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CHEBI:65902 - fomitopinic acid A

ChEBI IDCHEBI:65902
ChEBI Namefomitopinic acid A
Stars
DefinitionA tetracyclic triterpenoid that is lanost-8-ene substituted by hydroxy groups at positions 24 and 25 , a carboxylic acid at position 21 and an oxo grouo at position 3 (the 24S stereoisomer). Isolated from the fruit bodies of Fomitopsis pinicola, it exhibits antiinflammatory activity against cylooxygenase-1 (COX-1) and cylooxygenase-2 (COX-2).
Last Modified25 January 2013
DownloadsMolfile
FormulaC30H48O5
Net Charge0
Average Mass488.709
Monoisotopic Mass488.35017
SMILES[H][C@@]12CCC3=C(CC[C@@]4(C)[C@@]3(C)CC[C@]4([H])[C@@H](CC[C@H](O)C(C)(C)O)C(=O)O)[C@@]1(C)CCC(=O)C2(C)C
InChIInChI=1S/C30H48O5/c1-26(2)22-10-9-21-20(28(22,5)15-14-23(26)31)13-17-29(6)19(12-16-30(21,29)7)18(25(33)34)8-11-24(32)27(3,4)35/h18-19,22,24,32,35H,8-17H2,1-7H3,(H,33,34)/t18-,19-,22+,24+,28-,29-,30+/m1/s1
InChIKeyGCGLPSVDVGXRFN-AMKDLFIQSA-N
Species of MetaboliteComponentSourceComments
Fomitopsis pinicola (ncbitaxon:40483) fruit body (BTO:0000487) PubMed (15679320)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
cyclooxygenase 2 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
cyclooxygenase 1 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
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)
fomitopinic acid A (CHEBI:65902) has parent hydride lanostane (CHEBI:20265)
fomitopinic acid A (CHEBI:65902) has role cyclooxygenase 1 inhibitor (CHEBI:50630)
fomitopinic acid A (CHEBI:65902) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
fomitopinic acid A (CHEBI:65902) has role metabolite (CHEBI:25212)
fomitopinic acid A (CHEBI:65902) is a diol (CHEBI:23824)
fomitopinic acid A (CHEBI:65902) is a oxo monocarboxylic acid (CHEBI:35871)
fomitopinic acid A (CHEBI:65902) is a tetracyclic triterpenoid (CHEBI:26893)
IUPAC Name 
(24S)-24,25-dihydroxy-3-oxolanost-8-en-21-oic acid
Registry NumbersSources
Reaxys:10224261Reaxys
Citations