Ergocalciferol
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Basic Info
| Common Name | Ergocalciferol(F04733) |
| 2D Structure | |
| Description | Ergocalciferol is a form of Vitamin D, also called vitamin D2. It is created from viosterol, which in turn is created when ultraviolet light activates ergosterol. Ergocalciferol is used in the treatment of hypcalcemia and in dialysis-dependent renal failure. Ergoalcifediol is a fat soluble steroid hormone precursor of vitamin D that contributes to the maintenance of normal levels of calcium and phosphorus in the bloodstream. Vitamin D2 is the form of vitamin D most commonly added to foods and nutritional supplements. Vitamin D2 must be transformed (hydroxylated) into one of two active forms via the liver or kidney. Once transformed, it binds to the vitamin D receptor that then leads to a variety of regulatory roles. |
| FRCD ID | F04733 |
| CAS Number | 50-14-6 |
| PubChem CID | 5280793 |
| Formula | C28H44O |
| IUPAC Name | (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol |
| InChI Key | MECHNRXZTMCUDQ-RKHKHRCZSA-N |
| InChI | InChI=1S/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-20,22,25-27,29H,4,7-8,11,14-18H2,1-3,5-6H3/b10-9+,23-12+,24-13-/t20-,22+,25-,26+,27-,28+/m0/s1 |
| Canonical SMILES | CC(C)C(C)C=CC(C)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C |
| Isomeric SMILES | C[C@H](/C=C/[C@H](C)C(C)C)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](CCC3=C)O)C |
| Wikipedia | Ergocalciferol |
| Synonyms |
Oleovitamin D2
ergocalciferol
VITAMIN D2
Calciferol
Viosterol
Ercalciol
Ergorone
Detalup
Condocaps
Crystallina
|
| 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 | 396.659 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 5 |
| Complexity | 678 |
| Monoisotopic Mass | 396.339 |
| Exact Mass | 396.339 |
| XLogP | 7.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 29 |
| Defined Atom Stereocenter Count | 6 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 3 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9428 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.8323 |
| P-glycoprotein Substrate | Substrate | 0.6628 |
| P-glycoprotein Inhibitor | Inhibitor | 0.7614 |
| Non-inhibitor | 0.8391 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7960 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.5154 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8432 |
| CYP450 2D6 Substrate | Non-substrate | 0.9003 |
| CYP450 3A4 Substrate | Substrate | 0.7362 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9046 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8924 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9519 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.8784 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8142 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8163 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8502 |
| Non-inhibitor | 0.7513 | |
| AMES Toxicity | Non AMES toxic | 0.9401 |
| Carcinogens | Non-carcinogens | 0.9169 |
| Fish Toxicity | High FHMT | 0.9969 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9286 |
| Honey Bee Toxicity | High HBT | 0.8651 |
| Biodegradation | Not ready biodegradable | 0.9742 |
| Acute Oral Toxicity | I | 0.8502 |
| Carcinogenicity (Three-class) | Non-required | 0.5685 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.5363 | LogS |
| Caco-2 Permeability | 1.6350 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.6931 | LD50, mol/kg |
| Fish Toxicity | -0.1791 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.9458 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| How much is too much? Two contrasting cases of excessive vitamin D supplementation. | Clin Chim Acta | 2017 Oct | 28801091 |
| 25-hydroxyvitamin D circulates in different fractions of calf plasma if the parent compound is vitamin D₂ or vitamin D₃, respectively. | J Dairy Res | 2016 Feb | 26608575 |
| Vitamin D deficiency: appropriate replenishment therapies and the effects of vitamin D toxicity. | Consult Pharm | 2010 Mar | 20363711 |
| Very high-dose ergocalciferol is effective for correcting vitamin D deficiency in children and young adults with cystic fibrosis. | J Cyst Fibros | 2009 Jul | 19447079 |
| 25-hydroxycholecalciferol in poultry nutrition. | Poult Sci | 1995 Dec | 8825582 |
| A large dose of ergocalciferol does not cause deficient blood coagulation but is extremely toxic to rats. | Toxicol Lett | 1993 Sep | 8212066 |
| On the role of corticoids in conditioning the gastric mucosa to certain toxic actions of ergocalciferol. | Br J Nutr | 1957 | 13413121 |
Targets
- 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:
- Vitamin D2 is the form of vitamin D most commonly added to foods and nutritional supplements. Vitamin D2 must be transformed (hydroxylated) into one of two active forms via the liver or kidney. Once transformed, it binds to the vitamin D receptor that then leads to a variety of regulatory roles. Vitamin D plays an important role in maintaining calcium balance and in the regulation of parathyroid hormone (PTH). It promotes renal reabsorption of calcium, increases intestinal absorption of calcium and phosphorus, and increases calcium and phosphorus mobilization from bone to plasma. Vitamin D2 and its analogs appear to promote intestinal absorption of calcium through binding to a specific receptor in the mucosal cytoplasm of the intestine. Subsequently, calcium is absorbed through formation of a calcium-binding protein.
References
- Ramos-Lopez E, Bruck P, Jansen T, Pfeilschifter JM, Radeke HH, Badenhoop K: CYP2R1-, CYP27B1- and CYP24-mRNA expression in German type 1 diabetes patients. J Steroid Biochem Mol Biol. 2007 Mar;103(3-5):807-10. Epub 2007 Jan 16. [17223345 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- 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:
- Vitamin D2 is the form of vitamin D most commonly added to foods and nutritional supplements. Vitamin D2 must be transformed (hydroxylated) into one of two active forms via the liver or kidney. Once transformed, it binds to the vitamin D receptor that then leads to a variety of regulatory roles. Vitamin D plays an important role in maintaining calcium balance and in the regulation of parathyroid hormone (PTH). It promotes renal reabsorption of calcium, increases intestinal absorption of calcium and phosphorus, and increases calcium and phosphorus mobilization from bone to plasma. Vitamin D2 and its analogs appear to promote intestinal absorption of calcium through binding to a specific receptor in the mucosal cytoplasm of the intestine. Subsequently, calcium is absorbed through formation of a calcium-binding protein.
References
- Turunen MM, Dunlop TW, Carlberg C, Vaisanen S: Selective use of multiple vitamin D response elements underlies the 1 alpha,25-dihydroxyvitamin D3-mediated negative regulation of the human CYP27B1 gene. Nucleic Acids Res. 2007;35(8):2734-47. Epub 2007 Apr 10. [17426122 ]
- 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:
- Vitamin D2 is the form of vitamin D most commonly added to foods and nutritional supplements. Vitamin D2 must be transformed (hydroxylated) into one of two active forms via the liver or kidney. Once transformed, it binds to the vitamin D receptor that then leads to a variety of regulatory roles. Vitamin D plays an important role in maintaining calcium balance and in the regulation of parathyroid hormone (PTH). It promotes renal reabsorption of calcium, increases intestinal absorption of calcium and phosphorus, and increases calcium and phosphorus mobilization from bone to plasma. Vitamin D2 and its analogs appear to promote intestinal absorption of calcium through binding to a specific receptor in the mucosal cytoplasm of the intestine. Subsequently, calcium is absorbed through formation of a calcium-binding protein.
References
- Carvallo L, Henriquez B, Olate J, van Wijnen AJ, Lian JB, Stein GS, Onate S, Stein JL, Montecino M: The 1alpha,25-dihydroxy Vitamin D3 receptor preferentially recruits the coactivator SRC-1 during up-regulation of the osteocalcin gene. J Steroid Biochem Mol Biol. 2007 Mar;103(3-5):420-4. Epub 2007 Jan 10. [17218095 ]