1-[(1S,3R,6R,7S,8S,9S,10S,11S,14S,16S)-8,9,14-trihydroxy-7,11-dimethyl-2-oxapentacyclo[8.8.0.01,3.03,7.011,16]octadecan-6-yl]ethan-1-one

• ChemBase ID: 305515
• Molecular Formular: C21H32O5
• Molecular Mass: 364.47578
• Monoisotopic Mass: 364.22497412
• SMILES: C1[C@@H](C[C@H]2[C@](C1)([C@@H]1[C@@]3(CC2)[C@@]2([C@]([C@@H]([C@H]1O)O)([C@@H](CC2)C(=O)C)C)O3)C)O
• Canonical SMILES: O[C@H]1CC[C@]2([C@H](C1)CC[C@@]13[C@@H]2[C@H](O)[C@@H](O)[C@]2([C@]3(O1)CC[C@H]2C(=O)C)C)C
• InChI: InChI=1S/C21H32O5/c1-11(22)14-6-9-21-19(14,3)17(25)15(24)16-18(2)7-5-13(23)10-12(18)4-8-20(16,21)26-21/h12-17,23-25H,4-10H2,1-3H3/t12-,13-,14-,15-,16+,17+,18-,19-,20-,21+/m0/s1
• InChIKey: FWXVLSDGEDMLQU-APDNMBNPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(1S,3R,6R,7S,8S,9S,10S,11S,14S,16S)-8,9,14-trihydroxy-7,11-dimethyl-2-oxapentacyclo[8.8.0.0^1,^3.0^3,^7.0^1^1,^1^6]octadecan-6-yl]ethan-1-one
• IUPAC Traditional name: 1-[(1S,3R,6R,7S,8S,9S,10S,11S,14S,16S)-8,9,14-trihydroxy-7,11-dimethyl-2-oxapentacyclo[8.8.0.0^1,^3.0^3,^7.0^1^1,^1^6]octadecan-6-yl]ethanone
• Synonyms: Tenacigenin B

Database IDs

• CAS Number: 80508-42-5

CALCULATED PROPERTIES

• Acid pKa: 13.423147
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.79974514
• LogD (pH = 7.4): 0.7997448
• Log P: 0.7997452
• Molar Refractivity: 95.0 cm^3
• Polarizability: 38.424374 Å^3
• Polar Surface Area: 90.29 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder