Thapsigargin

• CAS: 67526-95-8
• Catalog Number: ACM67526958
• Category: Inhibitors
• Molecular Weight: 650.75
• Molecular Formula: C₃₄H₅₀O₁₂
• Description: Thapsigargin, an endoplasmic reticulum (ER) stress inducer, is an inhibitor of microsomal Ca2+-ATPase. Thapsigargin efficiently inhibits coronavirus (HCoV-229E, MERS-CoV, SARS-CoV-2) replication in different cell types.
• 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-buten-1-yl]oxy]-2-oxo-4-(1-oxobutoxy)azuleno[4,5-b]furan-7-yl ester;(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 octanoate;Octanoic acid [(3S)-6α-acetoxy-2,3,3a,4,5,6,6aα,7,8,9bβ-decahydro-3β,3aα-dihydroxy-3,6,9-trimethyl-8β-[[(Z)-2-methyl-1-oxo-2-butenyl]oxy]-2-oxo-4β-(1-oxobutoxy)azuleno[4,5-b]furan]-7α-yl ester;Thapsigargin,97%;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;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 (TG)
• IUPAC Name: [(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetyloxy-4-butanoyloxy-3,3a-dihydroxy-3,6,9-trimethyl-8-[(Z)-2-methylbut-2-enoyl]oxy-2-oxo-4,5,6a,7,8,9b-hexahydroazuleno[4,5-b]furan-7-yl]octanoate
• Canonical SMILES: CCCCCCCC(=O)OC1C2C(=C(C1OC(=O)C(=CC)C)C)C3C(C(CC2(C)OC(=O)C)OC(=O)CCC)(C(C(=O)O3)(C)O)O
• InChI Key: IXFPJGBNCFXKPI-FSIHEZPISA-N
• Appearance: liquid or film
• Storage: -20°C, sealed storage, away from moisture and light*In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light)
• EC Number: 614-076-3
• Exact Mass: 650.33000
• Hazard Statements: Xn,T
• Safety Description: 26-36/37/39
• Shipping: Can be shipped at room temperature, where not in use may vary.
• Source: PlantsUmbelliferaeThapsia garganica L.
• Supplemental Hazard Statements: H315-H319-H334-H335
• Symbol: GHS07,GHS08
• WGK Germany: 3

Custom Q&A

What is the molecular formula of thapsigargin?

The molecular formula of thapsigargin is C34H50O12.

What is the molecular weight of thapsigargin?

The molecular weight of thapsigargin is 650.8 g/mol.

What is the IUPAC name of thapsigargin?

The IUPAC name of thapsigargin is [(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetyloxy-4-butanoyloxy-3,3a-dihydroxy-3,6,9-trimethyl-8-[(Z)-2-methylbut-2-enoyl]oxy-2-oxo-4,5,6a,7,8,9b-hexahydroazuleno[4,5-b]furan-7-yl] octanoate.

What is the InChIKey of thapsigargin?

The InChIKey of thapsigargin is IXFPJGBNCFXKPI-FSIHEZPISA-N.

What is the CAS number of thapsigargin?

The CAS number of thapsigargin is 67526-95-8.

Is thapsigargin a natural product?

Yes, thapsigargin is a natural product found in Thapsia gymnesica, Thapsia villosa, and Thapsia garganica.

What is the role of thapsigargin?

Thapsigargin has a role as an EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor and a calcium channel blocker.

Where is thapsigargin isolated from?

Thapsigargin is isolated from the roots of Thapsia garganica L., Apiaceae.

How is thapsigargin used in traditional medicine?

Thapsigargin is used in traditional medicine as a counter-irritant.

What does thapsigargin inhibit?

Thapsigargin inhibits Ca(2+)-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum.