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CHEBI:65587 - caseamemebrol B

ChEBI IDCHEBI:65587
ChEBI Namecaseamemebrol B
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
FormulaC29H42O9
Net Charge0
Average Mass534.646
Monoisotopic Mass534.28288
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@H](O)C(=C)C=C
InChIInChI=1S/C29H42O9/c1-9-15(3)22(32)14-28(8)17(5)11-24(33)29-21(26(35-18(6)30)38-27(29)36-19(7)31)12-20(13-23(28)29)37-25(34)16(4)10-2/h9,12,16-17,20,22-24,26-27,32-33H,1,3,10-11,13-14H2,2,4-8H3/t16?,17-,20-,22-,23+,24+,26+,27-,28-,29-/m0/s1
InChIKeyFVXRSGIAXHNGNZ-DHKDGQATSA-N
Species of MetaboliteComponentSourceComments
Casearia membranacea (IPNI:779616-1)
twig (BTO:0001411) PubMed (14709876)
leaf (BTO:0000713) 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 B (CHEBI:65587) has role antineoplastic agent (CHEBI:35610)
caseamemebrol B (CHEBI:65587) has role metabolite (CHEBI:25212)
caseamemebrol B (CHEBI:65587) is a acetate ester (CHEBI:47622)
caseamemebrol B (CHEBI:65587) is a cyclic ether (CHEBI:37407)
caseamemebrol B (CHEBI:65587) is a diol (CHEBI:23824)
caseamemebrol B (CHEBI:65587) is a diterpenoid (CHEBI:23849)
caseamemebrol B (CHEBI:65587) is a organic heterotricyclic compound (CHEBI:26979)
caseamemebrol B (CHEBI:65587) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
(1R,3S,5R,6aR,7S,8S,10R,10aR)-1,3-bis(acetyloxy)-10-hydroxy-7-[(2S)-2-hydroxy-3-methylidenepent-4-en-1-yl]-7,8-dimethyl-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,12S,18S,19R)-18,19-diacetoxy-18,19-epoxy-6-hydroxy-2-(2-methylbutanoyloxy)-cleroda-12-hydroxy-3,13(16),14-trieneChEBI
Citations