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CHEBI:66520 - spiculoic acid A

ChEBI IDCHEBI:66520
ChEBI Namespiculoic acid A
Stars
DefinitionA carbobicyclic compound that is 2,3,3a,4,5,7a-hexahydro-1H-indene substituted by ethyl groups at positions 3, 4, 5 and 7, a methyl group at position 1, an oxo group at position 2, a 2-phenylethenyl group at position 5 and a carboxy group at position 4 (the 1R,3R,3aS,4S,5R,7aS stereoisomer). Isolated from Plakortis angulospiculatus, it exhibits cytotoxicity against human breast cancer MCF-7 cells.
Last Modified8 July 2013
DownloadsMolfile
FormulaC27H36O3
Net Charge0
Average Mass408.582
Monoisotopic Mass408.26645
SMILES[H][C@@]12[C@@H](CC)C(=O)[C@H](C)[C@@]1([H])C(CC)=C[C@](/C=C/c1ccccc1)(CC)[C@@]2(CC)C(=O)O
InChIInChI=1S/C27H36O3/c1-6-20-17-26(8-3,16-15-19-13-11-10-12-14-19)27(9-4,25(29)30)23-21(7-2)24(28)18(5)22(20)23/h10-18,21-23H,6-9H2,1-5H3,(H,29,30)/b16-15+/t18-,21-,22+,23-,26-,27-/m1/s1
InChIKeyALLQJQBDLUMIQH-UOVLAWSHSA-N
Species of MetaboliteComponentSourceComments
Plakortis angulospiculatus (ncbitaxon:295227) - PubMed (14703354)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
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)
spiculoic acid A (CHEBI:66520) has role antineoplastic agent (CHEBI:35610)
spiculoic acid A (CHEBI:66520) has role metabolite (CHEBI:25212)
spiculoic acid A (CHEBI:66520) is a carbobicyclic compound (CHEBI:36785)
spiculoic acid A (CHEBI:66520) is a cyclic ketone (CHEBI:3992)
spiculoic acid A (CHEBI:66520) is a oxo monocarboxylic acid (CHEBI:35871)
spiculoic acid A (CHEBI:66520) is a styrenes (CHEBI:26799)
IUPAC Name 
(1R,3R,3aS,4S,5R,7aS)-3,4,5,7-tetraethyl-1-methyl-2-oxo-5-[(E)-2-phenylethenyl]-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid
Registry NumbersSources
Reaxys:9666648Reaxys
Citations