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CHEBI:65902 - fomitopinic acid A

Default Structure
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:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
cyclooxygenase 1 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
cyclooxygenase 2 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
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