thapsigargin (CHEBI:9516)

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CHEBI:9516 - thapsigargin

ChEBI ID	CHEBI:9516
ChEBI Name	thapsigargin
Stars
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.
Secondary ChEBI IDs	CHEBI:45970, CHEBI:363811
Last Modified	26 August 2015
Downloads	Molfile

Formula	C34H50O12
Net Charge	0
Average Mass	650.762
Monoisotopic Mass	650.33023
SMILES	[H][C@]1(OC(=O)/C(C)=C\C)C(C)=C2[C@]3([H])OC(=O)[C@@](C)(O)[C@@]3(O)[C@@H](OC(=O)CCC)C[C@](C)(OC(C)=O)[C@@]2([H])[C@@H]1OC(=O)CCCCCCC
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

Wikipedia

Roles Classification

Biological Roles:

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.

ChEBI Ontology

Outgoing Relation(s)
	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	Source
Thapsigargin	KEGG COMPOUND
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
thapsigargine	ChEBI
Tg	ChEBI

Manual Xrefs	Databases
C09561	KEGG COMPOUND
TG1	PDBeChem
LMPR0103410001	LIPID MAPS
Thapsigargin	Wikipedia
C00003375	KNApSAcK

Registry Numbers	Sources
Reaxys:4649293	Reaxys
CAS:67526-95-8	ChemIDplus

Citations