6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-7-yl octanoate

• ChemBase ID: 105182
• Molecular Formular: C34H50O12
• Molecular Mass: 650.7536
• Monoisotopic Mass: 650.33022704
• SMILES: CCCCCCCC(=O)OC1C(OC(=O)/C(=C\C)/C)C(=C2C3OC(=O)C(C)(O)C3(O)C(CC(C)(OC(=O)C)C12)OC(=O)CCC)C
• Canonical SMILES: CCCCCCCC(=O)OC1C(OC(=O)/C(=C\C)/C)C(=C2C1C(C)(OC(=O)C)CC(C1(C2OC(=O)C1(C)O)O)OC(=O)CCC)C
• InChI: InChI=1S/C34H50O12/c1-9-12-13-14-15-17-24(37)43-28-26-25(20(5)27(28)44-30(38)19(4)11-3)29-34(41,33(8,40)31(39)45-29)22(42-23(36)16-10-2)18-32(26,7)46-21(6)35/h11,22,26-29,40-41H,9-10,12-18H2,1-8H3
• InChIKey: IXFPJGBNCFXKPI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-7-yl octanoate
• IUPAC Traditional name: 6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methylbut-2-enoyl)oxy]-2-oxo-4H,5H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-7-yl octanoate
• Synonyms: THAPSIGARGIN

Database IDs

• CAS Number: 67526-95-8
• PubChem SID: 162091980
• PubChem CID: 45934368

CALCULATED PROPERTIES

• Acid pKa: 11.135566
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 4.3845243
• LogD (pH = 7.4): 4.3844457
• Log P: 4.3845253
• Molar Refractivity: 163.8158 cm^3
• Polarizability: 65.89336 Å^3
• Polar Surface Area: 171.96 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: R:36/37/38
• Safety Statements: S:20-25-26-37/39

Product Information

• Purity: 99%

DETAILS

MP Biomedicals - 02158999

Purity: 99% Cell permeable sesquiterpene lactone tumor promoter. Inhibits endoplasmic reticulum Ca^2+ -ATPase which induces the release of independent intracellular Ca^2+ .

REFERENCES

• Fujiki, H., et al., Carcinogenesis, 7: 707, (1986).
• Takemura, H., et al., J. Biol. Chem., 264: 12266, (1989).
• Thastrup, O., et al., Proc. Natl. Acad. Sci. USA, 87: 2466, (1990).