CHEBI:69026 - preaustinoid A1

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ChEBI Name preaustinoid A1
ChEBI ID CHEBI:69026
Definition A meroterpenoid found in Penicillium rubrum and Penicillium species. It has been found to exhibit inhibitory activity against the production of interleukin 1-β from induced inflammasomes.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C26H36O7
Net Charge 0
Average Mass 460.567
Monoisotopic Mass 460.24610
InChI InChI=1S/C26H36O7/c1-14-23(5)13-16-22(4)11-10-17(27)33-21(2,3)15(22)9-12-24(16,6)26(14,20(30)32-8)19(29)25(7,31)18(23)28/h15-16,31H,1,9-13H2,2-8H3/t15-,16+,22-,23-,24+,25+,26+/m1/s1
InChIKey XBLDTXYFLHSWHN-RFMSQVAGSA-N
SMILES [H][C@@]12C[C@]3(C)C(=C)[C@@](C(=O)OC)(C(=O)[C@@](C)(O)C3=O)[C@@]1(C)CC[C@@]1([H])[C@@]2(C)CCC(=O)OC1(C)C
Metabolite of Species Details
Penicillium rubrum (NCBI:txid1266769) Chloroform extract See: PubMed
Penicillium sp. (NCBI:txid5081) See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via meroterpenoid )
cysteine protease inhibitor
Any protease inhibitor that restricts the action of a cysteine protease.
Penicillium metabolite
Any fungal metabolite produced during a metabolic reaction in Penicillium.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing preaustinoid A1 (CHEBI:69026) has role Penicillium metabolite (CHEBI:76964)
preaustinoid A1 (CHEBI:69026) has role cysteine protease inhibitor (CHEBI:64152)
preaustinoid A1 (CHEBI:69026) has role metabolite (CHEBI:25212)
preaustinoid A1 (CHEBI:69026) is a carboxylic ester (CHEBI:33308)
preaustinoid A1 (CHEBI:69026) is a cyclic terpene ketone (CHEBI:36130)
preaustinoid A1 (CHEBI:69026) is a meroterpenoid (CHEBI:64419)
preaustinoid A1 (CHEBI:69026) is a organic heterotetracyclic compound (CHEBI:38163)
preaustinoid A1 (CHEBI:69026) is a terpene lactone (CHEBI:37668)
preaustinoid A1 (CHEBI:69026) is a tertiary α-hydroxy ketone (CHEBI:139592)
preaustinoid A1 (CHEBI:69026) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
methyl (5aS,7aS,8R,10S,12R,13aS,13bS)-10-hydroxy-5,5,7a,10,12,13b-hexamethyl-14-methylidene-3,9,11-trioxotetradecahydro-8,12-methanocycloocta[3,4]benzo[1,2-c]oxepine-8(5H)-carboxylate
Synonym Source
preaustinoid A1 UniProt
Manual Xref Database
8SX PDBeChem
View more database links
Registry Number Type Source
21969350 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
14577628 PubMed citation Europe PMC
19678538 PubMed citation Europe PMC
21916432 PubMed citation Europe PMC
26396816 PubMed citation Europe PMC
29317628 PubMed citation Europe PMC
Last Modified
18 August 2020
General Comment
2020-08-18 The stereo-configuration of the structure changed from 5aR to 5aS due to evidence found in PMID:29317628. The crystal structure of ligand also supports this new configuration.