CHEBI:65902 - fomitopinic acid A

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ChEBI Name fomitopinic acid A
ChEBI ID CHEBI:65902
Definition A 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).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C30H48O5
Net Charge 0
Average Mass 488.69910
Monoisotopic Mass 488.35017
InChI InChI=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
InChIKey GCGLPSVDVGXRFN-AMKDLFIQSA-N
SMILES [H][C@@]1(CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CCC(=O)C(C)(C)[C@]1([H])CC3)[C@@H](CC[C@H](O)C(C)(C)O)C(O)=O
Metabolite of Species Details
Fomitopsis pinicola (NCBI:txid40483) Found in fruit body (BTO:0000487). 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): 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.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
10224261 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
15679320 PubMed citation Europe PMC
Last Modified
25 January 2013