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Ligands
Code Name Style Show Link
FZV Tert-butyl [(2s)-1-{[(2r)-1-oxo-3-phenyl-1-{[2-(pyridin-3-yl)ethyl]amino}propan-2-yl]sulfanyl}-3-phenylpropan-2-yl]carbamate
HEM Protoporphyrin ix containing Fe
Non-standard Residues
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Code : 6DAC   PDBj   RCSB PDB   PDBe
Header : OXIDOREDUCTASE/OXIDOREDUCTASE INHIBITOR
Title : Human CYP3A4 bound to an inhibitor
Release Data : 2019-04-03
Compound :
mol_id molecule chains synonym
1 Cytochrome P450 3A4 A 1,8-cineole 2-exo-monooxygenase,Albendazole monooxygenase,Albendazole sulfoxidase,CYPIIIA3,CYPIIIA4,Cholesterol 25-hydroxylase,Cytochrome P450 3A3,Cytochrome P450 HLp,Cytochrome P450 NF-25,Cytochrome P450-PCN1,Nifedipine oxidase,Quinine 3-monooxygenase,Taurochenodeoxycholate 6-alpha-hydroxylase
ec: 1.14.14.-,1.14.14.56,1.14.14.55
fragment: residues 23-503
Source :
mol_id organism_scientific organism_common expression_system
1 Homo sapiens  (taxid:9606) Human Escherichia coli  (taxid:562)
gene: CYP3A4, CYP3A3
Authors : Sevrioukova, I.F.
Keywords : OXIDOREDUCTASE, OXIDOREDUCTASE-OXIDOREDUCTASE INHIBITOR complex
Exp. method : X-RAY DIFFRACTION ( 2.550 Å )
Citation :

Structure-Activity Relationships of Rationally Designed Ritonavir Analogues: Impact of Side-Group Stereochemistry, Headgroup Spacing, and Backbone Composition on the Interaction with CYP3A4.

Samuels, E.R.,Sevrioukova, I.
(2019)  Biochemistry  58 : 2077 - 2087

PubMed: 30912932
DOI: 10.1021/acs.biochem.9b00156

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