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Cytochrome P450

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[[Image:2f9q.png|left|200px|thumb|Crystal Structure of Cytochrome P450 [[2f9q]]]]
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<StructureSection load='' size='350' side='right' caption='Cytochrome P450 CypC2 with heme C complex with warfarin (PDB entry [[1og5]])' scene='43/430105/Cv/2'>
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{{STRUCTURE_2f9q| PDB=2f9q | SIZE=400| SCENE=Cytochrome_P450/Cv/1 |right|CAPTION=Cytochrome P450 tetramer with heme and sulfate ions [[2f9q]] }}
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__TOC__
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== Function ==
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[[Cytochrome P450]] (P450) or '''cytochrome P450 monooxygenase''' catalyzes the oxidation of organic substances like lipids. The P450 contains a heme cofactor. The protein is numbered by its gene.<ref>PMID:12369887</ref> P450 CYP121 is called '''mycocyclosin synthase'''.
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* '''P450cam''', also known as camphor 5-monooxygenase, catalyzes the hydroxylation of camphor.<br />
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* '''P450nor''' is a Nitric Oxide Reductase P450.<br />
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* '''P450epoK''' converts epothilone D to epothilone B.<br />
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* '''P450cin''' monooxygenates 1,8-cineole which is similar to camphor.<br />
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* '''Bifunctional P450/NADPH P450 reductase''' (P450 BM3) is a fatty acid monooxygenase.<br />
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* '''P450 3A4''' see [[CYP3A4]].<br />
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* '''P450 19 family''' see [[Aromatase]].<br />
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* '''P450 17A1''' see [[Abiraterone acetate|Human steroidogenic cytochrome P450 17A1 with inhibitor abiraterone]]
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See also [[Hemeproteins]].
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Additional details on cytochrome P450 interactions with drugs see
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*[[Drug Metabolism by CYP450 Enzymes]]<br />
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*[[Montelukast]] - anti rhinitis
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*[[Noxafil]] - antifungal drug which binds to CYP51.
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*[[Cobicistat]] - anti HIV/AIDS drug which binds to CYP3A4.
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== Structural highlights ==
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The <scene name='43/430105/Cv/6'>heme moiety is stabilized by several side chains</scene>. The <scene name='43/430105/Cv/7'>heme iron is pentacoordinated with Cys as one ligand</scene>.<ref>PMID:12861225</ref>
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[[Cytochrome P450]] (P450) catalyzes the oxidation of organic substances like lipids. catalyzes the oxidation of organic substances like lipids. The P450 contains a heme cofactor. The protein is numbered by its gene. P450cam, also known as camphor 5-monooxygenase, catalyzes the hydroxylation of camphor. P450nor is a Nitric Oxide Reductase P450. P450epoK converts epothilone D to epothilone B. P450cin monooxygenates 1,8-cineole which is similar to camphor. The images at the left and at the right correspond to one representative P450, ''i.e.'' the crystal structure of human P4502 ([[2f9q]]). For details on the human P45019 family see [[Aromatase]]. Bifunctional P450/NADPH P450 reductase is a fatty acid monooxygenase. Additional details in [[Drug Metabolism by CYP450 Enzymes]].
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{{TOC limit|limit=2}}
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== 3D Structures of Cytochrome P450 ==
== 3D Structures of Cytochrome P450 ==
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[[Cytochrome P450 3D structures]]
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Updated on {{REVISIONDAY2}}-{{MONTHNAME|{{REVISIONMONTH}}}}-{{REVISIONYEAR}}
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</StructureSection>
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=== human P450 1 family ===
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[[2hi4]] – hP4501A2+naphthoflavone - human<br />
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[[4i8v]] - hP4501A1 +naphthoflavone<br />
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[[3pm0]] - hP4501B1+naphthoflavone<br />
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=== human P450 2 family ===
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[[2pg5]], [[2pg6]], [[2pg7]] – hP4502A6 (mutant)<br />
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[[3ebs]] – hP4502A6 (mutant)+phenacetin<br />
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[[2fdu]], [[2fdv]], [[2fdw]], [[2fdy]] - hP4502A6+pyridine derivative<br />
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[[1z10]] - hP4502A6 catalytic domain+coumarin<br />
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[[4ejj]] - hP4502A6 + nicotine<br />
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[[3t3q]], [[3t3r]] - hP4502A6 (mutant) + pilocarpine<br />
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[[2z10]] – hP4502A6+coumarin<br />
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[[1z11]] - hP4502A6+methoxalen<br />
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[[3t3s]] - hP4502A13 + pilocarpine<br />
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[[4ejg]] - hP4502A13 + nicotine<br />
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[[4ejh]], [[4eji]] - hP4502A13 + pyridine derivative<BR />
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[[2p85]] – hP4502A13 (mutant)+indole<br />
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[[3tk3]] - hP4502B4 (mutant) + imidazole derivative<br />
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[[4jlt]] - hP4502B4 (mutant) + drug<br />
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[[3ibd]] – hP4502B6 (mutant)+4-(4-chlorophenyl)imidazole<br />
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[[3ua5]] – hP4502B6 (mutant) + amlodipine<br />
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[[4i91]] - hP4502B6 (mutant) + pinine<br />
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[[2nnh]] – hP4502C8+retinoic acid<br />
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[[2nni]] - hP4502C8+montelukast<br />
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[[2nnj]] - hP4502C8+felodipine<br />
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[[1pq2]] - hP4502C8<br />
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[[1og2]], [[1og5]] – hP4502C9 (mutant)<br />
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[[1r9o]] – hP4502C9 (mutant)+flurbiprofen<br />
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[[4gqs]] - hP4502C19 catalytic domain<br />
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[[2f9q]], [[3qm4]] – hP4502D6<br />
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[[3tbg]] – hP4502D6 + thioridazine<br />
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[[3tda]] – hP4502D6 + prinomastat<br />
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[[3gph]], [[3koh]], [[3lc4]] – hP4502E1 fragment +imidazole derivative<br />
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[[3e6i]] – hP4502E1 fragment+indazole<br />
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[[3e4e]] – hP4502E1 fragment+methylpyrazole<br />
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[[3t3z]] - hP4502E1 + pilocarpine<br />
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[[3czh]], [[3dl9]], [[3c6g]] – hP4502R1+vitamin D<br />
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=== human P450 3 family ===
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[[2v0m]] – hP4503A4+ketoconazole<br />
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[[2j0d]] - hP4503A4+erythromycin<br />
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[[3nxu]], [[3tjs]] - hP4503A4+ritonavir<br />
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[[4i4g]], [[4i4h]], [[4k9t]], [[4k9u]], [[4k9v]], [[4k9w]], [[4k9x]] - hP4503A4 (mutant) +ritonavir derivative<br />
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[[3ua1]] - hP4503A4 + ergocryptine<br />
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[[1tqn]], [[1w0e]], [[1w0f]], [[1w0g]] – hP4503A4<br />
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[[4i3q]] - hP4503A4 (mutant) <br />
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=== human P450 7 family ===
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[[3dax]] – hP4507A1<br />
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[[3sn5]] - hP4507A1 + cholest-4-en-3-one
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===human P450 11 family===
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[[4dvq]] - hP45011B2 + corticosterone<br />
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[[4fdh]] - hP45011B2 + fadrozole<br />
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=== human P450 19 family (aromatase)===
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[[3eqm]], [[3s79]], [[4kq8]] - hP45019A1+androstenedione<br />
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[[3s7s]] - hP45019A1 + exemestane<br />
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[[4gl5]], [[4gl7]] - hP45019A1 + inhibitor
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=== human P450 46 family ===
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[[2q9f]] – hP45046A1+cholesterol<br />
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[[2q9d]], [[2q9g]] - hP45046A1<br />
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[[2vn0]] – hP450105A1+troglitazone<br />
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[[2zby]] - hP450105A1 (mutant)
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=== P450 from ''Mycobacterium tuberculosis'' ===
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[[2vku]], [[1h5z]] – MtP45051 - ''Mycobacterium tuberculosis''<br />
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[[2ci0]], [[2cib]], [[1u13]] - MtP45051 (mutant)<br />
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[[1x8v]] - MtP45051 (mutant)+estriol<br />
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[[1ea1]] - MtP45051 (mutant)+ fluconazole<br />
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[[1e9x]] - MtP45051 (mutant)+ phenylimidazole<br />
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[[3cxv]], [[3cxx]], [[3cxy]], [[3cxz]], [[3cy0]], [[3cy1]] - MtP450121 (mutant)<br />
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[[3g5f]], [[3g5h]], [[2ij5]], [[1n40]] – MtP450121<br />
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[[2ij7]] - MtP450121+fluconazole<br />
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[[1n4g]], [[4ktf]], [[4ktj]], [[4ktk]], [[4ktl]] - MtP450121+pyrazole derivative<br />
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[[4ict]], [[4ips]], [[4ipw]], [[4iq7]], [[4iq9]] - MtP450121 + piperazine derivative<br />
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[[4g1x]], [[4g2g]], [[4g44]], [[4g45]], [[4g46]], [[4g47]], [[4g48]] - MtP450121 + inhibitor<br />
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[[3ivi]], [[3iw0]], [[3ivy]] – MtP450125 <br />
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[[3iw1]] - MtP450125+androstenedione<br />
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[[3iw2]] - MtP450125+econazole<br />
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[[2uvn]] - MtP450130+econazole<br />
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[[2wgy]] – MtP450130 (mutant)<br />
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[[2w09]], [[2w0b]], [[2w0a]] - MtP450130 (mutant)+pyridine inhibitor<br />
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[[2uuq]] – MtP450130
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=== P450cam ===
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[[2qbl]], [[2qbm]], [[2qbn]], [[2gqx]], [[2gr6]], [[2frz]], [[2h7s]], [[6cp4]], [[2cp4]], [[3cp4]], [[4cp4]], [[1c8j]], [[1geb]], [[2a1o]],[[3p6q]], [[3p6r]], [[3p6s]], [[3p6t]], [[3p6u]], [[3p6v]], [[3p6w]], [[3p6x]], [[4ek1]] – PpP450cam(mutant) – ''Pseudomona putida''<br />
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[[1dz4]], [[1dz8]], [[1dz6]], [[1dz9]], [[5cp4]], [[1phc]], [[2cpp]], [[1yrc]], [[1yrd]], [[3l61]], [[3l62]], [[3l63]] - PpP450cam<br />
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[[2qbo]] - PpP450cam (mutant)+cyanide<br />
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[[1qmq]] - PpP450cam (mutant)+Ru substrate<br />
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[[2h7q]] - PpP450cam+imidazole<br />
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[[1cp4]] - PpP450cam+benzene<br />
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[[1akd]], [[1iwi]], [[1noo]], [[7cpp]], [[8cpp]], [[2zwt]], [[2zwu]] - PpP450cam+1S-camphor derivative<br />
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[[1iwj]], [[1iwk]], [[2zuh]], [[2zui]], [[2zuj]], [[3fwf]], [[3fwg]], [[3fwi]], [[3fwj]] - PpP450cam (mutant)+1Scamphor<br />
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[[4l49]], [[4l4a]], [[4l4b]], [[4l4c]] - PpP450cam (mutant)+ camphor<br />
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[[4l4d]], [[4l4e]], [[4l4f]], [[4l4g]] - PpP450cam (mutant)+ camphor + CN<br />
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[[2l8m]] – PpP450cam+camphor+CO<br />
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[[4g3r]] – PpP450cam+camphor+NO<br />
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[[2fe6]], [[2fer]], [[2feu]] - PpP450cam+Mn protoporphyrin IX<br />
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[[1uyu]] - PpP450cam+ Xe<br />
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[[1o76]] - PpP450cam+cyanide<br />
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[[4cpp]] - PpP450cam+adamantine<br />
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[[5cpp]] - PpP450cam+adamantanone<br />
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[[6cpp]] - PpP450cam+camphene<br />
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[[1p2y]], [[1p7r]] - PpP450cam+nicotine<br />
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[[1re9]], [[1rf9]] - PpP450cam +fluorescent probe<br />
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[[2z97]], [[2zaw]], [[2zax]] - PpP450cam+methyl depropionated hemin<br />
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[[3cpp]], [[2lqd]] - PpP450cam+CO<br />
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[[1pha]], [[1phb]], [[1phd]], [[1phe]], [[1phf]], [[1phg]] - PpP450cam+imidazole derivative<br />
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[[1gek]], [[1gem]] - PpP450cam+N-butyl-isocyanide<br />
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[[1lwl]] - PpP450cam+fluorescent probe<br />
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[[2h7r]] - PpP450cam (mutant)+imidazole<br />
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[[1k2o]] - PpP450cam (mutant)+pyridine derivative<br />
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[[1gjm]] - PpP450cam (mutant)+sulphydryl reagent<br />
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[[2a1m]], [[2a1n]], [[2a10]] - PpP450cam (mutant)+ferrous dioxygen<br />
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[[1t85]], [[1t86]], [[1t87]], [[1t88]] - PpP450cam (mutant)+ferrous CO<br />
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[[1j51]] - PpP450cam (mutant)+trichlorobenzene<br />
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[[1mpw]] - PpP450cam (mutant)+trimethylbicycloheptene<br />
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[[3oia]], [[3ol5]], [[3p6m]], [[3p6n]], [[3p6o]], [[3p6p]], [[3poq]], [[3por]], [[3pos]], [[3pot]], [[3pou]], [[3pov]], [[3pow]], [[3pox]] - PpP450cam (mutant)+substrate analog<br />
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[[4jws]], [[4jwu]] - PpP450cam (mutant)+ putidaredoxin<br />
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[[4jx1]] - PpP450cam (mutant)+ putidaredoxin + camphor + hydroxycamphor<br />
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[[2m56]] - PpP450cam + putidaredoxin + camphor <br />
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[[3w9c]] - PpP450cam (mutant)+ putidaredoxin <br />
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[[3oft]], [[4c9m]], [[3lxh]], [[3lxi]], [[3ofu]] – NaP450 – ''Novosphignobium aromaticivorans''<br />
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[[4c9p]] - NaP450cam (mutant) + camphor <br />
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[[4c9k]] - NaP450cam + camphor + hydroxycamphor<br />
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[[4c9n]] - NaP450cam (mutant) + camphor + hydroxycamphor<br />
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[[4c9l]] - NaP450cam + camphor + CN<br />
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[[4c9o]] - NaP450cam (mutant) + camphor + CN<br />
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=== P450nor ===
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[[1cl6]], [[1rom]] – FoP450nor - ''Fusarium oxysporum''<br />
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[[2rom]] - FoP450nor+CO<br />
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[[1cmj]], [[1cmn]], [[1ehg]] - FoP450nor (mutant)<br />
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[[1xqd]] – FoP450nor+pyridinealdehyde adenine<br />
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[[1jfb]], [[1jfc]], [[1ged]], [[1ehe]] - FoP450nor<br />
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[[1gej]], [[1gei]] - FoP450nor+N-butyl-isocyanide<br />
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[[1ulw]] - FoP450nor (mutant)
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===P450epoK===
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[[1pkf]] – P450epoK+epothilone D – ''Sorangium cellulosum''
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===P450cin===
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[[3bdz]], [[3be0]] – CbP450cin – ''Citrobacter braakii''<br />
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[[4fyz]] - CbP450cin
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=== rabbit P450 ===
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[[2bdm]] – rP4502B4 – rabbit<br />
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[[1po5]], [[3mvr]], [[3r1a]], [[3r1b]] - rP4502B4 (mutant)<br />
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[[1suo]],[[3g5n]], [[3g93]], [[2q6n]] - rP4502B4 (mutant)+imidazole derivative<br />
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[[3kw4]], [[3me6]], [[3tmz]], [[4h1n]] - rP4502B4 (mutant)+anti-platelet drug<br />
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[[3uas]] - rP4502B4 (mutant)+ inactivator<br />
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[[1dt6]] - rP4502C5 (mutant)<br />
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[[1nr6]] – rP4502C5+diclofenac<br />
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[[1n6b]] - rP4502C5+sulfaphenazole
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===P450 BM3===
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[[3cbd]] – BmP450 heme domain – ''Bacillus megaterium''<br />
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[[3dgi]], [[3hf2]], [[3kx3]], [[3kx4]], [[3kx5]], [[3m4v]], [[3npl]], [[3psx]], [[4dty]], [[4dua]], [[4duc]], [[4dud]], [[1jme]], [[1p0v]], [[1p0w]], [[1p0x]], [[1smi]], [[1yqp]], [[1yqo]], [[1zo4]], [[2nnb]], [[4hgj]], [[4h23]], [[4h24]], [[4kpb]], [[4kf0]], [[4kf2]] - BmP450 heme domain (mutant)<br />
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[[4dtw]], [[4due]], [[4duf]] - BmP450 heme domain (mutant) + serotonin<br />
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[[4dtz]], [[4du2]], [[4dub]] - BmP450 heme domain (mutant) + dopamine<br />
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[[1jpz]], [[1zo9]], [[1zoa]], [[4kpa]] - BmP450 heme domain + palmitate derivative<br />
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[[1smj]] - BmP450 heme domain (mutant) + palmitoleate<br />
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[[2x7y]], [[2x80]] - BmP450 heme domain (mutant) + DMSO<br />
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[[4hgf]], [[4hgg]], [[4hgh]], [[4hgi]] - BmP450 heme domain (mutant) + styrene<br />
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[[4kew]], [[4key]] - BmP450 heme domain (mutant) + omeprazole<br />
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[[3ekb]], [[3ekd]], [[3ekf]], [[2ij3]], [[2ij4]] - BmP450102 heme domain (mutant)<br />
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[[2ij2]], [[2hpd]] - BmP450102 heme domain<br />
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[[4dqk]] - BmP450 FAD domain + FAD<br />
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[[4dql]] - BmP450 FAD domain + NADP + FAD<br />
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[[2uwh]] - BmP450102+palmitic acid<br />
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[[3ben]] - BmP450102 + imidazole derivative<br />
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[[2j1m]], [[2j4s]] - BmP450102+DMSO<br />
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[[1bvy]], [[1bu7]] – BmP450102A1 FMN domain<br />
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[[1fag]] – BmP450102A1+ palmitic acid<br />
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[[1fah]] – BmP450102A1 (mutant)<br />
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[[2bmh]] - BmP450102A1<br />
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=== Other CYPs ===
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[[1ued]] – AoP450 oxyC – ''Amycolatopsis orientalis''<br />
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-
[[1lfk]], [[1lg9]], [[1lgf]] - AoP450 oxyB<br />
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[[1q5d]] – ScP450EPOK+epothilone – ''Sorangium cellulosum''<br />
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[[1q5e]] - ScP450EPOK<br />
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[[1io8]] – SsP450119 (mutant) – ''Sulfolobus solfataricus''<br />
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[[1io9]], [[1io7]], [[1f4u]] - SsP450119<br />
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[[1f4t]] - SsP450119+ phenylimidazole<br />
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[[1cpt]] – P450108 – ''Pseudomonas sp.''<br />
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[[4l0e]], [[4l0f]] - P450 SKY32– ''Streptomyces''<br />
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[[3aba]] – SaP450105P1+filipin I – ''Streptomyces avermitilis''<br />
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[[3abb]] – SaP450105D6<br />
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[[3e5j]], [[3e5l]] - SaP450105P1 (mutant)<br />
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[[3e5k]] - SaP450105P1 (mutant)+4-phenylimidazole<br />
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[[2whw]], [[2wi9]], [[2vz7]] – SvP450107L1 (mutant) – ''Streptomyces venezuelae''<br />
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[[2vzm]] – SvP450107L1 (mutant)+narbomycin<br />
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[[2c7x]] - SvP450107L1+narbomycin<br />
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[[2cd8]], [[2ca0]], [[2c6h]] – SvP450107L1+YC-17<br />
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[[2bvj]] - SvP450107L1<br />
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[[3p3l]], [[3p3o]], [[3p3x]], [[3p3z]] – P450 – ''Streptomyces thioluteus''<br />
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[[2zqj]] – BsP450152A1 – ''Bacillus subtilis''<br />
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[[2zqx]] - BsP450152A1+heptanoic acid<br />
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[[3nc3]], [[3nc5]], [[3nc6]], [[3nc7]] - BsP450134A1 (mutant)<br />
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[[1izo]] – BsP450 BS beta+ palmitoleic acid<br />
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[[1jin]], [[1jip]] - SeP450107A1+ ketoconazole - ''Saccharopolyspora erythraea''<br />
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[[1jio]], [[1oxa]] - SeP450107A1+6DEB<br />
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[[1eup]] – SeP450107A1+androstendione<br />
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[[1egy]] - SeP450107A1+aminophenanthrene<br />
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[[2jjn]], [[2jjo]] - SeP450113A1 (mutant)<br />
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[[2jjp]] - SeP450113A1 (mutant)+ketoconazole<br />
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[[2vrv]] - SeP450113A1 (mutant)+clotrimazole<br />
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[[3a1l]] – SsP450245A1+dichlorochrompyrrolic acid – ''Streptomyces sp.''<br />
+
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[[2z3t]] - SsP450245A1<br />
+
-
[[2z3u]] - SsP450245A1+chromopyrrolic acid<br />
+
-
[[3cv8]] – SgP450105A1 (mutant) – ''Streptomyces griseolus''<br />
+
-
[[3cv9]], [[2zbz]] - SgP450105A1 (mutant)+vitamin D3<br />
+
-
[[2zbx]] - SgP450105A1+imidazole<br />
+
-
[[3dam]], [[3dan]], [[3dbm]] – P45074A2 – ''Parthenium argentatum''<br />
+
-
[[2rch]], [[3dsi]] – AtP45074A+13(S)-HOD – ''Arabidopsis thaliana''<br />
+
-
[[3dsj]] - AtP45074A (mutant)+13(S)-HOD<br />
+
-
[[2rcl]] - AtP45074A+vernolic acid<br />
+
-
[[3dsk]] - AtP45074A (mutant)+ vernolic acid<br />
+
-
[[2rcm]], [[3cli]] - AtP45074A<br />
+
-
[[3r9b]] – MsP45016A2 – ''Mycobacterium smegmatis''<br />
+
-
[[3r9c]] – MsP45016A2 + econazole<br />
+
-
[[2rfb]] – PtP450 – ''Picrophilus torridus''<br />
+
-
[[2rfc]] – PtP450+phenylimidazole<br />
+
-
[[2nz5]], [[2nza]], [[2dkk]] – ScP450158A1 – ''Streptomyces coelicolor''<br />
+
-
[[1gwi]] - ScP450154C1<br />
+
-
[[1wiy]] – TtP450 – ''Thermus thermophilus''<br />
+
-
[[1n97]] – TtP450175A1<br />
+
-
[[3nv5]], [[3nv6]], [[4dxy]] - NaP240101D2<br />
+
-
[[3tkt]] – NaP450108D1<br />
+
-
[[3awm]] – SpP450-α + palmitic acid – ''Sphingomonas paucimobilis''<br />
+
-
[[3awp]], [[3awq]] - SpP450-α (mutant)<br />
+
-
[[3qoa]], [[2qu8]], [[3qu8]] – hP450 2b6 (mutant) + inhibitor<br />
+
-
[[3a4g]], [[3a4h]] – PaP450 VDH – ''Pseudonocardia autotrophica''<br />
+
-
[[3a4z]] - PaP450 VDH (mutant)<br />
+
-
[[3a50]], [[3a51]] - PaP450 VDH (mutant) + vitamin D3<br />
+
-
[[3qi8]] – P450 – synthetic<br />
+
-
[[4dnz]] – RpP450199A4 – ''Rhodopseudomonas palustris''<br />
+
-
[[4do1]], [[4egm]] – RpP450199A4 + benzoate derivative<br />
+
-
[[4egn]] – RpP450199A4 + veratric acid<br />
+
-
[[4egp]] – RpP450199A4 + naphthoic acid<br />
+
-
[[4ego]] – RpP450199A4 + indole derivative<br />
+
-
[[3o1a]] – P450 165D3 – ''Actinoplanes teichomyceticus''<br />
+
-
[[3wec]] – P450 + dihydroxy-aurachin Re – ''Rhodococcus erythropolis''<br />
+
 +
== References ==
 +
<references/>
[[Category:Topic Page]]
[[Category:Topic Page]]

Current revision

Cytochrome P450 CypC2 with heme C complex with warfarin (PDB entry 1og5)

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References

  1. ↑ Danielson PB. The cytochrome P450 superfamily: biochemistry, evolution and drug metabolism in humans. Curr Drug Metab. 2002 Dec;3(6):561-97. PMID:12369887
  2. ↑ Williams PA, Cosme J, Ward A, Angove HC, Matak Vinkovic D, Jhoti H. Crystal structure of human cytochrome P450 2C9 with bound warfarin. Nature. 2003 Jul 24;424(6947):464-8. Epub 2003 Jul 13. PMID:12861225 doi:http://dx.doi.org/10.1038/nature01862

Proteopedia Page Contributors and Editors (what is this?)

Michal Harel, Alexander Berchansky, Joel L. Sussman

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