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Information on EC 4.2.3.13 - (+)-delta-cadinene synthase
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4.2.3.13 (+)-delta-cadinene synthaseIUBMB Comments
The sesquiterpenoid (+)-delta-cadinene is an intermediate in phytoalexin biosynthesis. Mg2+ is required for activity.
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Word Map
- 4.2.3.13
- synthases
-
terpenoids
- sesquiterpenoids
- germacrene
-
geranyl
- linalool
- arboreum
-
+-delta-cadinene
- lavandula
- beta-caryophyllene
-
multiproduct
-
fragrant
- alpha-humulene
-
agarwood
-
e,e-farnesyl
-
e-beta-farnesene
- amorpha-4,11-diene
-
ddxxd
- aquilaria
- 5-epi-aristolochene
- synthesis
- agriculture
The enzyme appears in viruses and cellular organisms
Synonyms
sesquiterpene synthase, (+)-delta-cadinene synthase, cdn1-c1, cadinene synthase, delta-cadinene synthase, pntps2, cadinol/cadinene synthase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
2-trans,6-trans-farnesyl-diphosphate diphosphate-lyase (cyclizing, (+)-alpha-cadinene-forming)
-
-
-
-
cadinene synthase
Cop4
cyclase, delta-cadinene
-
-
-
-
delta-cadinene cyclase
-
-
-
-
delta-cadinene synthase
EC 4.6.1.11
-
-
formerly
-
farnesyl diphosphate-delta-cadinene cyclase
-
-
-
-
TPS1
delta-cadinene synthase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate = (+)-delta-cadinene + diphosphate
the sesquiterpenoid (+)-delta-cadinene is an intermediate in phytoalexin biosynthesis. Mg2+ is required for activity
-
-
-
(2E,6E)-farnesyl diphosphate = (+)-delta-cadinene + diphosphate
cyclization reaction
-
(2E,6E)-farnesyl diphosphate = (+)-delta-cadinene + diphosphate
cyclization reaction
-
(2E,6E)-farnesyl diphosphate = (+)-delta-cadinene + diphosphate
catalytic mechanism, overview
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
elimination of diphosphate
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl diphosphate diphosphate-lyase (cyclizing, (+)-delta-cadinene-forming)
The sesquiterpenoid (+)-delta-cadinene is an intermediate in phytoalexin biosynthesis. Mg2+ is required for activity.
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CAS REGISTRY NUMBER
COMMENTARY
166800-09-5
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate
(+)-delta-cadinene + germacradien-4-ol + diphosphate
-
-
-
?
(2E,6Z)-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
-
-
?
nerolidyl diphosphate
(+)-delta-cadinene + alpha-bisabolol + beta-bisabolene + beta-farnesene + ?
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
products are about 60% (-)-alpha-copaene, 40% (+)-delta-cadinene
-
?
(2E,6E)-farnesyl diphosphate
delta-cadinene + diphosphate
-
-
major product
-
?
(2E,6E)-farnesyl diphosphate
delta-cadinene + diphosphate
-
-
major product
-
?
(2E,6E)-farnesyl diphosphate
delta-cadinene + diphosphate
-
delta-cadinene is one of the two main products, while alpha-muuorlene, beta-caryophyllene, alpha-humulene and alpha-copaene are minor products
-
?
(2E,6E)-farnesyl diphosphate
delta-cadinene + diphosphate
-
bifunctional sesquiterpene synthase producing both alpha-copaene and delta-cadinene
-
?
(2E,6E)-farnesyl diphosphate + H2O
delta-cadinene + diphosphate
-
Cop4 generates a tertiary cadinyl cation which upon deprotonation yields its major cyclization product delta-cadinene. The cadinyl cation reacts further to yield other cyclization products (beta-cubebene, cubebol , beta-copaene, sativene)
-
-
?
(2E,6E)-farnesyl diphosphate + H2O
delta-cadinene + diphosphate
-
Cop4 generates a tertiary cadinyl cation which upon deprotonation yields its major cyclization product delta-cadinene. The cadinyl cation reacts further to yield other cyclization products (beta-cubebene, cubebol , beta-copaene, sativene)
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
the fungal-elicited production of a (+)-delta-cadinene synthase is consistent with a role for this enzyme as the first committed step in the pathways leading to the related phytoalexins gossypol and lacinilene C in cotton
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
amount of enzyme does not increase significantly in stems treated with Verticillium dahliae due to a high basal level of enzyme in untreated stems
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
the enzyme is encoded by a complex gene family that based on homology can be divided into two subfamilies, cad1-A and cad1-C
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
nerolidyl diphosphate is an intermediate
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
the first step enzyme in the conversion of farnesyl diphosphate to sesquiterpene phytoalexins. The reaction is induced by the infection of cotton with Verticillium dahliae
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
the product (+)-delta-cadinene is metabolically converted to deoxyhemigossypol, deoxyhemigossypol 6-methyl ether, hemigossypol and hemigossypol 6-methyl ether
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
transcription of cad1-C is activated in stems treated with Verticillium dahliae
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
the sesquiterpenoid (+)-alpha-cadinene is an intermediate in phytoalexin biosynthesis
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
the enzyme is encoded by a complex gene family that based on homology can be divided into two subfamilies, cad1-A and cad1-C
-
?
additional information
?
-
delta-cadinene synthase is a sesquiterpene cyclase that utilises the universal achiral precursor farnesyl diphosphate (FDP) to generate predominantly the bicyclic sesquiterpene delta-cadinene and about 2% germacradien-4-ol
-
-
?
additional information
?
-
-
products (in vivo expression in Saccharomyces cerevisiae): delta-cadinene and a compound with a cadinene skeleton, minor products: alpha-muurolene, beta-caryophyllene, alpha-humulene and alpha-copaene
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate
(+)-delta-cadinene + germacradien-4-ol + diphosphate
-
-
-
?
additional information
?
-
delta-cadinene synthase is a sesquiterpene cyclase that utilises the universal achiral precursor farnesyl diphosphate (FDP) to generate predominantly the bicyclic sesquiterpene delta-cadinene and about 2% germacradien-4-ol
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
the fungal-elicited production of a (+)-delta-cadinene synthase is consistent with a role for this enzyme as the first committed step in the pathways leading to the related phytoalexins gossypol and lacinilene C in cotton
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
amount of enzyme does not increase significantly in stems treated with Verticillium dahliae due to a high basal level of enzyme in untreated stems
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
the enzyme is encoded by a complex gene family that based on homology can be divided into two subfamilies, cad1-A and cad1-C
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
the first step enzyme in the conversion of farnesyl diphosphate to sesquiterpene phytoalexins. The reaction is induced by the infection of cotton with Verticillium dahliae
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
the product (+)-delta-cadinene is metabolically converted to deoxyhemigossypol, deoxyhemigossypol 6-methyl ether, hemigossypol and hemigossypol 6-methyl ether
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
-
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
transcription of cad1-C is activated in stems treated with Verticillium dahliae
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
the sesquiterpenoid (+)-alpha-cadinene is an intermediate in phytoalexin biosynthesis
-
?
2-trans,6-trans-farnesyl diphosphate
(+)-delta-cadinene + diphosphate
-
the enzyme is encoded by a complex gene family that based on homology can be divided into two subfamilies, cad1-A and cad1-C
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Infections
Antisense suppression of a (+)-delta-cadinene synthase gene in cotton prevents the induction of this defense response gene during bacterial blight infection but not its constitutive expression.
Infections
Medicago TERPENE SYNTHASE 10 Is Involved in Defense Against an Oomycete Root Pathogen.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00065
nerolidyl diphosphate
pH 7.5, 30ºC, recombinant CDN1-C1 enzyme
additional information
additional information
Michaelis-Menten steady-state kinetics, overview
-
0.00058
(2E,6E)-farnesyl diphosphate
wild type enzyme, at pH 7.5 and 25°C
0.00058
(2E,6E)-farnesyl diphosphate
recombinant His6-tagged wild-type enzyme, pH 7.5, 25°C
0.00145
(2E,6E)-farnesyl diphosphate
mutant enzyme W279E, at pH 7.5 and 25°C
0.00145
(2E,6E)-farnesyl diphosphate
recombinant mutant W279E, pH 7.5, 25°C
0.0019
(2E,6E)-farnesyl diphosphate
mutant enzyme W279M, at pH 7.5 and 25°C
0.0019
(2E,6E)-farnesyl diphosphate
recombinant mutant W279M, pH 7.5, 25°C
0.0022
(2E,6E)-farnesyl diphosphate
recombinant mutant W279A, pH 7.5, 25°C
0.00223
(2E,6E)-farnesyl diphosphate
mutant enzyme W279A, at pH 7.5 and 25°C
0.0032
(2E,6E)-farnesyl diphosphate
wild type enzyme, at pH 8.0 and 30°C
0.0032
(2E,6E)-farnesyl diphosphate
wild type enzyme, at pH 7.5 and 25°C
0.00428
(2E,6E)-farnesyl diphosphate
mutant enzyme W279Y, at pH 7.5 and 25°C
0.0043
(2E,6E)-farnesyl diphosphate
recombinant mutant W279Y, pH 7.5, 25°C
0.008
(2E,6E)-farnesyl diphosphate
mutant enzyme W279Q, at pH 7.5 and 25°C
0.008
(2E,6E)-farnesyl diphosphate
recombinant mutant W279Q, pH 7.5, 25°C
0.0092
(2E,6E)-farnesyl diphosphate
recombinant mutant W279D, pH 7.5, 25°C
0.00924
(2E,6E)-farnesyl diphosphate
mutant enzyme W279D, at pH 7.5 and 25°C
0.00945
(2E,6E)-farnesyl diphosphate
mutant enzyme W279L, at pH 7.5 and 25°C
0.0095
(2E,6E)-farnesyl diphosphate
recombinant mutant W279L, pH 7.5, 25°C
0.0184
(2E,6E)-farnesyl diphosphate
pH and temperature not specified in the publication
0.0017
2-trans,6-trans-farnesyl diphosphate
pH 7, 30°C, fusion protein composed of the pXC1-encoded protein and the histidine leader peptide derived from pET28
0.00605
2-trans,6-trans-farnesyl diphosphate
pH 7.5, 30ºC, recombinant CDN1-C1 enzyme
0.007
2-trans,6-trans-farnesyl diphosphate
-
isoenzyme CAD1-A, pH 8.7, 30°C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.033
2-trans,6-trans-farnesyl diphosphate
fusion protein composed of the pXC1-encoded protein and the histidine leader peptide derived from pET28, pH 7, 30°C
0.00059
(2E,6E)-farnesyl diphosphate
mutant enzyme W279E, at pH 7.5 and 25°C
0.00059
(2E,6E)-farnesyl diphosphate
recombinant mutant W279E, pH 7.5, 25°C
0.00067
(2E,6E)-farnesyl diphosphate
mutant enzyme W279D, at pH 7.5 and 25°C
0.00067
(2E,6E)-farnesyl diphosphate
recombinant mutant W279D, pH 7.5, 25°C
0.00073
(2E,6E)-farnesyl diphosphate
mutant enzyme W279Y, at pH 7.5 and 25°C
0.00073
(2E,6E)-farnesyl diphosphate
recombinant mutant W279Y, pH 7.5, 25°C
0.001
(2E,6E)-farnesyl diphosphate
wild type enzyme, at pH 7.5 and 25°C
0.00109
(2E,6E)-farnesyl diphosphate
mutant enzyme W279M, at pH 7.5 and 25°C
0.0011
(2E,6E)-farnesyl diphosphate
recombinant mutant W279M, pH 7.5, 25°C
0.00127
(2E,6E)-farnesyl diphosphate
His-tagged recombinant enzyme, at pH 7.5 and 25°C
0.00127
(2E,6E)-farnesyl diphosphate
recombinant His6-tagged wild-type enzyme, pH 7.5, 25°C
0.003
(2E,6E)-farnesyl diphosphate
mutant enzyme W279Q, at pH 7.5 and 25°C
0.003
(2E,6E)-farnesyl diphosphate
recombinant mutant W279Q, pH 7.5, 25°C
0.0031
(2E,6E)-farnesyl diphosphate
recombinant mutant W279A, pH 7.5, 25°C
0.00312
(2E,6E)-farnesyl diphosphate
mutant enzyme W279A, at pH 7.5 and 25°C
0.0038
(2E,6E)-farnesyl diphosphate
mutant enzyme W279L, at pH 7.5 and 25°C
0.0038
(2E,6E)-farnesyl diphosphate
recombinant mutant W279L, pH 7.5, 25°C
0.01
(2E,6E)-farnesyl diphosphate
wild type enzyme, at pH 8.0 and 30°C
0.694
(2E,6E)-farnesyl diphosphate
pH and temperature not specified in the publication
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.073
(2E,6E)-farnesyl diphosphate
recombinant mutant W279D, pH 7.5, 25°C
0.17
(2E,6E)-farnesyl diphosphate
recombinant mutant W279Y, pH 7.5, 25°C
0.38
(2E,6E)-farnesyl diphosphate
recombinant mutant W279Q, pH 7.5, 25°C
0.4
(2E,6E)-farnesyl diphosphate
recombinant mutant W279L, pH 7.5, 25°C
0.41
(2E,6E)-farnesyl diphosphate
recombinant mutant W279E, pH 7.5, 25°C
0.58
(2E,6E)-farnesyl diphosphate
recombinant mutant W279M, pH 7.5, 25°C
0.7
(2E,6E)-farnesyl diphosphate
mutant enzyme W279D, at pH 7.5 and 25°C
1.41
(2E,6E)-farnesyl diphosphate
recombinant mutant W279A, pH 7.5, 25°C
1.7
(2E,6E)-farnesyl diphosphate
mutant enzyme W279Y, at pH 7.5 and 25°C
2.2
(2E,6E)-farnesyl diphosphate
recombinant His6-tagged wild-type enzyme, pH 7.5, 25°C
2.5
(2E,6E)-farnesyl diphosphate
mutant enzyme W279Q, at pH 7.5 and 25°C
3.1
(2E,6E)-farnesyl diphosphate
wild type enzyme, at pH 8.0 and 30°C
4
(2E,6E)-farnesyl diphosphate
mutant enzyme W279L, at pH 7.5 and 25°C
4.1
(2E,6E)-farnesyl diphosphate
mutant enzyme W279E, at pH 7.5 and 25°C
5.7
(2E,6E)-farnesyl diphosphate
mutant enzyme W279M, at pH 7.5 and 25°C
14
(2E,6E)-farnesyl diphosphate
mutant enzyme W279A, at pH 7.5 and 25°C
21.7
(2E,6E)-farnesyl diphosphate
wild type enzyme, at pH 7.5 and 25°C
31
(2E,6E)-farnesyl diphosphate
wild type enzyme, at pH 7.5 and 25°C
37.7
(2E,6E)-farnesyl diphosphate
pH and temperature not specified in the publication
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
specific activity of the enzyme increases concomitantly with the cad1 transcripts in developing cottonseeds
additional information
-
specific activity of the enzyme increases concomitantly with the cad1 transcripts in developing cottonseeds
additional information
-
in roots the activity increases on day 7 post germination. In cotyledons and hypocotyls the activity decreases on day 7 post germination
additional information
-
in the early stages of infection with a defoliating isolate of the pathogen Verticillium dahliae, the enzyme activity in resistant plants increases more quickly than in susceptible plants
additional information
-
specific activity of the enzyme increases concomitantly with the cad1 transcripts in developing cottonseeds
additional information
-
enzyme activity appears between 26 and 33 days postanthesis, reaches a maximum at 38 days postanthesis and then sharply declines
additional information
-
in the early stages of infection with a defoliating isolate of the pathogen Verticillium dahliae, the enzyme activity in resistant plants increases more quickly than in susceptible plants
additional information
-
in roots the activity increases on day 7 post germination. In cotyledons and hypocotyls the activity decreases on day 7 post germination
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
