Metabolic Modeling Tutorial
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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Reaction: 1.14.13.119

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

EC Number: 1.14.13.119

Enzymes and Genes:
5-epi-aristolochene-1,3-dihydroxylase Inferred from experiment : EAH ( Nicotiana tabacum )

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

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

Sub-reactions:
(+)-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]

Summary:
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: ?

Unification Links: Rhea:28226

Relationship Links: BRENDA:EC:1.14.13.119 , ENZYME:EC:1.14.13.119 , IUBMB-ExplorEnz:EC:1.14.13.119

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


References

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 18.5 on Mon Nov 24, 2014, biocyc13.