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Information on EC 1.1.1.218 - morphine 6-dehydrogenase
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EC Tree
1.1.1.218 morphine 6-dehydrogenaseIUBMB Comments
Also acts on some other alkaloids, including codeine, normorphine and ethylmorphine, but only very slowly on 7,8-saturated derivatives such as dihydromorphine and dihydrocodeine. In the reverse direction, also reduces naloxone to the 6alpha-hydroxy analogue. Activated by 2-sulfanylethan-1-ol (2-mercaptoethanol).
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Word Map
- 1.1.1.218
- morphinone
-
dehydrogenation
-
aldo-keto
-
alicyclic
- normorphine
- ethylmorphine
- codeine
- steroid
- nadp
- hamster
-
congener
- barbital
-
lithocholic
- indomethacin
- pyrazole
- 2-mercaptoethanol
- dihydrocodeine
-
diethyl
-
nonenzymatically
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phenylarsine
- phe
- maleate
- ketones
- biliary
-
17beta-hydroxysteroids
- o-quinones
- dihydromorphine
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analgesia
-
nad+-dependent
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3alpha-hydroxysteroids
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
morphine 6-dehydrogenase, naloxone reductase, akr1c34, morphine-6-dehydrogenase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
morphine 6-dehydrogenase
-
-
-
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naloxone reductase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
morphine + NAD(P)+ = morphinone + NAD(P)H + H+
dehydrogenation of the 6-hydroxy group of morphine derivatives having a 7,8-unsaturated bond
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morphine + NAD(P)+ = morphinone + NAD(P)H + H+
dehydrogenation of the 6-hydroxy group of morphine derivatives having a 7,8-unsaturated bond
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morphine + NAD(P)+ = morphinone + NAD(P)H + H+
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-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dehydrogenation
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-
-
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oxidation
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-
-
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redox reaction
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-
-
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reduction
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-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
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SYSTEMATIC NAME
IUBMB Comments
morphine:NAD(P)+ 6-oxidoreductase
Also acts on some other alkaloids, including codeine, normorphine and ethylmorphine, but only very slowly on 7,8-saturated derivatives such as dihydromorphine and dihydrocodeine. In the reverse direction, also reduces naloxone to the 6alpha-hydroxy analogue. Activated by 2-sulfanylethan-1-ol (2-mercaptoethanol).
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CAS REGISTRY NUMBER
COMMENTARY
106640-77-1
deleted Reg.No.
97002-71-6
-
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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
3-hydroxyhexobarbital + NADP+
?
-
does not serve as a substrate for guinea pig enzyme
-
-
?
nalorphine + NAD(P)+
(5alpha)-3-hydroxy-17-(prop-2-en-1-yl)-7,8-didehydro-4,5-epoxymorphinan-6-one + NAD(P)H + H+
trans-1,4-decalindiol + NADP+
?
-
about 30% of the activity observed with morphine
-
-
?
codeine + NAD(P)+
codeinone + NAD(P)H
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oxidation at 80% the rate of morphine oxidation
-
-
?
codeine + NAD(P)+
codeinone + NAD(P)H
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oxidation at 80% the rate of morphine oxidation
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-
?
codeine + NAD(P)+
codeinone + NAD(P)H
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only weak enzyme activity for codeine
-
-
?
codeine + NAD(P)+
codeinone + NAD(P)H
-
oxidation at 120% the rate of morphine oxidation
at pH 6.5, + NADPH, reduction of codeinone to codeine
r
codeine + NAD(P)+
codeinone + NAD(P)H
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non-Theorell-Chance sequential ordered mechanism for codeine oxidation at pH 9.5
morphine dehydrogenase follows a Theorell-Chance mechanism for codeinone reduction at pH 7.0
?
codeine + NAD(P)+
codeinone + NAD(P)H
-
oxidation at 120% the rate of morphine oxidation
at pH 6.5, + NADPH, reduction of codeinone to codeine
r
codeine + NAD(P)+
codeinone + NAD(P)H
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non-Theorell-Chance sequential ordered mechanism for codeine oxidation at pH 9.5
morphine dehydrogenase follows a Theorell-Chance mechanism for codeinone reduction at pH 7.0
?
codeine + NADP+
codeinone + NADPH
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codeine as the sole carbon and energy source
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?
codeine + NADP+
codeinone + NADPH
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codeine as the sole carbon and energy source
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?
ethylmorphine + NAD(P)+
?
-
oxidation at 51% the rate of morphine oxidation
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-
?
morphine + NADP+
morphinone + NADPH
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highly specific alkaloid dehydrogenase, oxidizing only the C-6 hydroxy group of morphine and codeine, morphine as the sole carbon and energy source
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?
morphine + NADP+
morphinone + NADPH
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highly specific alkaloid dehydrogenase, oxidizing only the C-6 hydroxy group of morphine and codeine, morphine as the sole carbon and energy source
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-
?
morphine + NADP+
morphinone + NADPH
-
highly specific alkaloid dehydrogenase, oxidizing only the C-6 hydroxy group of morphine and codeine, morphine as the sole carbon and energy source
-
?
morphine + NADP+
morphinone + NADPH
-
highly specific alkaloid dehydrogenase, oxidizing only the C-6 hydroxy group of morphine and codeine, morphine as the sole carbon and energy source
-
-
?
morphine + NADP+
morphinone + NADPH + H+
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-
production of morphinone demonstrated in vitro experiments
?
morphine + NADP+
morphinone + NADPH + H+
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production of morphinone demonstrated in vitro experiments
?
morphine + NADP+
morphinone + NADPH + H+
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enzyme activity only with NAD+
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-
?
morphine + NADP+
morphinone + NADPH + H+
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enzyme acitivity with NAD+ four times that with NADP+
-
-
?
morphine + NADP+
morphinone + NADPH + H+
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enzyme activity only with NADP+
-
?
morphine + NADP+
morphinone + NADPH + H+
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enzyme activity only with NADP+
-
-
?
morphine + NADP+
morphinone + NADPH + H+
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enzyme activity only with NADP+
-
?
morphine + NADP+
morphinone + NADPH + H+
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enzyme activity only with NADP+
-
-
?
morphine + NADP+
morphinone + NADPH + H+
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+ NAD+: enzyme activity ten times that with NADP+
-
?
morphine + NADP+
morphinone + NADPH + H+
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+ NAD+: enzyme activity ten times that with NADP+
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?
nalorphine + NAD(P)+
(5alpha)-3-hydroxy-17-(prop-2-en-1-yl)-7,8-didehydro-4,5-epoxymorphinan-6-one + NAD(P)H + H+
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best substrate, oxidation at 120% the rate of morphine oxidation
-
-
?
nalorphine + NAD(P)+
(5alpha)-3-hydroxy-17-(prop-2-en-1-yl)-7,8-didehydro-4,5-epoxymorphinan-6-one + NAD(P)H + H+
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best substrate, oxidation at 120% the rate of morphine oxidation
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-
?
naloxone + NAD(P)H
6alpha-naloxol + NADP+
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stereospecific reduction
?
naloxone + NAD(P)H
6alpha-naloxol + NADP+
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stereospecific reduction
?
normorphine + NAD(P)+
?
-
about 3 times better substrate than morphine
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-
?
normorphine + NAD(P)+
?
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best substrate, oxidation at 139% the rate of morphine oxidation
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?
additional information
?
-
the enzyme AKR1C34 shows 3alpha/17beta/20alpha-hydroxysteroid dehydrogenase activities, EC 1.1.1.239, detailed overview. Ala54 plays a critical role in non-/recognition of the steroidal substrates. Reaction products identification by thin-layer chromatography (TLC) and liquid chromatography/mass spectrometry (LC/MS)
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-
?
additional information
?
-
-
the enzyme AKR1C34 shows 3alpha/17beta/20alpha-hydroxysteroid dehydrogenase activities, EC 1.1.1.239, detailed overview. Ala54 plays a critical role in non-/recognition of the steroidal substrates. Reaction products identification by thin-layer chromatography (TLC) and liquid chromatography/mass spectrometry (LC/MS)
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-
?
additional information
?
-
J7M9D0
the enzyme shows NAD+-dependent dehydrogenase activity towards other nonsteroidal alicyclic alcohols and 3alpha/17beta-hydroxy-C18/C19/C21-steroids, detailed overview
-
-
?
additional information
?
-
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the enzyme shows NAD+-dependent dehydrogenase activity towards other nonsteroidal alicyclic alcohols and 3alpha/17beta-hydroxy-C18/C19/C21-steroids, detailed overview
-
-
?
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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
codeine + NADP+
codeinone + NADPH
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codeine as the sole carbon and energy source
-
?
codeine + NADP+
codeinone + NADPH
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codeine as the sole carbon and energy source
-
?
morphine + NADP+
morphinone + NADPH
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highly specific alkaloid dehydrogenase, oxidizing only the C-6 hydroxy group of morphine and codeine, morphine as the sole carbon and energy source
-
?
morphine + NADP+
morphinone + NADPH
-
highly specific alkaloid dehydrogenase, oxidizing only the C-6 hydroxy group of morphine and codeine, morphine as the sole carbon and energy source
-
-
?
morphine + NADP+
morphinone + NADPH
-
highly specific alkaloid dehydrogenase, oxidizing only the C-6 hydroxy group of morphine and codeine, morphine as the sole carbon and energy source
-
?
morphine + NADP+
morphinone + NADPH
-
highly specific alkaloid dehydrogenase, oxidizing only the C-6 hydroxy group of morphine and codeine, morphine as the sole carbon and energy source
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
J7M9D0
the rabbit enzyme shows high coenzyme preference for NAD+ over NADP+. Also in the reverse reaction, the enzymes reduces several alpha-dicarbonyl compounds including S-camphorquinone using NADH as the coenzyme, exhibiting low Km values of 0.004-0.006 mM. The reductase activity of the enzyme determined with NADPH as the coenzyme is less than 40% of their NADH-linked activity
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additional information
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the rabbit enzyme shows high coenzyme preference for NAD+ over NADP+. Also in the reverse reaction, the enzymes reduces several alpha-dicarbonyl compounds including S-camphorquinone using NADH as the coenzyme, exhibiting low Km values of 0.004-0.006 mM. The reductase activity of the enzyme determined with NADPH as the coenzyme is less than 40% of their NADH-linked activity
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Phenylarsine oxide
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dithiol modifier, competitive inhibitor to cofactor binding and noncompetitively toward morphine binding
additional information
-
competitive inhibitors: testosterone, 5alpha-androstan-17beta-ol-3-one, 5beta-androsteran-17beta-ol-3-one; no inhibition by indomethacine; no or weak inhibition by pyrazole, barbital
-
additional information
no or poor inhibition by 7-hydroxyflavone, chrysin, quercetin, genistein, galangin, lithocholic acid, and zearalenone
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additional information
-
no or poor inhibition by 7-hydroxyflavone, chrysin, quercetin, genistein, galangin, lithocholic acid, and zearalenone
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additional information
-
5beta-dihydrotestosterone, lithocholic acid, androsterone and estradiol inhibit competitively toward morphine binding; little inhibitory effect: indomethacin, prostaglandins E2, D2; no or weak inhibition by pyrazole, barbital
-
additional information
-
competitive inhibition: NADP+ with respect to NADPH, codeine with respect to codeinone
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.002
5alpha-androstan-17beta-ol-3-one
-
similar values of other 17beta-hydroxysteroids
additional information
additional information
J7M9D0
Michaelis-Menten kinetics
-
additional information
additional information
-
Michaelis-Menten kinetics
-
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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
0.073
Hexestrol
Oryctolagus cuniculus
J7M9D0
pH 7.4, 25°C, recombinant enzyme