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CHEBI:66796 - pyripyropene K

ChEBI IDCHEBI:66796
ChEBI Namepyripyropene K
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
FormulaC33H41NO10
Net Charge0
Average Mass611.688
Monoisotopic Mass611.27305
SMILES[H][C@@]12C[C@H](OC(C)=O)[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/C33H41NO10/c1-7-25(36)40-17-32(5)22-15-24(41-18(3)35)33(6)29(31(22,4)12-11-23(32)43-26(37)8-2)28(38)27-21(44-33)14-20(42-30(27)39)19-10-9-13-34-16-19/h9-10,13-14,16,22-24,28-29,38H,7-8,11-12,15,17H2,1-6H3/t22-,23+,24+,28+,29-,31+,32+,33-/m1/s1
InChIKeyKVOOWOAVSBWHFM-TUMCFGMQSA-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 K (CHEBI:66796) has role Aspergillus metabolite (CHEBI:76956)
pyripyropene K (CHEBI:66796) has role acyl-CoA:cholesterol acyltransferase 2 inhibitor (CHEBI:64697)
pyripyropene K (CHEBI:66796) is a acetate ester (CHEBI:47622)
pyripyropene K (CHEBI:66796) is a organic heterotetracyclic compound (CHEBI:38163)
pyripyropene K (CHEBI:66796) is a pyridines (CHEBI:26421)
pyripyropene K (CHEBI:66796) is a sesquiterpenoid (CHEBI:26658)
IUPAC Name 
(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-6-(acetyloxy)-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]chromen-3-yl propanoate
Registry NumbersSources
Reaxys:7326609Reaxys
Citations