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
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Formula C34H50O12
Net Charge 0
Average Mass 650.75360
Monoisotopic Mass 650.330
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
Database Links Databases
C00003375 KNApSAcK
C09561 KEGG COMPOUND
LMPR0103410001 LIPID MAPS
TG1 PDBeChem
Thapsigargin Wikipedia
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Registry Numbers Types Sources
4649293 Beilstein Registry Number Beilstein
4649293 Reaxys Registry Number Reaxys
67526-95-8 CAS Registry Number ChemIDplus
Citations Waiting for 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