1.6.2.2 (+)-catechin - 2453 1.6.2.2 (+)-taxifolin - 33019 1.6.2.2 (-)-epicatechin - 1846 1.6.2.2 (5Z)-5-[(9H-fluoren-3-yl)methylidene]-1-(4-methylphenyl)-2-sulfanylidenedihydropyrimidine-4,6(1H,5H)-dione about 80% inhibition at 0.5 mM 219115 1.6.2.2 (5Z)-5-{[4-bromo-5-(morpholin-4-yl)furan-2-yl]methylidene}-1-(4-methylphenyl)-2-sulfanylidenedihydropyrimidine-4,6(1H,5H)-dione about 5% inhibition at 0.5 mM 219107 1.6.2.2 1,10-phenanthroline - 62 1.6.2.2 1-(2-fluorophenyl)-5-[(1-methyl-2,3-dihydro-1H-indol-3-yl)methyl]-2-sulfanylidenedihydropyrimidine-4,6(1H,5H)-dione about 75% inhibition at 0.5 mM 219097 1.6.2.2 2,2'-dipyridyl - 375 1.6.2.2 2-methyl-6-[(phenylsulfanyl)methyl]-2,5-dihydropyrimidin-4(3H)-one about 5% inhibition at 0.5 mM 219103 1.6.2.2 4-({[(2S)-2,3-dihydro-1,3-benzoxazol-2-yl]sulfanyl}methyl)tetrahydropyrimidine-2,5-dione about 45% inhibition at 0.5 mM 219127 1.6.2.2 5'-(p-fluorosulfonylbenzoyl)-adenosine - 91789 1.6.2.2 5-(prop-2-en-1-yl)-6-propyl-2-sulfanylidene-2,3-dihydropyrimidin-4(1H)-one about 75% inhibition at 0.5 mM 219121 1.6.2.2 5-propyl-2-thiouracil 25 mM, almost complete inhibition 108538 1.6.2.2 6-(pentyloxy)-2-sulfanylidene-2,3-dihydropyrimidin-4(1H)-one about 25% inhibition at 0.05 mM 219111 1.6.2.2 6-([[(2R)-2,3-dihydro-1,3-benzoxazol-2-yl]sulfanyl]methyl)-2-sulfanylidene-2,3-dihydropyrimidin-4(1H)-one complete inhibition at 0.05 mM 219125 1.6.2.2 6-benzyl-2-sulfanylidene-2,3-dihydropyrimidin-4(1H)-one about 3% inhibition at 0.5 mM 219109 1.6.2.2 6-pentyl-2-sulfanylidene-2,3-dihydropyrimidin-4(1H)-one about 25% inhibition at 0.5 mM 219117 1.6.2.2 6-Propyl-2-thiouracil about 20% residual activity at 0.009 mM 4773 1.6.2.2 6-[(phenylsulfanyl)methyl]-2-sulfanylidene-2,3-dihydropyrimidin-4(1H)-one complete inhibition at 0.05 mM 219101 1.6.2.2 6-[(phenylsulfanyl)methyl]pyrimidine-2,4(1H,3H)-dione about 50% inhibition at 0.5 mM 219119 1.6.2.2 6-{[(2,6-dichlorophenyl)sulfanyl]methyl}-2-sulfanylidene-2,3-dihydropyrimidin-4(1H)-one complete inhibition at 0.05 mM 219099 1.6.2.2 6-{[(4-bromophenyl)sulfanyl]methyl}-2-sulfanylidene-2,3-dihydropyrimidin-4(1H)-one about 10% inhibition at 0.05 mM 219113 1.6.2.2 6-{[(4-methylphenyl)sulfanyl]methyl}-2-sulfanylidene-2,3-dihydropyrimidin-4(1H)-one about 85% inhibition at 0.05 mM 219105 1.6.2.2 6-{[(propan-2-yl)sulfanyl]methyl}-2-sulfanylidene-2,3-dihydropyrimidin-4(1H)-one about 18% inhibition at 0.05 mM 219123 1.6.2.2 acetate - 47 1.6.2.2 Acrynol - 31002 1.6.2.2 Acrynol 0.1 mM, 75% inhibition 31002 1.6.2.2 Acrynol 0.1 mM, 88% inhibition 31002 1.6.2.2 adenine nucleotides - 16056 1.6.2.2 ADP - 13 1.6.2.2 ADP 5 mM, 66% inhibition 13 1.6.2.2 Amytal - 3064 1.6.2.2 apigenin - 515 1.6.2.2 apocynin 90.1% inhibition at 0.2 mM 1735 1.6.2.2 Atebrin - 2721 1.6.2.2 Atebrin 1 mM, complete inhibition 2721 1.6.2.2 Atebrin 0.5 mM, complete inhibition 2721 1.6.2.2 Atebrin 0.1 mM, 44% inhibition 2721 1.6.2.2 benzoate complete inhibition at 1 mM 316 1.6.2.2 benzyl alcohol 100 mM, 52% inhibition, reversible, may be due to changes in membrane fluidity 260 1.6.2.2 Br- competitive vs. cytochrome b5, reversible by dilution 332 1.6.2.2 Ca2+ 23.5% residual activity at 1 mM 15 1.6.2.2 CaCl2 8 mM, 50% inhibition, competitive vs. cytochrome b5 218 1.6.2.2 citrate - 131 1.6.2.2 Cl- - 141 1.6.2.2 Cl- competitive vs. cytochrome b5, reversible by dilution 141 1.6.2.2 dicoumarol - 754 1.6.2.2 dicoumarol 0.3 mM, 57% inhibition 754 1.6.2.2 dithiothreitol 80% residual activity at 1 mM 45 1.6.2.2 ebselen almost complete inhibition at 0.02 mM 2514 1.6.2.2 F- competitive vs. cytochrome b5, reversible by dilution 174 1.6.2.2 hemin - 822 1.6.2.2 Hg2+ - 33 1.6.2.2 I- competitive vs cytochrome b5, reversible by dilution 507 1.6.2.2 Inositol hexaphosphate - 12563 1.6.2.2 iodoacetamide 1 mM, complete inhibition 67 1.6.2.2 iodoacetamide 23.5% residual activity at 1 mM 67 1.6.2.2 iodoacetate 27.3% residual activity at 1 mM 93 1.6.2.2 iodoacetic acid 5 mM, complete inhibition 213 1.6.2.2 K+ high ionic strength reduction of cytochrome b5 or dichlorphenolindophenol 50055 1.6.2.2 K+ high ionic strength - 50055 1.6.2.2 luteolin - 436 1.6.2.2 luteolin-7-O-glucoside - 18642 1.6.2.2 Mepacrin - 98049 1.6.2.2 Mersalyl complete inhibition at 1.0 mM 1982 1.6.2.2 MgCl2 78.1 mM, 50% inhibition, competitive vs. cytochrome b5 196 1.6.2.2 additional information not inhibited by NAD+ and ferrocyanide 2 1.6.2.2 additional information high levels of H2O2 inhibit enzyme expression 2 1.6.2.2 additional information inhibitory potencies of flavonoids on the enzyme, structure-activity relationship, overview. No inhibition by naringenin, naringin, and chrysin. Flavonoids containing two hydroxyl groups in ring B and a carbonyl group at C-4 in combination with a double bond between C-2 and C-3 produced a much stronger inhibition, whereas substitution of a hydroxyl group at C-3 is associated with a less inhibitory effect 2 1.6.2.2 additional information species-specific sensitivity to methemoglobin induction, in vitro induction of methemoglobin by 1 mM NaNO2, overview 2 1.6.2.2 additional information enzyme inhibition by dietary flavonoids: inhibitor structure-activity analysis, overview. No inhibition by morin, apigenin, (+)-catechin, (-)-epicatechin, naringenin and naringin 2 1.6.2.2 additional information the enzyme is not inhibited by Mg2+, Mn2+, or EDTA 2 1.6.2.2 morin - 1145 1.6.2.2 myricetin - 484 1.6.2.2 myricetin noncompetitive versus NADH, non-linear relationship indicating non-Michaelis-Menten kinetic binding with respect to cytochrome b5 484 1.6.2.2 N-ethylmaleimide - 49 1.6.2.2 N-ethylmaleimide 10 mM, 89% inhibition 49 1.6.2.2 N-ethylmaleimide 8 mM, 70% inhibition 49 1.6.2.2 N-ethylmaleimide 1 mM, 90% inhibition 49 1.6.2.2 NaCN 91.4% residual activity at 1 mM 860 1.6.2.2 NAD+ competitive 7 1.6.2.2 NAD+ competitive, stronger inhibition of mutant enzymes compared to wild type enzyme 7 1.6.2.2 NADP+ - 10 1.6.2.2 nitric oxide - 662 1.6.2.2 p-chloromercuribenzoate - 43 1.6.2.2 p-chloromercuribenzoate 0.001 mM, complete inhibition 43 1.6.2.2 p-chloromercuribenzoate 0.005 mM, complete inhibition 43 1.6.2.2 p-chloromercuribenzoate complete inhibition at 0.4 mM 43 1.6.2.2 p-hydroxymercuribenzoate 0.1 mM, complete inhibition 98 1.6.2.2 p-hydroxymercuribenzoate 0.1 mM, almost complete inhibition 98 1.6.2.2 p-hydroxymercuribenzoate complete inhibition at 1 mM 98 1.6.2.2 para-chloromercuribenzenesulfonate - 125038 1.6.2.2 Pentachlorophenol - 1077 1.6.2.2 peroxynitrite - 1220 1.6.2.2 phosphate competitive inhibition 16 1.6.2.2 Phytohemagglutinin - 31273 1.6.2.2 Proflavin 0.1 mM, 86% inhibition 15932 1.6.2.2 Proflavin 0.1 mM, 74% inhibition 15932 1.6.2.2 Proflavin 0.1 mM, 98% inhibition 15932 1.6.2.2 propylthiouracil complete inhibition at 0.5 mM 5321 1.6.2.2 quercetin - 137 1.6.2.2 quercetin about 20% residual activity at 0.02 mM 137 1.6.2.2 quercitrin - 1936 1.6.2.2 rutin - 1095 1.6.2.2 succinate - 58 1.6.2.2 taurodeoxycholate - 1833 1.6.2.2 taurodeoxycholate 20 mM, 84% inhibition 1833 1.6.2.2 Thenoyltrifluoroacetone - 5619 1.6.2.2 Tris reduction of cytochrome b5 317 1.6.2.2 Wheat germ agglutinin - 46617 1.6.2.2 ZINC39395747 - 219124