2.3.1.85: fatty-acid synthase system
This is an abbreviated version!
For detailed information about fatty-acid synthase system, go to the full flat file.
Word Map on EC 2.3.1.85
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2.3.1.85
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mycobacterium
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tuberculosis
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mycolic
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lipogenic
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enoyl
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fasciclin
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cerulenin
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beta-ketoacyl-acyl
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malonyl-coa
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triclosan
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isoniazid
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transacylase
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enoyl-acyl
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beta-ketoacyl
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thiolactomycin
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malonyl-acp
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condensing
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acyl-acps
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malonyl
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srebp-1c
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fabgs
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medicine
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apicoplast
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boutons
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phosphopantetheinylation
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4'-phosphopantetheine
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ketoacyl
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antituberculous
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thiacetazone
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nutrition
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analysis
- 2.3.1.85
- mycobacterium
- tuberculosis
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mycolic
-
lipogenic
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enoyl
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fasciclin
- cerulenin
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beta-ketoacyl-acyl
- malonyl-coa
- triclosan
- isoniazid
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transacylase
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enoyl-acyl
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beta-ketoacyl
- thiolactomycin
- malonyl-acp
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condensing
- acyl-acps
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malonyl
- srebp-1c
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fabgs
- medicine
- apicoplast
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boutons
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phosphopantetheinylation
- 4'-phosphopantetheine
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ketoacyl
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antituberculous
- thiacetazone
- nutrition
- analysis
Reaction
Synonyms
F09E10.3 protein, FAS, FAS-II, FASI, FASII, FASN, fatty acid synthase, fatty acid synthase I, fatty acid synthase II, fatty acid synthase type 2, fatty-acid synthase, type 2 dissociative FAS, type 2 fatty acid synthase, type II fatty acid synthase, yeast fatty acid synthase
ECTree
2.3.1.85 fatty-acid synthase systemAdvanced search results
results (
results (Inhibitors
Inhibitors on EC 2.3.1.85 - fatty-acid synthase system
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INHIBITOR 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
IMAGE
(+)-catechin
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50% inhibition of overall enzyme reaction at 1.6 mM, 50% inhibition of ketoacyl reduction reaction at 7.4 mM
(-)-catechin gallate
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50% inhibition at 0.0015 mg/ml, B ring, C ring and gallate ring of inhibitor react with acyl transferase domain
(-)-epicatechin
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50% inhibition of overall enzyme reaction at 3.8 mM, 50% inhibition of ketoacyl reduction reaction at 9.38 mM
(-)-epicatechin gallate
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50% inhibition of overall enzyme reaction at 0.042 mM, 50% inhibition of ketoacyl reduction reaction at 0.068 mM, two-step inhibition mechanism with reversible initial inhibition and irreversible subsequent inactivation
(-)-epigallocatechin gallate
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0.5 mM, 20% residual activity, 50% inhibition of overall enzyme reaction at 0.052 mM, 50% inhibition of ketoacyl reduction reaction at 0.1 mM
(10E,12Z)-octadec-10,12-dienoic acid
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more potent inhibitor than (9Z,11E)-octadec-9,11-dienoic acid
1,1'-[methanediylbis(2,4,6-trihydroxy-5-methylbenzene-3,1-diyl)]dibutan-1-one
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IC50: 0.0254 mM
1,2,3,4,6-penta-O-galloyl-beta-D-glucose
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compound is transported across cancer cell membrane to further down-regulate FAS and activate caspase-3 in MDA-MB-231 cells. Compared with other FAS inhibitors, including catechin gallate and morin, 1,2,3,4,6-penta-O-galloyl-beta-D-glucose involves a higher reversible fast-binding inhibition with an irreversible slow-binding inhibition, i.e. saturation kinetics with a dissociation constant of 0.59 microM and a limiting rate constant of 0.16 per min. The major reacting site of PGG is on the beta-ketoacyl reduction domain of FAS. Compound exhibits different types of inhibitions against the three substrates in the FAS overall reaction
2,2'-methanediylbis(3,5-dihydroxy-4,4-dimethyl-6-propanoylcyclohexa-2,5-dien-1-one)
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IC50: 0.0602 mM
2,3-trans-octenoyl-CoA
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competitively inhibits malonyl-transferase reaction
2-(3-butanoyl-2,4,6-trihydroxy-5-methylbenzyl)-3,5-dihydroxy-4,4-dimethyl-6-propanoylcyclohexa-2,5-dien-1-one
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IC50: 0.0231 mM
2-acetyl-6-(3-butanoyl-2,4,6-trihydroxy-5-methylbenzyl)-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one
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IC50: 0.0287 mM
2-acetyl-6-(3-butanoyl-2,4,6-trihydroxybenzyl)-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one
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IC50: 0.0297 mM
2-acetyl-6-[(2,4-dihydroxy-3,3-dimethyl-6-oxo-5-propanoylcyclohexa-1,4-dien-1-yl)methyl]-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one
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IC50: 0.0717 mM
2-acetyl-6-{3-butanoyl-5-[(2,4-dihydroxy-3,3-dimethyl-6-oxo-5-propanoylcyclohexa-1,4-dien-1-yl)methyl]-2,4,6-trihydroxybenzyl}-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one
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IC50: 0.031 mM
2-butanoyl-6-(3-butanoyl-2,6-dihydroxy-4-methoxy-5-methylbenzyl)-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one
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IC50: 0.0326 mM
2-butanoyl-6-[(2,4-dihydroxy-3,3-dimethyl-6-oxo-5-propanoylcyclohexa-1,4-dien-1-yl)methyl]-3,5-dihydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one
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IC50: 0.0561 mM
2-[(Z)-[2-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]hydrazinylidene]methyl]pyridine
good inhibition activity against two enzyme overexpressing cancer cell lines. IC50 value for MDA-MB-468 cell 0.0083 mM, for SW-480 cell 0.0015 mM
3,4-dihydroxybenzoic acid
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50% inhibition of overall enzyme reaction at 9.0 mM, 50% inhibition of ketoacyl reduction reaction at 30 mM
3-hydroxynaphthalen-1-yl 3,4,5-trihydroxybenzoate
analog of (-)-epigallocatechin 3-gallate. Compound displays moderate to high cytotoxicity and significantly blocks FASN activity, diminishes FASN protein expression levels and induces apoptosis
4-hydroxynaphthalen-2-yl 3,4,5-trihydroxybenzoate
analog of (-)-epigallocatechin 3-gallate. Compound displays moderate to high cytotoxicity and significantly blocks FASN activity, diminishes FASN protein expression levels and induces apoptosis
adriamycin
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cytotoxic activity against cancer cells, IC50 value for MCF-7 cell 0.0035 mM, for A-549 cell 0.0018 mM, for HL-60 cell 0.0008 mM
catechin gallate
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very potent inhibitor, acts mainly on an acyl transferase domain. IC50 of 0.0015 mg/ml
catechol
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50% inhibition of overall enzyme reaction at 7.4 mM, 50% inhibition of ketoacyl reduction reaction at 21 mM
dutasteride
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at clinically relevant levels, inhibits FASN mRNA, protein expression and enzymatic activity in prostate cancer cells
gallic acid
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50% inhibition of overall enzyme reaction at 21 mM, 50% inhibition of ketoacyl reduction reaction at 26 mM
grape skin extract
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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
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N-ethylmaleimide
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inhibition of elongation process and malonyl transfer at 10 mM
naphthalene-1,3-diyl bis(3,4,5-trihydroxybenzoate)
analog of (-)-epigallocatechin 3-gallate. Compound displays moderate to high cytotoxicity and significantly blocks FASN activity, diminishes FASN protein expression levels
nordihydroguaiaretic acid
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inhibits competitively with respect to acetyl-CoA, noncompetitively with respect to malonyl-CoA, and in a mixed manner with respect toNADPH.IC50 = 0.093 mM
procyanidin
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procyanidins isolated from seeds of Hippophae rhamnoides inhibits the activity of FAS and reduces MDA-MB-231 cell viability with an IC50 value of 37.5 microg/ml. Procyanidins induce MDA-MB-231 cell apoptosis
propyl gallate
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50% inhibition of overall enzyme reaction at 0.5 mM, 50% inhibition of ketoacyl reduction reaction at 1.4 mM
propyl p-hydroxylbenzoate
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50% inhibition of overall enzyme reaction at 1.1 mM, 50% inhibition of ketoacyl reduction reaction at 2.6 mM
Zn2+
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80% loss of activity at 0.008 mM, interacts with SH groups, substrates of the reaction protect, malonyl-CoA being the most effective, addition of dithiothreitol leads to a recovery of 70% enzyme activity; below 0.004 mM, rapid and irreversible inactivation, above 0.004 mM, cross-linking of enzyme involving phosphopantheine SH group. All three substrates, acetyl-CoA, malonyl-CoA, NADPH, protect. Renaturation by dithiothreitol
[1,1'-biphenyl]-4,4'-diyl bis(3,4,5-trihydroxybenzoate)
analog of (-)-epigallocatechin 3-gallate. Compound displays moderate to high cytotoxicity and significantly blocks FASN activity
1,3-Dibromo-2-propanone
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acetyl-CoA, not malonyl-CoA, protects against inactivation, both protect against cross-linking of the subunits; covalently cross-links subunits, inactivates beta-ketoacyl synthetase- and overall-fatty acid synthase reaction
1,3-Dibromo-2-propanone
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acetyl-CoA, not malonyl-CoA, protects against inactivation, both protect against cross-linking of the subunits
C75
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0.05 mM, 90% reduction of enzyme activity, dramatic reduction of visible lipid droplet accumulation, reduction of enzyme mRNA
C75
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inactivation of beta-ketoacyl synthase, enoyl reductase and thioesterase partial activites, mechanism
C75
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i.e. 3-carboxy-4-octyl-2-methylenebutyrolactone, 50% inhibition of enzyme at 0.2 mM
cerulenin
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0.01 mM, 75% reduction of enzyme activity, dramatic reduction of visible lipid droplet accumulation, reduction of enzyme mRNA
ginkgolic acid C15:1
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DELTA8 and DELTA10 isomers, at ratio 1:2. Cytotoxic activity against cancer cells, IC50 value for MCF-7 cell 0.146 mM, for A-549 cell 0.066 mM, for HL-60 cell 0.005 mM
ginkgolic acid C17:1
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double bond positions not specified. Cytotoxic activity against cancer cells, IC50 value for MCF-7 cell 0.093 mM, for A-549 cell 0.050 mM, for HL-60 cell 0.004 mM
ginkgolic acid C17:2
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double bond positions not specified. Cytotoxic activity against cancer cells, IC50 value for MCF-7 cell 0.108 mM, for A-549 cell 0.056 mM, for HL-60 cell 0.004 mM
iodoacetamide
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beta-ketoacyl synthetase activity, acetyl-CoA but not malonyl-CoA protects
iodoacetamide
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beta-ketoacyl synthetase activity, acetyl-CoA but not malonyl-CoA protects
iodoacetamide
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beta-ketoacyl synthetase activity, acetyl-CoA but not malonyl-CoA protects
iodoacetamide
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kinetics, 50% inactivation after 5 min at 1 mM and after 0.5 min at 20 mM
iodoacetamide
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beta-ketoacyl synthetase activity, acetyl-CoA but not malonyl-CoA protects
iodoacetamide
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beta-ketoacyl synthetase activity, acetyl-CoA but not malonyl-CoA protects
iodoacetamide
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inhibits beta-ketoacyl synthetase activity, acetyl-CoA but not malonyl CoA protects
iodoacetamide
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beta-ketoacyl synthetase activity, acetyl-CoA but not malonyl-CoA protects
iodoacetamide
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beta-ketoacyl synthetase activity, acetyl-CoA but not malonyl-CoA protects
iodoacetamide
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beta-ketoacyl synthetase activity, acetyl-CoA but not malonyl-CoA protects
iodoacetamide
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beta-ketoacyl synthetase activity, acetyl-CoA but not malonyl-CoA protects
quercetin
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50% inhibition at 0.0024 mg/ml, mixed type inhibition for substrate NADPH, competitive with substrate acetyl-CoA, noncompetitive with malonyl-CoA
resveratrol
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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
S-(4-bromo-2,3-dioxobutyl)-CoA
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irreversible, acetyl transacetylase and beta-ketoacyl synthase activity, 4 mol inhibitor per mol enzyme complex, mechanism, dithiothreitol protects
S-(4-bromo-2,3-dioxobutyl)-CoA
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irreversible, 50% inhibition after 10 s at 0.02 mM, 6.5 s at 0.06 mM and 4.5 s at 0.09 mM, specific for acetyl transacetylase and beta-ketoacyl synthase activity, 4 mol inhibitor per mol enzyme complex, acetyl-CoA, malonyl-CoA, cysteine and pantetheine protect
triclosan
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0.05 mM, 70% reduction of enzyme activity, dramatic reduction of visible lipid droplet accumulation, reduction of enzyme mRNA
triclosan
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inititation of mammary carcinogenesis is reduced in animals fed with triclosan, triclosan also inhibits enzyme activity in tumor cell homogenates
Urea
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enzyme forms inactive aggregates in the presence of urea, cyclodextrins prevent aggregation
Urea
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non-competitive inhibitor for NADPH, competitive inhibitor for acetyl-CoA and malonyl-CoA, complete inactivation occurs at lower concentration than obvious conformational changes, aggregation occurs at 3-4 M
additional information
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the enzyme is potently inhibited by green tea extract
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additional information
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a common model is proposed that is possibly shared by all FAS polyphenol inhibitors. The model includes two almost planar aromatic rings with their respective hydroxyl groups, and a proper ester linkage between the two rings that possibly causes the inhibition of FAS by irreversibly inhibiting the beta-ketoacyl reductase domain
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additional information
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FAS is potently inhibited by extracts of Taxillus chinensis Danser. Potent, reversible and a fast irreversible inhibition. IC50: 480 ng/ml
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additional information
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inhibition by extract from rhizome of Alpinia officinarum, i.e. galangal. Inhibition consists of both reversible inhibition with an IC50-value of 0.0017 mg dried extract per ml, and biphasic slow-binding inactivation
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additional information
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black tea extract shows more potent inhibitory activity on fatty acid synthase than green tea extract. Inhibitory ability of the black tea extract depends on the extracting solvent and the conditions used. Only 1023% of the inhibitory activity from the black tea is extracted by the general method of boiling with water. The results suggest that the main fatty acid synthase inhibitors in black tea might be theaflavins
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