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Information on EC 1.14.11.11 - hyoscyamine (6S)-dioxygenase
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EC Tree
1.14.11.11 hyoscyamine (6S)-dioxygenaseIUBMB Comments
Requires Fe2+ and ascorbate.
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Word Map
- 1.14.11.11
- scopolamine
-
tropane
- hyoscyamus
- niger
- belladonna
-
atropa
-
anisodus
-
anticholinergic
-
hairy
- acutangulus
-
anisodamine
-
epoxidation
-
2-oxoglutarate-dependent
-
aerial
-
6beta-hydroxylase
-
solanaceous
- tanguticus
-
agrobacterium-mediated
- metel
- putrescine
- datura
- n-methyltransferase
- tabacum
-
chemotype
-
high-value
-
catharanthus
- pericycle
- roseus
- tropinone
-
genetically-engineered
-
biofunctional
-
gst-tag
- vindoline
-
underground
-
bolt
-
2.1.1.53
- drug development
- pharmacology
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
aah6h, hnh6h, dih6h, ath6h, 
more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
H6H
hyoscyamine 6-hydroxylase
-
-
-
-
hyoscyamine 6beta-hydroxylase
hyoscyamine-6beta-hydroxylase
oxygenase, hyoscyamine 6beta-di-
-
-
-
-
hyoscyamine 6beta-hydroxylase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
L-hyoscyamine + 2-oxoglutarate + O2 = (6S)-hydroxyhyoscyamine + succinate + CO2
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-
-
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L-hyoscyamine + 2-oxoglutarate + O2 = (6S)-hydroxyhyoscyamine + succinate + CO2
proposed mechanism of epoxidation catalyzed by the enzyme, overview
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
decarboxylation
-
-
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epoxidation
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-
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hydroxylation
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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hydroxylation
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-
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hydroxylation
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converts L-hyoscyamine to 6beta-hydroxyhyoscyamine and then to scopolamine
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
L-hyoscyamine,2-oxoglutarate:oxygen oxidoreductase ((6S)-hydroxylating)
Requires Fe2+ and ascorbate.
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CAS REGISTRY NUMBER
COMMENTARY
103865-33-4
-
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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
(6S)-hydroxyhyoscyamine + succinate + CO2
L-hyoscyamine + 2-oxoglutarate + O2
-
-
-
r
2-hydroxy-3-phenylpropionyltropine + 2-oxoglutarate + O2
2-hydroxy-3-phenylpropionyl-6-hydroxytropine + succinate + CO2
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15% of the activity with L-hyoscyamine
-
?
2-oxoglutarate + p-hydroxyatropine + O2
?
-
26% of the activity with L-hyoscyamine
-
-
?
2-oxoglutarate + trans-cinnamoyltropine + O2
succinate + trans-cinnamoyl-6-hydroxytropine + CO2
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39% of the activity with L-hyoscyamine
-
?
3-hydroxy-3-phenylpropionyltropine + 2-oxoglutarate + O2
3-hydroxy-3-phenylpropionyl-6-hydroxytropine + succinate + CO2
-
56% of the activity with L-hyoscyamine
-
?
6,7-dehydrohyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
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119% of the activity with L-hyoscyamine
-
?
6beta-hydroxyhyoscyamine
scopolamine
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weak epoxidase activity, 2-5% of the hydroxylase activity
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-
?
8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-(4-(dimethylamino)phenyl)acetate + 2-oxoglutarate + O2
?
-
-
-
-
?
8-methyl-8-azabicyclo[3.2.1]octan-3-yl benzoate + 2-oxoglutarate + O2
?
-
-
-
-
?
apoatropine + 2-oxoglutarate + O2
6-hydroxyapoatropine + succinate + CO2
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45% of the activity with L-hyoscyamine
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?
hyoscyamine + O2 + 2-oxoglutarate + O2
scopolamine + succinate + CO2
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-
-
-
?
isobutyltropine + 2-oxoglutarate + O2
?
-
15% of the activity with L-hyoscyamine
-
-
?
L-homatropine + 2-oxoglutarate + O2
6-hydroxyhomatropine + succinate + CO2
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81% of the activity with L-hyoscyamine
-
?
L-norhyoscyamine + 2-oxoglutarate + O2
6-hydroxynorhyoscyamine + succinate + CO2
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81% of the activity with L-hyoscyamine
-
?
noratropine-N-acetic acid + 2-oxoglutarate + O2
?
-
17% of the activity with L-hyoscyamine
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-
?
phenylacetyltropine + 2-oxoglutarate + O2
6-hydroxyphenylacetyltropine + succinate + CO2
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81% of the activity with L-hyoscyamine
-
?
phenylalanyltropine + 2-oxoglutarate + O2
?
-
8% of the activity with L-hyoscyamine
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-
?
(6S)-6-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
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-
-
?
(6S)-6-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
key enzyme in the biosynthesis pathway of scopolamine
-
-
?
(6S)-6-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
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-
-
?
(6S)-6-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
-
-
-
-
?
(6S)-6-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
-
-
-
-
ir
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO
-
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO
the bifunctional enzyme also catalyzes the conversion of (6S)-6beta-hydroxyhyoscyamine to scopolamine, cf. EC 1.14.20.13
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
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-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
-
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
the enzyme catalyzes the hydroxylation of (-)-hyoscyamine and the subsequent epoxidation of 6beta-hydroxyhyoscyamine to form scopolamine, a natural alkaloid
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
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-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
MH392211
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-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
-
-
H6H produces 6beta-hydroxyhyoscyamine and its derivative, scopolamine, the DmrH6H epoxidase activity is low compared to the hydroxylase activity
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
-
the binding of the substrates, hyoscyamine and 2-oxoglutarate, to the enzyme induces significant conformational changes
H6H produces 6beta-hydroxyhyoscyamine and its derivative, scopolamine, the DmrH6H epoxidase activity is low compared to the hydroxylase activity
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
Glu116 interacts with the tertiary amine located on the hyoscyamine tropane moiety and Tyr326 forms CH-pi hydrogen bonds with the hyoscyamine phenyl ring
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
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-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
key enzyme in the biosynthesis pathway of scopolamine
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-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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-
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?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
Hyoscyamus gyorffi
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-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
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-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
-
-
-
ir
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
only the L-isomer of hyoscyamine serves as substrate, D-hyoscyamine is nearly inactive
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
the enzyme catalyzes two consecutive oxidation reactions leading from hyoscyamine to scopolamine
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
enzyme is involved in biosynthetic pathway leading to scopolamine
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
-
-
?
additional information
?
-
the enzyme also catalyzes the reaction of EC 1.14.11.14
-
-
?
additional information
?
-
-
the enzyme also catalyzes the reaction of EC 1.14.11.14
-
-
?
additional information
?
-
-
the enzyme also catalyzes the reaction of EC 1.14.11.14
-
-
?
additional information
?
-
-
hyoscyamine 6beta-hydroxylase, a 2-oxoglutarate-dependent dioxygenase, converts L-hyoscyamine to its 6,7-epoxy derivative, scopolamine, in two sequential steps. 6,7-Dehydrohyoscyamine, a potential precursor for the last step of epoxidation, is an obligatory intermediate in the biosynthesis of scopolamine
-
-
?
additional information
?
-
-
hyoscyamine 6beta-hydroxylase, a 2-oxoglutarate-dependent dioxygenase, converts L-hyoscyamine to its 6,7-epoxy derivative, scopolamine, in two sequential steps. The catalytic efficiency of AbH6H, especially for the second oxidation, which is the reaction of EC 1.14.11.14, is low. The epoxidation step is much slower than the hydroxylation step. Substrate analogues 1-methylpiperidin-4-yl 2-phenylacetate, 8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-phenylpropanoate, 8-oxabicyclo[3.2.1]octan-3-yl 2-phenylacetate, and 4 are no substrates for the enzyme
-
-
?
additional information
?
-
the enzyme also catalyzes the reaction of EC 1.14.11.14
-
-
?
additional information
?
-
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high specificity for 2-oxoglutarate in hydroxylation
-
-
?
additional information
?
-
the enzyme also catalyzes the reaction of EC 1.14.11.14
-
-
?
additional information
?
-
-
the enzyme also catalyzes the reaction of EC 1.14.11.14
-
-
?
additional information
?
-
-
methyl jasmonate and salicylic acid increase the expression of the enzyme
-
-
?
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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
(6S)-6-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
key enzyme in the biosynthesis pathway of scopolamine
-
-
?
(6S)-6-hydroxyhyoscyamine + 2-oxoglutarate + O2
scopolamine + succinate + CO2
-
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO
-
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
-
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
the enzyme catalyzes the hydroxylation of (-)-hyoscyamine and the subsequent epoxidation of 6beta-hydroxyhyoscyamine to form scopolamine, a natural alkaloid
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
-
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
MH392211
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
-
-
H6H produces 6beta-hydroxyhyoscyamine and its derivative, scopolamine, the DmrH6H epoxidase activity is low compared to the hydroxylase activity
-
?
L-hyoscyamine + 2-oxoglutarate + O2
(6S)-hydroxyhyoscyamine + succinate + CO2
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
key enzyme in the biosynthesis pathway of scopolamine
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
-
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
the enzyme catalyzes two consecutive oxidation reactions leading from hyoscyamine to scopolamine
-
-
?
L-hyoscyamine + 2-oxoglutarate + O2
6beta-hydroxyhyoscyamine + succinate + CO2
-
enzyme is involved in biosynthetic pathway leading to scopolamine
-
?
additional information
?
-
-
hyoscyamine 6beta-hydroxylase, a 2-oxoglutarate-dependent dioxygenase, converts L-hyoscyamine to its 6,7-epoxy derivative, scopolamine, in two sequential steps. 6,7-Dehydrohyoscyamine, a potential precursor for the last step of epoxidation, is an obligatory intermediate in the biosynthesis of scopolamine
-
-
?
additional information
?
-
-
methyl jasmonate and salicylic acid increase the expression of the enzyme
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
Fe2+
without addition of Fe2+, only 1.3% of the activity is detected
Fe2+
-
dependent, about 25-30% decreased production of scopolamine and hyoscyamine in absence of iron in medium
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(1R,2R,4S,5S,7s)-7-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.02,4]nonane
-
slight inhibition by the substrate analogue
8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-(4-(dimethylamino)phenyl)acetate
-
-
additional information
-
synthesis and inhibitory potencies of substrate analogues, overview. No inhibition by substrate analogues 1-methylpiperidin-4-yl 2-phenylacetate, 8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-phenylpropanoate, and 8-oxabicyclo[3.2.1]octan-3-yl 2-phenylacetate
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.05
L-hyoscyamine