(1S,2S,7R,10S,11R,17S)-17-hydroxy-2,6,6,10,11-pentamethyl-14-[(2R,4S,5R)-4,5,6-trihydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.02,7.011,15]heptadec-14-en-5-one

• ChemBase ID: 159650
• Molecular Formular: C30H50O5
• Molecular Mass: 490.715
• Monoisotopic Mass: 490.3658247
• SMILES: C1C(=O)C([C@H]2[C@](C1)([C@H]1[C@](CC2)([C@@]2(C(=C(CC2)[C@@H](C[C@@H]([C@H](C(O)(C)C)O)O)C)C[C@@H]1O)C)C)C)(C)C
• Canonical SMILES: O[C@H]([C@H](C(O)(C)C)O)C[C@H](C1=C2C[C@H](O)[C@@H]3[C@]([C@]2(CC1)C)(C)CC[C@@H]1[C@]3(C)CCC(=O)C1(C)C)C
• InChI: InChI=1S/C30H50O5/c1-17(15-21(32)25(34)27(4,5)35)18-9-13-29(7)19(18)16-20(31)24-28(6)12-11-23(33)26(2,3)22(28)10-14-30(24,29)8/h17,20-22,24-25,31-32,34-35H,9-16H2,1-8H3/t17-,20+,21+,22+,24+,25-,28+,29+,30+/m1/s1
• InChIKey: HNOSJVWYGXOFRP-UNPOXIGHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,7R,10S,11R,17S)-17-hydroxy-2,6,6,10,11-pentamethyl-14-[(2R,4S,5R)-4,5,6-trihydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-14-en-5-one
• IUPAC Traditional name: (1S,2S,7R,10S,11R,17S)-17-hydroxy-2,6,6,10,11-pentamethyl-14-[(2R,4S,5R)-4,5,6-trihydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-14-en-5-one
• Synonyms: (8α,9β,11β,14β,23S,24R)-11,23,24,25-Tetrahydroxydammar-13(17)-en-3-one; (23S,24R)- 1β,23,24,25-Tetrahydroxy-8α,9β,14β-dammar-13(17)-en-3-one; Alisol A

Database IDs

• CAS Number: 19885-10-0
• PubChem SID: 162253785
• PubChem CID: 15558616

CALCULATED PROPERTIES

• Acid pKa: 13.026905
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 3.7460926
• LogD (pH = 7.4): 3.746092
• Log P: 3.746093
• Molar Refractivity: 139.024 cm^3
• Polarizability: 55.37563 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A535960

A hypocholesterolemic triterpenoid.

REFERENCES

• Hikino, H. et al.: Shoyak. Zas., 36, 150 (1982)
• Kubo, M. et al.: Biol. Pharmac. Bull., 20, 511 (1982)