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Literature summary extracted from

  • Brasil, E.M.; Canavieira, L.M.; Cardoso, E.T.C.; Silva, E.O.; Lameira, J.; Nascimento, J.L.M.; Eifler-Lima, V.L.; Macchi, B.M.; Sriram, D.; Bernhardt, P.V.; Silva, J.R.A.; Williams, C.M.; Alves, C.N.
    Inhibition of tyrosinase by 4H-chromene analogs Synthesis, kinetic studies, and computational analysis (2017), Chem. Biol. Drug Des., 90, 804-810 .
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.14.18.1 2-(chloromethyl)-10-(2-fluorophenyl)-7,7-dimethyl-6,7,8,10-tetrahydropyrano[3,2-b]chromene-4,9-dione
-
 Agaricus bisporus
1.14.18.1 2-(chloromethyl)-10-(4-fluorophenyl)-7,7-dimethyl-6,7,8,10-tetrahydropyrano[3,2-b]chromene-4,9-dione i.e. DHPC04, binding mode of R-DHPC04 and S-DHPC04 on the catalytic site of the enzyme, interactions between DHPC04 and residues His243 and Asn260 Agaricus bisporus
1.14.18.1 2-(hydroxymethyl)-7,7-dimethyl-10-phenyl-6,7,8,10-tetrahydropyrano[3,2-b]chromene-4,9-dione weak inhibition Agaricus bisporus
1.14.18.1 4-(2-(hydroxymethyl)-7,7-dimethyl-4,9-dioxo-4,6,7,8,9,10-hexahydropyrano[3,2-b]chromen-10-yl)benzonitrile
-
 Agaricus bisporus
1.14.18.1 kojic acid binding mode on the catalytic site of the enzyme Agaricus bisporus
1.14.18.1 additional information inhibition of tyrosinase by 4H-chromene analogues, synthesis, kinetic studies, and computational analysis, overview. Dihydropyrano[3,2-b] chromenediones (DHPCs), which are considered 4H-chromenes, are an important class of fused oxygenated heterocycles that are synthesized via a one-pot three-component reaction of kojic acid, an aldehyde and a 1,3-dione. Molecular docking and molecular modeling using the enzyme crystal structure, PDB ID 2Y9X, as template Agaricus bisporus
1.14.18.1 tropolone
-
 Agaricus bisporus

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
1.14.18.1 Cu2+ a binuclear copper enzyme. In the catalytic site of TYR, the bivalent copper ions are chelated by three individual histidine residues, overview Agaricus bisporus

Molecular Weight [Da]

EC Number Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
1.14.18.1 128000
-
-
 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 additional information Agaricus bisporus the enzyme catalyzes the oxidation of both monophenols (cresolase or monophenolase activity) and o-diphenols (catecholase or diphenolase activity) into reactive o-quinones ?
-
 ?
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 additional information the enzyme catalyzes the oxidation of both monophenols (cresolase or monophenolase activity) and o-diphenols (catecholase or diphenolase activity) into reactive o-quinones Agaricus bisporus ?
-
 ?
1.14.18.1 tyrosine + O2
-
 Agaricus bisporus dopaquinone + H2O
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.18.1 AbTYR
-
 Agaricus bisporus
1.14.18.1 mushroom tyrosinase
-
 Agaricus bisporus
1.14.18.1 tyr
-
 Agaricus bisporus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.14.18.1 7.2
-
 assay at Agaricus bisporus

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
1.14.18.1 additional information
-
 additional information inhibition kinetics Agaricus bisporus
1.14.18.1 0.005
-
 kojic acid pH 7.2, temperature not specified in the publication Agaricus bisporus
1.14.18.1 0.006
-
 4-(2-(hydroxymethyl)-7,7-dimethyl-4,9-dioxo-4,6,7,8,9,10-hexahydropyrano[3,2-b]chromen-10-yl)benzonitrile pH 7.2, temperature not specified in the publication Agaricus bisporus
1.14.18.1 0.009
-
 2-(chloromethyl)-10-(2-fluorophenyl)-7,7-dimethyl-6,7,8,10-tetrahydropyrano[3,2-b]chromene-4,9-dione pH 7.2, temperature not specified in the publication Agaricus bisporus
1.14.18.1 0.8
-
 tropolone pH 7.2, temperature not specified in the publication Agaricus bisporus
1.14.18.1 2.4
-
 2-(hydroxymethyl)-7,7-dimethyl-10-phenyl-6,7,8,10-tetrahydropyrano[3,2-b]chromene-4,9-dione pH 7.2, temperature not specified in the publication Agaricus bisporus

General Information

EC Number General Information Comment Organism
1.14.18.1 metabolism tyrosinase is a rate-limiting enzyme for controlling the production of melanin. The melanogenesis begins with the conversion of the amino acid L-tyrosine to L-3,4-dihydroxyphenylalanine (L-DOPA) catalyzed by tyrosinase (TYR). The regulation of the TYR activity is directly connected with melanin biosynthesis Agaricus bisporus