VITAMIN D-3
General Information
| Mainterm | VITAMIN D-3 |
| Doc Type | ASP |
| CAS Reg.No.(or other ID) | 67-97-0 |
| Regnum |
184.1950 172.380 582.5953 |
From www.fda.gov
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 5280795 |
| 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 | 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 |
| InChI Key | QYSXJUFSXHHAJI-YRZJJWOYSA-N |
| Canonical SMILES | CC(C)CCCC(C)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C |
| Molecular Formula | C27H44O |
| Wikipedia | cholecalciferol |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 384.648 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 6 |
| Complexity | 610.0 |
| CACTVS Substructure Key Fingerprint | A A A D c f B 4 I A A A A A A A A A A A A A A A A A A A A Y A A A A A w Y A A A A A A A A G A A A A A A G g A A C A A A D x S g g A I C A A A A A g C A A i B C A A A A A A A g A A A A C A A A A A g I E A I A A Q A A Q A A E w A A I g A O A w M A P g A A A A A A A A A A A A A A A A C A A A Q A A C A A A A A = = |
| Topological Polar Surface Area | 20.2 |
| Monoisotopic Mass | 384.339 |
| Exact Mass | 384.339 |
| XLogP3 | None |
| XLogP3-AA | 7.9 |
| Compound Is Canonicalized | True |
| 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 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| 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 |
From admetSAR
ADMET Predicted Profile --- Regression
| 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 |
From admetSAR
Toxicity Profile
| Route of Exposure | Oral, readily absorbed |
|---|---|
| Mechanism of Toxicity | 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. |
| Metabolism | Within the liver, cholecalciferal is hydroxylated to calcidiol (25-hydroxycholecalciferol) by the enzyme 25-hydroxylase. Within the kidney, calcidiol serves as a substrate for 1-alpha-hydroxylase, yielding calcitriol (1,25-dihydroxycholecalciferol), the biologically active form of vitamin D3. Half Life: Several weeks |
| Toxicity Values | None |
| Lethal Dose | None |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
| Minimum Risk Level | None |
| Health Effects | None |
| Treatment | None |
| Reference |
|
From T3DB
Taxonomic Classification
| 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. |
From ClassyFire
Targets
- 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
References
- Tokar EJ, Webber MM: Cholecalciferol (vitamin D3) inhibits growth and invasion by up-regulating nuclear receptors and 25-hydroxylase (CYP27A1) in human prostate cancer cells. Clin Exp Metastasis. 2005;22(3):275-84. [16158255 ]
- 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
References
- Yamamoto N, Naraparaju VR: Role of vitamin D3-binding protein in activation of mouse macrophages. J Immunol. 1996 Aug 15;157(4):1744-9. [8759764 ]
- 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
References
- Segura-Aguilar J: Peroxidase activity of liver microsomal vitamin D 25-hydroxylase and cytochrome P450 1A2 catalyzes 25-hydroxylation of vitamin D3 and oxidation of dopamine to aminochrome. Biochem Mol Med. 1996 Jun;58(1):122-9. [8809353 ]
- 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
- Eloranta JJ, Hiller C, Juttner M, Kullak-Ublick GA: The SLCO1A2 gene, encoding human organic anion-transporting polypeptide 1A2, is transactivated by the vitamin D receptor. Mol Pharmacol. 2012 Jul;82(1):37-46. doi: 10.1124/mol.112.077909. Epub 2012 Apr 3. [22474172 ]
From T3DB