(1S,2R,5S,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-(18O)ol

• ChemBase ID: 164729
• Molecular Formular: C27H46O
• Molecular Mass: 388.653301
• Monoisotopic Mass: 388.35911247
• 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)CCCC(C)C)C)[18OH]
• 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)[18OH])C)C
• 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/i28+2
• InChIKey: HVYWMOMLDIMFJA-XLQSOFFQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,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-(^1^8O)ol
• IUPAC Traditional name: (1S,2R,5S,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-(^1^8O)ol
• Synonyms: (3β)-Cholest-5-en-3-ol-18O; Cholesterol-3-18O

Database IDs

• CAS Number: 59613-51-3
• PubChem SID: 162258864
• PubChem CID: 71314853

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 - C432493

[18O] Cholesterol can be used as a practical tracer for studies of cholesterol metabolism in humans.

REFERENCES

• Hudgins, L.C., et al.: Biomed. Environ. Mass Spect., 17, 463 (1988)