Brand  (β version)

PDB ID: 3NXU

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Ligands
Code Name Style Show Link
DMS Dimethyl sulfoxide PoSSuM
HEM Protoporphyrin ix containing Fe PoSSuM
RIT Ritonavir PoSSuM
Non-standard Residues
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Glycosylation
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Structure summary

Code : 3NXU   PDBj   RCSB PDB   PDBe
Header : OXIDOREDUCTASE/OXIDOREDUCTASE INHIBITOR
Title : Crystal structure of human cytochrome P4503A4 bound to an inhibitor ritonavir
Release Data : 2010-10-20
Compound :
mol_id molecule chains synonym
1 Cytochrome P450 3A4 A,B Quinine 3-monooxygenase, CYPIIIA4, Nifedipine oxidase, Cytochrome P450 3A3, CYPIIIA3, Cytochrome P450 HLp, Taurochenodeoxycholate 6-alpha-hydroxylase, Cytochrome P450 NF-25, Cytochrome P450-PCN1, Albendazole monooxygenase, Albendazole sulfoxidase
ec: 1.14.13.67, 1.14.13.97, 1.14.13.32
fragment: UNP residues 1-2 and 25-503
Source :
mol_id organism_scientific organism_common expression_system
1 Homo sapiens  (taxid:9606) Human Escherichia coli  (taxid:469008)
gene: CYP3A3, CYP3A4
expression_system_strain: BL21(DE3)
Authors : Sevrioukova, I.F., Poulos, T.L.
Keywords : alpha beta protein, cytochrome P450 fold, hemoprotein, monooxygenase, cytochrome P450 reductase, endoplasmic reticulum, OXIDOREDUCTASE-OXIDOREDUCTASE INHIBITOR complex
Exp. method : X-RAY DIFFRACTION ( 2.0 Å )
Citation :

Structure and mechanism of the complex between cytochrome P4503A4 and ritonavir.

Sevrioukova, I.F.,Poulos, T.L.
(2010)  Proc.Natl.Acad.Sci.USA  107 : 18422 - 18427

PubMed: 20937904
DOI: 10.1073/pnas.1010693107

Reaction

Chain : A, B
UniProt : P08684 (CP3A4_HUMAN)
Reaction: EC: Evidence:
Physiological Direction:
an organic molecule + reduced [NADPH--hemoprotein reductase] + O2 = an alcohol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) 1.14.14.1 PubMed:11555828, PubMed:12865317, PubMed:2732228, PubMed:9435160
left-to-right
17beta-estradiol + reduced [NADPH--hemoprotein reductase] + O2 = 2-hydroxy-17beta-estradiol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:11555828, PubMed:12865317
left-to-right
17beta-estradiol + reduced [NADPH--hemoprotein reductase] + O2 = 4-hydroxy-17beta-estradiol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:12865317
left-to-right
17beta-estradiol + reduced [NADPH--hemoprotein reductase] + O2 = 16alpha,17beta-estriol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:12865317, PubMed:14559847
left-to-right
17beta-estradiol + reduced [NADPH--hemoprotein reductase] + O2 = 16beta,17beta-estriol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:12865317
left-to-right
estrone + reduced [NADPH--hemoprotein reductase] + O2 = 2- hydroxyestrone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:12865317
left-to-right
estrone + reduced [NADPH--hemoprotein reductase] + O2 = 4- hydroxyestrone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:12865317
left-to-right
estrone + reduced [NADPH--hemoprotein reductase] + O2 = 16alpha-hydroxyestrone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:12865317, PubMed:14559847
left-to-right
testosterone + reduced [NADPH--hemoprotein reductase] + O2 = 1beta-hydroxytestosterone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:15373842
left-to-right
testosterone + reduced [NADPH--hemoprotein reductase] + O2 = 2beta-hydroxytestosterone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:15373842
left-to-right
testosterone + reduced [NADPH--hemoprotein reductase] + O2 = 6beta,17beta-dihydroxyandrost-4-en-3-one + oxidized [NADPH-- hemoprotein reductase] + H2O + H(+) - PubMed:15764715, PubMed:20702771, PubMed:2732228
left-to-right PubMed:2732228
testosterone + reduced [NADPH--hemoprotein reductase] + O2 = 11beta,17beta-dihydroxyandrost-4-ene-3-one + oxidized [NADPH-- hemoprotein reductase] + H2O + H(+) - PubMed:15764715
left-to-right
17beta-hydroxy-5alpha-androstan-3-one + reduced [NADPH-- hemoprotein reductase] + O2 = 17beta,18-dihydroxy-3-oxo-5alpha- androstanone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:22773874
left-to-right
17beta-hydroxy-5alpha-androstan-3-one + reduced [NADPH-- hemoprotein reductase] + O2 = 17beta,19-dihydroxy-3-oxo-5alpha- androstanone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:22773874
left-to-right
androst-4-ene-3,17-dione + reduced [NADPH--hemoprotein reductase] + O2 = 6beta-hydroxyandrost-4-ene-3,17-dione + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:2732228
left-to-right
progesterone + reduced [NADPH--hemoprotein reductase] + O2 = 6beta-hydroxyprogesterone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:2732228
left-to-right
progesterone + reduced [NADPH--hemoprotein reductase] + O2 = 16alpha-hydroxyprogesterone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:2732228
left-to-right
cortisone + reduced [NADPH--hemoprotein reductase] + O2 = 6beta-hydroxycortisone + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:21490593
left-to-right
cortisol + reduced [NADPH--hemoprotein reductase] + O2 = 6beta-hydroxycortisol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:21490593
left-to-right
cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = 25-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:21576599
left-to-right
cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = 4beta-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:21576599
left-to-right
cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (22R)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:21576599
left-to-right
cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = (24R)-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:21576599
left-to-right
cholesterol + reduced [NADPH--hemoprotein reductase] + O2 = 26-hydroxycholesterol + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:21576599
left-to-right
(9Z,12Z)-octadecadienoate + reduced [NADPH--hemoprotein reductase] + O2 = 11-hydroxy-(9Z,12Z)-octadecadienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:9435160
left-to-right
(5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH-- hemoprotein reductase] + O2 = 7-hydroxy-(5Z,8Z,11Z,14Z)- eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:9435160
left-to-right
(5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH-- hemoprotein reductase] + O2 = 10-hydroxy-(5Z,8Z,11Z,14Z)- eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:9435160
left-to-right
(5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH-- hemoprotein reductase] + O2 = 13-hydroxy-(5Z,8Z,11Z,14Z)- eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:9435160
left-to-right
(5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH-- hemoprotein reductase] + O2 = (14R,15S)-epoxy-(5Z,8Z,11Z)- eicosatrienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:19965576
left-to-right
(5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH-- hemoprotein reductase] + O2 = (14S,15R)-epoxy-(5Z,8Z,11Z)- eicosatrienoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:19965576
left-to-right
(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + reduced [NADPH-- hemoprotein reductase] + O2 = (17R,18S)-epoxy-(5Z,8Z,11Z,14Z)- eicosatetraenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:19965576
left-to-right
(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + reduced [NADPH-- hemoprotein reductase] + O2 = (19R,20S)-epoxy-(4Z,7Z,10Z,13Z,16Z)- docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:19965576
left-to-right
(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + reduced [NADPH-- hemoprotein reductase] + O2 = (19S,20R)-epoxy-(4Z,7Z,10Z,13Z,16Z)- docosapentaenoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:19965576
left-to-right
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + reduced [NADPH--hemoprotein reductase] + O2 = N-(8,9-epoxy-5Z,11Z,14Z- eicosatrienoyl)-ethanolamine + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:20702771
left-to-right
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + reduced [NADPH--hemoprotein reductase] + O2 = N-(11,12-epoxy-5Z,8Z,14Z- eicosatrienoyl)-ethanolamine + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:20702771
left-to-right
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine + reduced [NADPH--hemoprotein reductase] + O2 = N-(14,15-epoxy-5Z,8Z,11Z- eicosatrienoyl)-ethanolamine + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:20702771
left-to-right
all-trans-retinol + reduced [NADPH--hemoprotein reductase] + O2 = all-trans-retinal + oxidized [NADPH--hemoprotein reductase] + 2 H2O + H(+) - PubMed:10681376
left-to-right
all-trans-retinoate + reduced [NADPH--hemoprotein reductase] + O2 = all-trans-4-hydroxyretinoate + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:11093772
left-to-right
quinine + reduced [NADPH--hemoprotein reductase] + O2 = 3- hydroxyquinine + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) 1.14.14.55 PubMed:8968357
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fenbendazole + reduced [NADPH--hemoprotein reductase] + O2 = fenbendazole S-oxide + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) 1.14.14.73 PubMed:10759686
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albendazole + reduced [NADPH--hemoprotein reductase] + O2 = albendazole S-oxide + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) 1.14.14.73 PubMed:10759686
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1,8-cineole + reduced [NADPH--hemoprotein reductase] + O2 = 2- exo-hydroxy-1,8-cineole + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) 1.14.14.56 PubMed:11159812
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1,4-cineole + reduced [NADPH--hemoprotein reductase] + O2 = 2- exo-hydroxy-1,4-cineole + oxidized [NADPH--hemoprotein reductase] + H2O + H(+) - PubMed:11695850
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Cofactor: Evidence: Note:
heme ECO:0000269 | PubMed:15256616
ECO:0000269 | PubMed:15258162
-