(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-{[(2Z)-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: 132263
• Molecular Formular: C34H50O12
• Molecular Mass: 650.7536
• Monoisotopic Mass: 650.33022704
• SMILES: CCCCCCCC(=O)O[C@H]1[C@H]2C(=C([C@@H]1OC(=O)/C(=C\C)/C)C)[C@H]1[C@]([C@H](C[C@]2(C)OC(=O)C)OC(=O)CCC)([C@](C(=O)O1)(C)O)O
• Canonical SMILES: CCCCCCCC(=O)O[C@@H]1[C@@H](OC(=O)/C(=C\C)/C)C(=C2[C@H]1[C@@](C)(OC(=O)C)C[C@@H]([C@]1([C@H]2OC(=O)[C@@]1(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/b19-11-/t22-,26+,27-,28-,29-,32-,33+,34+/m0/s1
• InChIKey: IXFPJGBNCFXKPI-FSIHEZPISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-{[(2Z)-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: thapsigargin
• Synonyms: Thapsigargin; Octanoic Acid (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-(Acetyloxy)-2,3,3a,4,5,6,6a,7,8,9b- decahydro-3,3a-dihydroxy-3,6,9-trimethyl-8-[[(2Z)-2-methyl-1-oxo-2-butenyl]oxy]-2-oxo-4-(1-oxobutoxy)azuleno[4,5-b]furan-7-yl Ester; (-)-Thapsigargin; Octanoic Acid [3S-[3α,3aβ,4α,6β,6aβ,7β,8α(Z),9bα]]-6-(Acetyloxy)-2,3,3a,4,5,6,6a,7,8,9b-decahydro-3,3a-dihydroxy-3,6,9-trimethyl-8-[(2-methyl-1-oxo-2-butenyl)oxy]-2-oxo-4-(1-oxobutoxy)azuleno[4,5-b]furan-7-yl Ester; Thapsigargin

Database IDs

• CAS Number: 67526-95-8
• MDL Number: MFCD00083511
• PubChem SID: 162226540; 24278762
• PubChem CID: 446378

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

Physical Property

• Solubility: Chloroform; DMSO: soluble; ethanol: soluble
• Apperance: Off-White Solid; solid film
• Melting Point: 84-90°C

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 36/37/38-42
• Safety Statements: 26-36/37/39
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H319-H334-H335
• GHS Precautionary statements: P261-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Quality Level: PREMIUM

DETAILS

Sigma Aldrich - T9033

Biochem/physiol Actions
Potent, cell-permeable, IP3-independent intracellular calcium releaser. Blocks the transient increase in intracellular Ca2+ induced by angiostatin and endostatin. Induces apoptosis by disrupting intracellular free Ca2+ levels; incorporated into chemotherapeutic prodrug formulations.

Sigma Aldrich - T124

Biochem/physiol Actions
Potent, cell-permeable, IP3-independent intracellular calcium releaser. Blocks the transient increase in intracellular Ca2+ induced by angiostatin and endostatin. Induces apoptosis by disrupting intracellular free Ca2+ levels; incorporated into chemotherapeutic prodrug formulations.

Toronto Research Chemicals - T339250

A widely used inhibitor of the ubiquitous sarco-endoplasmic reticulum Ca(2+)-ATPases in mammalian cells. It acts as a potent, cell-permeable, IP3-independent intracellular calcium releaser that blocks the transient increase in intracellular Ca2+ induced b

REFERENCES

• Treiman, M. et al.: Trends Pharmacol. Sci., 19, 131 (1998)
• Korge, P. et al.: Eur. J. Biochem., 265, 273 (1998)
• Tsukamoto, A. Cell Biol. Int., 17, 969 (1998)
• Kutinova C.N. et al.: Cell Biol. Toxicol., 23, 337 (1998)