Calcidiol
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Basic Info
| Common Name | Calcidiol(F04731) |
| 2D Structure | |
| Description | The major circulating metabolite of vitamin D3 (cholecalciferol). It is produced in the liver and is the best indicator of the body's vitamin D stores. It is effective in the treatment of rickets and osteomalacia, both in azotemic and non-azotemic patients. Calcifediol also has mineralizing properties. |
| FRCD ID | F04731 |
| CAS Number | 19356-17-3 |
| PubChem CID | 5283731 |
| Formula | C27H44O2 |
| 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 |
| InChI Key | JWUBBDSIWDLEOM-DTOXIADCSA-N |
| InChI | InChI=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 |
| Canonical SMILES | CC(CCCC(C)(C)O)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C |
| Isomeric 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 |
| Wikipedia | Calcidiol |
| Synonyms |
Calcifediol
Calcidiol
25-hydroxyvitamin D3
25-Hydroxycholecalciferol
Calcifediol anhydrous
19356-17-3
Hidroferol
25-Hydroxyvitamin D
Calcifediolum
Didrogyl
|
| Classifies |
Predicted: Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Lipids and lipid-like molecules |
| Class | Steroids and steroid derivatives |
| Subclass | Vitamin D and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Vitamin D and derivatives |
| Alternative Parents | |
| Molecular Framework | Aliphatic homopolycyclic compounds |
| Substituents | Triterpenoid - Tertiary alcohol - Cyclic alcohol - Secondary alcohol - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Alcohol - Aliphatic homopolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as vitamin d and derivatives. These are compounds containing a secosteroid backbone, usually secoergostane or secocholestane. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 400.647 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 6 |
| Complexity | 655 |
| Monoisotopic Mass | 400.334 |
| Exact Mass | 400.334 |
| XLogP | 6.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 29 |
| Defined Atom Stereocenter Count | 5 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 2 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9164 |
| Human Intestinal Absorption | HIA+ | 0.9953 |
| Caco-2 Permeability | Caco2+ | 0.8891 |
| P-glycoprotein Substrate | Substrate | 0.7454 |
| P-glycoprotein Inhibitor | Inhibitor | 0.5209 |
| Inhibitor | 0.6087 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7849 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4758 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8379 |
| CYP450 2D6 Substrate | Non-substrate | 0.9004 |
| CYP450 3A4 Substrate | Substrate | 0.7815 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8874 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9229 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9488 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7885 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.7968 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.5600 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8189 |
| Non-inhibitor | 0.7589 | |
| AMES Toxicity | Non AMES toxic | 0.8612 |
| Carcinogens | Non-carcinogens | 0.9170 |
| Fish Toxicity | High FHMT | 0.9954 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9899 |
| Honey Bee Toxicity | High HBT | 0.8457 |
| Biodegradation | Not ready biodegradable | 0.9910 |
| Acute Oral Toxicity | I | 0.5667 |
| Carcinogenicity (Three-class) | Non-required | 0.6374 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.4276 | LogS |
| Caco-2 Permeability | 1.4574 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 4.1429 | LD50, mol/kg |
| Fish Toxicity | 0.0567 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.1261 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| [Disturbances of calcium metabolism and vitamin D supplementation in sarcoidosis - two-way street]. | Pol Merkur Lekarski | 2018 Mar 27 | 29601566 |
| Plasma 25-hydroxyvitamin D concentration and risk of type 2 diabetes andpre-diabetes: 12-year cohort study. | PLoS One | 2018 Apr 19 | 29672520 |
| Experimental study on 1,25(OH)<sub>2</sub> D<sub>3</sub> amelioration of oral lichen planus through regulating NF-κB signaling pathway. | Oral Dis | 2017 Sep | 28231625 |
| Effect of vitamin D on HbA1c levels of children and adolescents with diabetesmellitus type 1. | Minerva Pediatr | 2017 Oct | 25411949 |
| Effects of vitamin D and its metabolites on cell viability and Staphylococcusaureus invasion into bovine mammary epithelial cells. | Vet Microbiol | 2017 May | 28619151 |
| Effects of 25-hydroxycholecalciferol supplementation in maternal diets on milkquality and serum bone status markers of sows and bone quality of piglets. | Anim Sci J | 2017 Mar | 27364313 |
| Vitamin D3 supplementation using an oral spray solution resolves deficiency buthas no effect on VO2 max in Gaelic footballers: results from a randomised,double-blind, placebo-controlled trial. | Eur J Nutr | 2017 Jun | 27015912 |
| Therapeutic impact of dietary vitamin D supplementation for preventing rightventricular remodeling and improving survival in pulmonary hypertension. | PLoS One | 2017 Jul 7 | 28686688 |
| Relative biological value of 1α-hydroxycholecalciferol to25-hydroxycholecalciferol in broiler chicken diets. | Poult Sci | 2017 Jul 1 | 28339866 |
| Concentrations of calcium and 25-hydroxycholecalciferol (vitamin D3) in plasma ofwild kākāpō (Strigops habroptilus) living on two islands in New Zealand. | N Z Vet J | 2017 Jul | 28372517 |
| Vitamin D, Calcium, and Cardiovascular Disease: A"D"vantageous or "D"etrimental? An Era of Uncertainty. | Curr Atheroscler Rep | 2017 Jan | 28127710 |
| A micronutrient-fortified young-child formula improves the iron and vitamin Dstatus of healthy young European children: a randomized, double-blind controlled trial. | Am J Clin Nutr | 2017 Feb | 28052885 |
| Vitamin D supplementation to palliative cancer patients shows positive effects onpain and infections-Results from a matched case-control study. | PLoS One | 2017 Aug 31 | 28859173 |
| No Severe Hypercalcemia with Daily Vitamin D3 Supplementation of up to 30 µgduring the First Year of Life. | Horm Res Paediatr | 2017 | 28647736 |
| Hypercalcemia, hypercalciuria, and kidney stones in long-term studies of vitamin D supplementation: a systematic review and meta-analysis. | Am J Clin Nutr | 2016 Oct | 27604776 |
| Preferred natural food of breeding Kakapo is a high value source of calcium andvitamin D. | J Steroid Biochem Mol Biol | 2016 Nov | 26515407 |
| How well are the optimal serum 25OHD concentrations reached in high-doseintermittent vitamin D therapy? a placebo-controlled study on comparison between 100 000 IU and 200 000 IU of oral D3 every 3 months in elderly women. | Clin Endocrinol (Oxf) | 2016 Jun | 26725707 |
| [Vitamin D and calcium in the mirror of clinical evidence]. | Orv Hetil | 2016 Jul | 27476520 |
| Using Multicountry Ecological and Observational Studies to Determine Dietary RiskFactors for Alzheimer's Disease. | J Am Coll Nutr | 2016 Jul | 27454859 |
| Impact of Increasing Dietary Calcium Levels on Calcium Excretion and Vitamin DMetabolites in the Blood of Healthy Adult Cats. | PLoS One | 2016 Feb 12 | 26870965 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. Transcription factor that mediates the action of vitamin D3 by controlling the expression of hormone sensitive genes. Recruited to promoters via its interaction with BAZ1B/WSTF which mediates the interaction with acetylated histones, an essential step for VDR-promoter association. Plays a central role in calcium homeostasis.
- Gene Name:
- VDR
- Uniprot ID:
- P11473
- Molecular Weight:
- 48288.64 Da
- Mechanism of Action:
- Calcidiol is transformed in the kidney by 25-hydroxyvitamin D3-1-(alpha)-hydroxylase to calcitriol, the active form of vitamin D3. Calcitriol binds to intracellular receptors that then function as transcription factors to modulate gene expression. Like the receptors for other steroid hormones and thyroid hormones, the vitamin D receptor has hormone-binding and DNA-binding domains. The vitamin D receptor forms a complex with another intracellular receptor, the retinoid-X receptor, and that heterodimer is what binds to DNA. In most cases studied, the effect is to activate transcription, but situations are also known in which vitamin D suppresses transcription. Calcitriol increases the serum calcium concentrations by: increasing GI absorption of phosphorus and calcium, increasing osteoclastic resorption, and increasing distal renal tubular reabsorption of calcium. Calcitriol appears to promote intestinal absorption of calcium through binding to the vitamin D receptor in the mucosal cytoplasm of the intestine. Subsequently, calcium is absorbed through formation of a calcium-binding protein.
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Iron ion binding
- Specific Function:
- Catalyzes the conversion of 25-hydroxyvitamin D3 (25(OH)D) to 1-alpha,25-dihydroxyvitamin D3 (1,25(OH)2D) plays an important role in normal bone growth, calcium metabolism, and tissue differentiation.
- Gene Name:
- CYP27B1
- Uniprot ID:
- O15528
- Molecular Weight:
- 56503.475 Da
- Mechanism of Action:
- Calcidiol is transformed in the kidney by 25-hydroxyvitamin D3-1-(alpha)-hydroxylase to calcitriol, the active form of vitamin D3. Calcitriol binds to intracellular receptors that then function as transcription factors to modulate gene expression. Like the receptors for other steroid hormones and thyroid hormones, the vitamin D receptor has hormone-binding and DNA-binding domains. The vitamin D receptor forms a complex with another intracellular receptor, the retinoid-X receptor, and that heterodimer is what binds to DNA. In most cases studied, the effect is to activate transcription, but situations are also known in which vitamin D suppresses transcription. Calcitriol increases the serum calcium concentrations by: increasing GI absorption of phosphorus and calcium, increasing osteoclastic resorption, and increasing distal renal tubular reabsorption of calcium. Calcitriol appears to promote intestinal absorption of calcium through binding to the vitamin D receptor in the mucosal cytoplasm of the intestine. Subsequently, calcium is absorbed through formation of a calcium-binding protein.
References
- Diesel B, Radermacher J, Bureik M, Bernhardt R, Seifert M, Reichrath J, Fischer U, Meese E: Vitamin D(3) metabolism in human glioblastoma multiforme: functionality of CYP27B1 splice variants, metabolism of calcidiol, and effect of calcitriol. Clin Cancer Res. 2005 Aug 1;11(15):5370-80. [16061850 ]