(3R,4R,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4-carboxylic acid

• ChemBase ID: 172048
• Molecular Formular: C30H46O4
• Molecular Mass: 470.68384
• Monoisotopic Mass: 470.33960995
• SMILES: C1C[C@H]([C@](C2[C@]1([C@@H]1[C@@](CC2)([C@]2(C(=CC1=O)[C@H]1[C@@](CC2)(CC[C@H]([C@@H]1C)C)C)C)C)C)(C)C(=O)O)O
• Canonical SMILES: C[C@@H]1CC[C@]2([C@@H]([C@H]1C)C1=CC(=O)[C@H]3[C@@]([C@@]1(CC2)C)(C)CCC1[C@]3(C)CC[C@H]([C@]1(C)C(=O)O)O)C
• InChI: InChI=1S/C30H46O4/c1-17-8-11-26(3)14-15-28(5)19(23(26)18(17)2)16-20(31)24-27(4)12-10-22(32)30(7,25(33)34)21(27)9-13-29(24,28)6/h16-18,21-24,32H,8-15H2,1-7H3,(H,33,34)/t17-,18+,21?,22-,23+,24-,26-,27+,28-,29-,30-/m1/s1
• InChIKey: YIMHGPSYDOGBPI-YEIMTCQQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4-carboxylic acid
• IUPAC Traditional name: (3R,4R,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-14-oxo-1,2,3,4a,5,6,7,8,9,10,11,12,12a,14a-tetradecahydropicene-4-carboxylic acid
• Synonyms: 11-Oxo-β-boswellic Acid; 11-keto-β-Boswellic Acid; 11-Keto β-Boswellic Acid; (3α,4β)-3-Hydroxy-11-oxours-12-en-23-oic Acid; 3α-Hydroxy-11-oxours-12-en-24-oic Acid

Database IDs

• CAS Number: 17019-92-0
• PubChem SID: 164227958
• PubChem CID: 71749672

CALCULATED PROPERTIES

• Acid pKa: 4.3979464
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.8848214
• LogD (pH = 7.4): 3.128715
• Log P: 6.0183
• Molar Refractivity: 134.342 cm^3
• Polarizability: 53.29785 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - K175200

A constitutent of frankincense (olibanum) with anti-inflammatory properties. It has been shown to trigger apoptosis via a pathway dependent on caspase-8 activation but independent on Fas/Fas ligand interaction in colon cancer HT-29 cells.

REFERENCES

• Liu, J. et al.: Carcinogen., 23, 2087 (2002)
• Sharma, S. et al.: Phytomed., 11, 255 (2002)
• Siemoneit, U., et al.: Eur. J. Pharmacol., 606, 246 (2002)