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CHEBI:141316 - rhizopycnolide A

Default Structure
ChEBI IDCHEBI:141316
ChEBI Namerhizopycnolide A
Stars
DefinitionA 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.
Last Modified15 November 2018
SubmitterR. Stephan
DownloadsMolfile
FormulaC19H20O9
Net Charge0
Average Mass392.360
Monoisotopic Mass392.11073
SMILESCOc1cc(O)c2c(=O)oc3c(c2c1)[C@@](C)(O)C[C@@H](OC)[C@@]31C[C@@H](O)C(=O)O1
InChIInChI=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
InChIKeyDXDVGVFRBGQXNB-WPZAJUNFSA-N
Species of MetaboliteComponentSourceComments
Rhizopycnis vagum (ncbitaxon:1589764) - PubMed (27441892)
Roles Classification
Biological Roles:
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 Relation(s)
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 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)
rhizopycnolide A (CHEBI:141316) is a γ-lactone (CHEBI:37581)
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
Citations