sodium (1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexyl sulfate

• ChemBase ID: 179535
• Molecular Formular: C28H43NaO4S
• Molecular Mass: 498.69339
• Monoisotopic Mass: 498.27797514
• 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)OS(=O)(=O)[O-].[Na+]
• Canonical SMILES: CC([C@H](/C=C/[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)C.[Na+]
• InChI: InChI=1S/C28H44O4S.Na/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(14-11-21(24)4)32-33(29,30)31;/h9-10,12-13,19-20,22,25-27H,4,7-8,11,14-18H2,1-3,5-6H3,(H,29,30,31);/q;+1/p-1/b10-9+,23-12+,24-13-;/t20-,22+,25-,26+,27-,28+;/m0./s1
• InChIKey: VNINQFWZCBNKBF-WNFKWOOTSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexyl sulfate
• IUPAC Traditional name: sodium (1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexyl sulfate
• Synonyms: (3β,5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-ol Hydrogen Sulfate; Ergocalciferol Hydrogen Sulfate; Vitamin D2 3β-Sulfate; Vitamin D2 Sulfate; Vitamin D2 Sulfate Sodium Salt

Database IDs

• CAS Number: 1784-46-9
• PubChem SID: 164235445
• PubChem CID: 71752968

CALCULATED PROPERTIES

• Acid pKa: -1.4908444
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.7291555
• LogD (pH = 7.4): 4.7291455
• Log P: 7.105544
• Molar Refractivity: 137.7598 cm^3
• Polarizability: 54.3417 Å^3
• Polar Surface Area: 66.43 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - V676030

A biliary metabolite of Vitamin D2 (V676040). The sulfate metabolite is not biologically active except at the highest doses tested.

REFERENCES

• Kumar R., et al.: J. Steroid Biochem., 17, 495 (1982)