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Thapsigargin

CAT: 0926-FT45561-05Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0926-FT45561-05Size:10 mg
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CAS Number
67526-95-8
MDL Number
MFCD00083511
Smiles
CCCCCCCC (=O) O[C@H]1[C@H]2C (=C ([C@@H]1OC (=O) /C (=C\C) /C) C) [C@H]3[C@] ([C@H] (C[C@]2 (C) OC (=O) C) OC (=O) CCC) ([C@] (C (=O) O3) (C) O) O
Molecular Formula
C34H50O12
Molecular Weight
650.75 g/mol
Controlled
No

Chemical Information

Thapsigargin

Thapsigargin is 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 used in experimentation examining the impacts of increasing cytosolic calcium concentrations. It has a role as a calcium channel blocker and an EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor. It is an organic heterotricyclic compound, a sesquiterpene lactone and a butyrate ester.

CAS Number67526-95-8
PubChem CID446378
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
Molecular FormulaC34H50O12
Molecular Weight650.8
XLogP3.6
Topological Polar Surface Area172
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count12
Rotatable Bond Count17
Heavy Atom Count46
Formal Charge0
Complexity1270
SMILES
CCCCCCCC(=O)O[C@H]1[C@H]2C(=C([C@@H]1OC(=O)/C(=C\C)/C)C)[C@H]3[C@]([C@H](C[C@]2(C)OC(=O)C)OC(=O)CCC)([C@](C(=O)O3)(C)O)O
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
Chemical Structure
2D Structure
2D structure of Thapsigargin
CAS: 67526-95-8
CID: 446378
Formula: C34H50O12
MW: 650.8
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight650.8
XLogP33.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count12
Rotatable Bond Count17
Exact Mass650.33022703
Monoisotopic Mass650.33022703
Topological Polar Surface Area172 Ų
Heavy Atom Count46
Formal Charge0
Complexity1270
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
TBZ1976Thapsigargin

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