CHEBI:66520 - spiculoic acid A

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ChEBI Name spiculoic acid A
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C27H36O3
Net Charge 0
Average Mass 408.57290
Monoisotopic Mass 408.26645
InChI InChI=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
SMILES [H][C@@]12[C@@H](C)C(=O)[C@H](CC)[C@@]1([H])[C@](CC)(C(O)=O)[C@@](CC)(C=C2CC)\C=C\c1ccccc1
Metabolite of Species Details
Plakortis angulospiculatus (NCBI:txid295227) See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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)
(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 Number Type Source
9666648 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
14703354 PubMed citation Europe PMC
16320993 PubMed citation Europe PMC
17007398 PubMed citation Europe PMC
17107066 PubMed citation Europe PMC
22801647 PubMed citation Europe PMC
Last Modified
08 July 2013