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Literature summary for 1.14.15.4 extracted from

  • Voets, M.; Antes, I.; Scherer, C.; Mueller-Vieira, U.; Biemel, K.; Marchais-Oberwinkler, S.; Hartmann, R.W.
    Synthesis and evaluation of heteroaryl-substituted dihydronaphthalenes and indenes: potent and selective inhibitors of aldosterone synthase (CYP11B2) for the treatment of congestive heart failure and myocardial fibrosis (2006), J. Med. Chem., 49, 2222-2231.
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
expression of CYP11B2 in Schizosaccharomyces pombe and in V79 MZh cells Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
1-(1H-inden-2-yl)-1H-imidazole CYP11B2 IC50: 448 nM, no inhibition of CYP11B1, recombinant enzymes Homo sapiens
1-(3,4-dihydronaphthalen-2-yl)-1H-imidazole CYP11B1 IC50: 639 nM, CYP11B2 IC50: 334 nM, recombinant enzymes Homo sapiens
1-(6-methoxy-3,4-dihydronaphthalen-2-yl)-1H-imidazole CYP11B1 IC50: 763 nM, CYP11B2 IC50: 411 nM, recombinant enzymes Homo sapiens
3-(1-ethyl-3,4-dihydronaphthalen-2-yl)-pyridine CYP11B1 IC50: 2117 nM, CYP11B2 IC50: 30 nM, recombinant enzymes Homo sapiens
3-(1-methyl-3,4-dihydronaphthalen-2-yl)-pyridine CYP11B1 IC50: 1268 nM, CYP11B2 IC50: 7 nM, recombinant enzymes Homo sapiens
3-(3,4-dihydronaphthalen-2-yl)pyridine CYP11B1 IC50: 1729 nM, CYP11B2 IC50: 7 nM, recombinant enzymes Homo sapiens
3-(3-methyl-3,4-dihydronaphthalen-2-yl)pyridine CYP11B1 IC50: 503 nM, CYP11B2 IC50: 5 nM, recombinant enzymes Homo sapiens
3-(4-ethyl-3,4-dihydronaphthalen-2-yl)pyridine CYP11B1 IC50: 1615 nM, CYP11B2 IC50: 176 nM, recombinant enzymes Homo sapiens
3-(4-methyl-3,4-dihydronaphthalen-2-yl)pyridine CYP11B1 IC50: 1291 nM, CYP11B2 IC50: 13 nM, recombinant enzymes Homo sapiens
3-(6-methoxy-1H-inden-2-yl)pyridine competitive, CYP11B1 IC50: 5684 nM, CYP11B2 IC50: 4 nM, recombinant enzymes Homo sapiens
3-(6-methoxy-3,4-dihydronaphthalen-2-yl)pyridine competitive, CYP11B1 IC50: 578 nM, CYP11B2 IC50: 2 nM, recombinant enzymes Homo sapiens
3-(7-methoxy-3,4-dihydronaphthalen-2-yl)pyridine CYP11B2 IC50: 45 nM, no inhibition of CYP11B1, recombinant enzymes Homo sapiens
3-[(Z)-2-phenylvinyl]pyridine CYP11B1 IC50: 288 nM, CYP11B2 IC50: 735 nM, no inhibition by the 3-[(E)-2-phenylvinyl]pyridine isomer, recombinant enzymes Homo sapiens
4-(6-methoxy-3,4-dihydronaphthalen-2-yl)pyridine CYP11B1 IC50: 2529 nM, CYP11B2 IC50: 2834 nM, recombinant enzymes Homo sapiens
6-methoxydihydronaphthalene
-
Homo sapiens
atenolol potent inhibition of CYP11B2, recombinant enzyme Homo sapiens
erythromycin potent inhibition of CYP11B2, recombinant enzyme Homo sapiens
fadrozole CYP11B2 IC50: 1 nM, CYP11B1 IC50: 10 nM, recombinant enzymes Homo sapiens
ketoconazole CYP11B2 IC50: 81 nM, CYP11B1 IC50: 224 nM, recombinant enzymes Homo sapiens
ketoprofene potent inhibition of CYP11B2, recombinant enzyme Homo sapiens
additional information synthesis and evaluation of heteroaryl-substituted dihydronaphthalenes and indenes: potent and selective inhibitors of CYP11B2 for the treatment of congestive heart failure and myocardial fibrosis, ligand-protein interactions, docking and molecular dynamics studies using homology-modeled CYP11B2 structure, overview Homo sapiens
testosterone potent inhibition of CYP11B2, recombinant enzyme Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
11-deoxycortisol + reduced adrenal ferredoxin + O2 Homo sapiens CYP11B1 cortisol + oxidized adrenal ferredoxin + H2O
-
?
18-hydroxycorticosterone + reduced adrenal ferredoxin + O2 Homo sapiens CYP11B2 aldosterone + oxidized adrenal ferredoxin + H2O
-
?

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
11-deoxycortisol + reduced adrenal ferredoxin + O2 CYP11B1 Homo sapiens cortisol + oxidized adrenal ferredoxin + H2O
-
?
18-hydroxycorticosterone + reduced adrenal ferredoxin + O2 CYP11B2 Homo sapiens aldosterone + oxidized adrenal ferredoxin + H2O
-
?

Synonyms

Synonyms Comment Organism
Aldosterone synthase
-
Homo sapiens
CYP11B1
-
Homo sapiens
CYP11B2
-
Homo sapiens

Cofactor

Cofactor Comment Organism Structure
reduced adrenal ferredoxin
-
Homo sapiens

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.0000013
-
6-methoxydihydronaphthalene recombinant enzyme Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000001
-
CYP11B2 IC50: 1 nM Homo sapiens fadrozole
0.000002
-
CYP11B2 IC50: 2 nM, recombinant enzymes Homo sapiens 3-(6-methoxy-3,4-dihydronaphthalen-2-yl)pyridine
0.000004
-
CYP11B2 IC50: 4 nM, recombinant enzymes Homo sapiens 3-(6-methoxy-1H-inden-2-yl)pyridine
0.000005
-
CYP11B2 IC50: 5 nM, recombinant enzymes Homo sapiens 3-(3-methyl-3,4-dihydronaphthalen-2-yl)pyridine
0.000007
-
CYP11B2 IC50: 7 nM, recombinant enzymes Homo sapiens 3-(3,4-dihydronaphthalen-2-yl)pyridine
0.000007
-
CYP11B2 IC50: 7 nM, recombinant enzymes Homo sapiens 3-(1-methyl-3,4-dihydronaphthalen-2-yl)-pyridine
0.00001
-
CYP11B1 IC50: 10 nM, recombinant enzymes Homo sapiens fadrozole
0.000013
-
, CYP11B2 IC50: 13 nM, recombinant enzymes Homo sapiens 3-(4-methyl-3,4-dihydronaphthalen-2-yl)pyridine
0.00003
-
CYP11B2 IC50: 30 nM, recombinant enzymes Homo sapiens 3-(1-ethyl-3,4-dihydronaphthalen-2-yl)-pyridine
0.000045
-
CYP11B2 IC50: 45 nM, no inhibition of CYP11B1, recombinant enzymes Homo sapiens 3-(7-methoxy-3,4-dihydronaphthalen-2-yl)pyridine
0.000081
-
CYP11B2 IC50: 81 nM Homo sapiens ketoconazole
0.000176
-
CYP11B2 IC50: 176 nM, recombinant enzymes Homo sapiens 3-(4-ethyl-3,4-dihydronaphthalen-2-yl)pyridine
0.000224
-
IC50 CYP11B1 IC50: 224 nM, recombinant enzymes Homo sapiens ketoconazole
0.000288
-
CYP11B1 IC50: 288 nM Homo sapiens 3-[(Z)-2-phenylvinyl]pyridine
0.000334
-
CYP11B2 IC50: 334 nM, recombinant enzymes Homo sapiens 1-(3,4-dihydronaphthalen-2-yl)-1H-imidazole
0.000411
-
CYP11B2 IC50: 411 nM, recombinant enzymes Homo sapiens 1-(6-methoxy-3,4-dihydronaphthalen-2-yl)-1H-imidazole
0.000448
-
CYP11B2 IC50: 448 nM, no inhibition of CYP11B1, recombinant enzymes Homo sapiens 1-(1H-inden-2-yl)-1H-imidazole
0.000503
-
CYP11B1 IC50: 503 nM Homo sapiens 3-(3-methyl-3,4-dihydronaphthalen-2-yl)pyridine
0.000578
-
competitive, CYP11B1 IC50: 578 nM Homo sapiens 3-(6-methoxy-3,4-dihydronaphthalen-2-yl)pyridine
0.000639
-
CYP11B1 IC50: 639 nM Homo sapiens 1-(3,4-dihydronaphthalen-2-yl)-1H-imidazole
0.000735
-
CYP11B2 IC50: 735 nM, no inhibition by the 3-[(E)-2-phenylvinyl]pyridine isomer, recombinant enzymes Homo sapiens 3-[(Z)-2-phenylvinyl]pyridine
0.000763
-
CYP11B1 IC50: 763 nM Homo sapiens 1-(6-methoxy-3,4-dihydronaphthalen-2-yl)-1H-imidazole
0.001268
-
CYP11B1 IC50: 1268 nM Homo sapiens 3-(1-methyl-3,4-dihydronaphthalen-2-yl)-pyridine
0.001291
-
CYP11B1 IC50: 1291 nM Homo sapiens 3-(4-methyl-3,4-dihydronaphthalen-2-yl)pyridine
0.001615
-
CYP11B1 IC50: 1615 nM Homo sapiens 3-(4-ethyl-3,4-dihydronaphthalen-2-yl)pyridine
0.001729
-
CYP11B1 IC50: 1729 nM Homo sapiens 3-(3,4-dihydronaphthalen-2-yl)pyridine
0.002117
-
CYP11B1 IC50: 2117 nM Homo sapiens 3-(1-ethyl-3,4-dihydronaphthalen-2-yl)-pyridine
0.002529
-
CYP11B1 IC50: 2529 nM Homo sapiens 4-(6-methoxy-3,4-dihydronaphthalen-2-yl)pyridine
0.002834
-
CYP11B2 IC50: 2834 nM, recombinant enzymes Homo sapiens 4-(6-methoxy-3,4-dihydronaphthalen-2-yl)pyridine
0.005684
-
competitive, CYP11B1 IC50: 5684 nM Homo sapiens 3-(6-methoxy-1H-inden-2-yl)pyridine