CHEBI:9516 - thapsigargin

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ChEBI Name thapsigargin
ChEBI ID CHEBI:9516
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:45970, CHEBI:363811
Supplier Information ChemicalBook:CB2852025, ChemicalBook:CB61017625, ChemicalBook:CB4362168, eMolecules:475725, ZINC000005133329
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Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group (−C6H5) bonded to a hydroxy group (−OH). Mildly acidic, it requires careful handling because it can cause chemical burns. Phenol was first extracted from coal tar, but today is produced on a large scale (about 7 million tonnes a year) from petroleum-derived feedstocks. It is an important industrial commodity as a precursor to many materials and useful compounds. It is primarily used to synthesize plastics and related materials. Phenol and its chemical derivatives are essential for production of polycarbonates, epoxies, explosives such as picric acid, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceutical drugs.
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Formula C34H50O12
Net Charge 0
Average Mass 650.75360
Monoisotopic Mass 650.33023
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
SMILES [H][C@@]1(OC(=O)C(\C)=C/C)[C@@H](OC(=O)CCCCCCC)[C@@]2([H])C(=C1C)[C@]1([H])OC(=O)[C@@](C)(O)[C@@]1(O)[C@H](C[C@]2(C)OC(C)=O)OC(=O)CCC
Roles Classification
Biological Role(s): EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor
An EC 3.6.3.* (acid anhydride hydrolase catalysing transmembrane movement of substances) inhibitor that interferes with the action of Ca2+-transporting ATPase (EC 3.6.3.8).
calcium channel blocker
One of a class of drugs that acts by selective inhibition of calcium influx through cell membranes or on the release and binding of calcium in intracellular pools.
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ChEBI Ontology
Outgoing thapsigargin (CHEBI:9516) has role calcium channel blocker (CHEBI:38215)
thapsigargin (CHEBI:9516) has role EC 3.6.3.8 (Ca2+-transporting ATPase) inhibitor (CHEBI:60186)
thapsigargin (CHEBI:9516) is a butyrate ester (CHEBI:50477)
thapsigargin (CHEBI:9516) is a organic heterotricyclic compound (CHEBI:26979)
thapsigargin (CHEBI:9516) is a sesquiterpene lactone (CHEBI:37667)
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-2,3,3a,4,5,6,6a,7,8,9b-decahydroazuleno[4,5-b]furan-7-yl octanoate
Synonyms Sources
octanoic acid {3S-[3α,3aβ,4α,6β,6aβ,7β,8α(Z),9bα]}-6-(acetoxy)-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 ChEBI
Tg ChEBI
Thapsigargin KEGG COMPOUND
thapsigargine ChEBI
Manual Xrefs Databases
C00003375 KNApSAcK
C09561 KEGG COMPOUND
LMPR0103410001 LIPID MAPS
TG1 PDBeChem
Thapsigargin Wikipedia
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Registry Numbers Types Sources
4649293 Reaxys Registry Number Reaxys
67526-95-8 CAS Registry Number ChemIDplus
Citations Types Sources
10477042 PubMed citation Europe PMC
12410314 PubMed citation Europe PMC
16874404 PubMed citation Europe PMC
17825049 PubMed citation Europe PMC
20357004 PubMed citation Europe PMC
24598360 PubMed citation Europe PMC
9014219 PubMed citation Europe PMC
Last Modified
26 August 2015