Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
IUBMB CommentsA group of P-450 heme-thiolate proteins, acting on a wide range of substrates including many xenobiotics, steroids, fatty acids, vitamins and prostaglandins; reactions catalysed include hydroxylation, epoxidation, N-oxidation, sulfooxidation, N-, S- and O-dealkylations, desulfation, deamination, and reduction of azo, nitro and N-oxide groups. Together with EC 1.6.2.4, NADPH---hemoprotein reductase, it forms a system in which two reducing equivalents are supplied by NADPH. Some of the reactions attributed to EC 1.14.15.3, alkane 1-monooxygenase, belong here.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
6 beta-hydroxylase
-
-
-
-
6-beta-testosterone hydroxylase
-
-
-
-
7-alkoxycoumarin O-dealkylase
-
-
Aldehyde oxygenase
-
-
-
-
Arachidonic acid epoxygenase
-
-
-
-
aryl hydrocarbon hydroxylase
-
-
-
-
aryl-4-monooxygenase
-
-
-
-
Coumarin 7-hydroxylase
-
-
-
-
CYP6B1V1/CYP6B1V2/ CYP6B1V3
-
-
-
-
CYP6B3V1/CYP6B3V2
-
-
-
-
CYP6B4V1/CYP6B4V2
-
-
-
-
cytochrome P-450 4 enzyme
-
-
cytochrome P450 monooxygenase
-
-
Cytochrome P450-D2
-
-
-
-
cytochrome P450-dependent monooxygenase
-
-
Debrisoquine 4-hydroxylase
-
-
-
-
Estrogen synthetase
-
-
-
-
flavoprotein monooxygenase
-
-
-
-
flavoprotein-linked monooxygenase
-
-
-
-
Hepatic cytochrome P-450MC1
-
-
-
-
Laurate omega-1 hydroxylase
-
-
-
-
Lauric acid omega-6-hydroxylase
-
-
-
-
Mephenytoin 4-hydroxylase
-
-
-
-
microsomal monooxygenase
-
-
-
-
Ovarian aromatase
-
-
-
-
oxygenase, flavoprotein-linked mono-
-
-
-
-
P450 types B0 and B1
-
-
-
-
P450-PB1 and P450-PB2
-
-
-
-
Progesterone 21-hydroxylase
-
-
-
-
Prostaglandin omega-hydroxylase
-
-
-
-
S-mephenytoin 4-hydroxylase
-
-
-
-
sertraline N-demethylase
-
-
Steroid hormones 7-alpha-hydroxylase
-
-
-
-
Testosterone 15-alpha-hydroxylase
-
-
-
-
Testosterone 16-alpha hydroxylase
-
-
-
-
Testosterone 6-beta-hydroxylase
-
-
-
-
Testosterone 7-alpha-hydroxylase
-
-
-
-
xenobiotic monooxygenase
-
-
-
-
CYP1A1
-
-
-
-
CYP2E1
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
7-ethoxyresorufin + [reduced NADPH-hemoprotein reductase] + O2
?
-
-
-
?
okadaic acid + NADPH + O2
?
-
-
-
?
6beta-hydroxytestosterone + [reduced NADPH-hemoprotein reductase] + O2
?
-
-
-
?
7-ethoxycoumarin + [reduced NADPH-hemoprotein reductase] + O2
7-hydroxycoumarin + [oxidized NADPH-hemoprotein reductase] + H2O + ?
-
wild-type enzyme and recombinant enzyme CYP1A1 fused to yeast reductase and expressed in transgenic tobacco plants
-
-
?
7-ethoxycoumarin + [reduced NADPH-hemoprotein reductase] + O2
?
-
-
-
-
?
7-ethoxyresorufin + O2 + reduced donor
?
-
7-ethoxyresorufin O-deethylation
-
-
?
7-hydroxycoumarin + [reduced NADPH-hemoprotein reductase] + O2
?
-
-
-
-
?
7-methoxycoumarin + [reduced NADPH-hemoprotein reductase] + O2
?
-
-
-
-
?
7-propoxycoumarin + [reduced NADPH-hemoprotein reductase] + O2
?
-
-
-
-
?
adrenic acid + [reduced NADPH-hemoprotein reductase] + O2
?
-
i.e. all-cis-7,10,13,16-docosatetraenoic acid
-
-
?
arachidonic acid + O2 + NADPH
20-hydroxyeicosatetraenoic acid + H2O + NADP+
-
-
i.e. 20-HETE, a potent constrictor of renal microvessels and inhibits Na+ reabsorption in the proximal tubule and thick ascending limb, i.e.20-HETE
-
?
arachidonic acid + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxyeicosatetraenoic acid + 19-hydroxyeicosatetraenoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
ratio 12:1
-
?
aryl hydrocarbons + [reduced NADPH-hemoprotein reductase] + O2
?
-
prostaglandins
-
-
?
benzo-pyrene + [reduced NADPH-hemoprotein reductase] + O2
?
-
recombinant enzyme CYP1A1 fused to yeast reductase and expressed in transgenic tobacco plants
-
-
?
chlorotoluron + [reduced NADPH-hemoprotein reductase] + O2
?
-
a combination of oxidative N-demethylation and hydroxylation of the ring-methyl group, recombinant enzyme CYP1A1 fused to yeast reductase and expressed in transgenic tobacco plants
-
-
?
docosahexaenoic acid + [reduced NADPH-hemoprotein reductase] + O2
22-hydroxydocosahexaenoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
eicosapentaenoic acid + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxyeicosapentaenoic acid + 19-hydroxyeicosapentaenoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
ratio 4:3
-
?
linoleic acid + [reduced NADPH-hemoprotein reductase] + O2
(9Z,12Z)-18-hydroxyoctadeca-9,12-dienoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
-
-
?
okadaic acid + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase]
-
-
-
?
p-nitrophenol + [reduced NADPH-hemoprotein reductase] + O2
?
-
-
-
?
sertraline + [reduced NADPH-hemoprotein reductase] + O2
demethylsertraline + formaldehyde + [oxidized NADPH-hemoprotein reductase] + H2O
-
i.e. (1S,4S)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthylamine, a one-step oxidative N-demethylation
-
-
?
tolbutamide + [reduced NADPH-hemoprotein reductase] + O2
?
-
-
-
?
vandetanib + [reduced NADPH-hemoprotein reductase] + H+ + O2
N-desmethylvandetanib + [oxidized NADPH-hemoprotein reductase] + ?
-
-
-
?
additional information
?
-
additional information
?
-
-
no fluctuations between the light and dark periods under ad libitum and restricted feeding conditions, effects on P450 monooxygenase activities in male rats, overview
-
-
?
additional information
?
-
-
the cytochrome P-450 4, CYP4, family catalyze the omega-hydroxylation of fatty acids, metabolic regulation, overview, PPARalpha agonist increased the transcription activity of rat CYP4A1
-
-
?
additional information
?
-
-
the enzyme performs dealkylation of 7-alkoxycoumarin
-
-
?
additional information
?
-
-
CYP4A enzymes predominantly function as AA omega-hydroxylases, hydroxy metabolites are roduced by the individual CYP isoforms in a regio- and stereoselective manner. CYP isoforms that do not produce 20-hydroxyeicosatetraenoic acid but function predominantly as AA (omega-1)-hydroxylases include CYP1A1, but also act regioselective
-
-
?
additional information
?
-
-
the enzyme shows (omega-1)-hydroxylase activity against arachidonic acid, linoleic acid, and especially against eicosapentaenoic acid and docosahexaenoic acid, substrate specificities of isozymes, overview
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
7-ethoxycoumarin + [reduced NADPH-hemoprotein reductase] + O2
7-hydroxycoumarin + [oxidized NADPH-hemoprotein reductase] + H2O + ?
-
wild-type enzyme and recombinant enzyme CYP1A1 fused to yeast reductase and expressed in transgenic tobacco plants
-
-
?
arachidonic acid + O2 + NADPH
20-hydroxyeicosatetraenoic acid + H2O + NADP+
-
-
i.e. 20-HETE, a potent constrictor of renal microvessels and inhibits Na+ reabsorption in the proximal tubule and thick ascending limb
-
?
benzo-pyrene + [reduced NADPH-hemoprotein reductase] + O2
?
-
recombinant enzyme CYP1A1 fused to yeast reductase and expressed in transgenic tobacco plants
-
-
?
chlorotoluron + [reduced NADPH-hemoprotein reductase] + O2
?
-
a combination of oxidative N-demethylation and hydroxylation of the ring-methyl group, recombinant enzyme CYP1A1 fused to yeast reductase and expressed in transgenic tobacco plants
-
-
?
sertraline + [reduced NADPH-hemoprotein reductase] + O2
demethylsertraline + formaldehyde + [oxidized NADPH-hemoprotein reductase] + H2O
-
i.e. (1S,4S)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthylamine, a one-step oxidative N-demethylation
-
-
?
additional information
?
-
additional information
?
-
-
no fluctuations between the light and dark periods under ad libitum and restricted feeding conditions, effects on P450 monooxygenase activities in male rats, overview
-
-
?
additional information
?
-
-
the cytochrome P-450 4, CYP4, family catalyze the omega-hydroxylation of fatty acids, metabolic regulation, overview, PPARalpha agonist increased the transcription activity of rat CYP4A1
-
-
?
additional information
?
-
-
CYP4A enzymes predominantly function as AA omega-hydroxylases, hydroxy metabolites are roduced by the individual CYP isoforms in a regio- and stereoselective manner. CYP isoforms that do not produce 20-hydroxyeicosatetraenoic acid but function predominantly as AA (omega-1)-hydroxylases include CYP1A1, but also act regioselective
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Theoharides, A.D.; Kupfer, D.
Evidence for different hepatic microsomal monooxygenases catalyzing omega- and (omega-1)-hydroxylations of prostaglandins E1 and E2. Effects of inducers of monooxygenase on the kinetic constants of prostaglandin hydroxylation
J. Biol. Chem.
256
2168-2175
1981
Rattus norvegicus
brenda
Cashman, J.R.; Lattard, V.; Lin, J.
Effect of total parenteral nutrition and choline on hepatic flavin-containing and cytochrome P-450 monooxygenase activity in rats
Drug Metab. Dispos.
32
222-229
2004
Rattus norvegicus
brenda
Gorinova, N.; Nedkovska, M.; Atanassov, A.
Cytochrome P450 monooxygenase as a tool for metabolizing of herbicides in plants
Biotechnol. Biotechnol. Equip.
19
105-115
2005
Homo sapiens, Lolium rigidum, Nicotiana tabacum, Phelipanche ramosa, Rattus norvegicus, Solanum tuberosum, Sorghum sp., Triticum aestivum, Zea mays
-
brenda
Chan, P.K.; Lu, S.Y.; Liao, J.W.; Wei, C.F.; Tsai, Y.; Ueng, T.H.
Induction and inhibition of cytochrome P450-dependent monooxygenases of rats by fungicide bitertanol
Food Chem. Toxicol.
44
2047-2057
2006
Rattus norvegicus
brenda
Hirao, J.; Arakawa, S.; Watanabe, K.; Ito, K.; Furukawa, T.
Effects of restricted feeding on daily fluctuations of hepatic functions including P450 monooxygenase activities in rats
J. Biol. Chem.
281
3165-3171
2006
Rattus norvegicus
brenda
Ito, O.; Nakamura, Y.; Tan, L.; Ishizuka, T.; Sasaki, Y.; Minami, N.; Kanazawa, M.; Ito, S.; Sasano, H.; Kohzuki, M.
Expression of cytochrome P-450 4 enzymes in the kidney and liver: regulation by PPAR and species-difference between rat and human
Mol. Cell. Biochem.
284
141-148
2006
Homo sapiens, Rattus norvegicus
brenda
Pekthong, D.; Blanchard, N.; Abadie, C.; Bonet, A.; Heyd, B.; Mantion, G.; Berthelot, A.; Richert, L.; Martin, H.
Effects of Andrographis paniculata extract and Andrographolide on hepatic cytochrome P450 mRNA expression and monooxygenase activities after in vivo administration to rats and in vitro in rat and human hepatocyte cultures
Chem. Biol. Interact.
179
247-255
2009
Homo sapiens, Homo sapiens (P05177), Rattus norvegicus (P04799), Rattus norvegicus (P04800), Rattus norvegicus (P05182), Rattus norvegicus (P08683)
brenda
Acharya, P.; Engel, J.C.; Correia, M.A.
Hepatic CYP3A suppression by high concentrations of proteasomal inhibitors: a consequence of endoplasmic reticulum (ER) stress induction, activation of RNA-dependent protein kinase-like ER-bound eukaryotic initiation factor 2alpha (eIF2alpha)-kinase (PERK)
Mol. Pharmacol.
76
503-515
2009
Rattus norvegicus
brenda
Nayeem, M.A.; Zeldin, D.C.; Boegehold, M.A.; Morisseau, C.; Marowsky, A.; Ponnoth, D.S.; Roush, K.P.; Falck, J.R.
Modulation by salt intake of the vascular response mediated through adenosine A(2A) receptor: role of CYP epoxygenase and soluble epoxide hydrolase
Am. J. Physiol. Regul. Integr. Comp. Physiol.
299
R325-R333
2010
Homo sapiens, Mus musculus, Rattus norvegicus
brenda
Kobayashi, K.; Yamamoto, T.; Taguchi, M.; Chiba, K.
High-performance liquid chromatography determination of N- and O-demethylase activities of chemicals in human liver microsomes: application of postcolumn fluorescence derivatization using Nash reagent
Anal. Biochem.
284
342-347
2000
Homo sapiens, Rattus norvegicus
brenda
Kolrep, F.; Hessel, S.; These, A.; Ehlers, A.; Rein, K.; Lampen, A.
Differences in metabolism of the marine biotoxin okadaic acid by human and rat cytochrome P450 monooxygenases
Arch. Toxicol.
90
2025-2036
2016
Homo sapiens, Rattus norvegicus (P04799), Rattus norvegicus (P04800)
brenda
Indra, R.; Pompach, P.; Vavrova, K.; Jaklova, K.; Heger, Z.; Adam, V.; Eckschlager, T.; Kopeckova, K.; Arlt, V.A.; Stiborova, M.
Cytochrome P450 and flavin-containing monooxygenase enzymes are responsible for differential oxidation of the anti-thyroid-cancer drug vandetanib by human and rat hepatic microsomal systems
Environ. Toxicol. Pharmacol.
74
103310
2020
Rattus norvegicus (P08683)
brenda