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Thapsigargin

CAT: 0804-HY-13433-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-13433-01Size:1 mg
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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[1][2][3][4][5].
CAS Number
67526-95-8
UNSPSC
12352005
Hazard Statement
H315, H319, H334, H335
Target
Apoptosis; Calcium Channel; SARS-CoV
Type
Natural Products
Related Pathways
Anti-infection; Apoptosis; Membrane Transporter/Ion Channel; Neuronal Signaling
Applications
Cancer-programmed cell death
Field of Research
Cancer; Infection
Assay Protocol
https://www.medchemexpress.com/Thapsigargin.html
Purity
99.95
Solubility
DMSO : 50 mg/mL (ultrasonic)
Smiles
CCCCCCCC(O[C@@H]1[C@@H](OC(/C(C)=C\C)=O)C(C)=C2[C@@]1([H])[C@@](C)(OC(C)=O)C[C@H](OC(CCC)=O)[C@@]([C@@]3(O)C)(O)[C@@]2([H])OC3=O)=O
Molecular Formula
C34H50O12
Molecular Weight
650.75
Precautions
H315, H319, H334, H335
References & Citations
2+
Shipping Conditions
Blue Ice
Storage Conditions
-20°C (Powder, sealed storage, away from moisture and light)
Scientific Category
Natural Products
Clinical Information
No Development Reported

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

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