5.1.99.4: alpha-methylacyl-CoA racemase
This is an abbreviated version!
For detailed information about alpha-methylacyl-CoA racemase, go to the full flat file.
Word Map on EC 5.1.99.4
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5.1.99.4
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prostate
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adenocarcinoma
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papillary
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cytokeratins
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high-grade
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gleason
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prostatectomy
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neoplasia
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needle
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clinicopathologic
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vimentin
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intraepithelial
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prostate-specific
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eosinophilic
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urothelial
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acinar
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pathologist
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immunophenotype
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34betae12
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hgpin
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chromophobe
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atypia
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pristanic
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oncocytic
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suspicious
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oncocytomas
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transurethral
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nucleoli
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drug development
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tmprss2-erg
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metanephric
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fuhrman
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immunomarkers
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chrcc
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cribriform
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analysis
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nephrogenic
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medicine
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psammoma
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pharmacology
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sarcomatoid
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hobnail
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tubulocystic
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immunoprofile
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adenosis
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phytanic
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diagnostics
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tubulopapillary
- 5.1.99.4
- prostate
- adenocarcinoma
-
papillary
-
cytokeratins
-
high-grade
-
gleason
-
prostatectomy
- neoplasia
-
needle
-
clinicopathologic
- vimentin
-
intraepithelial
-
prostate-specific
-
eosinophilic
-
urothelial
-
acinar
-
pathologist
-
immunophenotype
-
34betae12
-
hgpin
-
chromophobe
-
atypia
-
pristanic
-
oncocytic
-
suspicious
- oncocytomas
-
transurethral
-
nucleoli
- drug development
-
tmprss2-erg
-
metanephric
-
fuhrman
-
immunomarkers
-
chrcc
-
cribriform
- analysis
-
nephrogenic
- medicine
-
psammoma
- pharmacology
-
sarcomatoid
-
hobnail
-
tubulocystic
-
immunoprofile
-
adenosis
-
phytanic
- diagnostics
-
tubulopapillary
Reaction
Synonyms
2-arylpropionyl-CoA epimerase, 2-methylacyl-CoA racemase, alpha-methyl CoA racemase, alpha-Methylacyl CoA racemase, alpha-methylacyl coenzyme A racemase, alpha-methylacyl-CoA racemase, alpha-methylacyl-CoA racemase 1A, alpha-methylacyl-coenzyme A racemase, AMACR, AMACR 1A, AMACR IA, amacr/P504S, GenBank U89905-derived protein GI2145184, GenBank U89906-derived protein GI 2145186, ibuprofenoyl-CoA epimerase, MCR, P504S, Racemase, alpha-methylacyl coenzyme A, Racemase, alpha-methylacyl coenzyme A (Mus musculus clone 3), Racemase, alpha-methylacyl coenzyme A (Rattus norvegicus clone 11)
ECTree
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Inhibitors
Inhibitors on EC 5.1.99.4 - alpha-methylacyl-CoA racemase
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(24S,25R)-(3R,7R,12R)-trihydroxy-24-fluoro-5beta-cholestan-26-oyl-CoA
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competitive inhibition
(25-R,S)-3,7,12-trihydroxycoprostanoic acid
competitive inhibition
5,5'-dithiobis(2-nitrobenzoate)
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inhibition is reversed by incubation of the inactivated enzyme with 10 mM dithiothreitol
alpha-trifluoromethyltetradecanoic acid
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inhibits growth of cancer cell lines PC3, CWR22 Rv1, and Du145 in a dose-dependent manner due to AMACR inhibition
beta-fluorinated branched chain alpha-methylacyl coenzyme A esters analogues
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reversible competitive inhibitors, presence of beta-fluorine on the alpha-methyl group or the acyl chain results in a significant lowering of the Ki value compared with nonfluorinated analogs, and this is attributed to a lowering of the pKa of the alpha-proton, facilitating enolization and binding, competitive
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decanoyl-CoA
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non-competitive substrate inhibition at higher substrate concentrations
Ibuprofen
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chemopreventive effects of ibuprofen on prostate cancer risk, which may be enhanced by AMACR genetic variants
octyl-beta-D-glucopyranoside
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concentrations greater than 0.6% octyl-beta-D-glucopyranoside cause a reduction in enzyme activity
2-(4-Isobutylphenyl)propionic acid
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i.e. ibuprofen, strongest of all competitive inhibitors tested
additional information
enzyme-bound enolate mimic inhibitor design and synthesis, overview
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additional information
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enzyme-bound enolate mimic inhibitor design and synthesis, overview
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additional information
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N,N-dialkylcarbamoyl-CoA substrate-product analogues inactivate MCR. Binding exceeds that of the substrate, (S)-ibuprofenoyl-CoA, up to 250fold and is proportional to the alkyl chain length (4-12 carbons). The presence of two decyl chains enhances binding over a single decyl chain by 204fold
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additional information
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design of mechanism-based irreversible inhibitors, 2-methylmyrist-2-enoyl CoA is not an inhibitor, mechanism, overview
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