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1.14.14.1: unspecific monooxygenase

This is an abbreviated version!
For detailed information about unspecific monooxygenase, go to the full flat file.

Word Map on EC 1.14.14.1

Reaction

RH
+
[reduced NADPH-hemoprotein reductase]
+
O2
=
ROH
+
[oxidized NADPH-hemoprotein reductase]
+
H2O

Synonyms

3AH15, 6 beta-hydroxylase, 6-beta-testosterone hydroxylase, 7-alkoxycoumarin O-dealkylase, 7-ethoxycoumarin-O-deethylase, 7-ethoxyresorufin-O-deethylase, AA omega-hydroxylase, Aldehyde oxygenase, Arachidonic acid epoxygenase, aromatase, aryl hydrocarbon hydroxylase, aryl-4-monooxygenase, BG04_163, BM3, BPH, Brain aromatase, class IV cytochrome P450 monooxygenase, clavine oxidase, CLOA, Clone PF26, Clone PF3/46, Coumarin 7-hydroxylase, CP2D6, Cyp, CYP monooxygenase, CYP102, CYP102 monooxygenase, CYP1027H1, CYP102A1, CYP102A2, CYP102A3, CYP102A7, CYP102B1, CYP106, CYP107, CYP1074A2, CYP109, CYP116B3, CYP116B4, CYP116B46, CYP134, CYP150A20, CYP152, CYP154H1, CYP19, CYP197, CYP1A, CYP1A1, CYP1A2, CYP1A3, CYP1B1, CYP24A1, CYP27A1, CYP28A5, CYP2A3, CYP2A6, CYP2B, CYP2B4, CYP2B6, CYP2C11, CYP2C19, CYP2C8, CYP2C9, CYP2D6, CYP2E1, CYP305A1, CYP3A, CYP3A1, CYP3A4, CYP3A5, CYP3A7, CYP4, CYP4502F4, CYP4A, CYP4A4, CYP4A6, CYP4A7, CYP4AA1, CYP4E2, CYP4F, CYP4F2, CYP4F3A, CYP4F3B, CYP5035A2, CYP5035A3, CYP5035A5, CYP5035C1, CYP5036A1, CYP5036A3, CYP5037B2, CYP505D1, CYP505D2, CYP505D3, CYP505D4, CYP51, CYP512B5, CYP512H1, CYP5136A2, CYP5136A3, CYP5136A5, CYP5139A1, CYP5141A1, CYP5141D1, CYP5142A3, CYP5142C1, CYP5144A3, CYP5144A7, CYP5144A9, CYP5144C7, CYP5144D4, CYP5145A3, CYP5147A1, CYP5150B1, CYP53A15, CYP53C2, CYP53D2, CYP5A1, CYP63A2, CYP6B1, CYP6B1v1, CYP6B1V1/CYP6B1V2/ CYP6B1V3, CYP6B3V1/CYP6B3V2, CYP6B4V1/CYP6B4V2, CYP6B5V1, CYP714D1, CYP82E2, CYP82E3, CYP82E4v1, CYP82E4v2, CYP8A1, CYP9F2, CYPIA1, CYPIA2, CYPIA4, CYPIA5, CYPIB1, CYPIIA1, CYPIIA10, CYPIIA11, CYPIIA12, CYPIIA13, CYPIIA2, CYPIIA3, CYPIIA4, CYPIIA5, CYPIIA6, CYPIIA7, CYPIIA8, CYPIIA9, CYPIIB1, CYPIIB10, CYPIIB11, CYPIIB12, CYPIIB19, CYPIIB2, CYPIIB20, CYPIIB3, CYPIIB4, CYPIIB5, CYPIIB6, CYPIIB9, CYPIIC1, CYPIIC10, CYPIIC11, CYPIIC12, CYPIIC13, CYPIIC14, CYPIIC15, CYPIIC16, CYPIIC17, CYPIIC18, CYPIIC19, CYPIIC2, CYPIIC20, CYPIIC21, CYPIIC22, CYPIIC23, CYPIIC24, CYPIIC25, CYPIIC26, CYPIIC27, CYPIIC28, CYPIIC29, CYPIIC3, CYPIIC30, CYPIIC31, CYPIIC37, CYPIIC38, CYPIIC39, CYPIIC4, CYPIIC40, CYPIIC41, CYPIIC42, CYPIIC5, CYPIIC6, CYPIIC7, CYPIIC8, CYPIIC9, CYPIID1, CYPIID10, CYPIID11, CYPIID14, CYPIID15, CYPIID16, CYPIID17, CYPIID18, CYPIID19, CYPIID2, CYPIID3, CYPIID4, CYPIID5, CYPIID6, CYPIID9, CYPIIE1, CYPIIF1, CYPIIF3, CYPIIF4, CYPIIG1, CYPIIH1, CYPIIH2, CYPIIIA1, CYPIIIA10, CYPIIIA11, CYPIIIA12, CYPIIIA13, CYPIIIA14, CYPIIIA15, CYPIIIA16, CYPIIIA17, CYPIIIA18, CYPIIIA19, CYPIIIA2, CYPIIIA21, CYPIIIA24, CYPIIIA25, CYPIIIA27, CYPIIIA28, CYPIIIA29, CYPIIIA3, CYPIIIA30, CYPIIIA31, CYPIIIA5, CYPIIIA6, CYPIIIA7, CYPIIIA8, CYPIIIA9, CYPIIJ1, CYPIIJ2, CYPIIJ3, CYPIIJ5, CYPIIJ6, CYPIIK1, CYPIIK3, CYPIIK4, CYPIIL1, CYPIIM1, CYPIVA4, CYPIVA8, CYPIVB1, CYPIVC1, CYPIVF1, CYPIVF11, CYPIVF12, CYPIVF4, CYPIVF5, CYPIVF6, CYPIVF8, CYPVIA1, CYPVIB1, CYPVIB2, CYPVIB4, CYPVIB5, CYPVIB6, CYPVIB7, CYPXIX, CYPXIXA1, CYPXIXA2, CYPXIXA3, Cyt P450, cytochrome P-450 4 enzyme, cytochrome P-450 BM3, cytochrome P-450 monooxygenase, cytochrome P450 2B4, cytochrome P450 3A, cytochrome P450 3A4, cytochrome P450 aromatase, cytochrome P450 BM3, cytochrome P450 monooxygenase, cytochrome P450 monooxygenase 116B3, cytochrome P450 monooxygenase 2A6, cytochrome P450 monooxygenase 2C8, cytochrome P450 monooxygenase 2C9, cytochrome P450 monooxygenase 3A4, cytochrome P450 monooxygenase pc-2, cytochrome P450 monooxygenase pc-4, cytochrome P450 monooxygenase pc-5, cytochrome P450 monooxygenase pc-6, cytochrome P450 monooxygenase PC-foxy1, cytochrome P450 oxidoreductase, cytochrome P450 reductase, Cytochrome P450-D2, cytochrome P450-dependent monooxygenase, cytochrome P450-dependent monooxygenase 1A2, cytochrome P450-monooxygenase, cytochrome-P450 hydroxylase, DAH1, DAH2, Debrisoquine 4-hydroxylase, EC 1.14.1.1, EC 1.14.14.2, EC 1.14.99.8, EC 1.99.1.1, ECOD, Ema, EROD, Estrogen synthetase, EUI, fatty acid hydroxylase, flavocytochrome P450BM-3, flavoprotein monooxygenase, flavoprotein-linked monooxygenase, FMO3, FraEuI1c_1415, FraEuI1c_2494, FraEuI1c_5334, GA 16a,17-epoxidase, GA-deactivating enzyme, Hepatic cytochrome P-450MC1, HLp, HMPREF1624_01477, IIA3, Isozyme 3A, Laurate omega-1 hydroxylase, Lauric acid omega-6-hydroxylase, liver cytochrome P450-dependent monooxygenase, LMC1, Mephenytoin 4-hydroxylase, MFO, microsomal monooxygenase, microsomal P-450, mixed function oxygenase, monooxygenase 3, monooxygenase P450 BM-3, More, N-demethylase, nicotine oxidase, O-demethylase, OLF2, Olfactive, Os05g0482400 protein, Ovarian aromatase, oxygenase, flavoprotein-linked mono-, P(3)450, P-448, P-450 PHPAH1, P-450(M-1), P-450-MK2, P-450AROM, P-450IB, P-450IIIAM1, P-450MC, P-450MP, P-450UT, P1-88, P24, P450, P450 17-alpha, P450 19A1, P450 1A1, P450 1A2, P450 1B1, P450 2A6, P450 2B6, P450 2C19, P450 2C9, P450 2D-29/2D-35, P450 2D6, P450 2E1, P450 2J2, P450 3A4, P450 4A11, P450 4F2, P450 BM3, P450 CM3A-10, P450 DUT2, P450 FA, P450 FI, P450 form 3B, P450 form HP1, P450 HSM1, P450 HSM2, P450 HSM3, P450 HSM4, P450 IIB1, P450 IIC2, P450 LM4, P450 LM6, P450 LMC2, P450 MD, P450 monooxygenase, P450 MP-12/MP-20, P450 P49, P450 PB1, P450 PB4, P450 PBC1, P450 PBC2, P450 PBC3, P450 PBC4, P450 PCHP3, P450 PCHP7, P450 TCDDAA, P450 TCDDAHH, P450 type B2, P450 types B0 and B1, P450(I), P450-11A, P450-15-alpha, P450-15-COH, P450-16-alpha, P450-254C, P450-3C, P450-6B/29C, P450-A3, P450-AFB, P450-ALC, P450-BM3, P450-CMF1A, P450-CMF1B, P450-CMF2, P450-CMF3, P450-DB1, P450-DB2, P450-DB3, P450-DB4, P450-DB5, P450-HFLA, P450-HP, P450-IIA10, P450-IIA11, P450-IIA3.1, P450-IIA3.2, P450-IIA4, P450-KP1, P450-LM2, P450-MC1, P450-MC4, P450-MK1, P450-MKJ1, P450-MKMP13, P450-MKNF2, P450-NMB, P450-OLF1, P450-OLF3, P450-P1, P450-P2/P450-P3, P450-P3, P450-PB1 and P450-PB2, P450-PCN1, P450-PCN2, P450-PCN3, P450-PM4, P450-PP1, P450-PROS2, P4501A1, P450arom, P450cam, P450CB, P450CMEF, P450E, P450EF, P450F, P450H, P450I, P450IIC5, P450MT2, P450RAP, P450RLM6, P450s 3A, P450SMO, P52, PB15, PHP2, PHP3, PikC, PikC hydroxylase, Progesterone 21-hydroxylase, Prostaglandin omega-hydroxylase, PTF1, PTF2, S-mephenytoin 4-hydroxylase, Sam5, sertraline N-demethylase, SIAM614_30676, Steroid hormones 7-alpha-hydroxylase, Testosterone 15-alpha-hydroxylase, Testosterone 16-alpha hydroxylase, Testosterone 6-beta-hydroxylase, Testosterone 7-alpha-hydroxylase, xenobiotic monooxygenase

ECTree

     1 Oxidoreductases
         1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
             1.14.14 With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
                1.14.14.1 unspecific monooxygenase

Substrates Products

Substrates Products on EC 1.14.14.1 - unspecific monooxygenase

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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-camphor + [reduced NADPH-hemoprotein reductase] + O2
(+)-exo-5-hydroxycamphor + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
(-)-alpha-pinene + [reduced NADPH-hemoprotein reductase] + O2
myrtenol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(-)-alpha-pinene + [reduced NADPH-hemoprotein reductase] + O2
pinene oxide + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(-)-alpha-pinene + [reduced NADPH-hemoprotein reductase] + O2
verbenol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(-)-beta-pinene + [reduced NADPH-hemoprotein reductase] + O2
myrtanal + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(-)-beta-pinene + [reduced NADPH-hemoprotein reductase] + O2
pino-carveol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(1R)-cis-permethrin + O2 + [reduced NADPH-hemoprotein reductase]
3-phenoxybenzyl alcohol + 3-(4'-hydroxyphenoxy)-benzyl alcohol + [oxidized NADPH-hemoprotein reductase]
show the reaction diagram
-
-
-
-
?
(1R)-trans-permethrin + O2 + [reduced NADPH-hemoprotein reductase]
3-phenoxybenzyl alcohol + 3-(4'-hydroxyphenoxy)-benzyl alcohol + [oxidized NADPH-hemoprotein reductase]
show the reaction diagram
-
-
-
-
?
(1S)-cis-permethrin + O2 + [reduced NADPH-hemoprotein reductase]
3-phenoxybenzyl alcohol + 3-(4'-hydroxyphenoxy)-benzyl alcohol + [oxidized NADPH-hemoprotein reductase]
show the reaction diagram
-
-
-
-
?
(1S)-trans-permethrin + O2 + [reduced NADPH-hemoprotein reductase]
3-phenoxybenzyl alcohol + 3-(4'-hydroxyphenoxy)-benzyl alcohol + [oxidized NADPH-hemoprotein reductase]
show the reaction diagram
-
-
-
-
?
(methylsulfanyl)benzene + [reduced NADPH-hemoprotein reductase] + H+ + O2
methyl(phenyl)sulfaniumolate + [oxidized NADPH-hemoprotein reductase] + ?
show the reaction diagram
(R)-(+)-limonene + 2 O2 + 2 NADPH
(R)-cis-1,2-limonene epoxide + cis-carveol + 2 NADP+ + 2 H2O
show the reaction diagram
(S)-(-)-limonene + NADPH + O2
(S)-trans-1,2 limonene epoxide + NADP+ + H2O
show the reaction diagram
(S)-nicotine + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
substrate of CYP3A4, the reaction involves electron transfer via FMN
-
-
?
1,4-dimethoxybenzene + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
-
?
1-chloro-4-(methylsulfanyl)benzene + [reduced NADPH-hemoprotein reductase] + H+ + O2
(4-chlorophenyl)(methyl)sulfaniumolate + [oxidized NADPH-hemoprotein reductase] + ?
show the reaction diagram
1-chloro-4-ethenylbenzene + [reduced NADPH-hemoprotein reductase] + H+ + O2
(4-chlorophenyl)acetaldehyde + 2-(4-chlorophenyl)oxirane + 2-(4-chlorophenyl)ethan-1-ol + [oxidized NADPH-hemoprotein reductase] + ?
show the reaction diagram
1-indanone + [reduced NADPH-hemoprotein reductase] + O2
(S)-3-hydroxy-1-indanone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
1-methoxy-4-(methylsulfanyl)benzene + [reduced NADPH-hemoprotein reductase] + H+ + O2
(4-methoxyphenyl)(methyl)sulfaniumolate + [oxidized NADPH-hemoprotein reductase] + ?
show the reaction diagram
1-tetralone + [reduced NADPH-hemoprotein reductase] + O2
(S)-4-hydroxy-1-tetralone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
10-p-nitrophenoxydecanoic acid + NADPH + O2
?
show the reaction diagram
11-oxoprogesterone + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
?
12-methyl-myristic acid + NADPH + O2
?
show the reaction diagram
-
CYP102A7
-
-
?
12-methyl-tetradecanoic acid + NADPH + O2
?
show the reaction diagram
-
CYP102A7
-
-
?
13-methyl-myristic acid + NADPH + O2
?
show the reaction diagram
-
CYP102A7
-
-
?
13-methyl-tetradecanoic acid + NADPH + O2
?
show the reaction diagram
-
CYP102A7
-
-
?
2 3,5,4'-trimethoxy-trans-stilbene + 2 [reduced NADPH-hemoprotein reductase] + 2 O2
3-hydroxy-5,4'-dimethoxy-trans-stilbene + 3,5-dihydroxy-4'-methoxy-trans-stilbene + 2 [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
2,3-dihydroindene + [reduced NADPH-hemoprotein reductase] + H+ + O2
(1S)-2,3-dihydroinden-1-ol + 2,3-dihydroinden-1-one + [oxidized NADPH-hemoprotein reductase] + ?
show the reaction diagram
Roseibium aggregatum
-
-
-
?
2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
CYP1A2 catalyzes the first step of activation of the xenobiotic compound and its genotoxic effect, the second step is catalyzed by the sulfotransferase 1A1-1
-
-
?
2-amino-3-methylimidazo[4,5-f]quinoline + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
CYP1A2 catalyzes the first step of activation of the xenobiotic compound and its genotoxic effect, the second step is catalyzed by the N(O)-acetyltransferase.
-
-
?
2-hydroxy-1-(4-hydroxyphenyl)guanidine + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
?
3 geranylacetone + 3 NADPH + 3 H+ + 3 O2
9,10-epoxygeranylacetone + 11-hydroxygeranylacetone + 5,6-epoxygeranylacetone + 3 NADP+ + 3 H2O
show the reaction diagram
-
CYP102A7, high activity
-
-
?
3,5-dimethoxy-trans-stilbene + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
3,7-dimethyl-1-octanol + [reduced NADPH-hemoprotein reductase] + O2
6-hydroxy-3,7-dimethyl-1-octanol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
3-cyano-7-ethoxycoumarin + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
3-methoxybenzoic acid + [reduced NADPH-hemoprotein reductase] + O2
3,4-dihydroxybenzoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
when reconstituted with cytochrome P450 reductase 2, CYP53A15 converts 3-methoxybenzoic acid to 3,4-dihydroxybenzoic acid
-
-
?
3-methoxybenzoic acid + [reduced NADPH-hemoprotein reductase] + O2
3-hydroxybenzoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
when reconstituted with cytochrome P450 reductase 1, CYP53A15 converts 3-methoxybenzoic acid to 3-hydroxybenzoic acid
-
-
?
3-[2-(N,N-diethyl-N-methylammonium)ethyl]-7-methoxy-4-methylcoumarin + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
?
4-(methylnitrosamino)-1-(3pyridyl)-1-butanone + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
4-androstene-3,17-dione + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
4-chlorothioanisole + [reduced NADPH-hemoprotein reductase] + H+ + O2
4-chlorothioanisole sulfoxide + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
Roseibium aggregatum
-
-
-
?
4-chlorothioanisole + [reduced NADPH-hemoprotein reductase] + O2
4-chlorothioanisole sulfoxide + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
enantioselectivity for the biosulfoxidation catalyzed by the recombinant enzyme expressed from an improved engineered Escherichia coli strain
-
-
?
4-fluorothioanisole + [reduced NADPH-hemoprotein reductase] + O2
4-fluorothioanisole sulfoxide + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
enantioselectivity for the biosulfoxidation catalyzed by the recombinant enzyme expressed from an improved engineered Escherichia coli strain
-
-
?
4-methoxythioanisole + [reduced NADPH-hemoprotein reductase] + O2
4-methoxythioanisole sulfoxide + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
enantioselectivity for the biosulfoxidation catalyzed by the recombinant enzyme expressed from an improved engineered Escherichia coli strain
-
-
?
4-nitroanisole + [reduced NADPH-hemoprotein reductase] + H+ + O2
4-nitrophenol + [oxidized NADPH-hemoprotein reductase] + ?
show the reaction diagram
Roseibium aggregatum
-
-
-
?
4-tert-butylcyclohexyl acetate + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
4-tolylmethylsulfide + [reduced NADPH-hemoprotein reductase] + O2
4-tolylmethylsulfoxide + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
enantioselectivity for the biosulfoxidation catalyzed by the recombinant enzyme expressed from an improved engineered Escherichia coli strain
-
-
?
6-methoxy-1-tetralone + [reduced NADPH-hemoprotein reductase] + O2
(S)-4-hydroxy-6-methoxy-1-tetralone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
6beta-hydroxytestosterone + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
?
7-ethoxy-4-trifluoromethylcoumarin + [reduced NADPH-hemoprotein reductase] + O2
7-hydroxy-4-trifluoromethylcoumarin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
CYP1A2 cooperates with NADPH-cytochrome P450 reductase, which provides NADPH for the reaction. Interaction with their redox partner, NADPH-cytochrome P450 reductase, i.e. CPR, in a 1:1 molar ratio
-
-
?
7-ethoxy-trifluoromethylcoumarin + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
O-deethylation
-
-
?
7-ethoxycoumarin + NADPH + H+ + O2
7-hydroxycoumarin + NADP+ + H2O + ?
show the reaction diagram
7-ethoxycoumarin + [reduced NADPH-hemoprotein reductase] + H+
coumarin + [oxidized NADPH-hemoprotein reductase] + ?
show the reaction diagram
Roseibium aggregatum
-
-
-
?
7-ethoxycoumarin + [reduced NADPH-hemoprotein reductase] + O2
7-hydroxycoumarin + [oxidized NADPH-hemoprotein reductase] + H2O + ?
show the reaction diagram
7-ethoxycoumarin + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
7-ethoxyresorufin + O2 + reduced donor
?
show the reaction diagram
-
7-ethoxyresorufin O-deethylation
-
-
?
7-ethoxyresorufin + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
7-ethoxyresorufin + [reduced NADPH-hemoprotein reductase] + O2
resorufin + ethanol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
7-hydroxycoumarin + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
-
?
7-methoxy-1-tetralone + [reduced NADPH-hemoprotein reductase] + O2
(S)-4-hydroxy-7-methoxy-1-tetralone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
7-methoxy-4-(trifluoromethyl)-coumarin + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
7-methoxycoumarin + [reduced NADPH-hemoprotein reductase] + H+
coumarin + [oxidized NADPH-hemoprotein reductase] + ?
show the reaction diagram
Roseibium aggregatum
-
-
-
?
7-methoxycoumarin + [reduced NADPH-hemoprotein reductase] + O2
7-hydroxycoumarin + [oxidized NADPH-hemoprotein reductase] + ?
show the reaction diagram
-
-
-
-
?
7-methoxycoumarin + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
-
?
7-methoxyresorufin + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
-
?
7-propoxycoumarin + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
-
?
acenaphthene + [reduced NADPH-hemoprotein reductase] + O2
1-acenaphthenol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
adrenic acid + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
aflatoxin B1 + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
alpha-ionone + NADPH + O2
?
show the reaction diagram
-
CYP102A7, high activity
-
-
?
alpha-ionone + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
alpha-santonin + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
ambroxide + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
aminopyrine + [reduced NADPH-hemoprotein reductase] + O2
? + formaldehyde + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
amiprofos-methyl + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
androsterone + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
anisole + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
-
?
anthraquinone-1,5-disulfonic acid + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
anthraquinone-1,8-disulfonic acid + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
anthraquinone-1-sulfonic acid + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
anthraquinone-2,6-disulfonic acid + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
anthraquinone-2-sulfonic acid + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
apigenin + [reduced NADPH-hemoprotein reductase] + O2
3',8-dihydroxyapigenin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
arachidonic acid + O2 + NADPH
20-hydroxyeicosatetraenoic acid + H2O + NADP+
show the reaction diagram
arachidonic acid + [reduced NADPH-hemoprotein reductase] + O2
18-hydroxyarachidonic acid + 14,15-epoxyeicosa-5,8,11-trienoic acid + 11,12-epoxyeicosa-5,8,14-trienoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
arachidonic acid + [reduced NADPH-hemoprotein reductase] + O2
18-hydroxyarachidonic acid + 14,15-epoxyeicosa-5,8,11-trienoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
arachidonic acid + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxyeicosatetraenoic acid + 19-hydroxyeicosatetraenoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
ratio 12:1
-
?
arachidonic acid + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
aryl hydrocarbons + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
avermectin + [reduced NADPH-hemoprotein reductase] + O2
4''-oxo-avermectin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
bentazon + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
ring-hydroxylation
-
-
?
benzo(a)pyrene + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
-
?
benzo(ghi)perylene + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
-
?
benzo-pyrene + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
recombinant enzyme CYP1A1 fused to yeast reductase and expressed in transgenic tobacco plants
-
-
?
benzoic acid + [reduced NADPH-hemoprotein reductase] + O2
3,4-dihydroxybenzoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
when reconstituted with cytochrome P450 reductase 2, CYP53A15 converts benzoic acid to 3,4-dihydroxybenzoic acid
-
-
?
benzoic acid + [reduced NADPH-hemoprotein reductase] + O2
4-hydroxybenzoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
when reconstituted with cytochrome P450 reductase 1, CYP53A15 converts benzoic acid to 4-hydroxybenzoic acid
-
-
?
benzyl methyl sulfide + [reduced NADPH-hemoprotein reductase] + O2
benzyl methyl sulfoxide + benzyl methyl sulfone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
50% conversion
product ratio of 78:22
-
?
bergapten + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
beta-damasone + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
beta-ionol + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
beta-ionone + NADPH + O2
4-hydroxy-beta-ionone + NADP+ + H2O
show the reaction diagram
-
CYP102A7, high activity
-
-
?
beta-ionone + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
beta-ionone + [reduced NADPH-hemoprotein reductase] + O2
4-hydroxy-beta-ionone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
beta-ionone + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
substrate only for mutant A74G/F88V/S189Q
-
-
?
bispyribac-sodium + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
-
?
bornyl acetate + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
capric acid + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
?
capric acid + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
about 10% of the activity with palmitic acid, wild-type
-
-
?
caprylic acid + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
substrate only for mutant A74G/F88V/S189Q
-
-
?
chlormadinone acetate + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
?
chlorotoluron + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
chlorotoluron + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
chlorzoxazone + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
-
?
cholesterol + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
cinnamic acid + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
?
cis-nerolidol + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
compactin + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
?
coumarin + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
cytochrome c + NADH + H+ + O2
?
show the reaction diagram
cytochrome c + O2 + NADH
?
show the reaction diagram
cytochrome c + O2 + NADH
? + NAD+ + ?
show the reaction diagram
Roseibium aggregatum
-
-
-
?
daidzein + [reduced NADPH-hemoprotein reductase] + O2
3'-hydroxydaidzein + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
decanoic acid + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
dehydroepiandrosterone + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
dibenzylfluorescein + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
diclofop + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
ring-hydroxylation
-
-
?
dimethylaniline + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
substrate of CYP3A4
-
-
?
docosahexaenoic acid + [reduced NADPH-hemoprotein reductase] + O2
22-hydroxydocosahexaenoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
dodecanoic acid + NADPH + O2
?
show the reaction diagram
-
CYP102A7
-
-
?
dodecanoic acid + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
isozyme CYP52A17, good substrate
-
-
?
eicosapentaenoic acid + NADPH + H+ + O2
20-hydroxyeicosapentaenoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
eicosapentaenoic acid + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxyeicosapentaenoic acid + 19-hydroxyeicosapentaenoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
ratio 4:3
-
?
eicosapentaenoic acid + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxyeicosapentaenoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
eicosenoic acid + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
elymoclavine + [reduced NADPH-hemoprotein reductase] + O2
paspalic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
eriodictyol + [reduced NADPH-hemoprotein reductase] + O2
6-hydroxyeriodictyol + 8-hydroxyeriodictyol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
erythromycin + [reduced NADPH-hemoprotein reductase] + O2
? + formaldehyde + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
estrone + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
ethyl methyl sulfide + [reduced NADPH-hemoprotein reductase] + O2
ethyl methyl sulfoxide + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
enantioselectivity for the biosulfoxidation catalyzed by the recombinant enzyme expressed from an improved engineered Escherichia coli strain
-
-
?
ethyl phenyl sulfide + [reduced NADPH-hemoprotein reductase] + O2
ethyl phenyl sulfoxide + ethyl phenyl sulfone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
70% conversion
product ratio of 52:18
-
?
ethylbenzene + [reduced NADPH-hemoprotein reductase] + H+ + O2
(1S)-1-phenylethan-1-ol + 1-phenylethan-1-one + [oxidized NADPH-hemoprotein reductase] + ?
show the reaction diagram
Roseibium aggregatum
-
-
-
?
ethylbenzene + [reduced NADPH-hemoprotein reductase] + O2
(R)-1-phenylethanol + 1-phenylethanone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
product ratio of 88:12
-
?
ethylbenzene + [reduced NADPH-hemoprotein reductase] + O2
1-phenylethyl alcohol + 2-phenylethyl alcohol + [reduced NADPH-hemoprotein reductase] + O2
show the reaction diagram
recombinant enzyme
-
-
?
farnesol + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
CYP102A1 oxidizes farnesol to three products (2,3-epoxyfarnesol, 10,11-epoxyfarnesol, and 9-hydroxyfarnesol), whereas CYP4C7 produces 12-hydroxyfarnesol as the major product. Chimeric proteins C(78-82,F87L) and C(78-82,F87L,328-330) show the most complete change in substrate selectivity from fatty acids to farnesol, and both retain superior enzyme activity with respect to CYP102A1 approximately 5times and approximately 2times greater, respectively. C(78-82,F87L,328-330) produces 12-hydroxyfarnesol as the major metabolite, as does CYP4C7
-
-
?
fenchyl acetate + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
fenoxaprop-ethyl + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
-
?
fenthion + NADPH + H+ + O2
fenthion-oxon + sulfur + NADP+ + H2O
show the reaction diagram
-
-
-
r
fenthion + NADPH + H+ + O2
fenthion-sulfoxide + NADP+ + H2O
show the reaction diagram
-
-
-
r
fenthion + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
fenthion-sulfoxide and fenthion-oxon, are formed by some CYPs although at very different levels, depending on the relative CYP hepatic content. Fenthion-oxon formation is favored and at low fenthion concentrations CYP2B6 and CYP1A2 are mainly involved in its formation. At higher levels, a more widespread CYP involvement is evident, as in the case of fenthion-sulfoxide
-
-
?
fenthion-sulfoxide + [reduced NADPH-hemoprotein reductase] + O2
fenthion-sulfone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
fluoranthene + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
-
?
fluorene + [reduced NADPH-hemoprotein reductase] + O2
9-fluorenol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
fluoxetine + [reduced NADPH-hemoprotein reductase] + O2
? + formaldehyde + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
genistein + [reduced NADPH-hemoprotein reductase] + O2
3',8-dihydroxygenistein + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
geraniol + [reduced NADPH-hemoprotein reductase] + O2
8-hydroxygeraniol + 10-hydroxygeraniol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
giberellic acid GA12 + [reduced NADPH-hemoprotein reductase] + O2
16alpha,17-epoxy GA12 + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
product identification by GC-MS, the epoxid is transformed into 16,17-dihydro-16alpha,17-dihydroxy-GA4 under acidic conditions with acidic acid
-
?
giberellic acid GA4 + [reduced NADPH-hemoprotein reductase] + O2
16alpha,17-epoxy GA4 + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
giberellic acid GA9 + [reduced NADPH-hemoprotein reductase] + O2
16alpha,17-epoxy GA9 + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
product identification by GC-MS, the epoxid is transformed into 16,17-dihydro-16alpha,17-dihydroxy-GA4 under acidic conditions with acidic acid
-
?
hexadecanoic acid + NADPH + O2
?
show the reaction diagram
-
CYP102A7, highest binding affinity
-
-
?
indane + [reduced NADPH-hemoprotein reductase] + O2
(S)-3-hydroxy-indane + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
indene + [reduced NADPH-hemoprotein reductase] + H+ + O2
(S)-inden-1-ol + 2,3-dihydroinden-1-one + [oxidized NADPH-hemoprotein reductase] + ?
show the reaction diagram
Roseibium aggregatum
-
-
-
?
indene + [reduced NADPH-hemoprotein reductase] + O2
indenol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
indole + [reduced NADPH-hemoprotein reductase] + O2
(2Z)-2-(3-oxo-1,3-dihydro-2H-indol-2-ylidene)-1,2-dihydro-3H-indol-3-one + (3Z)-3-(3-oxo-1,3-dihydro-2H-indol-2-ylidene)-1,3-dihydro-2H-indol-2-one + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
isopimpinellin + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
ketoconazole + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
lauric acid + NADPH + O2
?
show the reaction diagram
-
CYP102A7
-
-
?
lauric acid + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
lauric acid + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
linoleic acid + NADPH + O2
?
show the reaction diagram
-
CYP102A1, CYP102A2, CYP102A3 and CYP102A7. CYP102A7 with high binding affinity
-
-
?
linoleic acid + [reduced NADPH-hemoprotein reductase] + O2
(9Z,12Z)-18-hydroxyoctadeca-9,12-dienoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
linoleic acid + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
isozyme CYP52A17, good substrate, isozyme CYP52A13, good substrate
-
-
?
losartan + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
luteolin + [reduced NADPH-hemoprotein reductase] + O2
3',8-dihydroxyapigenin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
m-xylene + [reduced NADPH-hemoprotein reductase] + O2
3-methylbenzyl alcohol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
recombinant enzyme
-
-
?
macrolide YC-17 + [reduced NADPH-hemoprotein reductase] + O2
methymycin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
Hydroxylation of C-10 position yield methymycin and of the C-12 neomethymycin. Hydroxylation at both positions yields novamethymycin.
-
-
?
macrolide YC-17 + [reduced NADPH-hemoprotein reductase] + O2
neomethymycin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
Hydroxylation of C-10 position yield methymycin and of the C-12 neomethymycin. Hydroxylation at both positions yields novamethymycin.
-
-
?
macrolide YC-17 + [reduced NADPH-hemoprotein reductase] + O2
novamethymycin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
Hydroxylation of C-10 position yield methymycin and of the C-12 neomethymycin. Hydroxylation at both positions yields novamethymycin.
-
-
?
medroxyprogesterone acetate + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
?
mefenacet + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
methyl 10,11-epoxyfarnesoate + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
the major product of C(78-82,F87L,328-330) during 10,11-epoxymethylfarnesoate oxidation is determined to be the 12-hydroxy isomer
-
-
?
methyl 4-methylphenyl sulfide + [reduced NADPH-hemoprotein reductase] + O2
methyl 4-methylphenyl sulfoxide + methyl 4-methylphenyl sulfone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
41% conversion
product ratio of 95:5
-
?
methyl farnesoate + O2 + NADPH
?
show the reaction diagram
the major product of C(78-82,F87L,328-330) during methylfarnesoate oxidation is determined to be the 12-hydroxy isomer
-
-
?
methyl phenyl sulfide + O2 + NADH
methyl phenyl sulfoxide + methyl phenyl sulfone + NAD+ + H2O
show the reaction diagram
-
55% conversion
product ratio of 77:23
-
?
methyltestosterone + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
?
metolachlor + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
Sorghum sp.
-
de-ethylation
-
-
?
midazolam + [reduced NADPH-hemoprotein reductase] + O2
1'-hydroxymidazolam + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
myristic acid + NADPH + O2
?
show the reaction diagram
-
CYP102A7
-
-
?
myristic acid + [reduced NADPH-hemoprotein reductase] + O2
omega-hydroxy-myristic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
isozyme CYP52A17, best substrate
isoform CYP52A17, additional fornmation of about 15% dicarbonic acid
-
?
N'-nitrosonornicotine + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
N-acetylindole + [reduced NADPH-hemoprotein reductase] + O2
1-acetyl-1,2-dihydro-3H-indol-3-one + 1-acetyl-1,3-dihydro-2H-indol-2-one + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
naphthalene + [reduced NADPH-hemoprotein reductase] + O2
1-naphthol + H2O + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
regioselective oxidation
-
-
?
naphthalene + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
substrate only for mutant A74G/F88V/S189Q
-
-
?
narbomycin + [reduced NADPH-hemoprotein reductase] + O2
pikromycin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
naringenin + [reduced NADPH-hemoprotein reductase] + O2
eriodictyol + 6-hydroxyeriodictyol + 8-hydroxyeriodictyol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
neryl acetate + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
nerylacetone + NADPH + O2
9,10-epoxynerylacetone + 5,6-epoxynerylacetone + NADP+ + H2O
show the reaction diagram
-
CYP102A7, high activity
-
-
?
nonylphenol + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
nootkatone + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
norflurazon + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
octane + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
substrate only for mutant A74G/F88V/S189Q and for mutant A74G/S189Q
-
-
?
okadaic acid + NADPH + O2
?
show the reaction diagram
okadaic acid + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase]
show the reaction diagram
-
-
-
?
oleandomycin + [reduced NADPH-hemoprotein reductase] + O2
4-hydroxy-oleandomycin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
oleic acid + NADPH + O2
?
show the reaction diagram
-
CYP102A1, CYP102A2, CYP102A3 and CYP102A7
-
-
?
oleic acid + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
oleic acid + [reduced NADPH-hemoprotein reductase] + O2
omega-hydroxy oleic acid + n-decan-dicarboxylic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
isozyme CYP52A13, best substrate,isozyme CYP52A17, good substrate
isozyme CYP52A13, products in ratio 1:1, CYP52A17, ratio 3:7 of hydroxy- and dicarboxy-product
-
?
omega-(p-nitrophenyl)decanoic acid + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
omega-(p-nitrophenyl)dodecanoic acid + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
omega-(p-nitrophenyl)octanoic acid + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
p-chlorothioanisole + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
-
?
p-fluorothioanisole + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
-
?
p-methoxythioanisole + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
-
?
p-nitrophenol + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
p-tolyl methyl sulfide + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
-
?
p-xylene + O2 + [reduced NADPH-hemoprotein reductase]
2,5-dimethylphenol + H2O + [oxidized NADPH-hemoprotein reductase]
show the reaction diagram
paclitaxel + [reduced NADPH-hemoprotein reductase] + O2
6alpha-hydroxypaclitaxel + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
palmitic acid + NADPH + O2
?
show the reaction diagram
-
CYP102A7
-
-
?
palmitic acid + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
palmitic acid + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
palmitoleic acid + NADPH + O2
?
show the reaction diagram
-
CYP102A7
-
-
?
pendimethalin + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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?
phenanthrene + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
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-
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?
phenyl ethyl sulfide + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
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-
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-
?
phenyl methyl sulfide + [reduced NADPH-hemoprotein reductase] + O2
phenyl methyl sulfoxide + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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enantioselectivity for the biosulfoxidation catalyzed by the recombinant enzyme expressed from an improved engineered Escherichia coli strain
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?
pilocarpine + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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?
pregnenolone + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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-
-
?
progesterone + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
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-
-
?
propylbenzene + [reduced NADPH-hemoprotein reductase] + O2
(R)-1-phenyl-1-propanol + (R)-1-phenyl-1-propanol + 1-phenylpropan-1-one + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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product ratio of 79:7:14
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?
prostaglandin + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-prostaglandin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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physiological functions are the metabolic inactivation of prostaglandins and the production of 20-hydroxyeicosatetraenoic acid, CYP4A4
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?
prostaglandin A1 + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-prostaglandin A1 + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
prostaglandin A2 + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-prostaglandin A2 + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
prostaglandin D2 + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-prostaglandin D2 + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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CYP4A4
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-
?
prostaglandin E1 + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-prostaglandin E1 + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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CYP4A4
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-
?
prostaglandin E2 + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-prostaglandin E2 + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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CYP4A4
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-
?
prostaglandin F2alpha + [reduced NADPH-hemoprotein reductase] + O2
20-hydroxy-prostaglandin F2alpha + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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CYP4A4
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-
?
psoralen + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
pyrene + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
-
?
pyributicarb + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
quinine + [reduced NADPH-hemoprotein reductase] + O2
3-hydroxyquinine + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
RH + [reduced NADPH-hemoprotein reductase] + O2
ROH + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
rivaroxaban + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
S-mephenytoin + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
-
-
-
?
sclareolide + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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-
-
?
sertraline + [reduced NADPH-hemoprotein reductase] + O2
demethylsertraline + formaldehyde + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
simvastatin + [reduced NADPH-hemoprotein reductase] + O2
6-beta-hydroxy-methyl-simvastatin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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-
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?
stanolone + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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-
-
?
stearic acid + NADPH + O2
?
show the reaction diagram
-
CYP102A7
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?
stearic acid + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
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-
-
-
?
stearic acid + [reduced NADPH-hemoprotein reductase] + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
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?
styrene + O2 + H2O2
(R)-styrene oxide + (S)-styrene oxide + H2O
show the reaction diagram
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engineered CYP102A1 heme domain which utilizes H2O2 as electron donor instead of NADPH
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?
styrene + O2 + NAD(P)H
(R)-styrene oxide + (S)-styrene oxide + H2O + NAD(P)+
show the reaction diagram
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enantioselective styrene oxidation with different CYP102A1 mutants, 25% S-isomer for the wild-type enzyme, 58% S-isomer for mutant A74E/F87V/P386S, 49% R-isomer for mutant F87A, 65% R-isomer for mutant A74G/F87V/L188Q, and 92% R-isomer for mutant F87G
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?
styrene + O2 + reduced putidaredoxin
(S)-styrene oxide + 2-phenylethanol + oxidized putidaredoxin + H2O
show the reaction diagram
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-
product ratio of 81:19
-
?
testosterone + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
testosterone + [reduced NADPH-hemoprotein reductase] + O2
6beta-hydroxytestosterone + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
testosterone + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
testosterone enanthate + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
CYP107
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?
tetradecanoic acid + NADPH + O2
?
show the reaction diagram
-
CYP102A7, highest activity
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?
tetralin + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
tetralin + [reduced NADPH-hemoprotein reductase] + O2
(S)-4-hydroxy-tetralin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
thiobencarb + O2 + reduced flavoprotein
?
show the reaction diagram
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-
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-
?
tolbutamide + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
toluene + O2 + NAD(P)H + cytochrome c
benzyl alcohol + H2O + NAD(P)+ + reduced cytochrome c
show the reaction diagram
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-
-
?
toluene + O2 + NADH
?
show the reaction diagram
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?
toluene + [reduced NADPH-hemoprotein reductase] + H+ + O2
benzylalcohol + benzaldehyde + [oxidized NADPH-hemoprotein reductase] + ?
show the reaction diagram
Roseibium aggregatum
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?
trans-decahydronaphthalene + [reduced NADPH-hemoprotein reductase] + H+ + O2
? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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-
-
?
trifluralin + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
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-
?
vandetanib + [reduced NADPH-hemoprotein reductase] + H+ + O2
N-desmethylvandetanib + [oxidized NADPH-hemoprotein reductase] + ?
show the reaction diagram
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-
?
xanthotoxin + reduced flavoprotein + O2
? + oxidized flavoprotein + H2O
show the reaction diagram
additional information
?
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