isoaigialone B (CHEBI:141363)

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ChEBI Name	isoaigialone B

ChEBI ID	CHEBI:141363

Definition	A γ-lactone that is 3,4,5,7-tetrahydro-2H-furo[3,4-b]pyran substituted by heptyl, methyl, hydroxy, hydroxy, oxo and methyl groups at positions 2R, 3S, 3S, 4R, 5 and 7R, respectively. It is isolated from the endophytic fungus Phaeoacremonium sp. and exhibits antifungal activities.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	R. Stephan

Supplier Information

Download	Molfile XML SDF

Formula

C16H26O5

Net Charge

Average Mass

298.379

Monoisotopic Mass

298.17802

InChI

InChI=1S/C16H26O5/c1-4-5-6-7-8-9-11-16(3,19)14(17)12-13(21-11)10(2)20-15(12)18/h10-11,14,17,19H,4-9H2,1-3H3/t10-,11-,14-,16-/m1/s1

InChIKey

VVQFDQXQOOFTTF-MMYVAXCBSA-N

SMILES

CCCCCCC[C@H]1OC2=C([C@@H](O)[C@]1(C)O)C(=O)O[C@@H]2C

Metabolite of Species	Details
Phaeoacremonium sp. (NCBI:txid1769363)	See: PubMed

Roles Classification
Biological Role(s):	antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce. fungal metabolite Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.

ChEBI Ontology
Outgoing	isoaigialone B (CHEBI:141363) has role antifungal agent (CHEBI:35718) isoaigialone B (CHEBI:141363) has role fungal metabolite (CHEBI:76946) isoaigialone B (CHEBI:141363) is a γ-lactone (CHEBI:37581) isoaigialone B (CHEBI:141363) is a diol (CHEBI:23824) isoaigialone B (CHEBI:141363) is a organic heterobicyclic compound (CHEBI:27171) isoaigialone B (CHEBI:141363) is a secondary alcohol (CHEBI:35681) isoaigialone B (CHEBI:141363) is a tertiary alcohol (CHEBI:26878)

IUPAC Name

(2R,3S,4R,7R)-2-heptyl-3,4-dihydroxy-3,7-dimethyl-2,3,4,7-tetrahydro-5H-furo[3,4-b]pyran-5-one

Last Modified

20 April 2021