Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-05-15 10:21:04 UTC
Update Date2025-10-07 16:07:05 UTC
Metabolite IDMMDBc0020347
Metabolite Identification
Common NameDehydrorabelomycin
DescriptionDehydrorabelomycin is a member of the angucycline chemical class, characterized by its complex polycyclic structure. This metabolite serves as an intermediate in various biosynthetic pathways, notably in the production of other angucyclines. Enzymatic studies have shown that different enzyme groups can convert dehydrorabelomycin into distinct products, highlighting functional differentiation among them (PMID:40500926 ). Additionally, the optimization of oviedomycin production has been achieved by reducing the accumulation of dehydrorabelomycin through substrate channeling, utilizing the CipB scaffold protein (PMID:40127858 ). The compound also requires FADH2/FMNH2 as cofactors for its conversion, emphasizing its role in redox reactions (PMID:38887580 ). The flavoprotein monooxygenase FlsO1 has been shown to convert prejadomycin to dehydrorabelomycin, while also facilitating the formation of xanthone-containing products through multiple oxidation steps (PMID:35194755 ). Furthermore, the biosynthetic gene clusters associated with typical angucyclines utilize FAD-dependent oxygenases to catalyze hydroxylation and dehydration reactions that lead to dehydrorabelomycin formation (PMID:30533539 ). Overall, dehydrorabelomycin plays a crucial role in the intricate biosynthetic pathways of angucyclines.
Structure
SynonymsNot Available
Molecular FormulaC19H12O5
Average Mass320.3
Monoisotopic Mass320.068473486
IUPAC Name1,6,8-trihydroxy-3-methyl-7,12-dihydrotetraphene-7,12-dione
Traditional Namedehydrorabelomycin
CAS Registry NumberNot Available
SMILES
CC1=CC(O)=C2C(=C1)C=C(O)C1=C2C(=O)C2=CC=CC(O)=C2C1=O
InChI Identifier
InChI=1S/C19H12O5/c1-8-5-9-7-13(22)16-17(14(9)12(21)6-8)18(23)10-3-2-4-11(20)15(10)19(16)24/h2-7,20-22H,1H3
InChI KeyPQVIKROZFPIERS-UHFFFAOYSA-N