ChemSpider 2D Image | Thapsigargin | C34H50O12

Thapsigargin

  • Molecular FormulaC34H50O12
  • Average mass650.754 Da
  • Monoisotopic mass650.330200 Da
  • ChemSpider ID393753

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 8 of 8 defined stereocentres

More details:

Featured data source
Natural Product Updates

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(-)-Thapsigargin
(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-2,3,3a,4,5,6,6a,7,8,9b-decahydroazuleno[4,5-b]furan-7-yl octanoate
(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
(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-Acetoxy-4-(butyryloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-{[(2Z)-2-methyl-2-butenoyl]oxy}-2-oxo-2,3,3a,4,5,6,6a,7,8,9b-decahydroazuleno[4,5-b]furan-7-yl octanoate [ACD/IUPAC Name]
(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-Acetoxy-4-(butyryloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-{[(2Z)-2-methyl-2-butenoyl]oxy}-2-oxo-2,3,3a,4,5,6,6a,7,8,9b-decahydroazuleno[4,5-b]furan-7-yl-octanoat [German] [ACD/IUPAC Name]
(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-Acetoxy-4-(butyryloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-{[(2Z)-2-methylbut-2-enoyl]oxy}-2-oxo-2,3,3a,4,5,6,6a,7,8,9b-decahydroazuleno[4,5-b]furan-7-yl octanoate
MFCD00083511
Octanoate de (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acétoxy-4-(butyryloxy)-3,3a-dihydroxy-3,6,9-triméthyl-8-{[(2Z)-2-méthyl-2-butenoyl]oxy}-2-oxo-2,3,3a,4,5,6,6a,7,8,9b-décahydroazuléno[4,5-b]furan-7-yle [French] [ACD/IUPAC Name]
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]f uran-7-yl ester [ACD/Index Name]
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
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

4649293 [DBID]
C09561 [DBID]
EU-0101262 [DBID]
T9033_SIGMA [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      An organic heterotricyclic compound that is a hexa-oxygenated 6,7-guaianolide isolated fron the roots of <ital>Thapsia garganica</ital> L., <ital>Apiaceae</ital>. A potent skin irritant, it is used in traditional medicine as a counter-irritant. Thapsigargin inhibits <element>Ca</element><smallsup>2+</smallsup>-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is u sed in experimentation examining the impacts of increasing cytosolic calcium concentrations. ChEBI CHEBI:9516
      An organic heterotricyclic compound that is a hexa-oxygenated 6,7-guaianolide isolated fron the roots of Thapsia garganica L., Apiaceae. A potent skin irritant, it is used in traditional medicine as a counter-irritant. Thapsigargin inhibits Ca(2+)-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is used in experimentation examining the impacts of increasing cytos olic calcium concentrations. ChEBI CHEBI:9516
      An organic heterotricyclic compound that is a hexa-oxygenated 6,7-guaianolide isolated fron the roots of Thapsia garganica L., Apiaceae. A potent skin irritant, it is used in; traditional medicine as a counter-irritant. Thapsigargin inhibits Ca2+-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is u; sed in experimentation examining the impacts of increasing cyt osolic calcium concentrations. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9516
      Intracellular Calcium EU-OpenScreen [T 9033]

    • Bio Activity:

      ATPase Tocris Bioscience 1138
      ATPases/GTPases Tocris Bioscience 1138
      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio HB1118
      Cell signaling/Ca<sup>2+</sup> signaling/Ca<sup>2+</sup>-ATPase (SERCA) Hello Bio HB1118
      Enzymes Tocris Bioscience 1138
      Enzymes/ATPase / GTPase/Ca<sup>2+</sup>-ATPase (SERCA) Hello Bio HB1118
      Potent and non-competitive sarco-endoplasmic Ca<sup>2+</sup>-ATPase (SERCA) inhibitor. Activates endoplasmic reticulum stress mechanisms. Induces apoptosis in most cells. Shows anticancer and neuroprotective actions. Hello Bio HB1118
      Potent inhibitor of sarco-endoplasmic reticulum Ca2+-ATPases. Causes ER stress; can be used to induce autophagy in mammalian cells. Tocris Bioscience 1138
      Potent inhibitor of SERCA ATPase Tocris Bioscience 1138
      Potent, non-competitive SERCA inhibitor Hello Bio HB1118

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.2±0.1 g/cm3
Boiling Point: 691.9±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±4.9 mmHg at 25°C
Enthalpy of Vaporization: 115.9±6.0 kJ/mol
Flash Point: 206.1±25.0 °C
Index of Refraction: 1.539
Molar Refractivity: 164.8±0.4 cm3
#H bond acceptors: 12
#H bond donors: 2
#Freely Rotating Bonds: 17
#Rule of 5 Violations: 3
ACD/LogP: 6.98
ACD/LogD (pH 5.5): 6.73
ACD/BCF (pH 5.5): 76981.93
ACD/KOC (pH 5.5): 109460.16
ACD/LogD (pH 7.4): 6.73
ACD/BCF (pH 7.4): 76922.95
ACD/KOC (pH 7.4): 109376.31
Polar Surface Area: 172 Å2
Polarizability: 65.3±0.5 10-24cm3
Surface Tension: 51.4±5.0 dyne/cm
Molar Volume: 525.8±5.0 cm3

Click to predict properties on the Chemicalize site


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