CHEBI:66654 - (+)-makassaric acid

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ChEBI Name (+)-makassaric acid
ChEBI ID CHEBI:66654
Definition A meroterpenoid isolated from the marine sponge Acanthodendrilla sp. It exhibits inhibitory activity against the enzyme mitogen-activated protein kinase-activated protein kinase 2 (EC 2.7.11.1).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C27H38O3
Net Charge 0
Average Mass 410.58880
Monoisotopic Mass 410.28210
InChI InChI=1S/C27H38O3/c1-17-7-10-23-26(4,14-11-22-25(2,3)12-6-13-27(22,23)5)20(17)16-19-15-18(24(29)30)8-9-21(19)28/h7-9,15,20,22-23,28H,6,10-14,16H2,1-5H3,(H,29,30)/t20-,22+,23+,26+,27+/m1/s1
InChIKey VIOMEESUKISOEL-XDEZJFBHSA-N
SMILES [H][C@@]12CC[C@@]3(C)[C@H](Cc4cc(ccc4O)C(O)=O)C(C)=CC[C@]3([H])[C@@]1(C)CCCC2(C)C
Metabolite of Species Details
Acanthodendrilla (NCBI:txid558782) 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): protein kinase inhibitor
An EC 2.7.* (P-containing group transferase) inhibitor that interferes with the action of protein kinases.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via meroterpenoid )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (+)-makassaric acid (CHEBI:66654) has role metabolite (CHEBI:25212)
(+)-makassaric acid (CHEBI:66654) has role protein kinase inhibitor (CHEBI:37699)
(+)-makassaric acid (CHEBI:66654) is a carbotricyclic compound (CHEBI:38032)
(+)-makassaric acid (CHEBI:66654) is a meroterpenoid (CHEBI:64419)
(+)-makassaric acid (CHEBI:66654) is a monohydroxybenzoic acid (CHEBI:25389)
IUPAC Name
3-{[(14β)-8,13-dimethylpodocarp-12-en-14-yl]methyl}-4-hydroxybenzoic acid
Synonym Source
4-hydroxy-3-{[(1R,4aR,4bS,8aS,10aS)-2,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl}benzoic acid IUPAC
Registry Number Type Source
11308967 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
15620270 PubMed citation Europe PMC
Last Modified
28 November 2012