Information on EC 1.1.1.100 - 3-oxoacyl-[acyl-carrier-protein] reductase

29454% relative activity compared to acetophenone

-

?

ethyl acetoacetate + NADPH

? + NADP+

-

706142

-

?

ethyl acetoacetate + NADPH

ethyl 3-hydroxybutyrate + NADP+

ethylbenzoylacetate + NADPH

? + NADP+

892% relative activity compared to acetophenone

-

?

methyl acetoacetate + NADPH

? + NADP+

-

is not a good substrate as ethyl acetoacetate

-

?

propiophenone + NADPH

? + NADP+

123% relative activity compared to acetophenone

-

?

propyl acetoacetate + NADPH

? + NADP+

-

as substrate it is limited to its weak solubility

-

?

additional information

?

-

26 entries

(3R)-3-hydroxyacyl-[acyl-carrier protein] + NADP+

3-oxoacyl-[acyl-carrier protein] + NADPH + H+

Pseudomonas putida

A5HIF6

beta-oxidation pathway

693287

-

?

3-oxoacyl-[acyl-carrier protein] + NADPH

(3R)-3-hydroxyacyl-[acyl-carrier protein] + NADP+

8 entries

3-oxoacyl-[acyl-carrier protein] + NADPH

3-hydroxyacyl-[acyl-carrier protein] + NADP+

Vibrio cholerae serotype O1

3-oxoacyl-[acyl-carrier protein] + NADPH + H+

(3R)-3-hydroxyacyl-[acyl-carrier protein] + NADP+

-

740630

-

?

a 3-oxoacyl-[acyl-carrier protein] + NADPH + H+

a (3R)-3-hydroxyacyl-[acyl-carrier protein] + NADP+

acetoacetyl-CoA + NADPH

3-hydroxybutyryl-CoA + NADP+

Streptococcus pneumoniae

-

667646

-

?

acetoacetyl-CoA + NADPH + H+

3-hydroxybutyryl-CoA + NADP+

beta-ketoacyl-[acyl-carrier protein] + NADPH

beta-hydroxyacyl-[acyl-carrier protein] + NADP+

beta-ketoacyl-[acyl-carrier protein] + NADPH + H+

beta-hydroxyacyl-[acyl-carrier protein] + NADP+

additional information

?

-

NADH

NADP+

NADPH

additional information

-

additional information

(E)-1-(4-methylpiperidin-1-yl)-3-phenylprop-2-en-1-one

80% residual activity

(E)-2-nitrophenyl cinnamate

-

(E)-3-phenoxybenzyl 3-(benzo[d][1,3]dioxol-5-yl)acrylate

61% residual activity

(E)-4-cyanophenyl 3-(benzo[d][1,3]dioxol-5-yl)acrylate

-

(E)-benzyl 3-(benzo[d][1,3]dioxol-5-yl)acrylate

71% residual activity

(E)-phenyl 3-(benzo[d][1,3]dioxol-5-yl)acrylate

69% residual activity

1,2,3,4,6-penta-O-galloyl-beta-D-glucose

4 entries

3-hydroxybutyryl-CoA

4-acetoxyanthecotulide

Plasmodium falciparum K1

-

most active linear sesquiterpene lactone from Anthemis auriculata against FabG

4-hydroxyanthecotulide

Plasmodium falciparum K1

-

linear sesquiterpene lactone from Anthemis auriculata

Acyl carrier protein

Lactococcus lactis

-

beta-ketobutyryl-CoA reductase activity of FabG1 is inhibited, activity of FabG2 is unaffected

654725

acyl-carrier protein

-

inhibition of wild-type with increasing concentrations

anthecotulide

Plasmodium falciparum K1

-

linear sesquiterpene lactone from Anthemis auriculata

bithionol

over 75% inhibition at 0.02 mM, IC50: 0.010 mM

bromochlorophen

an anthelmintic agent, over 75% inhibition at 0.02 mM, IC50: 0.0154 mM

chlorogenic acid

-

IC50: 0.881-0.948 mM

669013

di-resorcinol sulfide

over 75% inhibition at 0.02 mM, IC50: 0.0038 mM

DL-3-hydroxybutyryl-CoA

Streptococcus pneumoniae

-

competitive product inhibition

667646

epigallocatechin gallate

-

grape skin extract

Gallus gallus

-

inhibits the overall reaction and beta-ketoacyl reductase reaction of FAS with IC50 values of 4.61 microg/ml and 20.3 microg/ml, respectively. Inhibits the overall reaction of FAS competitively with acetyl-CoA, noncompetitively with malonyl-CoA and in a mixed manner with NADPH

735850

-

Guanidinium chloride

-

FabG is fully unfolded at 4 M, approximately 90% of the enzyme activity can be recovered on dialyzing the denaturant. In presence of NADPH, there is no stabilization of FabG in case of equilibrium unfolding with guanidinium chloride

706639

Hexachlorophene

an anthelmintic and antimicrobial agent, over 75% inhibition at 0.02 mM, IC50: 0.002 mM

kaempferol

synthetic construct

-

704843

N-(1,3-dioxoisoindolin-2-yl)-2-oxo-2H-chromene-3-carboxamide

69% residual activity

NADP+

p-chloromercuribenzoate

-

Phenylglyoxal

quercetin

resveratrol

-

inhibits the overall reaction and beta-ketoacyl reductase reaction of FAS with IC50 values of 11.1 microg/ml and 21.9 microg/ml, respectively. In 3 T3-L1 preadipocytes, resveratrol reduces lipid accumulation remarkably

735850

RNAi

Arabidopsis thaliana

-

suppresses KCR activity, which results in a reduction of cuticular wax load and affects very-long-chain fatty acid composition of sphingolipids, seed triacylglycerols, and root glycerolipids. RNAi-suppressed Arabidopsis KCR1 plants display fused vegetative and reproductive organs, an abnormal root morphology and have abnormal trichome and epidermal cell morphology

700827

-

Tannic acid

16 entries

Urea

-

FabG is fully unfolded at 6 M, approximately 90% of the enzyme activity can be recovered on dialyzing the denaturant. Two states in the reversible unfolding process of FabG in presence of NADPH, one is an activity-enhanced state and the other, an inactive state in case of equilibrium unfolding with urea

706639

additional information

26 entries

-

additional information

-

89.2

1,1,1-trifluoroacetone

with 4 mM NADPH, in 0.1 M sodium phosphate buffer, pH 7.0

5.72

2',3',4',5',6'-pentafluoroacetophenone

with 4 mM NADPH, in 0.1 M sodium phosphate buffer, pH 7.0

7.38

3'-fluoroacetophenone

with 4 mM NADPH, in 0.1 M sodium phosphate buffer, pH 7.0

14.34

4'-chloroacetophenone

with 4 mM NADPH, in 0.1 M sodium phosphate buffer, pH 7.0

12.29

4'-fluoroacetophenone

with 4 mM NADPH, in 0.1 M sodium phosphate buffer, pH 7.0

0.0057 - 2.2

acetoacetyl-CoA

22 entries

48

acetoacetyl-N-acetylcysteamine

-

0.003 - 0.017

acetoacetyl-[acyl-carrier protein]

5 entries

46.92

acetophenone

with 4 mM NADPH, in 0.1 M sodium phosphate buffer, pH 7.0

2.71

alpha-chloroacetophenone

with 4 mM NADPH, in 0.1 M sodium phosphate buffer, pH 7.0

0.29 - 4.06

beta-ketobutyryl-CoA

8.31

ethyl 4-chloroacetoacetate

with 4 mM NADPH, in 0.1 M sodium phosphate buffer, pH 7.0

0.127

ethyl acetoacetate

-

1.92

ethylbenzoylacetate

with 4 mM NADPH, in 0.1 M sodium phosphate buffer, pH 7.0

0.035

N-(2-sulfanylethyl)acetamide

Brassica napus

-

285673

0.29

NADP+

Pseudomonas aeruginosa

O54438

with 3-hydroxydecanoyl-N-acetylcysteamine as cosubstrate, pH and temperature not specified in the publication

739774

0.0093 - 0.617

NADPH

21 entries

6.03

propiophenone

with 4 mM NADPH, in 0.1 M sodium phosphate buffer, pH 7.0

additional information

7 entries

-

0.014 - 361

acetoacetyl-CoA

11 entries

0.3

ethyl acetoacetate

-

0.59 - 361

NADPH

15 entries

15200 - 26500

acetoacetyl-CoA

585 - 862

NADPH

0.0102

3-hydroxybutyryl-CoA

pH 6.8, 25°C, recombinant enzyme

additional information

-

0.45

(E)-2-nitrophenyl cinnamate

Escherichia coli

pH 7.0

0.18

(E)-4-cyanophenyl 3-(benzo[d][1,3]dioxol-5-yl)acrylate

Escherichia coli

pH 7.0

0.18

(E)-phenyl 3-(benzo[d][1,3]dioxol-5-yl)acrylate

Escherichia coli

pH 7.0

0.5

4-acetoxyanthecotulide

Plasmodium falciparum K1

-

pH 7.0, 25°C

0.75

4-hydroxyanthecotulide

Plasmodium falciparum K1

-

pH 7.0, 25°C

1

anthecotulide

Plasmodium falciparum K1

-

pH 7.0, 25°C

0.01

bithionol

Plasmodium falciparum

over 75% inhibition at 0.02 mM, IC50: 0.010 mM

0.0154

bromochlorophen

Plasmodium falciparum

an anthelmintic agent, over 75% inhibition at 0.02 mM, IC50: 0.0154 mM

0.881 - 0.948

chlorogenic acid

Escherichia coli

-

IC50: 0.881-0.948 mM

669013

0.0038

di-resorcinol sulfide

Plasmodium falciparum

over 75% inhibition at 0.02 mM, IC50: 0.0038 mM

0.00554 - 0.1223

epigallocatechin gallate

7 entries

0.002

Hexachlorophene

Plasmodium falciparum

an anthelmintic and antimicrobial agent, over 75% inhibition at 0.02 mM, IC50: 0.002 mM

0.0212

kaempferol

synthetic construct

-

pH 7.0

704843

0.215

N-(1,3-dioxoisoindolin-2-yl)-2-oxo-2H-chromene-3-carboxamide

Escherichia coli

pH 7.0

0.3048

quercetin

synthetic construct

-

pH 7.0

704843

0.00078

Tannic acid

Escherichia coli

-

706142

additional information

grape skin extract

-

0.0017 - 0.0018

-

recombinant refolded enzyme

670774

0.0019

-

recombinant soluble enzyme

0.0032

-

0.005

-

0.0132

-

0.0168

-

0.0189

-

0.0192

-

0.0197

-

0.02

with 2-octanone as substrate, 4 mM NADPH, in 0.1 M sodium phosphate buffer, pH 7.0

0.0366

-

0.06

mutant enzyme K173A, with acetoacetyl-CoA and NADH, pH 7.4 and 25°C

0.08

with 4'-fluoroacetophenone as substrate, 4 mM NADPH, in 0.1 M sodium phosphate buffer, pH 7.0

0.13

0.15

with 4'-chloroacetophenone as substrate, 4 mM NADPH, in 0.1 M sodium phosphate buffer, pH 7.0

0.16

with propiophenone as substrate, 4 mM NADPH, in 0.1 M sodium phosphate buffer, pH 7.0

0.44

0.46

mutant enzyme K152A, with 9,10-phenanthrene quinone and NADP+, pH 7.4 and 25°C

0.5

mutant enzyme Q126E/R168E/K169E, with acetoacetyl-CoA and NADPH, pH 7.4 and 25°C

0.65

mutant enzyme Y169A, with acetoacetyl-CoA and NADH, pH 7.4 and 25°C

0.85

mutant enzyme Y169A, with 9,10-phenanthrene quinone and NAD+, pH 7.4 and 25°C

1.03

with 1,1,1-trifluoroacetone as substrate, 4 mM NADPH, in 0.1 M sodium phosphate buffer, pH 7.0

1.16

with ethylbenzoylacetate as substrate, 4 mM NADPH, in 0.1 M sodium phosphate buffer, pH 7.0

1.2

mutant enzyme K173A, with 9,10-phenanthrene quinone and NAD+, pH 7.4 and 25°C

1.3

mutant enzyme K169E, with 9,10-phenanthrene quinone and NADP+, pH 7.4 and 25°C

1.6

mutant enzyme R168E, with 9,10-phenanthrene quinone and NADP+, pH 7.4 and 25°C

1.7

mutant enzyme Q126E/K169E, with 9,10-phenanthrene quinone and NADP+, pH 7.4 and 25°C

136000

Brassica napus

-

purified enzyme, protein determination by calculation from absorption at 280 nm

285673

14.8

mutant enzyme Q126E/R168E/K169E, with acetoacetyl-CoA and NADH, pH 7.4 and 25°C

15.7

mutant enzyme K169E, with 9,10-phenanthrene quinone and NAD+, pH 7.4 and 25°C

17.4

mutant enzyme Q126E/K169E, with 9,10-phenanthrene quinone and NAD+, pH 7.4 and 25°C

180400

Cuphea lanceolata

-

recombinant protein, cosubstrate NADPH, pH 7.0, phosphate buffer

285679

19.3

mutant enzyme K169E, with acetoacetyl-CoA and NADH, pH 7.4 and 25°C

2

2.4

mutant enzyme K173A, with acetoacetyl-CoA and NADPH, pH 7.4 and 25°C

2.45

with alpha-chloroacetophenone as substrate, 4 mM NADPH, in 0.1 M sodium phosphate buffer, pH 7.0

2.6

wild type enzyme, with 9,10-phenanthrene quinone and NADP+, pH 7.4 and 25°C

20

mutant enzyme D42A, with acetoacetyl-CoA and NADPH, pH 7.4 and 25°C

20.5

wild type enzyme, with acetoacetyl-CoA and NADH, pH 7.4 and 25°C

20.7

mutant enzyme R34A, with 9,10-phenanthrene quinone and NAD+, pH 7.4 and 25°C

20.8

wild type enzyme, with 9,10-phenanthrene quinone and NAD+, pH 7.4 and 25°C

21

mutant enzyme R34A, with acetoacetyl-CoA and NADH, pH 7.4 and 25°C

21.7

mutant enzyme R168E, with acetoacetyl-CoA and NADH, pH 7.4 and 25°C

22

mutant enzyme K152A, with acetoacetyl-CoA and NADH, pH 7.4 and 25°C

25.5

mutant enzyme K152A, with 9,10-phenanthrene quinone and NAD+, pH 7.4 and 25°C

280

-

acetoacetyl-N-acetylcysteamine

3

-

mutant R187A/R230A, acyl-carrier protein-dependent spectroscopic assay

3.1

mutant enzyme Y169A, with 9,10-phenanthrene quinone and NADP+, pH 7.4 and 25°C

3.5

wild type enzyme, with acetoacetyl-CoA and NADPH, pH 7.4 and 25°C

3.93

with 2',3',4',5',6'-pentafluoroacetophenone as substrate, 4 mM NADPH, in 0.1 M sodium phosphate buffer, pH 7.0

31.8

mutant enzyme Q126E/K169E, with acetoacetyl-CoA and NADH, pH 7.4 and 25°C

38.29

with ethyl 4-chloroacetoacetate as substrate, 4 mM NADPH, in 0.1 M sodium phosphate buffer, pH 7.0

3839

Cuphea lanceolata

-

recombinant protein, cosubstrate NADH, pH 7.0, phosphate buffer

285679

4

-

mutant R230E, acyl-carrier protein-dependent spectroscopic assay

4.3

mutant enzyme Q126E/K169E, with acetoacetyl-CoA and NADPH, pH 7.4 and 25°C

4.5

mutant enzyme K173A, with 9,10-phenanthrene quinone and NADP+, pH 7.4 and 25°C

42.6

-

mutant R187E/R230E, acyl-carrier protein-independent spectroscopic assay

45.6

-

mutant R187A/R230A, acyl-carrier protein-independent spectroscopic assay

450

-

acetoacetyl-CoA

4930

-

purified enzyme

285672

5.4

mutant enzyme D42A, with 9,10-phenanthrene quinone and NADP+, pH 7.4 and 25°C

5.5

mutant enzyme K169E, with acetoacetyl-CoA and NADPH, pH 7.4 and 25°C

530

-

acetoacteyl-ACP

54.2

-

mutant R230E, acyl-carrier protein-independent spectroscopic assay

54.5

-

mutant R187E, acyl-carrier protein-independent spectroscopic assay

55.3

-

mutant R230A, acyl-carrier protein-independent spectroscopic assay

57.9

-

mutant R187A, acyl-carrier protein-independent spectroscopic assay

59.8

6.1

-

mutant R230A, acyl-carrier protein-dependent spectroscopic assay

6.3

6.9

-

mutant R187A, acyl-carrier protein-dependent spectroscopic assay

7.3

mutant enzyme D42A, with acetoacetyl-CoA and NADH, pH 7.4 and 25°C

7.9

mutant enzyme R168E, with 9,10-phenanthrene quinone and NAD+, pH 7.4 and 25°C

7.95

Spinacia oleracea

-

285668

70.6

-

wild-type, acyl-carrier protein-dependent spectroscopic assay

74.6

mutant enzyme D42A, with 9,10-phenanthrene quinone and NAD+, pH 7.4 and 25°C

8.4

mutant enzyme Q126E/R168E/K169E, with 9,10-phenanthrene quinone and NAD+, pH 7.4 and 25°C

83140

Cuphea lanceolata

-

cosubstrate NADPH, pH 8.35, carbonate buffer

285679

9401

-

purified enzyme, protein determination by amino acid analysis

additional information

5.7 - 6.2

-

6 - 7

-

6.5

-

6.8

7

7.5