loading...| Preferred Name |
thapsigargin |
|
| Synonyms |
(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 Thapsigargin octanoic acid {3S-[3alpha,3abeta,4alpha,6beta,6abeta,7beta,8alpha(Z),9balpha]}-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 thapsigargine Tg |
|
| Definitions |
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 Ca(2+)-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is used in experimentation examining the impacts of increasing cytosolic calcium concentrations. |
|
| ID |
http://purl.obolibrary.org/obo/CHEBI_9516 |
|
| charge |
0 |
|
| database_cross_reference |
PMID:10477042 PDBeChem:TG1 PMID:17825049 LIPID_MAPS_instance:LMPR0103410001 PMID:9014219 KNApSAcK:C00003375 PMID:12410314 PMID:20357004 Wikipedia:Thapsigargin KEGG:C09561 Reaxys:4649293 PMID:24598360 Beilstein:4649293 CAS:67526-95-8 PMID:16874404 |
|
| 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 Ca(2+)-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is used in experimentation examining the impacts of increasing cytosolic calcium concentrations. |
|
| formula |
C34H50O12 |
|
| has_alternative_id |
CHEBI:363811 CHEBI:45970 |
|
| has_exact_synonym |
(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 Thapsigargin |
|
| has_obo_namespace |
chebi_ontology |
|
| has_related_synonym |
octanoic acid {3S-[3alpha,3abeta,4alpha,6beta,6abeta,7beta,8alpha(Z),9balpha]}-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 thapsigargine Tg |
|
| id |
CHEBI:9516 |
|
| in_subset | ||
| 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 |
|
| label |
thapsigargin |
|
| mass |
650.75360 |
|
| monoisotopicmass |
650.33023 |
|
| notation |
CHEBI:9516 |
|
| prefLabel |
thapsigargin |
|
| 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 |
|
| subClassOf |