(1R,2R,5R,9R,10R,13R,14R,17S,19R)-1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.02,10.05,9.014,19]henicosan-17-ol

• ChemBase ID: 172434
• Molecular Formular: C30H50O
• Molecular Mass: 426.7174
• Monoisotopic Mass: 426.38616622
• SMILES: C1[C@@H](C([C@H]2[C@](C1)([C@@H]1[C@@](CC2)([C@]2([C@H](CC1)[C@@H]1[C@@](CC2)(CCC1C(=C)C)C)C)C)C)(C)C)O
• Canonical SMILES: CC(=C)C1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)O)C
• InChI: InChI=1S/C30H50O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20?,21-,22+,23-,24+,25-,27-,28+,29-,30-/m1/s1
• InChIKey: MQYXUWHLBZFQQO-VVSKNWLOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,5R,9R,10R,13R,14R,17S,19R)-1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^2,^1^0.0^5,^9.0^1^4,^1^9]henicosan-17-ol
• IUPAC Traditional name: (1R,2R,5R,9R,10R,13R,14R,17S,19R)-1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^2,^1^0.0^5,^9.0^1^4,^1^9]henicosan-17-ol
• Synonyms: (3β)-Lup-20(29)-en-3-ol; Lup-20(29)-en-3β-ol; Monogynol B; (+)-Lupeol; 3β-Hydroxylup-20(29)-ene; Clerodol; Fagarasterol; Fagarsterol; Lupenol; NSC 90487; β-Viscol; Lupeol

Database IDs

• CAS Number: 545-47-1
• PubChem SID: 164228344
• PubChem CID: 71749855

CALCULATED PROPERTIES

• Acid pKa: 19.489433
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 7.448046
• LogD (pH = 7.4): 7.4480467
• Log P: 7.4480467
• Molar Refractivity: 130.9083 cm^3
• Polarizability: 52.777435 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - L474850

Abundant plant triterpene. Occurs in the skin of lupin seeds, in circle, in the latex of fig trees and of rubber plants. It was detected in cocoons of Bombyx mori.

REFERENCES

• Owen, R., et al.: Food Chem. Toxicol., 38, 647 (2000)
• Salvador, M., et al.: Food Chem., 80, 359 (2000)
• Chiavaro, E., et al.: J. Agric. Food Chem., 55, 10779 (2000)