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

• ChemBase ID: 172433
• Molecular Formular: C27H44O
• Molecular Mass: 384.63766
• Monoisotopic Mass: 384.33921603
• SMILES: C1[C@@H](CC2=CC=C3[C@H]([C@@]2(C1)C)CC[C@]1([C@H]3CC[C@@H]1[C@@H](CCCC(C)C)C)C)O
• Canonical SMILES: CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@@H]1C2=CC=C2[C@@]1(C)CC[C@@H](C2)O)C)C
• InChI: InChI=1S/C27H44O/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/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25-,26-,27-/m1/s1
• InChIKey: UCTLRSWJYQTBFZ-XMVWLVNMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-7,9-dien-5-ol
• IUPAC Traditional name: lumisterol 3
• Synonyms: (3β,9β,10α)-Cholesta-5,7-dien-3-ol; 9β,10α-Cholesta-5,7-dien-3β-ol; Lumisterol 3

Database IDs

• CAS Number: 5226-01-7
• PubChem SID: 164228343
• PubChem CID: 111049

CALCULATED PROPERTIES

• Acid pKa: 18.270805
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 6.7073097
• LogD (pH = 7.4): 6.7073097
• Log P: 6.7073097
• Molar Refractivity: 121.4665 cm^3
• Polarizability: 47.743767 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: WHite Solid
• Melting Point: 60-62°C

Safety Information

• Storage Condition: Amber Vial, Refrigerator

DETAILS

Toronto Research Chemicals - L474820

Lumisterol3 is an isomer of Vitamin D3 (V676045). Lumisterol3 is used in the preparation of vitamin D analogs.

REFERENCES

• Yamamoto, J., et al.: Biochemistry, 24, 3338 (1985)
• Takagi, K., et al.: Crit. Rev. Biochem. Mol. Biol., 28, 323 (1985)