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CHEBI:65588 - caseanigrescen A

ChEBI IDCHEBI:65588
ChEBI Namecaseanigrescen A
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
FormulaC30H42O10
Net Charge0
Average Mass562.656
Monoisotopic Mass562.27780
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@H](OC(C)=O)[C@@H](C)[C@@]2(C)CCC(=C)C=C
InChIInChI=1S/C30H42O10/c1-9-11-24(34)39-21-14-22-27(37-19(6)32)40-28(38-20(7)33)30(22)23(15-21)29(8,13-12-16(3)10-2)17(4)25(26(30)35)36-18(5)31/h10,14,17,21,23,25-28,35H,2-3,9,11-13,15H2,1,4-8H3/t17-,21+,23+,25-,26+,27+,28-,29-,30-/m1/s1
InChIKeyGFJLYOYUCCNCHS-XAOZSVRPSA-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 A (CHEBI:65588) has role antineoplastic agent (CHEBI:35610)
caseanigrescen A (CHEBI:65588) has role metabolite (CHEBI:25212)
caseanigrescen A (CHEBI:65588) is a acetate ester (CHEBI:47622)
caseanigrescen A (CHEBI:65588) is a butyrate ester (CHEBI:50477)
caseanigrescen A (CHEBI:65588) is a cyclic ether (CHEBI:37407)
caseanigrescen A (CHEBI:65588) is a diterpenoid (CHEBI:23849)
caseanigrescen A (CHEBI:65588) is a organic heterotricyclic compound (CHEBI:26979)
caseanigrescen A (CHEBI:65588) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
(1S,3R,5R,6aS,7S,8S,9R,10R,10aS)-1,3,9-tris(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
Registry NumbersSources
Reaxys:11042048Reaxys
Citations