Literature summary for 5.1.99.4 extracted from

Carnell, A.J.; Hale, I.; Denis, S.; Wanders, R.J.; Isaacs, W.B.; Wilson, B.A.; Ferdinandusse, S.
Design, synthesis, and in vitro testing of alpha-methylacyl-CoA racemase inhibitors (2007), J. Med. Chem., 50, 2700-2707.

Search for more literature for 5.1.99.4

Application

Application	Comment	Organism
pharmacology	the enzyme is partially validated as a potential therapeutic target by siRNA knockdown of the AMACR gene, overview	Rattus norvegicus

Inhibitors

Inhibitors	Comment	Organism	Structure
(24S,25R)-(3R,7R,12R)-trihydroxy-24-fluoro-5beta-cholestan-26-oyl-CoA	competitive inhibition	Rattus norvegicus
(2R,3S)-3-fluoro-2-methylhexadecanoyl-CoA	competitive inhibition	Rattus norvegicus
(2S,3R)-3-fluoro-2-methylhexadecanoyl-CoA	competitive inhibition	Rattus norvegicus
(R)-ibuprofenoyl-CoA	competitive inhibition	Rattus norvegicus
(S)-ibuprofenoyl-CoA	competitive inhibition	Rattus norvegicus
2-difluoromethylpentadecanoyl-CoA	competitive inhibition	Rattus norvegicus
2-methylmyristoyl CoA	competitive inhibition	Rattus norvegicus
2-methyloctanoyl CoA	competitive inhibition	Rattus norvegicus
2-trifluoromethyltetradecanoic acid	competitive inhibition	Rattus norvegicus
2-trifluoromethyltetradecanoyl-CoA	competitive inhibition	Rattus norvegicus
alpha-trifluoromethyltetradecanoic acid	inhibits growth of cancer cell lines PC3, CWR22 Rv1, and Du145 in a dose-dependent manner due to AMACR inhibition	Rattus norvegicus
beta-fluorinated branched chain alpha-methylacyl coenzyme A esters analogues	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	Rattus norvegicus
additional information	design of mechanism-based irreversible inhibitors, 2-methylmyrist-2-enoyl CoA is not an inhibitor, mechanism, overview	Rattus norvegicus

Localization

Localization	Comment	Organism	GeneOntology No.	Textmining
mitochondrion	-	Rattus norvegicus	5739	-
peroxisome	-	Rattus norvegicus	5777	-

Natural Substrates/ Products (Substrates)

Natural Substrates	Organism	Comment (Nat. Sub.)	Natural Products	Comment (Nat. Pro.)	Rev.	Reac.
(2S)-2-methylacyl-CoA	Rattus norvegicus	natural substrates are branched chain alpha-methylacyl coenzyme A esters	(2R)-2-methylacyl-CoA	-	?

Organism

Organism	UniProt	Comment	Textmining
Rattus norvegicus	-	-	-

Source Tissue

Source Tissue	Comment	Organism	Textmining
liver	-	Rattus norvegicus	-

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
(25S)-trihydroxycoprostanoyl-CoA	-	Rattus norvegicus	(25R)-trihydroxycoprostanoyl-CoA	-	?
(2S)-2-methylacyl-CoA	-	Rattus norvegicus	(2R)-2-methylacyl-CoA	-	?
(2S)-2-methylacyl-CoA	natural substrates are branched chain alpha-methylacyl coenzyme A esters	Rattus norvegicus	(2R)-2-methylacyl-CoA	-	?
(S)-Pristanoyl-CoA	-	Rattus norvegicus	(R)-Pristanoyl-CoA	-	?

Synonyms

Synonyms	Comment	Organism
alpha-methylacyl-CoA racemase	-	Rattus norvegicus
AMACR	-	Rattus norvegicus

Temperature Optimum [°C]

Temperature Optimum [°C]	Temperature Optimum Maximum [°C]	Comment	Organism
37	-	assay at	Rattus norvegicus

pH Optimum

pH Optimum Minimum	pH Optimum Maximum	Comment	Organism
7	-	assay at	Rattus norvegicus

Ki Value [mM]

Ki Value [mM]	Ki Value maximum [mM]	Inhibitor	Comment	Organism	Structure
additional information	-	additional information	inhibition kinetics	Rattus norvegicus
0.0009	-	2-trifluoromethyltetradecanoyl-CoA	pH 7.0, 37°C	Rattus norvegicus
0.0013	-	(2R,3S)-3-fluoro-2-methylhexadecanoyl-CoA	pH 7.0, 37°C	Rattus norvegicus
0.0023	-	(2S,3R)-3-fluoro-2-methylhexadecanoyl-CoA	pH 7.0, 37°C	Rattus norvegicus
0.0038	-	(24S,25R)-(3R,7R,12R)-trihydroxy-24-fluoro-5beta-cholestan-26-oyl-CoA	pH 7.0, 37°C	Rattus norvegicus
0.0054	-	(R)-ibuprofenoyl-CoA	pH 7.0, 37°C	Rattus norvegicus
0.0192	-	(S)-ibuprofenoyl-CoA	pH 7.0, 37°C	Rattus norvegicus
0.02	-	2-difluoromethylpentadecanoyl-CoA	pH 7.0, 37°C	Rattus norvegicus
0.045	-	2-methyloctanoyl CoA	pH 7.0, 37°C	Rattus norvegicus
0.137	-	2-methylmyristoyl CoA	pH 7.0, 37°C	Rattus norvegicus

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Release 2023.1 (January 2023)