Literature summary for 1.14.18.1 extracted from

Oyama, T.; Yoshimori, A.; Takahashi, S.; Yamamoto, T.; Sato, A.; Kamiya, T.; Abe, H.; Abe, T.; Tanuma, S.I.
Structural insight into the active site of mushroom tyrosinase using phenylbenzoic acid derivatives (2017), Bioorg. Med. Chem. Lett., 27, 2868-2872 .

Search for more literature for 1.14.18.1

Inhibitors

Inhibitors	Comment	Organism	Structure
4'-hydroxy-[1,1'-biphenyl]-2-carboxylic acid	-	Agaricus bisporus
4'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid	-	Agaricus bisporus
4'-hydroxy-[1,1'-biphenyl]-4-carboxylic acid	binding mode, modeling	Agaricus bisporus
4'-methoxy-[1,1'-biphenyl]-2-carboxylic acid	-	Agaricus bisporus
4'-methoxy-[1,1'-biphenyl]-3-carboxylic acid	-	Agaricus bisporus
4'-methoxy-[1,1'-biphenyl]-4-carboxylic acid	binding mode, modeling	Agaricus bisporus
additional information	both 4'-hydroxylation and methoxylation of 4-phenylbenzoic acid increase the inhibitory activity of phenylbenzoic acid isomers against mushroom tyrosinase, molecular inhibition mechanism involving the copper ions of the enzyme, overview. Arg268 fixes the angle of the aromatic ring of Phe264, and Val248 and is supposed to interact with the inhibitors as a hydrophobic manner. 4'-Hydroxylation but not methoxylation of 2-phenylbenzoic acid appears inhibitory activity. The interactions of Asn260 and Phe264 in the active site with the adequate-angled biphenyl group are involved in the inhibitory activities of the modified phenylbenzoic acid isomers by parallel and T-shaped Pi-Pi interactions, respectively	Agaricus bisporus
[1,1''-biphenyl]-3-carboxylic acid	little availability of the carboxylic acid group in 2-phenylbenzooic acid to chelate with cupric ions in the active site	Agaricus bisporus
[1,1'-biphenyl]-2-carboxylic acid	-	Agaricus bisporus
[1,1'-biphenyl]-4-carboxylic acid	-	Agaricus bisporus

Metals/Ions

Metals/Ions	Comment	Organism	Structure
Cu2+	a copper-containing enzyme	Agaricus bisporus

Natural Substrates/ Products (Substrates)

Natural Substrates	Organism	Comment (Nat. Sub.)	Natural Products	Comment (Nat. Pro.)	Rev.	Reac.
2 L-dopa + O2	Agaricus bisporus	-	2 dopaquinone + 2 H2O	-	?
tyrosine + O2	Agaricus bisporus	-	dopaquinone + H2O	-	?

Organism

Organism	UniProt	Comment	Textmining
Agaricus bisporus	-	-	-

Source Tissue

Source Tissue	Comment	Organism	Textmining
commercial preparation	-	Agaricus bisporus	-

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
2 L-dopa + O2	-	Agaricus bisporus	2 dopaquinone + 2 H2O	-	?
tyrosine + O2	-	Agaricus bisporus	dopaquinone + H2O	-	?

Synonyms

Synonyms	Comment	Organism
mushroom tyrosinase	-	Agaricus bisporus

Temperature Optimum [°C]

Temperature Optimum [°C]	Temperature Optimum Maximum [°C]	Comment	Organism
30	-	assay at	Agaricus bisporus

pH Optimum

pH Optimum Minimum	pH Optimum Maximum	Comment	Organism
6.5	-	assay at	Agaricus bisporus

IC50 Value

IC50 Value	IC50 Value Maximum	Comment	Organism	Inhibitor	Structure
0.00697	-	pH 6.5, 30°C	Agaricus bisporus	[1,1''-biphenyl]-3-carboxylic acid
0.01059	-	pH 6.5, 30°C	Agaricus bisporus	4'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid
0.0147	-	pH 6.5, 30°C	Agaricus bisporus	4'-hydroxy-[1,1'-biphenyl]-4-carboxylic acid
0.0153	-	pH 6.5, 30°C	Agaricus bisporus	4'-methoxy-[1,1'-biphenyl]-3-carboxylic acid
0.0153	-	pH 6.5, 30°C	Agaricus bisporus	4'-methoxy-[1,1'-biphenyl]-4-carboxylic acid
0.06324	-	pH 6.5, 30°C	Agaricus bisporus	[1,1'-biphenyl]-4-carboxylic acid
0.1	-	above, pH 6.5, 30°C	Agaricus bisporus	[1,1'-biphenyl]-2-carboxylic acid
0.1	-	above, pH 6.5, 30°C	Agaricus bisporus	4'-methoxy-[1,1'-biphenyl]-2-carboxylic acid
0.1	-	pH 6.5, 30°C	Agaricus bisporus	4'-hydroxy-[1,1'-biphenyl]-2-carboxylic acid

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Release 2023.1 (January 2023)