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:

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.

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).

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
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

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

Citations