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CHEBI:65591 - caseanigrescen D

ChEBI IDCHEBI:65591
ChEBI Namecaseanigrescen D
Stars
DefinitionA diterpenoid of the clerodane group isolated from the leaves and flowers of Casearia nigrescens. It exhibits cytotoxicity against A2780 human ovarian cancer cell line.
Last Modified7 December 2012
DownloadsMolfile
FormulaC28H40O8
Net Charge0
Average Mass504.620
Monoisotopic Mass504.27232
SMILES[H][C@@]12C[C@@H](OC(=O)CCC)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)CCC(=C)C=C
InChIInChI=1S/C28H40O8/c1-8-10-24(32)35-20-14-21-25(33-18(5)29)36-26(34-19(6)30)28(21)22(15-20)27(7,12-11-16(3)9-2)17(4)13-23(28)31/h9,14,17,20,22-23,25-26,31H,2-3,8,10-13,15H2,1,4-7H3/t17-,20+,22+,23+,25+,26-,27-,28-/m1/s1
InChIKeyOYLJTRVIXSOCPW-MGZSJDQHSA-N
Species of MetaboliteComponentSourceComments
Casearia nigrescens (IPNI:779628-1)
flower (BTO:0000469) PubMed (17315961)
leaf (BTO:0000713) PubMed (17315961)
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)
caseanigrescen D (CHEBI:65591) has role antineoplastic agent (CHEBI:35610)
caseanigrescen D (CHEBI:65591) has role metabolite (CHEBI:25212)
caseanigrescen D (CHEBI:65591) is a acetate ester (CHEBI:47622)
caseanigrescen D (CHEBI:65591) is a butyrate ester (CHEBI:50477)
caseanigrescen D (CHEBI:65591) is a cyclic ether (CHEBI:37407)
caseanigrescen D (CHEBI:65591) is a diterpenoid (CHEBI:23849)
caseanigrescen D (CHEBI:65591) is a organic heterotricyclic compound (CHEBI:26979)
caseanigrescen D (CHEBI:65591) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
(1S,3R,5R,6aS,7R,8R,10S,10aS)-1,3-bis(acetyloxy)-10-hydroxy-7,8-dimethyl-7-(3-methylidenepent-4-en-1-yl)-3,5,6,6a,7,8,9,10-octahydronaphtho[1,8a-c]furan-5-yl butanoate
Manual XrefsDatabases
17267181ChemSpider
Registry NumbersSources
Reaxys:11042051Reaxys
Citations