(1S,2R,5S,10S,11S,14R,15S)-2,15-dimethyl-14-[(2S)-6-(13C)methyl(4,5,6,7-13C4)heptan-2-yl]tetracyclo[8.7.0.02,7.011,15]heptadec-7-en-5-ol

• ChemBase ID: 164728
• Molecular Formular: C27H46O
• Molecular Mass: 391.61681419
• Monoisotopic Mass: 391.37164028
• 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](C)C[13CH2][13CH2][13CH]([13CH3])[13CH3])C)O
• Canonical SMILES: [13CH3][13CH]([13CH2][13CH2]C[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)O)C)[13CH3]
• InChI: InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1/i1+1,2+1,6+1,7+1,18+1
• InChIKey: HVYWMOMLDIMFJA-QVICAUPWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10S,11S,14R,15S)-2,15-dimethyl-14-[(2S)-6-(^1^3C)methyl(4,5,6,7-^1^3C₄)heptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-ol
• IUPAC Traditional name: (1S,2R,5S,10S,11S,14R,15S)-2,15-dimethyl-14-[(2S)-6-(^1^3C)methyl(4,5,6,7-^1^3C₄)heptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-ol
• Synonyms: (3β)-Cholest-5-en-3-ol-23,24,25,26,27-13C5; Cholesterol-13C5

Database IDs

• CAS Number: 150044-24-9
• PubChem SID: 162258863
• PubChem CID: 71314852

CALCULATED PROPERTIES

• Acid pKa: 18.20429
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 7.112889
• LogD (pH = 7.4): 7.112889
• Log P: 7.112889
• Molar Refractivity: 120.6165 cm^3
• Polarizability: 47.977962 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C432492

[13C] Cholesterol can be used as a practical tracer for studies of cholesterol metabolism in humans.

REFERENCES

• Prasad, V., et al.: J. Steroid Biochem., 21, 733 (1984)
• Duane, W., et al.: J. Clin. Invest., 92, 911 (1984)
• Lehmann, J., et al.: J. Biol. Chem., 272, 3137 (1984)
• Setchell, K., et al.: J. Clin. Invest., 102, 1690 (1984)
• Song, C., et al.: Endocrinology,