CYP1ALPHA
CYP27B
CYP27B1
UniProt:O15528 CYP27B1
CYP1A1
UniProt:P04798 CYP1A1
CYP17
CYP17A1
S17AH
UniProt:P05093 CYP17A1
CYP11A
CYP11A1
UniProt:P05108 CYP11A1
CYP1A2
UniProt:P05177 CYP1A2
CYP21
CYP21A2
CYP21B
UniProt:P08686 CYP21A2
ARO1
CYAR
CYP19
CYP19A1
UniProt:P11511 CYP19A1
CYP5
CYP5A1
TBXAS1
UniProt:P24557 TBXAS1
CYP27
CYP27A1
UniProt:Q02318 CYP27A1
CYP24
CYP24A1
UniProt:Q07973 CYP24A1
CYP1B1
UniProt:Q16678 CYP1B1
CYP51
CYP51A1
UniProt:Q16850 CYP51A1
CYP2R1
UniProt:Q6VVX0 CYP2R1
CYP2U1
UniProt:Q7Z449 CYP2U1
CYP2S1
UniProt:Q96SQ9 CYP2S1
CYP3A43
UniProt:Q9HB55 CYP3A43
ACAS2
ACSS2
UniProt:Q9NR19 ACSS2
CYP26A2
CYP26B1
P450RAI2
UniProt:Q9NR63 CYP26B1
ACAS2L
ACSS1
KIAA1846
UniProt:Q9NUB1 ACSS1
C20orf16
SMO
SMOX
UniProt:Q9NWM0 SMOX
CYP39A1
UniProt:Q9NYL5 CYP39A1
CYP46
CYP46A1
UniProt:Q9Y6A2 CYP46A1
25-Hydroxylation of vitamin D3 in liver
Further hydroxylation of calcidiol in kidney to form calcitriol
20alpha,22beta-hydroxycholesterol + NADPH + H+ + O2 => pregnenolone + isocaproaldehyde + NADP+ + H2O
20alpha,22beta-hydroxycholesterol is cleaved by CYP11A1 to yield pregnenolone and isocaproaldehyde
Hydroxylation of pregnenolone to form 17alpha-hydroxypregnenolone
pregnenolone + NADPH + H+ => 17alpha-hydroxypregnenolone + NADP+ + H2O
11-deoxycortisol + NADPH + H+ + O2 => cortisol + NADP+ + H2O
11-deoxycortisol is oxidised to cortisol by CYP11B1
21-hydroxylation of progesterone to form 11-deoxycorticosterone
progesterone + NAPDH + H+ + O2 => 11-deoxycorticosterone + NADP+ + H2O
Androstenedione is converted to estrone by Aromatase (CYP19A1)
Oxidative deamination of 5-Hydroxytryptamine by MAOA
Lanosterol is oxidatively demethylated to 4,4-dimethylcholesta-8(9),14,24-trien-3beta-ol
lanosterol + 3 NADPH + 3 H+ + 3 O2 => 4,4-dimethylcholesta-8(9),14,24-trien-3beta-ol + 3 NADP+ + 4 H2O + formate
Cholesterol + NADPH + H+ + O2 => 7-alpha-hydroxycholesterol + NADP+ + H2O
Cholesterol is hydroxylated to 7alpha-hydroxycholesterol by CYP7A1
4-Cholesten-7alpha-ol-3-one is 12alpha-hydroxylated to 7-alpha,12-alpha-dihydroxycholest-4-en-3-one
7-alpha-hydroxycholest-4-en-3-one + NADPH + H+ + O2 => 7-alpha,12-alpha-dihydroxycholest-4-en-3-one + NADP+ + H2O
Cholesterol is hydroxylated to 24-hydroxycholesterol by CYP46A1
cholesterol + NADPH + H+ + O2 => 24-hydroxycholesterol + NADP+ + H2O
24-hydroxycholesterol + NADPH + H+ + O2 => cholest-5-ene-3beta,7alpha,24-triol + NADP+ + H2O
24-hydroxycholesterol is 7alpha-hydroxylated to yield cholest-5-ene-3beta,7alpha,24-triol
4-Cholesten-7alpha,24(S)-diol-3-one + NADPH + H+ + O2 => 4-cholesten-7-alpha,12-alpha,24(S)-triol-3-one + NADP+ + H2O
4-Cholesten-7alpha,24(S)-diol-3-one is 12alpha-hydroxylated to 4-cholesten-7-alpha,12-alpha,24(S)-triol-3-one
Cholesterol is hydroxylated to 27-hydroxycholesterol by CYP27
cholesterol + NADPH + H+ + O2 => 27-hydroxycholesterol + H2O + NADP+
4-Cholesten-7alpha,27-diol-3-one + NADPH + H+ + O2 => 4-Cholesten-7alpha,12alpha,27-triol-3-one + NADP+ + H2O
4-Cholesten-7alpha,27-diol-3-one is 12alpha-hydroxylated to 4-Cholesten-7alpha,12alpha,27-triol-3-one
25-hydroxycholesterol is 7alpha-hydroxylated by CYP7B1
Arachidonic acid is oxidised to PGG2 by PTGS1
Arachidonic acid oxidised to PGG2
PGG2 is reduced to PGH2 by PTGS1
Peroxidative reduction of PGG2 to PGH2
PGH2 is isomerised to PGI2 by PTGIS
Prostacyclin synthase (CYP8A1) mediates the isomerization of prostaglandin H2 to prostaglandin I2
PGH2 is isomerised to TXA2 by TBXAS1
Thromboxane synthase (CYP5A1) mediates the isomerization of prostaglandin H2 to thromboxane A2
CYP4F2 omega-hydroxylates leukotriene B4, thus inactivating it
LTB4 is hydroxylated to 20oh-LTB4 by CYP4F2/4F3
N-acetylspermidine is oxidized to putrescine
N-acetylspermine is oxidised to spermidine
Spermine is oxidized to spermidine
CYP1B1 4-hydroxylates estradiol-17beta
11-deoxycorticosterone is oxidised to corticosterone by CYP11B2
Ethylene is oxidized to Ethylene oxide by CYP1A1
Ethylene oxidized to Ethylene oxide
N-atom dealkylation of caffeine
N-hydroxylation of 4-aminobiphenyl
Coumarin is 7-hydroxylated by CYP2A6
Coumarin is 7-hydroxylated by CYP2A13
Cyclophosphamide is 4-hydroxylated by CYP2B6
CYP2C8 inactivates paclitaxel by 6alpha-hydroxylation
CYP2C9 inactivates tolbutamide by 4methyl-hydroxylation
CYP2C18 initiates bioactivation of phenytoin by 4-hydroxylation
CYP2C19 5-hydroxylates omeprazole
Acetaminophen oxidised to N-acetylbenzoquinoneimine (NAPQI)
Benzene + O2 + NADPH + H+ -> Phenol + H2O + NADP+
Benzene is hydroxylated to phenol
Dehalogenation of carbon tetrachloride to form a free radical
Dehalogenation of the haloalkane CCl4 to form CCl3. free radical
Dehalogenation of the poly-halogenated hydrocarbon Halothane to form the acylhalide Trifluoroacetlychloride and hydrogen bromide
MEOS oxidizes ethanol to acetaldehyde
Vinyl chloride is oxidized to 2-Chloroethylene oxide
O-atom dealkylation of dextromethorphan
CYP2D6 4-hydroxylates debrisoquine
CYP2F1 dehydrogenates 3-methylindole
CYP3A4 can N-demethylate loperamide
CYP3A5 oxidises aflatoxin B1 to aflatoxin-8,9-oxide
CYP3A7 can 6beta-hydroxylate testosterone
CYP2J2 epoxygenates arachidonic acid
CYP4A11 omega-hydroxylates laurate
dodecanoic acid + O2 + NADPH + H+ -> 12-hydroxydodecanoic acid + H2O + NADP+
CYP4B1 can 12-hydroxylate arachidonic acid
CYP4F12 hydroxylates arachidonic acid
CYP4F8 hydroxylates prostaglandin H2
CYP24A1 catalyzes the initial step in the deactivation of the hormonally active form of vitamin D3
CYP26A1 breaks down all-trans-retinoic acid by 4-hydroxylation
CYP26B1 also deactivates all-trans-retinoic acid by 4-hydroxylation
CYP26C1 deactivates 9-cis-retinoic acid by 4-hydroxylation
CYP2S1 can deactivate all-trans-retinoic acid
CYP2U1 can omega-hydroxylate arachidonate
CYP2W1 can oxidize indole
CYP3A43 catalyzes the 6beta-hydroxylation of testosterone
CYP4F11 omega-hydroxylates 3-hydroxypalmitate
FMO1 N-oxidizes the anti-cancer drug tamoxifen
FMO2 S-oxidizes the antithyroid drug methimazole
FMO3 N-oxidizes the tertiary amine trimethylamine
Trimethylamine N-oxidised to Trimethylamine-N-oxide
Dietary tyramine is oxidatively deaminated to an aldehyde by MAOB
Oxidative deamination of Phenyethylamine by MAOB
Ethanol is oxidized by NAD+ to form acetaldehyde, NADH, and H+
ethanol + NAD+ => acetaldehyde + NADH + H+
acetaldehyde [cytosolic] => acetaldehyde [mitochondrial]
acetaldehyde + NAD+ => acetate + NADH + H+ [mitochondrial]
acetate + CoA + ATP => acetyl-CoA + AMP + pyrophosphate [mitochondrial]
acetaldehyde + NAD+ => acetate + NADH + H+ [cytosolic]
acetate + CoA + ATP => acetyl-CoA + AMP + pyrophosphate [cytosolic]
Phase 1 - Functionalization of compounds
Cytochrome P450 - arranged by substrate type
Endogenous sterols
Sterols are 12-hydroxylated by CYP8B1
Xenobiotics
Aromatic amines can be N-hydroxylated or N-dealkylated by CYP1A2
CYP2E1 reactions
Fatty acids
Eicosanoids
Vitamins
Miscellaneous substrates
FMO oxidizes nucleophiles
COX reactions
Amine Oxidase reactions
Monoamines are oxidized to aldehydes by MAOA and MAOB, producing NH3 and H2O2
Polyamines are oxidized to amines, aldehydes and H2O2 by PAOs
Alcohol catabolism
Ethanol oxidation