Cholecalciferol
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Basic Info
| Common Name | Cholecalciferol(F04739) |
| 2D Structure | |
| Description | Cholecalciferol is only found in individuals that have used or taken this drug. It is a derivative of 7-dehydroxycholesterol formed by ultraviolet rays breaking of the C9-C10 bond. It differs from ergocalciferol in having a single bond between C22 and C23 and lacking a methyl group at C24. [PubChem]The first step involved in the activation of vitamin D3 is a 25-hydroxylation which is catalysed by the 25-hydroxylase in the liver and then by other enzymes. The mitochondrial sterol 27-hydroxylase catalyses the first reaction in the oxidation of the side chain of sterol intermediates. 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. |
| FRCD ID | F04739 |
| CAS Number | 67-97-0 |
| PubChem CID | 5280795 |
| Formula | C27H44O |
| IUPAC Name | (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol |
| InChI Key | QYSXJUFSXHHAJI-YRZJJWOYSA-N |
| InChI | InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/b22-12+,23-13-/t21-,24+,25-,26+,27-/m1/s1 |
| Canonical SMILES | CC(C)CCCC(C)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C |
| Isomeric SMILES | C[C@H](CCCC(C)C)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](CCC3=C)O)C |
| Wikipedia | Cholecalciferol |
| Synonyms |
Colecalciferol
Vitamin D3
cholecalciferol
Calciol
67-97-0
VITAMIN D
Oleovitamin D3
Arachitol
Ricketon
Trivitan
|
| 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 - 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 | 384.648 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 6 |
| Complexity | 610 |
| Monoisotopic Mass | 384.339 |
| Exact Mass | 384.339 |
| XLogP | 7.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 28 |
| 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+ | 0.9590 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.8342 |
| P-glycoprotein Substrate | Substrate | 0.6706 |
| P-glycoprotein Inhibitor | Inhibitor | 0.7603 |
| Non-inhibitor | 0.5346 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7818 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.5091 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8384 |
| CYP450 2D6 Substrate | Non-substrate | 0.9116 |
| CYP450 3A4 Substrate | Substrate | 0.7302 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9256 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9071 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9551 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9026 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.7881 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7093 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.7730 |
| Non-inhibitor | 0.7589 | |
| AMES Toxicity | Non AMES toxic | 0.9132 |
| Carcinogens | Non-carcinogens | 0.9210 |
| Fish Toxicity | High FHMT | 0.9980 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9863 |
| Honey Bee Toxicity | High HBT | 0.8681 |
| Biodegradation | Not ready biodegradable | 0.9878 |
| Acute Oral Toxicity | I | 0.8559 |
| Carcinogenicity (Three-class) | Non-required | 0.6318 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.6731 | LogS |
| Caco-2 Permeability | 1.4885 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.9310 | LD50, mol/kg |
| Fish Toxicity | -0.5056 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.2238 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Case Study: The Effect of Nutritional Intervention on Body Composition andPhysical Performance of a Female Squash Player. | Int J Sport Nutr Exerc Metab | 2018 May 1 | 29091479 |
| [Disturbances of calcium metabolism and vitamin D supplementation in sarcoidosis - two-way street]. | Pol Merkur Lekarski | 2018 Mar 27 | 29601566 |
| Survival of viral pathogens in animal feed ingredients under transboundaryshipping models. | PLoS One | 2018 Mar 20 | 29558524 |
| Effects of Vitamin D Supplementation on Semen Quality, Reproductive Hormones, andLive Birth Rate: A Randomized Clinical Trial. | J Clin Endocrinol Metab | 2018 Mar 1 | 29126319 |
| Early Infant Feeding Practices as Possible Risk Factors for ImmunoglobulinE-Mediated Food Allergies in Kuwait. | Int J Pediatr | 2018 Jun 3 | 29971112 |
| Bone health in long-term gastric cancer survivors: A prospective study ofhigh-dose vitamin D supplementation using an easy administration scheme. | J Bone Miner Metab | 2018 Jul | 28766134 |
| Effects of dietary supplementation of arginine-silicate-inositol complex onabsorption and metabolism of calcium of laying hens. | PLoS One | 2018 Jan 23 | 29360830 |
| PTH(1-34) for Surgical Hypoparathyroidism: A 2-Year Prospective, Open-LabelInvestigation of Efficacy and Quality of Life. | J Clin Endocrinol Metab | 2018 Jan 1 | 29099939 |
| Food synergies for improving bioavailability of micronutrients from plant foods. | Food Chem | 2018 Jan 1 | 28867091 |
| Nutritional risk factors and status of serum 25(OH)D levels in patients withbreast cancer: A case control study in India. | J Steroid Biochem Mol Biol | 2018 Jan | 27687737 |
| Vitamin D deficiency causes rickets in an urban informal settlement in Kenya and is associated with malnutrition. | Matern Child Nutr | 2018 Jan | 28470840 |
| Calcium in the prevention of postmenopausal osteoporosis: EMAS clinical guide. | Maturitas | 2018 Jan | 29169584 |
| Vitamin D and cardiovascular diseases: Causality. | J Steroid Biochem Mol Biol | 2018 Jan | 28027913 |
| Effects of vitamin D status on oral health. | J Steroid Biochem Mol Biol | 2018 Jan | 28161532 |
| Protection of manganese oxide nanoparticles-induced liver and kidney damage byvitamin D. | Regul Toxicol Pharmacol | 2018 Aug 10 | 30102957 |
| Vitamin D, Calcium, or Combined Supplementation for the Primary Prevention ofFractures in Community-Dwelling Adults: Evidence Report and Systematic Review forthe US Preventive Services Task Force. | JAMA | 2018 Apr 17 | 29677308 |
| Calcium supplementation in osteoporosis: useful or harmful? | Eur J Endocrinol | 2018 Apr | 29440373 |
| The Impact of Sex and 25(OH)D Deficiency on Metabolic Function in Mice. | Nutrients | 2017 Sep 7 | 28880231 |
| Vitamin D supplementation during pregnancy: Improvements in birth outcomes and complications through direct genomic alteration. | Mol Cell Endocrinol | 2017 Sep 15 | 28188842 |
| Changes in vitamin D endocrinology during aging in adults. | Mol Cell Endocrinol | 2017 Sep 15 | 28602863 |
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
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
- General Function:
- Vitamin d3 25-hydroxylase activity
- Specific Function:
- Catalyzes the first step in the oxidation of the side chain of sterol intermediates; the 27-hydroxylation of 5-beta-cholestane-3-alpha,7-alpha,12-alpha-triol. Has also a vitamin D3-25-hydroxylase activity.
- Gene Name:
- CYP27A1
- Uniprot ID:
- Q02318
- Molecular Weight:
- 60234.28 Da
- Mechanism of Action:
- The first step involved in the activation of vitamin D3 is a 25-hydroxylation which is catalysed by the 25-hydroxylase in the liver and then by other enzymes. The mitochondrial sterol 27-hydroxylase catalyses the first reaction in the oxidation of the side chain of sterol intermediates. 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
- Lehmann B, Tiebel O, Meurer M: Expression of vitamin D3 25-hydroxylase (CYP27) mRNA after induction by vitamin D3 or UVB radiation in keratinocytes of human skin equivalents--a preliminary study. Arch Dermatol Res. 1999 Sep;291(9):507-10. [10541881 ]
- General Function:
- Vitamin transporter activity
- Specific Function:
- Involved in vitamin D transport and storage, scavenging of extracellular G-actin, enhancement of the chemotactic activity of C5 alpha for neutrophils in inflammation and macrophage activation.
- Gene Name:
- GC
- Uniprot ID:
- P02774
- Molecular Weight:
- 52963.025 Da
- Mechanism of Action:
- The first step involved in the activation of vitamin D3 is a 25-hydroxylation which is catalysed by the 25-hydroxylase in the liver and then by other enzymes. The mitochondrial sterol 27-hydroxylase catalyses the first reaction in the oxidation of the side chain of sterol intermediates. 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
- Nykjaer A, Dragun D, Walther D, Vorum H, Jacobsen C, Herz J, Melsen F, Christensen EI, Willnow TE: An endocytic pathway essential for renal uptake and activation of the steroid 25-(OH) vitamin D3. Cell. 1999 Feb 19;96(4):507-15. [10052453 ]
- General Function:
- Vitamin d3 25-hydroxylase activity
- Specific Function:
- Has a D-25-hydroxylase activity on both forms of vitamin D, vitamin D(2) and D(3).
- Gene Name:
- CYP2R1
- Uniprot ID:
- Q6VVX0
- Molecular Weight:
- 57358.82 Da
- Mechanism of Action:
- The first step involved in the activation of vitamin D3 is a 25-hydroxylation which is catalysed by the 25-hydroxylase in the liver and then by other enzymes. The mitochondrial sterol 27-hydroxylase catalyses the first reaction in the oxidation of the side chain of sterol intermediates. 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
- Flanagan JN, Young MV, Persons KS, Wang L, Mathieu JS, Whitlatch LW, Holick MF, Chen TC: Vitamin D metabolism in human prostate cells: implications for prostate cancer chemoprevention by vitamin D. Anticancer Res. 2006 Jul-Aug;26(4A):2567-72. [16886665 ]