Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-05-15 00:41:12 UTC
Update Date2025-10-07 16:05:20 UTC
Metabolite IDMMDBc0007531
Metabolite Identification
Common NameNorbikaverin
DescriptionNorbikaverin is a nonaketide pigment belonging to the chemical class of benzoxanthentrione compounds. This metabolite is notably produced by certain fungal species, including Gibberella fujikuroi, where it accumulates alongside its more prominent counterpart, bikaverin. Research indicates that norbikaverin is synthesized in mycelial cells when the fungi are cultivated on simple carbon and nitrogen sources, supplemented with additional cofactors (PMID:31748828 ). In various fungal isolates, including Fusarium oxysporum f.sp. vasinfectum, both bikaverin and norbikaverin are secreted, highlighting their role in the metabolic pathways of these organisms (PMID:12846324 ). Furthermore, norbikaverin is recognized as a precursor to bikaverin, which is produced in smaller quantities in some fungal species (PMID:20376635 ). The presence of these pigments in fungi suggests potential ecological roles, possibly related to pigmentation, signaling, or protection against environmental stressors (PMID:5168485 ). Overall, norbikaverin serves as an important component in the biosynthetic landscape of certain fungi, contributing to their metabolic diversity and ecological interactions.
Structure
SynonymsNot Available
Molecular FormulaC19H12O8
Average Mass368.297
Monoisotopic Mass368.053217346
IUPAC Name7,8,10-trihydroxy-3-methoxy-1-methyl-11,12-dihydro-6H-5-oxatetracene-6,11,12-trione
Traditional Name7,8,10-trihydroxy-3-methoxy-1-methyl-5-oxatetracene-6,11,12-trione
CAS Registry NumberNot Available
SMILES
COC1=CC2=C(C(C)=C1)C(=O)C1=C(O2)C(=O)C2=C(C(O)=CC(O)=C2O)C1=O
InChI Identifier
InChI=1S/C19H12O8/c1-6-3-7(26-2)4-10-11(6)16(23)14-17(24)12-8(20)5-9(21)15(22)13(12)18(25)19(14)27-10/h3-5,20-22H,1-2H3
InChI KeyGOQPBCJYIHERLE-UHFFFAOYSA-N