. Calcifediol is available as an oral medication in some countries to supplement vitamin D status.