CHEBI:141361 - aigialone

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ChEBI Name aigialone
ChEBI ID CHEBI:141361
Definition A furopyran that is 5,6-dihydro-4H-furo[2,3-b]pyran-3(2H)-one which is substituted by hydroxy groups at positions 4 and 5, methyl groups at positions 2 and 5, and a heptyl group at position 6 (the 2R,4R,5S,6R stereoisomer). Isolated from the mangrove fungus Aigialus parvus BCC 5311 and from Phaeoacremonium sp., an endophytic fungus from Senna spectabilis.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter R. Stephan
Supplier Information
Download Molfile XML SDF
Formula C16H26O5
Net Charge 0
Average Mass 298.379
Monoisotopic Mass 298.17802
InChI InChI=1S/C16H26O5/c1-4-5-6-7-8-9-11-16(3,19)14(18)12-13(17)10(2)20-15(12)21-11/h10-11,14,18-19H,4-9H2,1-3H3/t10-,11-,14-,16-/m1/s1
InChIKey YVCGKKHYXVEPMA-MMYVAXCBSA-N
SMILES [C@H]1(C2=C(O[C@@H]([C@]1(O)C)CCCCCCC)O[C@@H](C2=O)C)O
Metabolite of Species Details
Phaeoacremonium sp. See: PubMed
Roles Classification
Biological Role(s): fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing aigialone (CHEBI:141361) has role antifungal agent (CHEBI:35718)
aigialone (CHEBI:141361) has role fungal metabolite (CHEBI:76946)
aigialone (CHEBI:141361) is a cyclic ketone (CHEBI:3992)
aigialone (CHEBI:141361) is a furopyran (CHEBI:74927)
aigialone (CHEBI:141361) is a ketene acetal (CHEBI:145408)
aigialone (CHEBI:141361) is a secondary alcohol (CHEBI:35681)
aigialone (CHEBI:141361) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
(2R,4R,5S,6R)-6-heptyl-4,5-dihydroxy-2,5-dimethyl-5,6-dihydro-4H-furo[2,3-b]pyran-3(2H)-one
Synonym Source
(−)-aigialone KNApSAcK
Manual Xref Database
C00043254 KNApSAcK
View more database links
Registry Number Type Source
666735-72-4 CAS Registry Number KNApSAcK
Citation Waiting for Citations Type Source
28425292 PubMed citation SUBMITTER
Last Modified
18 November 2019