651734-12-2
Chemical Structure
20-Hydroxyvitamin D3
Synonym(s): 20(OH)D3; 20S-Hydroxyvitamin D3
- CAS No.: 651734-12-2
- Formula:C27H44O2
- Molecular Weight:400.64
IUPAC Name: (S,Z)-3-(2-((1S,3aS,7aS,E)-1-((S)-2-hydroxy-6-methylheptan-2-yl)-7a-methyloctahydro-4H-inden-4-ylidene)ethylidene)-4-methylenecyclohexan-1-ol
InChIKey: IQEQEOBGZMEDBQ-LBRHRNEPSA-N
SMILES: C=C1CC[C@H](O)C/C1=C/C=C2[C@@](CC[C@]3([H])[C@@](C)(O)CCCC(C)C)([H])[C@]3(C)CCC/2
Biological Activity: 20-Hydroxyvitamin D3 (20(OH)D3), a product of vitamin D3 hydroxylation, is a noncalcemic immunomodulator. 20-Hydroxyvitamin D3 binds to vitamin D receptor (VDR), activates VDR and aryl hydrocarbon receptor (AhR) signaling, stimulates CYP24A1 expression, and drives VDR nuclear translocation. 20-Hydroxyvitamin D3 inhibits NF-κB activity via IκBα upregulation. 20-Hydroxyvitamin D3 acts as a substrate for CYP27B1 and rat CYP24A1, undergoing hydroxylation to form dihydroxy-derivatives. 20-Hydroxyvitamin D3 inhibits cell proliferation, colony formation, migration, and tumor growth, and induces cell differentiation in cancer cells. 20-Hydroxyvitamin D3 can be used for the research of inflammatory and autoimmune diseases, melanoma, breast carcinomas, and hepatocarcinoma[1][2][3][4].
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20-Hydroxyvitamin D3 | 20-Hydroxyvitamin D3 (20(OH)D3), a product of vitamin D3 hydroxylation, is a noncalcemic immunomodulator. 20-Hydroxyvitamin D3 binds to vitamin D receptor (VDR), activates VDR and aryl hydrocarbon receptor (AhR) signaling, stimulates CYP24A1 expression, and drives VDR nuclear translocation. 20-Hydroxyvitamin D3 inhibits NF-κB activity via IκBα upregulation. 20-Hydroxyvitamin D3 acts as a substrate for CYP27B1 and rat CYP24A1, undergoing hydroxylation to form dihydroxy-derivatives. 20-Hydroxyvitamin D3 inhibits cell proliferation, colony formation, migration, and tumor growth, and induces cell differentiation in cancer cells. 20-Hydroxyvitamin D3 can be used for the research of inflammatory and autoimmune diseases, melanoma, breast carcinomas, and hepatocarcinoma. | |||||||||||||||||||||
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References
- [1]. Brzeminski P, et al. Chemical synthesis, biological activities and action on nuclear receptors of 20S(OH)D3, 20S,25(OH)2D3, 20S,23S(OH)2D3 and 20S,23R(OH)2D3. Bioorg Chem. 2022 Apr;121:105660. [Content Brief]
- [2]. Tieu EW, et al. Rat CYP24A1 acts on 20-hydroxyvitamin D(3) producing hydroxylated products with increased biological activity. Biochem Pharmacol. 2012;84(12):1696-1704. [Content Brief]
- [3]. Wang J, et al. 20-hydroxyvitamin D₃ inhibits proliferation of cancer cells with high efficacy while being non-toxic. Anticancer Res. 2012;32(3):739-746. [Content Brief]
- [4]. Skobowiat C, et al. Noncalcemic 20-hydroxyvitamin D3 inhibits human melanoma growth in in vitro and in vivo models. Oncotarget. 2017;8(6):9823-9834. [Content Brief]
