(1S,2S,5S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(5R)-6-(2H3)methyl-5-methyl(6,7,7,7-2H4)heptan-2-yl]tetracyclo[8.7.0.02,7.011,15]heptadecan-5-ol

• ChemBase ID: 163558
• Molecular Formular: C28H50O
• Molecular Mass: 402.696
• Monoisotopic Mass: 402.38616622
• SMILES: C1[C@@H](C[C@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](CC2)C(CC[C@H](C(C)C)C)C)C)C)O
• Canonical SMILES: O[C@H]1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2C(CC[C@H](C(C)C)C)C)C)C
• InChI: InChI=1S/C28H50O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h18-26,29H,7-17H2,1-6H3/t19-,20?,21+,22+,23+,24-,25+,26+,27+,28-/m1/s1
• InChIKey: ARYTXMNEANMLMU-SMPCNWHESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(5R)-6-(^2H₃)methyl-5-methyl(6,7,7,7-^2H₄)heptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-ol
• IUPAC Traditional name: (1S,2S,5S,7S,10R,11S,14R,15R)-2,15-dimethyl-14-[(5R)-6-(^2H₃)methyl-5-methyl(6,7,7,7-^2H₄)heptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-ol
• Synonyms: 5α-Cholestan-20(α/β)-methyl-3β-ol-25,26,26,26,27,27,27-d7; (3β,5α,24R)-Ergostan-3-ol; 24β-Ethylcholestanol; 24β-Methylcholestanol; 5α-Dihydrocampesterol; Chalinastanol; Dihydro-Neospongosterol; 20-(α/β)-Campestanol-d7

Database IDs

• PubChem SID: 162257693
• PubChem CID: 71314482

CALCULATED PROPERTIES

• Acid pKa: 18.296396
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 7.8054876
• LogD (pH = 7.4): 7.8054876
• Log P: 7.8054876
• Molar Refractivity: 124.3151 cm^3
• Polarizability: 50.058853 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C155303

A labelled phytosterol content in plant food which showed hypocholesterolemic and hypotriglyceridemic effects in hypercholesterolemic overweight volunteers. Used in the treatment of metabolic disorders.

REFERENCES

• Kasamo, K., et al.: Plant Physiol., 93, 1049 (1990)
• Davey, M., et al.: J. Sci. Food Agric., 80, 825 (1990)
• Nomura, T., et al.: J. Biol. Chem., 280, 17873 (1990)
• Matos, L., et al.: Food Chem., 102, 406 (1990)