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Information on EC 1.21.3.7 - tetrahydrocannabinolic acid synthase
for references in articles please use BRENDA:EC1.21.3.7
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EC Tree 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
IUBMB Comments
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 Δ9-THCA with lower efficiency. Whereas the product was originally called Δ1-tetrahydrocannabinolate, the recommended name according to systematic peripheral numbering is Δ9-tetrahydrocannabinolate.
The enzyme appears in viruses and cellular organisms
- 1.21.3.7
- cannabis
- cannabinoids
-
cannabigerolic
-
psychoactive
-
cannabidiolic
-
forensic
-
drug-type
-
chemotype
- hemp
-
cbcas
-
fiber-type
- marijuana
-
komagataella
-
seized
-
cannabichromenic
showSynonyms
thca synthase, thcas, tetrahydrocannabinolic acid synthase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
DELTA1-tetrahydrocannabinolic acid synthase
DELTA9-tetrahydrocannabinolic acid synthase
THCA synthase
THCAS
DELTA1-tetrahydrocannabinolic acid synthase
-
-
-
-
THCA synthase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cannabigerolate + O2 = DELTA9-tetrahydrocannabinolate + H2O2
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PATHWAY SOURCE
PATHWAYS
MetaCyc
cannabinoid biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
cannabigerolate:oxygen oxidoreductase (cyclizing, DELTA9-tetrahydrocannabinolate-forming)
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.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
cannabinerolate + O2
DELTA9-tetrahydrocannabinolate + H2O2
-
Substrates: -
Products: -
Products: -
?
additional information
?
-
-
Substrates: cannabigerol and cannabinero are no substrates
Products: -
Products: -
?
cannabigerolate + O2
DELTA9-tetrahydrocannabinolate + H2O2
-
Substrates: -
Products: -
Products: -
?
cannabigerolate + O2
DELTA9-tetrahydrocannabinolate + H2O2
-
Substrates: -
Products: -
Products: -
ir
cannabigerolate + O2
DELTA9-tetrahydrocannabinolate + H2O2
Substrates: -
Products: -
Products: -
?
cannabigerolate + O2
DELTA9-tetrahydrocannabinolate + H2O2
-
Substrates: -
Products: -
Products: -
?
cannabigerolate + O2
DELTA9-tetrahydrocannabinolate + H2O2
Substrates: -
Products: -
Products: -
?
cannabigerolate + O2
DELTA9-tetrahydrocannabinolate + H2O2
-
Substrates: -
Products: -
Products: -
?
cannabigerolate + O2
DELTA9-tetrahydrocannabinolate + H2O2
Substrates: -
Products: -
Products: -
?
cannabigerolate + O2
DELTA9-tetrahydrocannabinolate + H2O2
Substrates: -
Products: -
Products: -
ir
cannabigerolate + O2
DELTA9-tetrahydrocannabinolate + H2O2
-
Substrates: best substrate
Products: -
Products: -
?
cannabigerolate + O2
DELTA9-tetrahydrocannabinolate + H2O2
-
Substrates: about 98% conversion rate in 24 h
Products: -
Products: -
?
cannabigerolate + O2
DELTA9-tetrahydrocannabinolate + H2O2
-
Substrates: maximum conversion rate of about 98% in 24 h
Products: -
Products: -
?
cannabigerolate + O2
DELTA9-tetrahydrocannabinolate + H2O2
-
Substrates: -
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
cannabigerolate + O2
DELTA9-tetrahydrocannabinolate + H2O2
-
Substrates: -
Products: -
Products: -
?
cannabigerolate + O2
DELTA9-tetrahydrocannabinolate + H2O2
Substrates: -
Products: -
Products: -
?
cannabigerolate + O2
DELTA9-tetrahydrocannabinolate + H2O2
-
Substrates: -
Products: -
Products: -
?
cannabigerolate + O2
DELTA9-tetrahydrocannabinolate + H2O2
Substrates: -
Products: -
Products: -
?
cannabigerolate + O2
DELTA9-tetrahydrocannabinolate + H2O2
-
Substrates: -
Products: -
Products: -
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
FAD
-
the enzyme contains covalently attached FAD at a molar ratio of FAD to protein of 1:1
FAD
the enzyme contains covalently attached FAD cofactor at a molar ratio of FAD to protein of 1:1
additional information
-
NAD+, NADP+, FAD, and FMN do not stimulate the enzyme activity
-
additional information
-
the enzyme does not require any cofactors or coenzymes
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
the enzyme does not require any metal ions for activity
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
BSA
-
the addition of BSA has a slightly positive effect on the activity of the enzyme
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.254
cannabinerolate
-
at pH 6.0, temperature not specified in the publication
0.131
cannabigerolate
-
recombinant enzyme, in 100 mM sodium citrate (pH 5.5), at 30°C
0.134
cannabigerolate
-
at pH 6.0, temperature not specified in the publication
0.446
cannabigerolate
mutant enzyme R108A, in 100 mM sodium citrate buffer (pH 5.0), at 30°C
0.54
cannabigerolate
wild type enzyme, in 100 mM sodium citrate buffer (pH 5.0), at 30°C
0.783
cannabigerolate
mutant enzyme R110A, in 100 mM sodium citrate buffer (pH 5.0), at 30°C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.043
cannabigerolate
mutant enzyme R108A, in 100 mM sodium citrate buffer (pH 5.0), at 30°C
0.075
cannabigerolate
mutant enzyme R110A, in 100 mM sodium citrate buffer (pH 5.0), at 30°C
0.3
cannabigerolate
wild type enzyme, in 100 mM sodium citrate buffer (pH 5.0), at 30°C
0.888
cannabigerolate
-
recombinant enzyme, in 100 mM sodium citrate (pH 5.5), at 30°C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.096
cannabigerolate
mutant enzyme R108A, in 100 mM sodium citrate buffer (pH 5.0), at 30°C
0.096
cannabigerolate
mutant enzyme R110A, in 100 mM sodium citrate buffer (pH 5.0), at 30°C
0.556
cannabigerolate
wild type enzyme, in 100 mM sodium citrate buffer (pH 5.0), at 30°C
6.78
cannabigerolate
-
recombinant enzyme, in 100 mM sodium citrate (pH 5.5), at 30°C
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.078
-
unpurified recombinant enzyme, in 100 mM sodium citrate (pH 5.5), at 30°C
0.41
-
recombinant enzyme after 5250fold purification, in 100 mM sodium citrate (pH 5.5), at 30°C
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
the enzyme is localized to and functions in the storage cavity of glandular trichomes
brenda
additional information
-
samples composed of a mixture of leaves and tops of fresh adult cannabis plants and seized marijuana display the highest lowest tetrahydrocannybinolic acid synthase gene expression
brenda
-
fresh leaves from young cannabis plants display the lowest tetrahydrocannybinolic acid synthase gene expression
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
-
a key enzyme controlling the psychoactivity of cannabis
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). THCAS_CANSA
545
1
61927
Swiss-Prot
Secretory Pathway (Reliability: 1)
A0A084GE79_PSEDA
441
0
47357
TrEMBL
Secretory Pathway (Reliability: 1)
A0A142EGL7_CANSA
545
1
62050
TrEMBL
Secretory Pathway (Reliability: 1)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
58600
60000
75000
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
monomer
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POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
glycoprotein
glycoprotein
the enzyme contains eight possible Asn glycosylation sites
glycoprotein
-
the enzyme contains seven possible Asn glycosylation sites. Endoglycosidase treatment affords a deglycosylated enzyme with more catalytic activity than that of the glycosylated form
glycoprotein
the enzyme possesses at least eight potential N-linked glycosylation sites
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
sitting drop vapor diffusion method, in 0.09 M HEPES buffer pH 7.5 containing 1.26 M sodium citrate
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
H114A
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
DE-52 column chromatography, phenyl Sepharose CL-4B column chromatography, and hydroxylapatite column chromatography
-
diethylaminoethyl-cellulose column chromatography, phenyl Sepharose CL-4B column chromatography, and hydroxylapatite column chromatography
-
hydroxylapatite column chromatography
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21(DE3) and Pichia pastoris MutSKM71 KE1 cells
expressed in Saccharomyces cerevisiae strain CEN.PK2-1C and Pichia pastoris strain PichiaPink2
expressed in Sf9 insect cells
expressed using a baculovirus insect expression system and expressed in transgenic Nicotiana tabacum hairy roots and methylotrophic yeast Pichia pastoris
-
using a baculovirus-Sf9 insect cell expression system and expressed in Nicotiana tabacum hairy roots
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
the secreted enzyme activity in Pichia pastoris cultures is increased to 472% in the presence of 0.5% (w/v) casamino acids, 277% in the presence of proteinase inhibitors (10 mg/l 4-(2-aminoethyl) benzensulfonyl fluoride, 1 mg/l pepstatin A, and 1 mg/l E-64), 226% in the presence of 10 mg/ml FAD, 248% in the presence of 10 mg/ml FMN, 323% in the presence of 10 mg/ml riboflavin, and 298% in the presence of 1% (v/v) methanol
-
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Shoyama, Y.; Takeuchi, A.; Taura, F.; Tamada, T.; Adachi, M.; Kuroki, R.; Shoyama, Y.; Morimoto, S.
Crystallization of Delta1-tetrahydrocannabinolic acid (THCA) synthase from Cannabis sativa
Acta Crystallogr. Sect. F
61
799-801
2005
Cannabis sativa (Q8GTB6), Cannabis sativa
brenda
Taura, F.; Dono, E.; Sirikantaramas, S.; Yoshimura, K.; Shoyama, Y.; Morimoto, S.
Production of DELTA1-tetrahydrocannabinolic acid by the biosynthetic enzyme secreted from transgenic Pichia pastoris
Biochem. Biophys. Res. Commun.
361
675-680
2007
Cannabis sativa
brenda
Taura, F.
Studies on tetrahydrocannabinolic acid synthase that produces the acidic precursor of tetrahydrocannabinol, the pharmacologically active cannabinoid in marijuana
Drug Discov. Ther.
3
83-87
2009
Cannabis sativa
brenda
Taura, F.; Sirikantaramas, S.; Shoyama, Y.; Yoshikai, K.; Shoyama, Y.; Morimoto, S.
Cannabidiolic-acid synthase, the chemotype-determining enzyme in the fiber-type Cannabis sativa
FEBS Lett.
581
2929-2934
2007
Cannabis sativa
brenda
Taura, F.; Morimoto, S.; Shoyama, Y.; Mechoulam, R.
First direct evidence for the mechanism of DELTA1-tetrahydrocannabinolic acid biosynthesis
J. Am. Chem. Soc.
117
9766-9767
1995
Cannabis sativa
-
brenda
Sirikantaramas, S.; Morimoto, S.; Shoyama, Y.; Ishikawa, Y.; Wada, Y.; Shoyama, Y.; Taura, F.
The gene controlling marijuana psychoactivity: molecular cloning and heterologous expression of DELTA1-tetrahydrocannabinolic acid synthase from Cannabis sativa L.
J. Biol. Chem.
279
39767-39774
2004
Cannabis sativa (Q8GTB6), Cannabis sativa
brenda
Shoyama, Y.; Tamada, T.; Kurihara, K.; Takeuchi, A.; Taura, F.; Arai, S.; Blaber, M.; Shoyama, Y.; Morimoto, S.; Kuroki, R.
Structure and function of DELTA1-tetrahydrocannabinolic acid (THCA) synthase, the enzyme controlling the psychoactivity of Cannabis sativa
J. Mol. Biol.
423
96-105
2012
Cannabis sativa
brenda
Sirikantaramas, S.; Taura, F.; Tanaka, Y.; Ishikawa, Y.; Morimoto, S.; Shoyama, Y.
Tetrahydrocannabinolic acid synthase, the enzyme controlling marijuana psychoactivity, is secreted into the storage cavity of the glandular trichomes
Plant Cell Physiol.
46
1578-1582
2005
Cannabis sativa
brenda
Cascini, F.; Passerotti, S.; Boschi, I.
Analysis of THCA synthase gene expression in cannabis: a preliminary study by real-time quantitative PCR
Forensic Sci. Int.
231
208-212
2013
Cannabis sativa
brenda
Alaoui, M.A.; Ibrahimi, A.; Semlali, O.; Tarhda, Z.; Marouane, M.; Najwa, A.; Soulaymani, A.; Fahime, E.E.
Affinity comparison of different THCA synthase to CBGA using modeling computational approaches
Bioinformation
10
33-38
2014
Cannabis sativa (Q8GTB6), Cannabis sativa
brenda
Zirpel, B.; Stehle, F.; Kayser, O.
Production of DELTA9-tetrahydrocannabinolic acid from cannabigerolic acid by whole cells of Pichia (Komagataella) pastoris expressing DELTA9-tetrahydrocannabinolic acid synthase from Cannabis sativa L.
Biotechnol. Lett.
37
1869-1875
2015
Cannabis sativa (Q8GTB6)
brenda
Lange, K.; Poetsch, A.; Schmid, A.; Julsing, M.K.
Enrichment and identification of DELTA9-tetrahydrocannabinolic acid synthase from Pichia pastoris culture supernatants
Data Brief
4
641-649
2015
Cannabis sativa (Q8GTB6)
brenda
Lange, K.; Schmid, A.; Julsing, M.K.
DELTA9-Tetrahydrocannabinolic acid synthase production in Pichia pastoris enables chemical synthesis of cannabinoids
J. Biotechnol.
211
68-76
2015
Cannabis sativa (Q8GTB6)
brenda
Lange, K.; Schmid, A.; Julsing, M.K.
DELTA9-Tetrahydrocannabinolic acid synthase The application of a plant secondary metabolite enzyme in biocatalytic chemical synthesis
J. Biotechnol.
233
42-48
2016
Cannabis sativa
brenda
Zirpel, B.; Degenhardt, F.; Martin, C.; Kayser, O.; Stehle, F.
Engineering yeasts as platform organisms for cannabinoid biosynthesis
J. Biotechnol.
259
204-212
2017
Cannabis sativa
brenda
Cirovic, N.; Kecmanovic, M.; Keckarevic, D.; Keckarevic Markovic, M.
Differentiation of Cannabis subspecies by THCA synthase gene analysis using RFLP
J. Forensic Leg. Med.
51
81-84
2017
Cannabis sativa (Q8GTB6), Cannabis sativa, Cannabis sativa subsp. indica
brenda
Onofri, C.; de Meijer, E.P.M.; Mandolino, G.
Sequence heterogeneity of cannabidiolic- and tetrahydrocannabinolic acid-synthase in Cannabis sativa L. and its relationship with chemical phenotype
Phytochemistry
116
57-68
2015
Cannabis sativa (Q8GTB6), Cannabis sativa
brenda
EXTERNAL LINKS (specific for EC-Number 1.21.3.7)
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