(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R,3E,5R)-6-(2H3)methyl-5-methyl(7,7,7-2H3)hept-3-en-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol

• ChemBase ID: 179539
• Molecular Formular: C28H44O
• Molecular Mass: 396.64836
• Monoisotopic Mass: 396.33921603
• SMILES: C1[C@H](CCC(=C)/C/1=C\C=C/1\[C@H]2[C@](CCC1)([C@H](CC2)[C@@H](/C=C/[C@@H](C(C)C)C)C)C)O
• Canonical SMILES: O[C@H]1CCC(=C)/C(=C\C=C\2/CCC[C@]3([C@H]2CC[C@@H]3[C@@H](/C=C/[C@@H](C(C)C)C)C)C)/C1
• 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
• InChIKey: MECHNRXZTMCUDQ-RKHKHRCZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R,3E,5R)-6-(^2H₃)methyl-5-methyl(7,7,7-^2H₃)hept-3-en-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
• IUPAC Traditional name: (1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R,3E,5R)-6-(^2H₃)methyl-5-methyl(7,7,7-^2H₃)hept-3-en-2-yl]-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
• Synonyms: 3β,5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol-d6; Calciferol-d6; Ercalciol-d6; Ergosterol-d6 Irradiated; Ergocalciferol-d6; Oleovitamin D2-d6; Radiostol-d6; Radsterin-d6; (+)-Vitamin D2-d6; Viosterol-d6; Vio D-d6; Vitavel-D-d6; Vitamin D2-d6

Database IDs

• PubChem SID: 164235449
• PubChem CID: 71752975

CALCULATED PROPERTIES

• Acid pKa: 18.384342
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 7.050558
• LogD (pH = 7.4): 7.050558
• Log P: 7.050558
• Molar Refractivity: 128.8897 cm^3
• Polarizability: 49.86576 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - V676042

Labelled Vitamin D2 (V676040). The synthetic form of Vitamin D. Prepared from ergosterol by UV irradiation in a suitable solvent. Commercial solutions are usually made with propylene glycol or sesame oil. Antirachitic.

REFERENCES

• Knudson, B., et al.: J. Biol. Chem., 124, 287 (1938)
• Huber, B., et al.: J. Biol. Chem., 149, 125 (1938)
• Crowfoot, D., et al.: Nature, 162, 608 (1938)
• Suda, et al.: Biochem. Biophys. Res. Commun., 35, 182 (1938)