MetaCyc Reaction:

Superclasses: Reactions Classified By Conversion Type Simple Reactions Chemical Reactions Composite Reactions
Reactions Classified By Substrate Small-Molecule Reactions

EC Number:

Enzymes and Genes:

Nicotiana tabacum : 5-epi-aristolochene-1,3-dihydroxylase Inferred from experiment : EAH

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction in which it was curated.

Most BioCyc compounds have been protonated to a reference pH value of 7.3, and some reactions have been computationally balanced for hydrogen by adding free protons. Please see the PGDB Concepts Guide for more information.

Mass balance status: Balanced.

Enzyme Commission Primary Name: 5-epiaristolochene 1,3-dihydroxylase

Enzyme Commission Synonyms: 5-epi-aristolochene 1,3-dihydroxylase, EAH

Taxonomic Range: Viridiplantae

(+)-5-epi-aristolochene + NADPH + oxygen + H+ → 3-deoxy-capsidiol + NADP+ + H2O ,
3-deoxy-capsidiol + NADPH + oxygen + H+ → capsidiol + NADP+ + H2O ,
(+)-5-epi-aristolochene + NADPH + oxygen + H+ → 1-deoxy-capsidiol + NADP+ + H2O ,
1-deoxy-capsidiol + NADPH + oxygen + H+ → capsidiol + NADP+ + H2O

Standard Gibbs Free Energy (ΔrG in kcal/mol): -181.4065 Inferred by computational analysis [Latendresse13]

A heme-thiolate protein (P-450). Kinetic studies suggest that 3-deoxy-capsidiol is mainly formed first followed by hydroxylation at C-3. However the reverse order via 1-deoxy-capsidiol does occur.

Enzyme Commission Summary:
A heme-thiolate protein (P-450). Kinetic studies suggest that 1β-hydroxyepiaristolochene is mainly formed first followed by hydroxylation at C-3. However the reverse order via 3α-hydroxyepiaristolochene does occur.

Citations: [Ralston01, Takahashi05]

Gene-Reaction Schematic: ?

Gene-Reaction Schematic

Unification Links: Rhea:28226

Relationship Links: BRENDA:EC: , ENZYME:EC: , IUBMB-ExplorEnz:EC:

Created 07-Dec-2010 by Caspi R , SRI International


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

Ralston01: Ralston L, Kwon ST, Schoenbeck M, Ralston J, Schenk DJ, Coates RM, Chappell J (2001). "Cloning, heterologous expression, and functional characterization of 5-epi-aristolochene-1,3-dihydroxylase from tobacco (Nicotiana tabacum)." Arch Biochem Biophys 393(2);222-35. PMID: 11556809

Takahashi05: Takahashi S, Zhao Y, O'maille PE, Greenhagen BT, Noel JP, Coates RM, Chappell J (2005). "Kinetic and molecular analysis of 5-epiaristolochene 1,3-dihydroxylase, a cytochrome p450 enzyme catalyzing successive hydroxylations of sesquiterpenes." J Biol Chem 280(5);3686-96. PMID: 15522862

Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Fri Oct 9, 2015, biocyc14.