sodium (1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexyl sulfate

• ChemBase ID: 179543
• Molecular Formular: C27H43NaO4S
• Molecular Mass: 486.68269
• Monoisotopic Mass: 486.27797514
• SMILES: C1[C@H](CCC(=C)/C/1=C\C=C/1\[C@H]2[C@](CCC1)([C@H](CC2)[C@@H](CCCC(C)C)C)C)OS(=O)(=O)[O-].[Na+]
• Canonical SMILES: CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CCC/C/2=C\C=C/1\C[C@H](CCC1=C)OS(=O)(=O)[O-])C)C.[Na+]
• InChI: InChI=1S/C27H44O4S.Na/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(14-11-20(23)3)31-32(28,29)30;/h12-13,19,21,24-26H,3,6-11,14-18H2,1-2,4-5H3,(H,28,29,30);/q;+1/p-1/b22-12+,23-13-;/t21-,24+,25-,26+,27-;/m1./s1
• InChIKey: HZXPJUMUSRXXKW-DRFPHCMDSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexyl sulfate
• IUPAC Traditional name: sodium (1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexyl sulfate
• Synonyms: (1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(1R)-1,5-Dimethylhexyl]octahydro-7a-methyl-4H-inden-4-ylidene]ethylidene]-4-methylenecyclohexanol Sodium Salt; (3β,5Z,7E)-9,10-Secocholesta-5,7,10(19)-trien-3-ol Ηydrogen Sulfate Sodium Salt; Cholecalciferol Sulfate Sodium Salt; Vitamin D3 3β-Sulfate Sodium Salt; Vitamin D3 Sulfate Sodium Salt

Database IDs

• CAS Number: 78392-27-5
• PubChem SID: 164235453
• PubChem CID: 71752977

CALCULATED PROPERTIES

• Acid pKa: -1.4908444
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.804058
• LogD (pH = 7.4): 4.804048
• Log P: 7.1804466
• Molar Refractivity: 132.0946 cm^3
• Polarizability: 52.73922 Å^3
• Polar Surface Area: 66.43 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 113-114°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - V676055

The main metabolite of Vitamin D3. It has potent biological activity. Vitamin D3-sulfate had <5% of the activity of vitamin D3 to mobilize Ca from bone and .apprx.1% of the ability of Vitamin D3 to stimulate Ca transport, elevate serum P, or support bone

REFERENCES

• Bell, P.A., et al.: Biochem. J., et al.: 115, 663 (1969)
• Kumar, R.S., et al.: J. Clin. Invest., 65, 277 (1969)
• Reeve, L.E., et al.: J. Biol. Chem., 256, 823 (1969)
• Armas, L., et al.: J. Clin. Endocrinol. Metab., 89, 5387 (1969)