CHEBI:141316 - rhizopycnolide A

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ChEBI Name rhizopycnolide A
ChEBI ID CHEBI:141316
Definition A benzochromene that is benzo[c]chromen-6-one which is substituted by hydroxy groups at positions 1, 4 and 7, methoxy groups at positions 3 and 9, a methyl group at position 1, and a 2-carboxy-2-hydroxyethyl group at position 4, and in which the carboxy group has undergone condensation with the 4-hydroxy group to afford the corresponding spirocyclic lactone. It is active against the pathogenic bacteria Agrobacterium tumefaciens, Bacillus subtilis, Pseudomonas lachrymans, Ralstonia solanacearum, Staphylococcus hemolyticus, and Xanthomonas vesicatoria, with MIC values in the range 25-100 μg/mL.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter R. Stephan
Supplier Information
Download Molfile XML SDF
Formula C19H20O9
Net Charge 0
Average Mass 392.357
Monoisotopic Mass 392.11073
InChI InChI=1S/C19H20O9/c1-18(24)7-12(26-3)19(6-11(21)16(22)28-19)15-14(18)9-4-8(25-2)5-10(20)13(9)17(23)27-15/h4-5,11-12,20-21,24H,6-7H2,1-3H3/t11-,12-,18+,19+/m1/s1
InChIKey DXDVGVFRBGQXNB-WPZAJUNFSA-N
SMILES C1(=CC(=C2C(=C1)C3=C(OC2=O)[C@]4([C@@H](C[C@@]3(O)C)OC)OC([C@@H](C4)O)=O)O)OC
Metabolite of Species Details
Rhizopycnis vagum (NCBI:txid1589764) 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing rhizopycnolide A (CHEBI:141316) has role antifungal agent (CHEBI:35718)
rhizopycnolide A (CHEBI:141316) has role fungal metabolite (CHEBI:76946)
rhizopycnolide A (CHEBI:141316) is a γ-lactone (CHEBI:37581)
rhizopycnolide A (CHEBI:141316) is a benzochromene (CHEBI:38920)
rhizopycnolide A (CHEBI:141316) is a oxaspiro compound (CHEBI:37948)
rhizopycnolide A (CHEBI:141316) is a secondary alcohol (CHEBI:35681)
rhizopycnolide A (CHEBI:141316) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
(1S,3R,4S,4'R)-1,4',7-trihydroxy-3,9-dimethoxy-1-methyl-2,3,3',4'-tetrahydro-1H,5'H,6H-spiro[benzo[c]chromene-4,2'-furan]-5',6-dione
Citation Waiting for Citations Type Source
27441892 PubMed citation SUBMITTER
Last Modified
15 November 2018