(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-7-en-5-ol

• ChemBase ID: 177793
• Molecular Formular: C29H50O
• Molecular Mass: 414.7067
• Monoisotopic Mass: 414.38616622
• 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](CC[C@@H](C(C)C)CC)C)C)O
• Canonical SMILES: CC[C@H](C(C)C)CC[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
• InChI: InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21+,23+,24+,25-,26+,27+,28+,29-/m1/s1
• InChIKey: KZJWDPNRJALLNS-FBZNIEFRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-ol
• IUPAC Traditional name: clionasterol
• Synonyms: (3β)-Stigmast-5-en-3-ol; Nimbosterol; Stigmast-5-en-3β-ol; (-)-β-Sitosterol; (24R)-Ethylcholest-5-en-3β-ol; (24R)-Stigmast-5-en-3β-ol; 22,23-Dihydrostigmasterol; 24α-Ethylcholesterol; Angelicin; Azuprostat; Betaprost; Cinchol; Cupreol; Harzol; NSC 18173; Prostasal; Sobatum; Stigmasterol; 5-Stigmasten-3β-ol; α-Dihydrofucosterol; α-Phytosterol; β-Sitosterin; β-Sitosterol

Database IDs

• CAS Number: 83-46-5
• PubChem SID: 164233703
• PubChem CID: 457801

CALCULATED PROPERTIES

• Acid pKa: 18.20429
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 7.8444767
• LogD (pH = 7.4): 7.8444767
• Log P: 7.8444767
• Molar Refractivity: 129.7661 cm^3
• Polarizability: 51.670784 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - S497050

A common sterol in plants. Isolated from wheat germ oil, corn oil. Antilipemic. Used in the treatment of prostatic adenoma.

REFERENCES

• Tanaka, et al.: J. Biochem., 17, 483 (1933)
• Nigro, N.D., et al.: J. Natl. Cancer Inst., 69, 103 (1933)