Showing Metabocard for 5,6-trans-vitamin D3 (BASm0010588)
| Common Name | 5,6-trans-vitamin d3 |
|---|---|
| Description | 5,6-trans-vitamin D3 is the result of photodegradation of vitamin D3, and once formed in the skin, exposure to sunlight results in its rapid photodegradation to a variety of photoproducts. During chronic exposure to sunlight vitamin D3 in the skin can be photoisomerized to a variety of photoproducts, including 5,6-trans-vitamin D3. Because 5,6-Trans-vitamin D3 is a photoproduct of vitamin D3 and have a pseudo-1-alpha-hydroxyl structure due to the 180-degree rotation of the 3-hydroxyl group during isomerization. 5,6-trans-vitamin D3 can mimic the intestinal calcium transport activity of 1alpha,25(OH)2D (the active form of vitamine D). (PMID: 10876100 , 2541158 ). |
| Structure | |
| Molecular Formula | C27H44O |
| Average Mass | 384.63770 |
| Monoisotopic Mass | 384.33922 |
| IUPAC Name | (1S,3E)-3-{2-[(1R,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol |
| Traditional Name | (1s,3e)-3-{2-[(1r,4e,7ar)-7a-methyl-1-[(2r)-6-methylheptan-2-yl]-hexahydro-1h-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol |
| CAS Registry Number | 22350-41-0 |
| SMILES | C=C1CC[C@H](O)C/C1=C\C=C1/CCC[C@]2(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@@H]12 |
| InChI Identifier | 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-YYJGPZIQSA-N |
| CHEBI ID | CHEBI:145213 |
| HMDB ID | HMDB0006719 |
| State | Not Available |
| Water Solubility | 3.80e-04 g/l |
| logP | 7.98 |
| logS | -6.01 |
| pKa (Strongest Acidic) | 18.38 |
| pKa (Strongest Basic) | -1.32 |
| Hydrogen Acceptor Count | 1 |
| Hydrogen Donor Count | 1 |
| Polar Surface Area | 20.23 Ų |
| Rotatable Bond Count | 6 |
| Physiological Charge | 0 |
| Formal Charge | 0 |
| Refractivity | 123.22 m³·mol⁻¹ |
| Polarizability | 49.54 |