(1S,4S,5S,6R,9S,10R,13R)-5,9-dimethyl-6-{[(2E)-2-methylbut-2-enoyl]oxy}-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid

• ChemBase ID: 305896
• Molecular Formular: C25H36O4
• Molecular Mass: 400.55094
• Monoisotopic Mass: 400.26135963
• SMILES: C1[C@H]([C@]([C@@H]2[C@@](C1)([C@H]1[C@]3(CC2)CC(=C)[C@@H](CC1)C3)C)(C(=O)O)C)OC(=O)/C(=C/C)/C
• Canonical SMILES: C/C=C(/C(=O)O[C@@H]1CC[C@@]2([C@@H]([C@]1(C)C(=O)O)CC[C@@]13[C@H]2CC[C@@H](C3)C(=C)C1)C)\C
• InChI: InChI=1S/C25H36O4/c1-6-15(2)21(26)29-20-10-11-23(4)18(24(20,5)22(27)28)9-12-25-13-16(3)17(14-25)7-8-19(23)25/h6,17-20H,3,7-14H2,1-2,4-5H3,(H,27,28)/b15-6+/t17?,18-,19-,20+,23+,24-,25+/m0/s1
• InChIKey: HCVOJPQEMAKKFV-XHUUILEVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4S,5S,6R,9S,10R,13R)-5,9-dimethyl-6-{[(2E)-2-methylbut-2-enoyl]oxy}-14-methylidenetetracyclo[11.2.1.0^1,^1^0.0^4,^9]hexadecane-5-carboxylic acid
• IUPAC Traditional name: (1S,4S,5S,6R,9S,10R,13R)-5,9-dimethyl-6-{[(2E)-2-methylbut-2-enoyl]oxy}-14-methylidenetetracyclo[11.2.1.0^1,^1^0.0^4,^9]hexadecane-5-carboxylic acid
• Synonyms: ent-3β-Tigloyloxykaur-16-en-19-oic acid

Database IDs

• CAS Number: 79406-09-0

CALCULATED PROPERTIES

• Acid pKa: 4.6067376
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.845442
• LogD (pH = 7.4): 3.069189
• Log P: 5.789957
• Molar Refractivity: 112.7089 cm^3
• Polarizability: 44.65044 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Powder