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Enzyme Nomenclature
Information on EC 1.14.13.202 - methyl farnesoate epoxidase
for references in articles please use BRENDA:EC1.14.13.202
Word Map on EC 1.14.13.202
- 1.14.13.202
- juvenile
-
corpora
- allata
-
worker
-
epoxidation
-
larval
- cockroach
-
honey
-
queen
-
caste
-
o-methyltransferase
-
instar
-
vitellogenin
-
hemolymph
-
metamorphosis
- mellifera
-
eusocial
-
blattella
- germanica
-
rnai-mediated
- jhamt
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pupae
-
allatostatins
-
synthase-2
-
diapause
- punctata
- locust
-
diploptera
-
3-hydroxy-3-methylglutaryl
- agriculture
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
1.14.13.202
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RECOMMENDED NAME
GeneOntology No.
methyl farnesoate epoxidase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
methyl (2E,6E)-farnesoate + NADPH + H+ + O2 = juvenile hormone III + NADP+ + H2O
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-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
methyl (2E,6E)-farnesoate,NADPH:oxygen oxidoreductase
A heme-thiolate protein (cytochrome P-450). The enzyme, found in insects except for Lepidoptera (moths and butterflies) is specific for methyl farnesoate (cf. EC 1.14.13.203, farnesoate epoxidase) [1,2].
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
RNAi-mediated knockdown of CYP15A1 in the pre-final larval instar does not result in precocious metamorphosis to pupa. The double knockdown of juvenile hormone acid O-methyltransferase and TcCYP15A1 results in pupae and adults with shorter wings
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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
methyl (2E,6E)-farnesoate + NADPH + H+ + O2
?
-
epoxidation is 12% compared to epoxidation of methyl (2E,6E)-farnesoate
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-
?
additional information
?
-
-
no activity with farnesol, farnesal, farnesoic acid, juvenile hormone III, 3,7,11-trimethyl-dodecanol, geranyl geraniol, farnesyl methyl ether, and geraniol and the fatty acids, lauric acid, and arachidonic acid
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-
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methyl (2E,6E)-farnesoate + NADPH + H+ + O2
juvenile hormone III + NADP+ + H2O
the enzyme, found in insects except for Lepidoptera (moths and butterflies) is specific for methyl farnesoate
-
-
?
methyl (2E,6E)-farnesoate + NADPH + H+ + O2
juvenile hormone III + NADP+ + H2O
-
the enzyme, found in insects except for Lepidoptera (moths and butterflies) is specific for methyl farnesoate
-
-
?
methyl (2E,6E)-farnesoate + NADPH + H+ + O2
juvenile hormone III + NADP+ + H2O
-
the enzyme is specific for methyl (2E,6E)-farnesoate i.e. (2E,6E)-3,7,11-trimethyl-2,6-dodecatrienoate. The enzyme produces juvenile hormone III with a ratio of 98:2 in favor of the natural (10R)-epoxide enantiomer. No activity with methyl (2Z,6Z)-farnesoate, methyl (2Z,6E)-farnesoate
juvenile hormone III i.e. methyl (2E,6E,10R,11S)-10,11-epoxy-3,7,11-trimethyldodeca-2,6-dienoate
-
?
methyl (2E,6E)-farnesoate + NADPH + H+ + O2
juvenile hormone III + NADP+ + H2O
-
-
2E,6E isomer, product has 10R configuration
-
?
methyl (2E,6E)-farnesoate + NADPH + H+ + O2
juvenile hormone III + NADP+ + H2O
-
product has (10R)-configuration
-
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
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
methyl (2E,6E)-farnesoate + NADPH + H+ + O2
juvenile hormone III + NADP+ + H2O
Q6R7M4
the enzyme, found in insects except for Lepidoptera (moths and butterflies) is specific for methyl farnesoate
-
-
?
methyl (2E,6E)-farnesoate + NADPH + H+ + O2
juvenile hormone III + NADP+ + H2O
-
the enzyme, found in insects except for Lepidoptera (moths and butterflies) is specific for methyl farnesoate
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1-(2-methylpropyl)-5-[4-([4-[3-(trifluoromethyl)-3H-diaziren-3-yl]benzyl]oxy)phenyl]-1H-imidazole
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bifunctional compound, inhibits juvenile hormone III synthesis by intact glands as well as methyl farnesoate epoxidation by gland homogenates. Using the compound, a radiolabeled and photoactivatable diazirine or benzophenone group can be introduced to label the hydrophobic substrate binding site of the enzyme
5-(3-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]phenyl)-1-(2-methylpropyl)-1H-imidazole
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carbon monoxide/oxygen atmosphere
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half-maximal inhibition at a CO/O ratio of 4.0. Inhibition is reversed by white-light irradiation
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cytochrome c
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inhibition by oxidized cytochrome c, 20 microM, 52.4% residual activity
methyl (2E,6E)-3,7-dimethyl-8-(3,4-methylenedioxyphenoxy)-octadienoate
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inhibits juvenile hormone biosynthesis in vitro by spontaneously active glands, presumably by direct inhibition of the epoxidase, and also inhibits the production of total methyl ester
[4-([4-[1-(2-methylpropyl)-1H-imidazol-5-yl]phenoxy]methyl)phenyl](phenyl)methanone
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bifunctional compound, inhibits juvenile hormone III synthesis by intact glands as well as methyl farnesoate epoxidation by gland homogenates. Using the compound, a radiolabeled and photoactivatable diazirine or benzophenone group can be introduced to label the hydrophobic substrate binding site of the enzyme
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0109
1-(2-methylpropyl)-5-[4-([4-[3-(trifluoromethyl)-3H-diaziren-3-yl]benzyl]oxy)phenyl]-1H-imidazole
Diploptera punctata
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pH 7.3, 30°C
0.06
5-(2-(benzyloxy)phenyl)-1-(3,7-dimethyloct-6-en-1-yl)-1H-imidazole
Diploptera punctata
-
pH 7.7, 30°C, inhibition of methyl (2E,6E)-farnesoate epoxidation by recombinant CYP15A1 in a reconstituted system
0.0002
5-(3-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]phenyl)-1-(2-methylpropyl)-1H-imidazole
Diploptera punctata
-
pH 7.7, 30°C, inhibition of methyl (2E,6E)-farnesoate epoxidation by recombinant CYP15A1 in a reconstituted system
0.000025
5-[3-(benzyloxy)phenyl]-1-(2-methylpropyl)-1H-imidazole
Diploptera punctata
-
pH 7.7, 30°C, inhibition of methyl (2E,6E)-farnesoate epoxidation by recombinant CYP15A1 in a reconstituted system
0.0003
[4-([4-[1-(2-methylpropyl)-1H-imidazol-5-yl]phenoxy]methyl)phenyl](phenyl)methanone
Diploptera punctata
-
pH 7.3, 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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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
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CYP15A1 transcripts are detected only in the corpora allata of day 5-mated females. Highest CYP15A1 transcript levels are observed on days 3–6, at the time of maximal biosynthetic activity of the glands, whereas the message is barely detectable on days 10, 15, and 20, after oviposition and during pregnancy, when juvenile hormone synthesis is low
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clear relationship between methyl farnesoate levels and the total rate of juvenile hormone biosynthesis in individual pairs of glands. Methyl farnesoate levels rise 30fold during the spontaneous activity cycle, but never reach a level causing saturation of the methyl farnesoate epoxidase
additional information
-
CYP15A1 transcripts are not detected in the brain or fat body
additional information
level of CYP15A1 mRNA is high in the embryonic stage as well as in the middle of the final larval instar. In the embryonic stage, the transcript level of CYP15A1 starts to increase 30 h after egg laying and peaks 54-60 h after egg laying
additional information
-
level of CYP15A1 mRNA is high in the embryonic stage as well as in the middle of the final larval instar. In the embryonic stage, the transcript level of CYP15A1 starts to increase 30 h after egg laying and peaks 54-60 h after egg laying
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
agriculture
-
the enzyme may be useful in the design and screening of selective insect control agents
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.202)
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