Information on EC 1.1.1.245 - cyclohexanol dehydrogenase

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The expected taxonomic range for this enzyme is: Bacteria, Archaea

EC NUMBER
COMMENTARY hide
1.1.1.245
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RECOMMENDED NAME
GeneOntology No.
cyclohexanol dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
cyclohexanol + NAD+ = cyclohexanone + NADH + H+
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Caprolactam degradation
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cyclohexanol degradation
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Microbial metabolism in diverse environments
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cyclohexanol degradation
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SYSTEMATIC NAME
IUBMB Comments
cyclohexanol:NAD+ oxidoreductase
Also oxidizes some other alicyclic alcohols and diols.
CAS REGISTRY NUMBER
COMMENTARY hide
63951-98-4
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain NCIB 9871
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Manually annotated by BRENDA team
strain NCIB 9871
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
strain TK6
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Manually annotated by BRENDA team
strain TK6
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1,2-cycloheptanediol + NAD+
cycloheptane-1,2-dione + NADH
show the reaction diagram
-
relative oxidation activity at 25% the rate of cyclohexanol oxidation
-
-
?
1-butanol + NAD+
butanal + NADH
show the reaction diagram
1-decanol + NAD+
dodecanal + NADH
show the reaction diagram
-
poor substrate
-
-
?
1-dodecanol + NAD+
dodecanal + NADH
show the reaction diagram
-
poor substrate
-
-
?
1-heptanol + NAD+
heptanal + NADH
show the reaction diagram
1-hexanol + NAD+
hexanal + NADH
show the reaction diagram
1-octanol + NAD+
octanal + NADH
show the reaction diagram
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poor substrate
-
-
?
1-pentanol + NAD+
n-pentanal + NADH
show the reaction diagram
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relative activity at 23% the rate of cyclohexanol oxidation
-
-
?
1-propanol + NAD+
propionaldehyde + NADH
show the reaction diagram
2,3-butanediol + NAD+
? + NADH
show the reaction diagram
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relative activity at 4% the rate of cyclohexanol oxidation
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-
?
2,3-dimethylcyclohexanol + NAD+
2,3-methylcyclohexanone + NADH
show the reaction diagram
-
relative activity at 78% the rate of cyclohexanol oxidation
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-
?
2,6-dimethylcyclohexanol + NAD+
2,6-methylcyclohexanone + NADH
show the reaction diagram
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relative activity at 14% the rate of cyclohexanol oxidation
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-
?
2-butanol + NAD+
2-butanone + NADH
show the reaction diagram
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relative activity at 44% the rate of cyclohexanol oxidation
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?
2-cyclohexanol + NAD+
2-cyclohexenone + NADH
show the reaction diagram
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relative oxidation activity at 142% the rate of cyclohexanol oxidation
slow reduction
r
2-hydroxycyclohexanone + NADH
? + NAD+
show the reaction diagram
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relative activity at 50% the rate of cyclohexanone reduction
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2-methyl-1-butanol + NAD+
2-methyl-1-butanal + NADH
show the reaction diagram
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relative activity at 26% the rate of cyclohexanol oxidation
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?
2-methyl-1-pentanol + NAD+
2-methylpentanal + NADH
show the reaction diagram
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poor substrate
-
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?
2-methyl-1-propanol + NAD+
isobutyraldehyde + NADH
show the reaction diagram
-
relative activity at 17% the rate of cyclohexanol oxidation
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?
2-methyl-2-propanol + NAD+
? + NADH
show the reaction diagram
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relative activity at 16% the rate of cyclohexanol oxidation
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?
2-methylcyclohexanol + NAD+
2-methylcyclohexanone + NADH
show the reaction diagram
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relative activity at 51% the rate of cyclohexanol oxidation
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?
2-pentanol + NAD+
2-pentanone + NADH
show the reaction diagram
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relative activity at 43% the rate of cyclohexanol oxidation
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?
2-propanol + NAD+
acetone + NADH
show the reaction diagram
3-cyclohexyl-1-propanol + NAD+
3-cyclohexyl-1-propanal + NADH
show the reaction diagram
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poor substrate
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?
3-hexanol + NAD+
3-hexanone + NADH
show the reaction diagram
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relative activity at 196% the rate of cyclohexanol oxidation
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?
3-methylcyclohexanol + NAD+
3-methylcyclohexanone + NADH
show the reaction diagram
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relative activity at 74% the rate of cyclohexanol oxidation
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?
4-heptanol + NAD+
4-heptanone + NADH
show the reaction diagram
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relative activity at 125% the rate of cyclohexanol oxidation
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?
4-methyl-1-pentanol + NAD+
4-methylpentanal + NADH
show the reaction diagram
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poor substrate
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?
4-methylcyclohexanol + NAD+
4-methylcyclohexanone + NADH
show the reaction diagram
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relative activity at 66% the rate of cyclohexanol oxidation
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?
benzyl alcohol + NAD+
benzaldehyde + NADH
show the reaction diagram
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poor substrate
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?
benzyl alcohol + NAD+
benzylaldehyde + NADH
show the reaction diagram
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-
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?
cis-cyclopentane-1,2-diol + NAD+
? + NADH
show the reaction diagram
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relative activity at 27% the rate of cyclohexanol oxidation
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?
cycloheptanone + NADH
cycloheptanol + NAD+
show the reaction diagram
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relative activity at 10% the rate of cyclohexanone reduction
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cyclohexan-1,2-diol + NAD+
cyclohexane-1,2-dione + NADH
show the reaction diagram
cyclohexane-1,3-diol + NAD+
cyclohexane-1,3-dione + NADH
show the reaction diagram
cyclohexane-1,4-diol + NAD+
cyclohexane-1,4-dione + NADH
show the reaction diagram
cyclohexanol + NAD+
cyclohexanone + NADH
show the reaction diagram
cyclohexanol + NAD+
cyclohexanone + NADH + H+
show the reaction diagram
cyclooctanol + NAD+
cyclooctanone + NADH
show the reaction diagram
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relative activity at 500% the rate of cyclohexanol oxidation
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?
cyclopentanol + NAD+
cyclopentanone + NADH
show the reaction diagram
ethane-1,2-diol + NAD+
glyoxal + NADH
show the reaction diagram
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relative activity at 5% the rate of cyclohexanol oxidation
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?
ethanol + NAD+
acetaldehyde + NADH
show the reaction diagram
hexane-1,2-diol + NAD+
2-oxohexanal + NADH
show the reaction diagram
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relative activity at 84% the rate of cyclohexanol oxidation
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?
hexane-1,6-diol + NAD+
hexanedial + NADH
show the reaction diagram
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relative activity at 21% the rate of cyclohexanol oxidation
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?
methanol + NAD+
formaldehyde + NADH + H+
show the reaction diagram
propane-1,2-diol + NAD+
methylglyoxal + NADH
show the reaction diagram
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relative activity at 30% the rate of cyclohexanol oxidation
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?
propane-1,3-diol + NAD+
? + NADH
show the reaction diagram
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relative activity at 7% the rate of cyclohexanol oxidation
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?
trans-cyclopentane-1,2-diol + NAD+
? + NADH
show the reaction diagram
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relative activity at 114% the rate of cyclohexanol oxidation
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?
additional information
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
cyclohexanol + NAD+
cyclohexanone + NADH
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADH
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enzyme exhibits linearity of NAD(H) binding at pH 9.8 and at moderate ionic strength, in addition to positive cooperativity at pH 7.8 and 6.8, and at pH 9.8 in the presence of salt. NADH binding is positively cooperative below 20°C and negatively cooperative at 40–50°. Steady-state kinetic measurements show that SsADH displays standard Michaelis–Menten kinetics between 35°C and 45°C, but exhibits positive and negative cooperativity for NADH oxidation below and above this range of temperatures, respectively. Mutant N249Y displays non-cooperative behavious in coenzyme binding under the same experimental conditions used for the wild-type enzyme
NADP+
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ba2+
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increase of activity at 10 mM
Mg2+
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increase of activity at 10 mM
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Al3+
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almost complete inhibition of activity at 10 mM
Ca2+
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inhibition of activity at 10 mM
Co2+
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inhibition of activity at 10 mM
Cu2+
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almost complete inhibition of activity at 10 mM
Mn2+
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93% inhibition of activity at 10 mM
p-chloromercuribenzoate
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100% inhibition
Zn2+
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91% inhibition of activity at 10 mM
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.41
Cyclohexane-1,2-diol
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pH 10.3
0.5
Cyclohexane-1,3-diol
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pH 10.3
0.59
Cyclohexane-1,4-diol
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pH 10.3
0.0013 - 0.05
Cyclohexanol
0.0142
Cyclopentanol
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isoenzyme II at pH 7.6
0.0135
hexane-1,2-diol
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isoenzyme II at pH 7.6
0.024 - 0.04
NAD+
0.0028
trans-Cyclohexane-1,2-diol
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isoenzyme II at pH 7.6
0.0137
trans-cyclopentane-1,2-diol
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isoenzyme II at pH 7.6
additional information
additional information
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steady-state kinetic measurements show that SsADH displays standard Michaelis–Menten kinetics between 35°C and 45°C, but exhibits positive and negative cooperativity for NADH oxidation below and above this range of temperatures, respectively
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.04
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cell extract
0.28
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cell extract at pH 10
0.8
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oxidation of cyclohexanol at pH 7.8
1.9
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reduction of cyclohexanone at pH 7.8
2.5
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pH 10
127
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purified enzyme
143.5
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purified enzyme
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
10.1 - 10.5
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oxidation of alcohol
10.5
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
28000
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2 * 28000, SDS-PAGE, isoenzyme II
37500
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4 * 37500, SDS-PAGE
60000
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gel filtration, isoenzyme II
145000
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gel filtration
150000
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SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homotetramer
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4 * 37500, SDS-PAGE
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5 - 8.5
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stable
286383
10.5
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rapid inactivation above pH 10.5
12556
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4
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labile
40
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90% activity after incubation for 20 min
45
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1 min 50% loss of activity
50
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less than 20% activity after incubation for 20 min
55
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1 min 85% loss of activity
60
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1 min 95% loss of activity
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, stable for several days
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
126fold, affinity chromatograpy
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9.8fold, isoenzyme II
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
N249Y
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mutant N249Y displays non-cooperative behavious in coenzyme binding under the same experimental conditions used for the wild-type enzyme (that exhibits linearity of NAD(H) binding at pH 9.8 and at moderate ionic strength, in addition to positive cooperativity at pH 7.8 and 6.8, and at pH 9.8 in the presence of salt. NADH binding is positively cooperative below 20°C and negatively cooperative at 40–50°)