sodium (1S,2R,5R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.02,7.011,15]heptadec-7-en-5-yl sulfate

• ChemBase ID: 164730
• Molecular Formular: C27H45NaO4S
• Molecular Mass: 488.69857
• Monoisotopic Mass: 488.2936252
• SMILES: C1[C@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC[C@@H]1[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)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@H](C2)OS(=O)(=O)[O-])C)C.[Na+]
• InChI: InChI=1S/C27H46O4S.Na/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(31-32(28,29)30)13-15-26(20,4)25(22)14-16-27(23,24)5;/h9,18-19,21-25H,6-8,10-17H2,1-5H3,(H,28,29,30);/q;+1/p-1/t19-,21-,22+,23-,24+,25+,26+,27-;/m1./s1
• InChIKey: LMPVQXVJTZWENW-GCSFWTCKSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (1S,2R,5R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-yl sulfate
• IUPAC Traditional name: sodium cholesterol 3-sulfate
• Synonyms: (3β)-Cholest-5-en-3-ol 3-(Hydrogen Sulfate) Sodium Salt; Cholesterol Hydrogen Sulfate; Cholesteryl Sodium Sulfate; Sodium Cholesteryl Sulfate; Cholesterol 3-Sulfate Sodium Salt

Database IDs

• CAS Number: 2864-50-8
• PubChem SID: 162258865
• PubChem CID: 71314854

CALCULATED PROPERTIES

• Acid pKa: -1.3632758
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.79149
• LogD (pH = 7.4): 4.7914762
• Log P: 7.167875
• Molar Refractivity: 129.4866 cm^3
• Polarizability: 52.49241 Å^3
• Polar Surface Area: 66.43 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol (Sparingly)
• Apperance: White to Off-White Solid
• Melting Point: 178-180°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C432500

Principal sterol of the higher animals. Found in all body tissues, especial in the brain, spinal cord, and in animal fats or oils. Main constituent of gallstones.

REFERENCES

• Rosin, Z., et al.: Physiol. Chem., 124, 282 (1923)
• Schoenheimer, et al.: J. Biol. Chem., 105, 355 (1923)
• Gemant, et al.: Life Sci., 1, 233 (1923)
• Johnson, K., et al.: 4, 457 (1923)