CHEBI:194133 - hemiustilaginoidin F

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ChEBI Name hemiustilaginoidin F
ChEBI ID CHEBI:194133
Definition A naphtho-γ-pyrone which carries hydroxy substituents at positions C-5, C-6 and C-8 and a methyl group at C-2. Obtained from the laccase gene deletion mutant of Villosiclava virens (anamorph: Ustilaginoidea Virens), it is a precursor of ustilaginoidins used as the raw material for hapten synthesis through diazotization and Mannich reactions followed by bioconjugation with carrier proteins for complete antigen synthesis.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C14H12O5
Net Charge 0
Average Mass 260.245
Monoisotopic Mass 260.06847
InChI InChI=1S/C14H12O5/c1-6-2-9(16)13-11(19-6)4-7-3-8(15)5-10(17)12(7)14(13)18/h3-6,15,17-18H,2H2,1H3/t6-/m1/s1
InChIKey SESQTYVCZUNWHX-ZCFIWIBFSA-N
SMILES C[C@@H]1CC(=O)C2=C(O)C3=C(C=C(O)C=C3O)C=C2O1
Metabolite of Species Details
Ustilaginoidea virens (NCBI:txid1159556) See: PubMed
ChEBI Ontology
Outgoing hemiustilaginoidin F (CHEBI:194133) is a benzochromenone (CHEBI:64986)
hemiustilaginoidin F (CHEBI:194133) is a naphtho-γ-pyrone (CHEBI:64542)
hemiustilaginoidin F (CHEBI:194133) is a phenols (CHEBI:33853)
IUPAC Name
(2R)-5,6,8-trihydroxy-2-methyl-2,3-dihydro-4H-naphtho[2,3-b]pyran-4-one
Synonyms Sources
(2R)-2,3-dihydro-5,6,8-trihydroxy-2-methyl-4H-naphtho[2,3-b]pyran-4-one ChEBI
(2R)-5,6,8-trihydroxy-2-methyl-2,3-dihydro-4H-benzo[g]chromen-4-one IUPAC
Citation Waiting for Citations Type Source
36287930 PubMed citation Europe PMC
Last Modified
22 November 2022