CHEBI:72441 - englerin A

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ChEBI Name englerin A
ChEBI ID CHEBI:72441
Definition A guaiane sesquiterpenoid that is isolated from the bark of Phyllanthus engleri, a plant native to Tanzania and Zimbabwe. It acts as a potent and specific inhibitor of renal cancer cell growth.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Margaret Duesbury
Supplier Information
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Formula C26H34O6
Net Charge 0
Average Mass 442.54460
Monoisotopic Mass 442.23554
InChI InChI=1S/C26H34O6/c1-16(2)26-14-20(30-22(29)15-27)25(4,32-26)19-12-10-17(3)23(19)24(26)31-21(28)13-11-18-8-6-5-7-9-18/h5-9,11,13,16-17,19-20,23-24,27H,10,12,14-15H2,1-4H3/b13-11+/t17-,19-,20-,23-,24+,25+,26-/m1/s1
InChIKey GACOFEKSDCOVMV-RRYXBOBMSA-N
SMILES [H][C@@]12CC[C@@H](C)[C@@]1([H])[C@H](OC(=O)\C=C\c1ccccc1)[C@@]1(C[C@@H](OC(=O)CO)[C@@]2(C)O1)C(C)C
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing englerin A (CHEBI:72441) has role antineoplastic agent (CHEBI:35610)
englerin A (CHEBI:72441) has role metabolite (CHEBI:25212)
englerin A (CHEBI:72441) is a cinnamate ester (CHEBI:36087)
englerin A (CHEBI:72441) is a glycolate ester (CHEBI:37938)
englerin A (CHEBI:72441) is a guaiane sesquiterpenoid (CHEBI:36744)
IUPAC Name
(1R,3aR,4S,5R,7R,8S,8aR)-5-(glycoloyloxy)-7-isopropyl-1,4-dimethyldecahydro-4,7-epoxyazulen-8-yl (2E)-3-phenylacrylate
Manual Xrefs Databases
US2010286259 Patent
WO2009088854 Patent
WO2011120886 Patent
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Registry Number Type Source
21475559 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
19061394 PubMed citation Europe PMC
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23292997 PubMed citation Europe PMC
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Last Modified
18 February 2013