MetaCyc Compound: plumbagine

Synonyms: plumbagin, 5-hydroxy-2-methyl-1,4-naphthoquinone

Chemical Formula: C11H8O3

Molecular Weight: 188.18 Daltons

Monoisotopic Molecular Weight: 188.0473441231 Daltons

plumbagine compound structure

SMILES: CC2(C(C1(=CC=CC(=C1C(C=2)=O)O))=O)

InChI: InChI=1S/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3


Unification Links: ChEBI:8273 , ChemSpider:9790 , KEGG:C10387 , MetaboLights:MTBLC8273 , PubChem:10205

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 17.458965 Inferred by computational analysis [Latendresse13]

Reactions known to produce the compound:

plumbagin biosynthesis :
naphthylisoquinoline alkaloid precursor → plumbagine

Enzymes inhibited by plumbagine, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: benzophenone-3'-hydroxylase [Schmidt97] , xanthone synthase [Peters98] , xanthone-6-hydroxylase [Schmidt00] , xanthone-6-hydroxylase [Schmidt00] , xanthone synthase [Peters98] , pseudobaptigenin synthase [Clemens96]


Clemens96: Clemens S, Barz W, (1996) "Cytochrome P450-dependent methylendioxy bridge formation in Cicer arietinum." Phytochemistry (1996) 41(2), 457-460.

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Peters98: Peters S, Schmidt W, Beerhues L (1998). "Regioselective oxidative phenol couplings of 2,3',4,6-tetrahydroxybenzophenone in cell cultures of Centaurium erythraea RAFN and Hypericum androsaemum L." Planta, 204: 64-69.

Schmidt00: Schmidt W, Peters S, Beerhues L (2000). "Xanthone 6-hydroxylase from cell cultures of Centaurium erythraea RAFN and Hypericum androsaemium L." Phytochemistry 53(4);427-31. PMID: 10731018

Schmidt97: Schmidt W, Beerhues L (1997). "Alternative pathways of xanthone biosynthesis in cell cultures of Hypericum androsaemum L." FEBS Lett 420(2-3);143-6. PMID: 9459298

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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