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CHEBI:66794 - pyripyropene I

ChEBI IDCHEBI:66794
ChEBI Namepyripyropene I
Stars
DefinitionA sesquiterpenoid that consists of a heterotetracyclic system linked to a pyridine moiety. Isolated from the fungus, Aspergillus fumigatus, it exhibits inhibitory activity against acyl-CoA:cholesterol acyltransferase 2.
Last Modified13 January 2014
DownloadsMolfile
FormulaC34H43NO10
Net Charge0
Average Mass625.715
Monoisotopic Mass625.28870
SMILES[H][C@@]12C[C@H](OC(=O)CC)[C@@]3(C)Oc4cc(-c5cccnc5)oc(=O)c4[C@H](O)[C@]3([H])[C@@]1(C)CC[C@H](OC(=O)CC)[C@@]2(C)COC(=O)CC
InChIInChI=1S/C34H43NO10/c1-7-25(36)41-18-33(5)22-16-24(44-27(38)9-3)34(6)30(32(22,4)13-12-23(33)43-26(37)8-2)29(39)28-21(45-34)15-20(42-31(28)40)19-11-10-14-35-17-19/h10-11,14-15,17,22-24,29-30,39H,7-9,12-13,16,18H2,1-6H3/t22-,23+,24+,29+,30-,32+,33+,34-/m1/s1
InChIKeyBEQWYQUVYKTZHJ-FRXPNXMYSA-N
Species of MetaboliteComponentSourceComments
Aspergillus fumigatus (ncbitaxon:746128) - PubMed (7622436) Strain: FO 1289-2501
Roles Classification
Biological Roles:
acyl-CoA:cholesterol acyltransferase 2 inhibitor  A sterol O-acyltransferase inhibitor that specifically inhibits acyl-CoA:cholesterol acyltransferase 2.
Aspergillus metabolite  Any fungal metabolite produced during a metabolic reaction in the mould, Aspergillus .
ChEBI Ontology
Outgoing Relation(s)
pyripyropene I (CHEBI:66794) has role Aspergillus metabolite (CHEBI:76956)
pyripyropene I (CHEBI:66794) has role acyl-CoA:cholesterol acyltransferase 2 inhibitor (CHEBI:64697)
pyripyropene I (CHEBI:66794) is a carboxylic ester (CHEBI:33308)
pyripyropene I (CHEBI:66794) is a organic heterotetracyclic compound (CHEBI:38163)
pyripyropene I (CHEBI:66794) is a pyridines (CHEBI:26421)
pyripyropene I (CHEBI:66794) is a sesquiterpenoid (CHEBI:26658)
IUPAC Name 
(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-12-hydroxy-4,6a,12b-trimethyl-11-oxo-4-[(propanoyloxy)methyl]-9-(pyridin-3-yl)-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-benzo[f]pyrano[4,3-b]chromene-3,6-diyl dipropanoate
Registry NumbersSources
Reaxys:7327101Reaxys
Citations