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CHEBI:65589 - caseanigrescen B

ChEBI IDCHEBI:65589
ChEBI Namecaseanigrescen B
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
FormulaC28H40O9
Net Charge0
Average Mass520.619
Monoisotopic Mass520.26723
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](O)[C@@H](C)[C@@]2(C)CCC(=C)C=C
InChIInChI=1S/C28H40O9/c1-8-10-22(31)36-19-13-20-25(34-17(5)29)37-26(35-18(6)30)28(20)21(14-19)27(7,12-11-15(3)9-2)16(4)23(32)24(28)33/h9,13,16,19,21,23-26,32-33H,2-3,8,10-12,14H2,1,4-7H3/t16-,19+,21+,23-,24+,25+,26-,27-,28-/m1/s1
InChIKeyFACSSBRLFWVHQA-OISZFCHFSA-N
Species of MetaboliteComponentSourceComments
Casearia nigrescens (IPNI:779628-1)
leaf (BTO:0000713) PubMed (17315961)
flower (BTO:0000469) 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 B (CHEBI:65589) has role antineoplastic agent (CHEBI:35610)
caseanigrescen B (CHEBI:65589) has role metabolite (CHEBI:25212)
caseanigrescen B (CHEBI:65589) is a acetate ester (CHEBI:47622)
caseanigrescen B (CHEBI:65589) is a butyrate ester (CHEBI:50477)
caseanigrescen B (CHEBI:65589) is a cyclic ether (CHEBI:37407)
caseanigrescen B (CHEBI:65589) is a diol (CHEBI:23824)
caseanigrescen B (CHEBI:65589) is a diterpenoid (CHEBI:23849)
caseanigrescen B (CHEBI:65589) is a organic heterotricyclic compound (CHEBI:26979)
caseanigrescen B (CHEBI:65589) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
(1S,3R,5R,6aS,7S,8S,9R,10R,10aS)-1,3-bis(acetyloxy)-9,10-dihydroxy-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:11042049Reaxys
Citations