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CHEBI:65586 - caseamemebrol A

ChEBI IDCHEBI:65586
ChEBI Namecaseamemebrol A
Stars
DefinitionA diterpenoid of the clerodane group isolated from the leaves and twigs of Casearia membranacea. It exhibits significant cytotoxicity against human prostrate (PC-3) cancer cells.
Last Modified6 December 2012
DownloadsMolfile
FormulaC29H42O8
Net Charge0
Average Mass518.647
Monoisotopic Mass518.28797
SMILES[H][C@]12C[C@@H](OC(=O)C(C)CC)C=C3[C@H](OC(C)=O)O[C@H](OC(C)=O)[C@@]31[C@H](O)C[C@H](C)[C@]2(C)C/C=C(\C)C=C
InChIInChI=1S/C29H42O8/c1-9-16(3)11-12-28(8)18(5)13-24(32)29-22(26(34-19(6)30)37-27(29)35-20(7)31)14-21(15-23(28)29)36-25(33)17(4)10-2/h9,11,14,17-18,21,23-24,26-27,32H,1,10,12-13,15H2,2-8H3/b16-11+/t17?,18-,21-,23+,24+,26+,27-,28-,29-/m0/s1
InChIKeyFGGPIWICAGRSLN-WZBIUJGPSA-N
Species of MetaboliteComponentSourceComments
Casearia membranacea (IPNI:779616-1)
leaf (BTO:0000713) PubMed (14709876)
twig (BTO:0001411) PubMed (14709876)
Roles Classification
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
caseamemebrol A (CHEBI:65586) has role antineoplastic agent (CHEBI:35610)
caseamemebrol A (CHEBI:65586) has role metabolite (CHEBI:25212)
caseamemebrol A (CHEBI:65586) is a acetate ester (CHEBI:47622)
caseamemebrol A (CHEBI:65586) is a cyclic ether (CHEBI:37407)
caseamemebrol A (CHEBI:65586) is a diterpenoid (CHEBI:23849)
caseamemebrol A (CHEBI:65586) is a organic heterotricyclic compound (CHEBI:26979)
caseamemebrol A (CHEBI:65586) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
(1R,3S,5R,6aR,7S,8S,10R,10aR)-1,3-bis(acetyloxy)-10-hydroxy-7,8-dimethyl-7-[(2E)-3-methylpenta-2,4-dien-1-yl]-3,5,6,6a,7,8,9,10-octahydronaphtho[1,8a-c]furan-5-yl 2-methylbutanoate
Synonym  Source
(2R,5R,6R,8S,9S,10R,18S,19R)-18,19-diacetoxy-18,19-epoxy-6-hydroxy-2-(2-methylbutanoyloxy)cleroda-3,12,14-trieneChEBI
Citations