(1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.02,7.011,15]heptadec-9-en-5-ol

• ChemBase ID: 128025
• Molecular Formular: C27H46O
• Molecular Mass: 386.65354
• Monoisotopic Mass: 386.35486609
• SMILES: O[C@H]1CC[C@@]2([C@@H]3C(=CC[C@H]2C1)[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@]1(CC3)C)C
• Canonical SMILES: CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1C2=CC[C@@H]2[C@]1(C)CC[C@@H](C2)O)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/h10,18-21,23-25,28H,6-9,11-17H2,1-5H3/t19-,20+,21+,23-,24+,25+,26+,27-/m1/s1
• InChIKey: IZVFFXVYBHFIHY-SKCNUYALSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,5S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-9-en-5-ol
• IUPAC Traditional name: 7-cholesterol
• Synonyms: (3β,5α)-Cholest-7-en-3-ol; 3β-Hydroxy-5α-cholest-7-ene; 7-En-3-cholestanol; Cholest-7-en-3-ol; Lathosterol; Δ7-Cholestenol; γ-Cholestenol; 5α-Cholest-7-en-3β-ol; Lathosterol

Database IDs

• CAS Number: 80-99-9
• PubChem SID: 162222341
• PubChem CID: 65728
• CHEBI ID: 17168
• Chemspider ID: 59151
• Wikipedia Title: Lathosterol

CALCULATED PROPERTIES

• Acid pKa: 18.361778
• 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 - L177500

A Cholesterol (C432501) metabolite. Lathosterol (indicating cholesterol synthesis) and Sitosterol (indicating cholesterol absorption) also decreased with deteriorating health. Low Lathosterol, Sitosterol (S497050), and Cholesterol (C432501) predicted mort

REFERENCES

• Chyou, P., et al.: Age Ageing, 29, 69 (2000)
• Schatz, I., et al.: Lancet, 358, 351 (2000)
• Bjorkman, M., et al.: Eur. J. Endocrinol., 158, 749 (2000)