Information on EC 1.5.1.25 - thiomorpholine-carboxylate dehydrogenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.5.1.25
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RECOMMENDED NAME
GeneOntology No.
thiomorpholine-carboxylate dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
thiomorpholine 3-carboxylate + NAD(P)+ = 3,4-dehydro-thiomorpholine-3-carboxylate + NAD(P)H + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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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SYSTEMATIC NAME
IUBMB Comments
thiomorpholine-3-carboxylate:NAD(P)+ 5,6-oxidoreductase
The product is the cyclic imine of the 2-oxoacid corresponding to S-(2-aminoethyl)cysteine. In the reverse direction, a number of other cyclic unsaturated compounds can act as substrates, but more slowly.
CAS REGISTRY NUMBER
COMMENTARY hide
115232-54-7
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
physiological function
additional information
-
in silico docking of various substrates and small inhibitors into the active site of the X-ray structures of mouse ketimine reductase/CRYM in order to better understand the enzyme catalytic mechanism
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
show the reaction diagram
-
-
-
-
?
cystathionine ketimine + NADH
cyclothionine + NAD+
show the reaction diagram
cystathionine ketimine + NADPH
cyclothionine + NADP+
show the reaction diagram
DELTA1-piperideine 2-carboxylate + NADH
? + NAD+
show the reaction diagram
DELTA1-piperideine 2-carboxylate + NADPH
? + NADP+
show the reaction diagram
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
show the reaction diagram
DELTA1-pyrrolidine 2-carboxylate + NADPH + H+
L-proline + NADP+
show the reaction diagram
DELTA2-thiazoline-2-carboxylate + NADPH + H+
? + NADP+
show the reaction diagram
glyocylate + methylamine + NADPH + H+
sarcosine + NADP+
show the reaction diagram
-
-
-
?
lanthionine ketimine + NADH
1,4-thiomorpholine 3,5-dicarboxylic acid + NAD+
show the reaction diagram
lanthionine ketimine + NADPH
1,4-thiomorpholine 3,5-dicarboxylic acid + NADP+
show the reaction diagram
phenylpyruvate + methylamine + NADPH + H+
N-methyl-L-phenylalanine + NADP+
show the reaction diagram
-
-
-
?
pyruvate + ethylamine + NADPH + H+
N-ethyl-L-alanine + NADP+
show the reaction diagram
-
-
-
?
pyruvate + methylamine + NADPH + H+
N-methyl-L-alanine + NADP+
show the reaction diagram
-
-
-
?
pyruvate + NH3 + NADPH + H+
L-alanine + NADP+
show the reaction diagram
-
-
-
?
S-(2-aminoethyl)-L-cysteine ketimine + NADPH + H+
1,4-thiomorpholine-3-carboxylate + NADP+
show the reaction diagram
S-aminoethylcysteine ketimine + NADH
1,4-thiomorpholine 3-carboxylic acid + NAD+
show the reaction diagram
S-aminoethylcysteine ketimine + NADPH
1,4-thiomorpholine 3-carboxylic acid + NADP+
show the reaction diagram
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
show the reaction diagram
-
-
-
-
?
DELTA1-piperideine 2-carboxylate + NADPH + H+
L-pipecolate + NADP+
show the reaction diagram
DELTA1-pyrrolidine 2-carboxylate + NADPH + H+
L-proline + NADP+
show the reaction diagram
DELTA2-thiazoline-2-carboxylate + NADPH + H+
? + NADP+
show the reaction diagram
S-(2-aminoethyl)-L-cysteine ketimine + NADPH + H+
1,4-thiomorpholine-3-carboxylate + NADP+
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3,3',5'-L-triiodothyronine
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competitive inhibition
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3,5,3'-L-triiodothyronine
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competitive inhibition
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3,5,3'-triiodothyronine
3,5-diiodo-L-tyrosine
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low competitive inhibition
3,5-diiodothyronine
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competitive inhibition
4,5-dibromopyrrole-2-carboxylate
-
DELTA1-piperideine 2-carboxylate
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substrate inhibition
L-thyroxine
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competitive inhibition
L-tyrosine
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competitive inhibition
picolinate
pyrrole-2-carboxylate
S-(2-aminoethyl)-L-cysteine ketimine
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substrate inhibition
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Triton X-100
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irreversible inactivation
additional information
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in silico docking of substrates and inhibitors using ketimine reductase/CRYM cyrstal structure, PDB ID 4BVA, overview
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3 - 10
Cystathionine ketimine
0.013
DELTA1-piperideine 2-carboxylate
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pH 7.2, 37C
0.33
DELTA1-Piperidine 2-carboxylate
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reaction with DELTA1-piperidine-2-carboxylate
0.045
DELTA1-pyrrolidine 2-carboxylate
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pH 7.2, 37C
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0.021
DELTA2-thiazoline-2-carboxylate
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pH 7.2, 37C
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0.47 - 1.17
Lanthionine ketimine
0.015 - 0.26
NADH
0.028
S-(2-aminoethyl)-L-cysteine ketimine
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pH 7.2, 37C
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0.077 - 0.24
S-Aminoethylcysteine ketimine
additional information
additional information
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Michaelis-Menten kinetics
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4.4
DELTA1-piperideine 2-carboxylate
-
pH 7.2, 37C
6.6
DELTA1-pyrrolidine 2-carboxylate
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pH 7.2, 37C
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1.7
DELTA2-thiazoline-2-carboxylate
-
pH 7.2, 37C
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0.2
S-(2-aminoethyl)-L-cysteine ketimine
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pH 7.2, 37C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
339
DELTA1-piperideine 2-carboxylate
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pH 7.2, 37C
148
DELTA1-pyrrolidine 2-carboxylate
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pH 7.2, 37C
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80
DELTA2-thiazoline-2-carboxylate
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pH 7.2, 37C
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7
S-(2-aminoethyl)-L-cysteine ketimine
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pH 7.2, temperature 37C
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.000035
3,3',5'-L-triiodothyronine
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pH 7.2, 37C
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0.000278
3,5,3'-triiodothyronine
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with substrate S-(2-aminoethyl)-L-cysteine ketimine, pH 5.0, temperature not specified in the publication
0.313
3,5-diiodo-L-tyrosine
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pH 7.2, 37C
0.000032
3,5-diiodothyronine
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pH 7.2, 37C
0.038
4,5-dibromopyrrole-2-carboxylate
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pH 7.2, 37C
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1.8
DELTA1-piperideine 2-carboxylate
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pH 7.2, 37C
1.7
S-(2-aminoethyl)-L-cysteine ketimine
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pH 7.2, 37C
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0027
pyrrole-2-carboxylate
Homo sapiens
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pH 7.2, 37C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
16.3
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16.6
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additional information
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highly purified recombinantly expressed human CRYM possesses substantial ketimine reductase activity
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6
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reaction with cystathionine ketimine, acetate buffer or phosphate buffer
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
high enzyme expression level
Manually annotated by BRENDA team
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high enzyme expression level, expression of the CRYM transcript follows the hair growth cycle with a significant increase in expression during mid- and late anagen growth phases
Manually annotated by BRENDA team
additional information
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CRYM/KR mRNA in the mouse is most highly expressed in skin among the tissues evaluated, followed by brain and heart
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
-
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
45000
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2 * 45000, SDS-PAGE
73000
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gel filtration
76000
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non-denaturing PAGE
100000
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non-denaturing PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
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2 * 45000, SDS-PAGE
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
irreversible inactivation at protein concentration below 1 mg/ml. Complete loss of activity after 24 h at 4C. Higher protein concentrations or 10% glycerol prevent enzyme inactivation. 30% loss of activity aftter 7 days at 4C
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4C, purified enzyme is stable for at least 1 month
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
purified from bovine brain
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purified from lamb brain
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purified from porcine kidney
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purified from rat liver
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
steroid hormones have a marked effect on the expression of CRYM, e.g. androgens induce CRYM expression in bovine mammary glands
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steroid hormones have a marked effect on the expression of CRYM, e.g. androgens induce CRYM expression in human prostate cancer
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