EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:66654 - (+)-makassaric acid

ChEBI IDCHEBI:66654
ChEBI Name(+)-makassaric acid
Stars
DefinitionA 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).
Last Modified28 November 2012
DownloadsMolfile
FormulaC27H38O3
Net Charge0
Average Mass410.598
Monoisotopic Mass410.28210
SMILES[H][C@]12CC=C(C)[C@@H](Cc3cc(C(=O)O)ccc3O)[C@]1(C)CC[C@@]1([H])C(C)(C)CCC[C@]21C
InChIInChI=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
InChIKeyVIOMEESUKISOEL-XDEZJFBHSA-N
Species of MetaboliteComponentSourceComments
Acanthodendrilla (ncbitaxon:558782) - PubMed (15620270)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
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.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
(+)-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 acidIUPAC
Registry NumbersSources
Reaxys:11308967Reaxys
Citations