KEGG   ORTHOLOGY: K20501
Entry
K20501            Tight     KO                                     
Symbol
THCAS
Name
tetrahydrocannabinolic acid synthase [EC:1.21.3.7]
Pathway
map00999  Biosynthesis of various plant secondary metabolites
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00894  Cannabidiol biosynthesis, malonyl-CoA => cannabidiol/dronabinol
Reaction
R12101  cannabigerolate:oxygen oxidoreductase (cyclizing, Delta9-tetrahydrocannabinolate-forming)
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00999 Biosynthesis of various plant secondary metabolites
    K20501  THCAS; tetrahydrocannabinolic acid synthase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.21  Catalysing the reaction X-H + Y-H = X-Y
   1.21.3  With oxygen as acceptor
    1.21.3.7  tetrahydrocannabinolic acid synthase
     K20501  THCAS; tetrahydrocannabinolic acid synthase
Genes
CSAV: 115696884 115697880
AG: BAC41356(THCAS)
Reference
PMID:15190053
  Authors
Sirikantaramas S, Morimoto S, Shoyama Y, Ishikawa Y, Wada Y, Shoyama Y, Taura F
  Title
The gene controlling marijuana psychoactivity: molecular cloning and heterologous expression of Delta1-tetrahydrocannabinolic acid synthase from Cannabis sativa L.
  Journal
J Biol Chem 279:39767-74 (2004)
DOI:10.1074/jbc.M403693200
  Sequence
[ag:BAC41356]
LinkDB

KEGG   ENZYME: 1.21.3.7
Entry
EC 1.21.3.7                 Enzyme                                 
Name
tetrahydrocannabinolic acid synthase;
THCA synthase;
Delta1-tetrahydrocannabinolic acid synthase
Class
Oxidoreductases;
Catalysing the reaction X-H + Y-H = X-Y;
With oxygen as acceptor
Sysname
cannabigerolate:oxygen oxidoreductase (cyclizing, Delta9-tetrahydrocannabinolate-forming)
Reaction(IUBMB)
cannabigerolate + O2 = Delta9-tetrahydrocannabinolate + H2O2 [RN:R12101]
Reaction(KEGG)
R12101
Substrate
cannabigerolate [CPD:C20406];
O2 [CPD:C00007]
Product
Delta9-tetrahydrocannabinolate [CPD:C21903];
H2O2 [CPD:C00027]
Comment
A flavoprotein (FAD). The cofactor is covalently bound. Part of the cannabinoids biosynthetic pathway in the plant Cannabis sativa. The enzyme can also convert cannabinerolate (the (Z)-isomer of cannabigerolate) to Delta9-THCA with lower efficiency. Whereas the product was originally called Delta1-tetrahydrocannabinolate, the recommended name according to systematic peripheral numbering is Delta9-tetrahydrocannabinolate.
History
EC 1.21.3.7 created 2012
Pathway
ec00999  Biosynthesis of various plant secondary metabolites
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K20501  tetrahydrocannabinolic acid synthase
Genes
CSAV: 115696884 115697880
Reference
1
  Authors
Taura F, Morimoto S Shoyama Y, Mechoulam R.
  Title
First direct evidence for the mechanism of Delta1-tetrahydrocannabinolic acid biosynthesis.
  Journal
J Am Chem Soc 117:9766-9767 (1995)
Reference
2  [PMID:15190053]
  Authors
Sirikantaramas S, Morimoto S, Shoyama Y, Ishikawa Y, Wada Y, Shoyama Y, Taura F
  Title
The gene controlling marijuana psychoactivity: molecular cloning and heterologous expression of Delta1-tetrahydrocannabinolic acid synthase from Cannabis sativa L.
  Journal
J Biol Chem 279:39767-74 (2004)
DOI:10.1074/jbc.M403693200
  Sequence
[ag:BAC41356]
Reference
3  [PMID:16511162]
  Authors
Shoyama Y, Takeuchi A, Taura F, Tamada T, Adachi M, Kuroki R, Shoyama Y, Morimoto S
  Title
Crystallization of Delta1-tetrahydrocannabinolic acid (THCA) synthase from Cannabis sativa.
  Journal
Acta Crystallogr Sect F Struct Biol Cryst Commun 61:799-801 (2005)
DOI:10.1107/S1744309105023365
Reference
4  [PMID:22766313]
  Authors
Shoyama Y, Tamada T, Kurihara K, Takeuchi A, Taura F, Arai S, Blaber M, Shoyama Y, Morimoto S, Kuroki R
  Title
Structure and function of 1-tetrahydrocannabinolic acid (THCA) synthase, the enzyme controlling the psychoactivity of Cannabis sativa.
  Journal
J Mol Biol 423:96-105 (2012)
DOI:10.1016/j.jmb.2012.06.030
  Sequence
[ag:BAC41356]
Other DBs
ExplorEnz - The Enzyme Database: 1.21.3.7
IUBMB Enzyme Nomenclature: 1.21.3.7
ExPASy - ENZYME nomenclature database: 1.21.3.7
BRENDA, the Enzyme Database: 1.21.3.7
LinkDB

KEGG   REACTION: R12101
Entry
R12101                      Reaction                               
Name
cannabigerolate:oxygen oxidoreductase (cyclizing, Delta9-tetrahydrocannabinolate-forming)
Definition
Cannabigerolate + Oxygen <=> Delta9-Tetrahydrocannabinolate + Hydrogen peroxide
Equation
C20406 + C00007 <=> C21903 + C00027
Enzyme
1.21.3.7
Pathway
rn00999  Biosynthesis of various plant secondary metabolites
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00894  Cannabidiol biosynthesis, malonyl-CoA => cannabidiol/dronabinol
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  1.21  Catalysing the reaction X-H + Y-H = X-Y
   1.21.3  With oxygen as acceptor
    1.21.3.7
     R12101  Cannabigerolate + Oxygen <=> Delta9-Tetrahydrocannabinolate + Hydrogen peroxide
Orthology
K20501  tetrahydrocannabinolic acid synthase [EC:1.21.3.7]
Other DBs
RHEA: 34138
LinkDB

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