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Information on EC 4.1.2.19 - rhamnulose-1-phosphate aldolase
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4.1.2.19 rhamnulose-1-phosphate aldolaseSpecify your search results
Word Map
- 4.1.2.19
- dihydroxyacetone
- aldolases
- dhap
- l-fuculose-1-phosphate
-
dhap-dependent
-
one-pot
- d-sorbose
- l-rhamnose
- d-psicose
-
achiral
- l-fructose
- synthesis
The enzyme appears in viruses and cellular organisms
Synonyms
l-rhamnulose-1-phosphate aldolase, rhamnulose-1-phosphate aldolase, rhamnulose 1-phosphate aldolase, rha-1pa, tm1072, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
aldolase, rhamnulose phosphate
-
-
-
-
L-Rhamnulose-1-phosphate aldolase
L-Rhamnulose-1-phosphate L-lactaldehyde-lyase
-
-
-
-
RhaD
Rhamn-1PA
-
-
-
-
rhamnulose 1-phosphate aldolase
Rhamnulose phosphate aldolase
-
-
-
-
RhuA
TM1072
L-Rhamnulose-1-phosphate aldolase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
L-Rhamnulose 1-phosphate = glycerone phosphate + (S)-lactaldehyde
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
aldol addition
condensation
-
-
-
-
elimination
elimination
-
-
of an aldehyde, C-C bond cleavage
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
KEGG
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SYSTEMATIC NAME
IUBMB Comments
L-rhamnulose-1-phosphate (S)-lactaldehyde-lyase (glycerone-phosphate-forming)
-
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CAS REGISTRY NUMBER
COMMENTARY
9054-58-4
-
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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
(2R)-2,3-dihydroxy-4-nitrobutanal
(1R,2R,3S,4R,5S,6S)-1-hydroxymethyl-6-nitrocyclohexane-1,2,3,4,5-pentol + (1S,2R,3R,4R,5R,6R)-1-hydroxymethyl-6-nitrocyclohexane-1,2,3,4,5-pentol
-
-
-
-
r
(2S)-2,3-dihydroxy-4-nitrobutanal
(1R,2R,3S,4S,5S,6S)-1-hydroxymethyl-6-nitrocyclohexane-1,2,3,4,5-pentol + 1-hydroxymethyl-6-nitrocyclohexane-1,2,3,4,5-pentol
-
-
-
-
r
(2S,3S)-3-methyl-1-oxopentane-2-benzylcarbamate
(2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-((S)-sec-butyl)-3,4-diol + N-ethyl-(2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-((S)-sec-butyl)-3,4-diol
-
product ratio 55:45
-
?
(benzyloxy)acetaldehyde + dihydroxyacetone
(3R,4S)-5-(benzyloxy)-1,3,4-trihydroxypentan-2-one + (3R,4R)-5-(benzyloxy)-1,3,4-trihydroxypentan-2-one
favored direction of reaction
-
-
r
(R)-1-oxobutane-2-benzylcarbamate
(2S,3S,4S,5R)-2-(hydroxymethyl)pyrrolidine-5-ethyl-3,4-diol + (2R,3S,4R,5R)-2-(hydroxymethyl)pyrrolidine-5-ethyl-3,4-diol + N-ethyl-(2S,3S,4S,5R)-2-(hydroxymethyl)pyrrolidine-5-ethyl-3,4-diol + N-ethyl-(2R,3S,4R,5R)-2-(hydroxymethyl)pyrrolidine-5-ethyl-3,4-diol
-
product ratio 48:30:11:11
-
?
(R)-1-oxohexane-2-benzylcarbamate
(2S,3S,4S,5R)-2-(hydroxymethyl)pyrrolidine-5-propyl-3,4-diol + (2R,3S,4R,5R)-2-(hydroxymethyl)pyrrolidine-5-propyl-3,4-diol + N-ethyl-(2R,3S,4R,5R)-2-(hydroxymethyl)pyrrolidine-5-propyl-3,4-diol + N-ethyl-(2S,3S,4S,5R)-2-(hydroxymethyl)-pyrrolidine-5-propyl-3,4-diol
-
product ratio 28:63:5:5
-
?
(R)-1-oxopentane-2-benzylcarbamate
(2S,3S,4S,5R)-2-(hydroxymethyl)pyrrolidine-5-propyl-3,4-diol + (2R,3S,4R,5R)-2-(hydroxymethyl)pyrrolidine-5-propyl-3,4-diol + N-ethyl-(2S,3S,4S,5R)-2-(hydroxymethyl)pyrrolidine-5-propyl-3,4-diol + N-ethyl-(2R,3S,4R,5R)-2-(hydroxymethyl)pyrrolidine-5-propyl-3,4-diol
-
product ratio 44:34:11:10
-
?
(R)-3-methyl-1-oxobutane-2-benzylcarbamate
(2R,3S,4R,5R)-2-(hydroxymethyl)pyrrolidine-5-isopropyl-3,4-diol
-
-
-
?
(R)-4-methyl-1-oxopentane-2-benzylcarbamate
(2S,3S,4S,5R)-2-(hydroxymethyl)pyrrolidine-5-isobutyl-3,4-diol + (2R,3S,4R,5R)-2-(hydroxymethyl)pyrrolidine-5-isobutyl-3,4-diol + N-ethyl-(2R,3S,4R,5R)-2-(hydroxymethyl)pyrrolidine-5-isobutyl-3,4-diol + N-ethyl-(2S,3S,4S,5R)-2-(hydroxymethyl)pyrrolidine-5-isobutyl-3,4-diol
-
product ratio 32:43:16.9
-
?
(S)-1-oxo-3-phenylpropan-2-benzylcarbamate
(2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-benzyl-3,4-diol
-
-
-
?
(S)-1-oxobutane-2-benzylcarbamate
(2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-ethyl-3,4-diol
-
-
-
?
(S)-1-oxohexane-2-benzylcarbamate
(2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-butyl-3,4-diol + (2S,3S,4R,5S)-2-(hydroxymethyl)pyrrolidine-5-butyl-3,4-diol
-
product ratio 93:7
-
?
(S)-1-oxopentane-2-benzylcarbamate
(2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-propyl-3,4-diol
-
-
-
?
(S)-3-methyl-1-oxobutane-2-benzylcarbamate
(2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-isopropyl-3,4-diol + N-ethyl-(2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-isopropyl-3,4-diol
-
product ratio 84:16
-
?
(S)-4-methyl-1-oxopentane-2-benzylcarbamate
(2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-isobutyl-3,4-diol + (2S,3S,4R,5S)-2-(hydroxymethyl)pyrrolidine-5-isobutyl-3,4-diol + N-ethyl-(2S,3S,4S,5S)-2-(hydroxymethyl)pyrrolidine-5-isobutyl-3,4-diol
-
product ratio 71:6:23
-
?
2 glycerone phosphate + 2 D-glyceraldehyde
D-psicose 1-phosphate + D-sorbose 1-phosphate
-
-
-
?
2 glycerone phosphate + 2 L-glyceraldehyde
L-fructose 1-phosphate + L-tagatose 1-phosphate
-
-
-
?
2-methyl-1-oxopropane-2-benzylcarbamate
(2S,3S,4S)-2-(hydroxymethyl)pyrrolidine-5-dimethyl-3,4-diol + (2R,3S,4R)-2-(hydroxymethyl)pyrrolidine-5-dimethyl-3,4-diol
-
product ratio 44:56
-
?
3-hydroxy-4-nitrobutanal
(1R,2R,3S,5R,6S)-1-hydroxymethyl-6-nitrocyclohexane-1,2,3,5-tetraol + (1S,2R,3R,5S,6R)-1-hydroxymethyl-6-nitrocyclohexane-1,2,3,5-tetraol
-
-
-
-
r
4-nitrobutanal
(1R,2R,3S,6S)-1-hydroxymethyl-6-nitrocyclohexane-1,2,3-triol + (1S,2R,3R,6R)-1-hydroxymethyl-6-nitrocyclohexane-1,2,3-triol
-
-
-
-
?
6-Deoxy-L-sorbose 1-phosphate
Glycerone phosphate + D-lactaldehyde
-
0.8% of the activity with L-rhamnulose 1-phosphate
-
-
?
benzyl (2-oxoethyl)carbamate + dihydroxyacetone
benzyl [(2S,3R)-2,3,5-trihydroxy-4-oxopentyl]carbamate + benzyl [(2R,3R)-2,3,5-trihydroxy-4-oxopentyl]carbamate
favored direction of reaction
-
-
r
benzyl [(2R)-1-oxopropan-2-yl]carbamate + dihydroxyacetone
benzyl [(2R,3S,4R)-3,4,6-trihydroxy-5-oxohexan-2-yl]carbamate + benzyl [(2R,3R,4R)-3,4,6-trihydroxy-5-oxohexan-2-yl]carbamate
favored direction of reaction
-
-
r
D-Fructose 1-phosphate
?
-
1.7% of the activity with L-rhanmnulose 1-phosphate
-
-
?
D-Fructose-1,6-diphosphate
?
-
1.8% of the activity with L-rhanmnulose 1-phosphate
-
-
?
D-Ribulose 1,5-diphosphate
?
-
1.3% of the activity with L-rhanmnulose 1-phosphate
-
-
?
dihydroxyacetone + L-lactaldehyde
L-rhamnulose 1-phosphate
favored direction of reaction
-
-
r
dihydroxyacetone phosphate + N-Cbz-(2R)-2-amino-3-methylbutanal
N-Cbz-5-amino-1,3,4-trihydroxyoctan-2-one
-
-
yield 93%, ratio of (3R,4S) to (3S,4R) product is 2:98
-
?
dihydroxyacetone phosphate + N-Cbz-(2S)-2-amino-3-methylbutanal
N-Cbz-5-amino-1,3,4-trihydroxyoctan-2-one
-
-
yield 93%, ratio of (3R,4S) to (3S,4R) product is 98:2
-
?
dihydroxyacetone phosphate + N-Cbz-(2S)-2-aminobutanal
N-Cbz-5-amino-1,3,4-trihydroxyheptan-2-one
-
-
yield 94%, ratio of (3R,4S) to (3S,4R) product is 98:2
-
?
dihydroxyacetone phosphate + N-Cbz-(2S)-2-aminopropanal
N-Cbz-5-amino-1,3,4-trihydroxyhexan-2-one
-
-
yield 99%, ratio of (3R,4S) to (3S,4R) product is 98:2
-
?
dihydroxyacetone phosphate + N-Cbz-aminoacetaldehyde
N-Cbz-5-amino-1,3,4-trihydroxypentan-2-one
-
yield 91%, ratio of (3R,4S) to (3S,4R) product is 94:6
yield 91%, ratio of (3R,4S) to (3S,4R) product is 94:6
-
?
dimethoxyacetaldehyde + glycerone phosphate
(3R,4R)-3,4-dihydroxy-5,5-dimethoxy-2-oxopentyl phosphate
-
-
-
-
?
DL-glycerol 3-phosphate + D-glyceraldehyde
D-psicose + D-sorbose
-
-
-
?
DL-glycerol 3-phosphate + L-glyceraldehyde
L-fructose + D-tagatose
-
-
-
?
glycerone phosphate + benzyloxyacetaldehyde
(3R,4S)-5-(benzyloxy)-3,4-dihydroxy-2-oxopentyl phosphate
-
68% aldol formation at 45°C
-
-
?
glycerone phosphate + ethyl-3-methyl-4-oxocrotonate
(3R,4S,5E)-7-ethoxy-3,4-dihydroxy-5-methyl-2,7-dioxohept-5-en-1-yl phosphate
-
87% aldol formation at 45°C
-
-
?
glycerone phosphate + L-glyceraldehyde
L-fructose 1-phosphate
-
-
-
?
glycerone phosphate + L-glyceraldehyde
L-tagatose 1-phosphate
-
-
-
?
glycerone phosphate + phenylacetaldehyde
(3R,4S)-3,4-dihydroxy-2-oxo-5-phenylpentyl phosphate
-
53% aldol formation at 45°C
-
-
?
N-formylglycinal + dihydroxyacetone
N-[(2S,3R)-2,3,5-trihydroxy-4-oxopentyl]formamide + N-[(2R,3R)-2,3,5-trihydroxy-4-oxopentyl]formamide
-
-
-
r
dihydroxyacetone phosphate + L-lactaldehyde
L-rhamnulose 1-phosphate
-
-
-
-
r
dihydroxyacetone phosphate + L-lactaldehyde
L-rhamnulose 1-phosphate
-
-
-
r
dihydroxyacetone phosphate + L-lactaldehyde
L-rhamnulose 1-phosphate
favored direction of reaction
-
-
r
Glycerone phosphate + (S)-lactaldehyde
L-Rhamnulose 1-phosphate
-
-
-
-
?
Glycerone phosphate + (S)-lactaldehyde
L-Rhamnulose 1-phosphate
Escherichia coli B / ATCC 11303
-
-
-
?
Glycerone phosphate + (S)-lactaldehyde
L-Rhamnulose 1-phosphate
Escherichia coli B / ATCC 11303
-
-
-
-
?
Glycerone phosphate + (S)-lactaldehyde
L-Rhamnulose 1-phosphate
-
-
-
-
r
Glycerone phosphate + (S)-lactaldehyde
L-Rhamnulose 1-phosphate
-
more than 90% aldol formation at 45°C
-
-
r
Glycerone phosphate + acetaldehyde
5-Deoxy-L-xylulose 1-phosphate
-
-
-
?
Glycerone phosphate + acetaldehyde
5-Deoxy-L-xylulose 1-phosphate
-
at 10% of the activity with L-lactaldehyde
-
-
?
glycerone phosphate + D-glyceraldehyde
D-sorbose 1-phosphate
-
at 50% of the activity with L-lactaldehyde
-
-
?
Glycerone phosphate + D-lactaldehyde
6-Deoxy-D-sorbose 1-phosphate
-
-
-
?
Glycerone phosphate + D-lactaldehyde
6-Deoxy-D-sorbose 1-phosphate
-
at 10% of the activity with L-lactaldehyde
-
-
?
Glycerone phosphate + formaldehyde
D-Erythrulose 1-phosphate
-
at 10% of the activity with L-lactaldehyde
-
-
?
Glycerone phosphate + glycolaldehyde
L-Xylulose 1-phosphate
-
at 40% of the activity with L-lactaldehyde
-
-
?
L-Rhamnulose 1-phosphate
?
Arthrobacter pyridinolis
-
enzyme is involved in metabolism of L-rhamnose
-
-
?
L-Rhamnulose 1-phosphate
?
-
enzyme is involved in rhamnose catabolism
-
-
?
L-rhamnulose 1-phosphate
dihydroxyacetone phosphate + L-lactaldehyde
-
-
-
-
r
L-rhamnulose 1-phosphate
dihydroxyacetone phosphate + L-lactaldehyde
-
-
-
r
L-Rhamnulose 1-phosphate
Glycerone phosphate + (S)-lactaldehyde
Arthrobacter pyridinolis
-
-
-
-
?
L-Rhamnulose 1-phosphate
Glycerone phosphate + (S)-lactaldehyde
-
-
-
-
?
L-Rhamnulose 1-phosphate
Glycerone phosphate + (S)-lactaldehyde
-
-
-
-
?
L-Rhamnulose 1-phosphate
Glycerone phosphate + (S)-lactaldehyde
-
-
-
?
L-Rhamnulose 1-phosphate
Glycerone phosphate + (S)-lactaldehyde
-
-
-
?
L-Rhamnulose 1-phosphate
Glycerone phosphate + (S)-lactaldehyde
Escherichia coli B / ATCC 11303
-
-
-
?
L-Rhamnulose 1-phosphate
Glycerone phosphate + (S)-lactaldehyde
Escherichia coli B / ATCC 11303
-
-
-
-
?
L-Rhamnulose 1-phosphate
Glycerone phosphate + (S)-lactaldehyde
Escherichia coli W3110 / ATCC 27325
-
-
-
-
?
L-Rhamnulose 1-phosphate
Glycerone phosphate + (S)-lactaldehyde
-
-
-
-
?
L-Rhamnulose 1-phosphate
Glycerone phosphate + (S)-lactaldehyde
-
-
-
-
?
L-Rhamnulose 1-phosphate
Glycerone phosphate + (S)-lactaldehyde
-
-
-
-
r
L-Rhamnulose 1-phosphate
Glycerone phosphate + (S)-lactaldehyde
-
-
-
r
L-Sorbose 1-phosphate
Glycerone phosphate + D-glyceraldehyde
-
0.3% of the activity with L-rhanmnulose 1-phosphate
-
-
?
additional information
?
-
RhuA is highly stereoselective with (S)-N-Cbz-2-aminoaldehydes (90-100% syn (i.e., 3R,4S) adduct), whereas those with R configuration give mixtures of anti/syn adducts, for iPr and iBu substituents, RhuA furnishes the anti adduct with high stereoselectivity
-
-
?
additional information
?
-
-
RhuA is highly stereoselective with (S)-N-Cbz-2-aminoaldehydes (90-100% syn (i.e., 3R,4S) adduct), whereas those with R configuration give mixtures of anti/syn adducts, for iPr and iBu substituents, RhuA furnishes the anti adduct with high stereoselectivity
-
-
?
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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
Glycerone phosphate + (S)-lactaldehyde
L-Rhamnulose 1-phosphate
-
-
-
-
r
L-rhamnulose 1-phosphate
dihydroxyacetone phosphate + L-lactaldehyde
-
-
-
-
r
L-Rhamnulose 1-phosphate
?
Arthrobacter pyridinolis
-
enzyme is involved in metabolism of L-rhamnose
-
-
?
L-Rhamnulose 1-phosphate
?
-
enzyme is involved in rhamnose catabolism
-
-
?
L-Rhamnulose 1-phosphate
Glycerone phosphate + (S)-lactaldehyde
-
-
-
?
L-Rhamnulose 1-phosphate
Glycerone phosphate + (S)-lactaldehyde
-
-
-
-
r
L-Rhamnulose 1-phosphate
Glycerone phosphate + (S)-lactaldehyde
-
-
-
r
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Co2+
Cs+
-
Na+, Cs+, NH4+, Rb+ and K+, in the order of increasing effectiveness markedly enhance activity
K+
-
Na+, Cs+, NH4+, Rb+ and K+, in the order of increasing effectiveness markedly enhance activity
Mg2+
Mn2+
Na+
-
Na+, Cs+, NH4+, Rb+ and K+, in the order of increasing effectiveness markedly enhance activity
NH4+
-
Na+, Cs+, NH4+, Rb+ and K+, in the order of increasing effectiveness markedly enhance activity
Ni2+
-
restores activity of the enzyme after inactivation by dialysis against chelating agents or by treatment with SDS and 2-mercaptoethanol
Rb+
-
Na+, Cs+, NH4+, Rb+ and K+, in the order of increasing effectiveness markedly enhance activity
Zn
Zn2+
Co2+
-
restores activity of the enzyme after inactivation by dialysis against chelating agents or by treatment with SDS and 2-mercaptoethanol
Mg2+
-
restores activity of the enzyme after inactivation by dialysis against chelating agents or by treatment with SDS and 2-mercaptoethanol
Mn2+
-
restores activity of the enzyme after inactivation by dialysis against chelating agents or by treatment with SDS and 2-mercaptoethanol
Zn2+
-
restores activity of the enzyme after inactivation by dialysis against chelating agents or by treatment with SDS and 2-mercaptoethanol
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
phosphate
the aldol addition of dihydroxyacetobe is strongly inhibited by phosphate
SDS
-
competitive with L-rhamnulose 1-phosphate or glycerone phosphate, noncompetitive with L-lactaldehyde
1,10-phenanthroline
-
competitive with L-rhamnulose 1-phosphate or glycerone phosphate; noncompetitive with L-lactaldehyde
1,10-phenanthroline
-
competitive with L-rhamnulose 1-phosphate or glycerone phosphate
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
the enzyme contains 12 sulfhydryl groups per molecule
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1125
dihydroxyacetone
wild type enzyme, apparent value, at pH 7.0 and 25°C
1339
dihydroxyacetone
mutant enzyme N29D, apparent value, at pH 7.0 and 25°C
0.6
dihydroxyacetone phosphate
wild type enzyme, apparent value, at pH 7.0 and 25°C
7
dihydroxyacetone phosphate
mutant enzyme N29D, apparent value, at pH 7.0 and 25°C
1.9
L-rhamnulose 1-phosphate
mutant enzyme Q11W, in 60 mM Tris-HCl pH 7.5, 60 mM KCl
2
L-rhamnulose 1-phosphate
mutant enzyme K15W, in 60 mM Tris-HCl pH 7.5, 60 mM KCl
2
L-rhamnulose 1-phosphate
wild type enzyme, in 60 mM Tris-HCl pH 7.5, 60 mM KCl
2.5
L-rhamnulose 1-phosphate
mutant enzyme K15Y, in 60 mM Tris-HCl pH 7.5, 60 mM KCl
5.4
L-rhamnulose 1-phosphate
mutant enzyme L84W, in 60 mM Tris-HCl pH 7.5, 60 mM KCl
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM