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Literature summary 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 .
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.14.18.1 4'-hydroxy-[1,1'-biphenyl]-2-carboxylic acid
-
 Agaricus bisporus
1.14.18.1 4'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid
-
 Agaricus bisporus
1.14.18.1 4'-hydroxy-[1,1'-biphenyl]-4-carboxylic acid binding mode, modeling Agaricus bisporus
1.14.18.1 4'-methoxy-[1,1'-biphenyl]-2-carboxylic acid
-
 Agaricus bisporus
1.14.18.1 4'-methoxy-[1,1'-biphenyl]-3-carboxylic acid
-
 Agaricus bisporus
1.14.18.1 4'-methoxy-[1,1'-biphenyl]-4-carboxylic acid binding mode, modeling Agaricus bisporus
1.14.18.1 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
1.14.18.1 [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
1.14.18.1 [1,1'-biphenyl]-2-carboxylic acid
-
 Agaricus bisporus
1.14.18.1 [1,1'-biphenyl]-4-carboxylic acid
-
 Agaricus bisporus

Metals/Ions

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

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.18.1 2 L-dopa + O2 Agaricus bisporus
-
 2 dopaquinone + 2 H2O
-
 ?
1.14.18.1 tyrosine + O2 Agaricus bisporus
-
 dopaquinone + H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.14.18.1 Agaricus bisporus
-
-
-

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.14.18.1 commercial preparation
-
 Agaricus bisporus
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.18.1 2 L-dopa + O2
-
 Agaricus bisporus 2 dopaquinone + 2 H2O
-
 ?
1.14.18.1 tyrosine + O2
-
 Agaricus bisporus dopaquinone + H2O
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.18.1 mushroom tyrosinase
-
 Agaricus bisporus

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.14.18.1 30
-
 assay at Agaricus bisporus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.14.18.1 6.5
-
 assay at Agaricus bisporus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.14.18.1 0.00697
-
 pH 6.5, 30°C Agaricus bisporus [1,1''-biphenyl]-3-carboxylic acid
1.14.18.1 0.01059
-
 pH 6.5, 30°C Agaricus bisporus 4'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid
1.14.18.1 0.0147
-
 pH 6.5, 30°C Agaricus bisporus 4'-hydroxy-[1,1'-biphenyl]-4-carboxylic acid
1.14.18.1 0.0153
-
 pH 6.5, 30°C Agaricus bisporus 4'-methoxy-[1,1'-biphenyl]-3-carboxylic acid
1.14.18.1 0.0153
-
 pH 6.5, 30°C Agaricus bisporus 4'-methoxy-[1,1'-biphenyl]-4-carboxylic acid
1.14.18.1 0.06324
-
 pH 6.5, 30°C Agaricus bisporus [1,1'-biphenyl]-4-carboxylic acid
1.14.18.1 0.1
-
 above, pH 6.5, 30°C Agaricus bisporus [1,1'-biphenyl]-2-carboxylic acid
1.14.18.1 0.1
-
 above, pH 6.5, 30°C Agaricus bisporus 4'-methoxy-[1,1'-biphenyl]-2-carboxylic acid
1.14.18.1 0.1
-
 pH 6.5, 30°C Agaricus bisporus 4'-hydroxy-[1,1'-biphenyl]-2-carboxylic acid