Escherichia coli K-12 substr. MG1655 Compound Class: an anthraquinone

Superclasses: a redox electron carrier Membrane-Electron-Carriers an electron-transfer quinone
an aldehyde or ketone a ketone a cyclic ketone a quinone an electron-transfer quinone

Anthraquinone derivatives are found in microorganisms, fungi, plants, marine organisms, and insects. In higher plants, most anthraquinones occur as mono- or diglycosides. The yellow or red colored compounds have some commercial relevance as natural dyes. 1,8-dihydroxyanthraquinones serve as laxatives.

In fungi and some higher plants (Leguminosae, Rhamnaceae, Polygonaceae, and Caesalpiniaceae), anthraquinones are biosynthesized via a polyketide pathway which comprises the successive condensation of acetyl CoA with 7 molecules of malonyl CoA to form an octa-α-keto-acyl chain, which is converted to the anthraquinone system via decarboxylation, cyclization, and aromatization.

an anthraquinone compound structure

Chemical Formula: C14H8O2

Molecular Weight: 208.22 Daltons

Monoisotopic Molecular Weight: 208.052429501 Daltons

SMILES: C1(C=CC2(C(=O)C3(C=CC=CC(C(=O)C(C=1)=2)=3)))

InChI: InChI=1S/C14H8O2/c15-13-9-5-1-2-6-10(9)14(16)12-8-4-3-7-11(12)13/h1-8H

Unification Links: ChEBI:22580

Reactions known to consume the compound:

L-alanine degradation I :
D-alanine + an electron-transfer quinone[inner membrane] + H2O → ammonium + pyruvate + an electron-transfer quinol[inner membrane]

TCA cycle I (prokaryotic) :
(S)-malate + an electron-transfer quinone[inner membrane] → oxaloacetate + an electron-transfer quinol[inner membrane]

Not in pathways:
a D-amino acid + an electron-transfer quinone[inner membrane] + H2O → ammonium + a 2-oxo carboxylate + an electron-transfer quinol[inner membrane]
(S)-dihydroorotate + an electron-transfer quinone[inner membrane] → orotate + an electron-transfer quinol[inner membrane]
NADPH + an electron-transfer quinone[inner membrane] + H+ → NADP+ + an electron-transfer quinol[inner membrane]
an electron-transfer quinone[inner membrane] + NAD(P)H + H+ → an electron-transfer quinol[inner membrane] + NAD(P)+

Reactions known to both consume and produce the compound:

Not in pathways:
2 a quinone + NADPH + H+ ↔ 2 a semiquinone + NADP+

In Reactions of unknown directionality:

Not in pathways:
2 a quinone + NADH + H+ = 2 a semiquinone + NAD+

In Redox half-reactions:
an electron-transfer quinone[membrane] + 2 H+[in] + 2 e-[membrane] → an electron-transfer quinol[membrane]

Inhibits: ArcB sensory histidine kinase + ATP → ArcB sensory histidine kinase - his292 phosphorylated + ADP

Created 02-Nov-2010 by Caspi R , SRI International

Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by SRI International Pathway Tools version 19.0 on Fri May 22, 2015, BIOCYC14B.