CHEBI:66794 - pyripyropene I

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ChEBI Name pyripyropene I
ChEBI ID CHEBI:66794
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C34H43NO10
Net Charge 0
Average Mass 625.70590
Monoisotopic Mass 625.28870
InChI InChI=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
InChIKey BEQWYQUVYKTZHJ-FRXPNXMYSA-N
SMILES CCC(=O)OC[C@]1(C)[C@H](CC[C@@]2(C)[C@H]1C[C@H](OC(=O)CC)[C@@]1(C)Oc3cc(oc(=O)c3[C@H](O)[C@H]21)-c1cccnc1)OC(=O)CC
Metabolite of Species Details
Aspergillus fumigatus (NCBI:txid746128) of strain FO 1289-2501 See: PubMed
Roles Classification
Biological Role(s): 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 .
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Number Type Source
7327101 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
7622436 PubMed citation Europe PMC
Last Modified
13 January 2014