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Literature summary 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)

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

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.14.15.4 1-(1H-inden-2-yl)-1H-imidazole CYP11B2 IC50: 448 nM, no inhibition of CYP11B1, recombinant enzymes Homo sapiens
1.14.15.4 1-(3,4-dihydronaphthalen-2-yl)-1H-imidazole CYP11B1 IC50: 639 nM, CYP11B2 IC50: 334 nM, recombinant enzymes Homo sapiens
1.14.15.4 1-(6-methoxy-3,4-dihydronaphthalen-2-yl)-1H-imidazole CYP11B1 IC50: 763 nM, CYP11B2 IC50: 411 nM, recombinant enzymes Homo sapiens
1.14.15.4 3-(1-ethyl-3,4-dihydronaphthalen-2-yl)-pyridine CYP11B1 IC50: 2117 nM, CYP11B2 IC50: 30 nM, recombinant enzymes Homo sapiens
1.14.15.4 3-(1-methyl-3,4-dihydronaphthalen-2-yl)-pyridine CYP11B1 IC50: 1268 nM, CYP11B2 IC50: 7 nM, recombinant enzymes Homo sapiens
1.14.15.4 3-(3,4-dihydronaphthalen-2-yl)pyridine CYP11B1 IC50: 1729 nM, CYP11B2 IC50: 7 nM, recombinant enzymes Homo sapiens
1.14.15.4 3-(3-methyl-3,4-dihydronaphthalen-2-yl)pyridine CYP11B1 IC50: 503 nM, CYP11B2 IC50: 5 nM, recombinant enzymes Homo sapiens
1.14.15.4 3-(4-ethyl-3,4-dihydronaphthalen-2-yl)pyridine CYP11B1 IC50: 1615 nM, CYP11B2 IC50: 176 nM, recombinant enzymes Homo sapiens
1.14.15.4 3-(4-methyl-3,4-dihydronaphthalen-2-yl)pyridine CYP11B1 IC50: 1291 nM, CYP11B2 IC50: 13 nM, recombinant enzymes Homo sapiens
1.14.15.4 3-(6-methoxy-1H-inden-2-yl)pyridine competitive, CYP11B1 IC50: 5684 nM, CYP11B2 IC50: 4 nM, recombinant enzymes Homo sapiens
1.14.15.4 3-(6-methoxy-3,4-dihydronaphthalen-2-yl)pyridine competitive, CYP11B1 IC50: 578 nM, CYP11B2 IC50: 2 nM, recombinant enzymes Homo sapiens
1.14.15.4 3-(7-methoxy-3,4-dihydronaphthalen-2-yl)pyridine CYP11B2 IC50: 45 nM, no inhibition of CYP11B1, recombinant enzymes Homo sapiens
1.14.15.4 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
1.14.15.4 4-(6-methoxy-3,4-dihydronaphthalen-2-yl)pyridine CYP11B1 IC50: 2529 nM, CYP11B2 IC50: 2834 nM, recombinant enzymes Homo sapiens
1.14.15.4 6-methoxydihydronaphthalene
-
 Homo sapiens
1.14.15.4 atenolol potent inhibition of CYP11B2, recombinant enzyme Homo sapiens
1.14.15.4 erythromycin potent inhibition of CYP11B2, recombinant enzyme Homo sapiens
1.14.15.4 fadrozole CYP11B2 IC50: 1 nM, CYP11B1 IC50: 10 nM, recombinant enzymes Homo sapiens
1.14.15.4 ketoconazole CYP11B2 IC50: 81 nM, CYP11B1 IC50: 224 nM, recombinant enzymes Homo sapiens
1.14.15.4 ketoprofene potent inhibition of CYP11B2, recombinant enzyme Homo sapiens
1.14.15.4 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
1.14.15.4 testosterone potent inhibition of CYP11B2, recombinant enzyme Homo sapiens

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.15.4 11-deoxycortisol + reduced adrenal ferredoxin + O2 Homo sapiens CYP11B1 cortisol + oxidized adrenal ferredoxin + H2O
-
 ?
1.14.15.4 18-hydroxycorticosterone + reduced adrenal ferredoxin + O2 Homo sapiens CYP11B2 aldosterone + oxidized adrenal ferredoxin + H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.14.15.4 Homo sapiens
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.15.4 11-deoxycortisol + reduced adrenal ferredoxin + O2 CYP11B1 Homo sapiens cortisol + oxidized adrenal ferredoxin + H2O
-
 ?
1.14.15.4 18-hydroxycorticosterone + reduced adrenal ferredoxin + O2 CYP11B2 Homo sapiens aldosterone + oxidized adrenal ferredoxin + H2O
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.15.4 Aldosterone synthase
-
 Homo sapiens
1.14.15.4 CYP11B1
-
 Homo sapiens
1.14.15.4 CYP11B2
-
 Homo sapiens

Cofactor

EC Number Cofactor Comment Organism Structure
1.14.15.4 reduced adrenal ferredoxin
-
 Homo sapiens

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
1.14.15.4 0.0000013
-
 6-methoxydihydronaphthalene recombinant enzyme Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.14.15.4 0.000001
-
 CYP11B2 IC50: 1 nM Homo sapiens fadrozole
1.14.15.4 0.000002
-
 CYP11B2 IC50: 2 nM, recombinant enzymes Homo sapiens 3-(6-methoxy-3,4-dihydronaphthalen-2-yl)pyridine
1.14.15.4 0.000004
-
 CYP11B2 IC50: 4 nM, recombinant enzymes Homo sapiens 3-(6-methoxy-1H-inden-2-yl)pyridine
1.14.15.4 0.000005
-
 CYP11B2 IC50: 5 nM, recombinant enzymes Homo sapiens 3-(3-methyl-3,4-dihydronaphthalen-2-yl)pyridine
1.14.15.4 0.000007
-
 CYP11B2 IC50: 7 nM, recombinant enzymes Homo sapiens 3-(3,4-dihydronaphthalen-2-yl)pyridine
1.14.15.4 0.000007
-
 CYP11B2 IC50: 7 nM, recombinant enzymes Homo sapiens 3-(1-methyl-3,4-dihydronaphthalen-2-yl)-pyridine
1.14.15.4 0.00001
-
 CYP11B1 IC50: 10 nM, recombinant enzymes Homo sapiens fadrozole
1.14.15.4 0.000013
-
 , CYP11B2 IC50: 13 nM, recombinant enzymes Homo sapiens 3-(4-methyl-3,4-dihydronaphthalen-2-yl)pyridine
1.14.15.4 0.00003
-
 CYP11B2 IC50: 30 nM, recombinant enzymes Homo sapiens 3-(1-ethyl-3,4-dihydronaphthalen-2-yl)-pyridine
1.14.15.4 0.000045
-
 CYP11B2 IC50: 45 nM, no inhibition of CYP11B1, recombinant enzymes Homo sapiens 3-(7-methoxy-3,4-dihydronaphthalen-2-yl)pyridine
1.14.15.4 0.000081
-
 CYP11B2 IC50: 81 nM Homo sapiens ketoconazole
1.14.15.4 0.000176
-
 CYP11B2 IC50: 176 nM, recombinant enzymes Homo sapiens 3-(4-ethyl-3,4-dihydronaphthalen-2-yl)pyridine
1.14.15.4 0.000224
-
 IC50 CYP11B1 IC50: 224 nM, recombinant enzymes Homo sapiens ketoconazole
1.14.15.4 0.000288
-
 CYP11B1 IC50: 288 nM Homo sapiens 3-[(Z)-2-phenylvinyl]pyridine
1.14.15.4 0.000334
-
 CYP11B2 IC50: 334 nM, recombinant enzymes Homo sapiens 1-(3,4-dihydronaphthalen-2-yl)-1H-imidazole
1.14.15.4 0.000411
-
 CYP11B2 IC50: 411 nM, recombinant enzymes Homo sapiens 1-(6-methoxy-3,4-dihydronaphthalen-2-yl)-1H-imidazole
1.14.15.4 0.000448
-
 CYP11B2 IC50: 448 nM, no inhibition of CYP11B1, recombinant enzymes Homo sapiens 1-(1H-inden-2-yl)-1H-imidazole
1.14.15.4 0.000503
-
 CYP11B1 IC50: 503 nM Homo sapiens 3-(3-methyl-3,4-dihydronaphthalen-2-yl)pyridine
1.14.15.4 0.000578
-
 competitive, CYP11B1 IC50: 578 nM Homo sapiens 3-(6-methoxy-3,4-dihydronaphthalen-2-yl)pyridine
1.14.15.4 0.000639
-
 CYP11B1 IC50: 639 nM Homo sapiens 1-(3,4-dihydronaphthalen-2-yl)-1H-imidazole
1.14.15.4 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
1.14.15.4 0.000763
-
 CYP11B1 IC50: 763 nM Homo sapiens 1-(6-methoxy-3,4-dihydronaphthalen-2-yl)-1H-imidazole
1.14.15.4 0.001268
-
 CYP11B1 IC50: 1268 nM Homo sapiens 3-(1-methyl-3,4-dihydronaphthalen-2-yl)-pyridine
1.14.15.4 0.001291
-
 CYP11B1 IC50: 1291 nM Homo sapiens 3-(4-methyl-3,4-dihydronaphthalen-2-yl)pyridine
1.14.15.4 0.001615
-
 CYP11B1 IC50: 1615 nM Homo sapiens 3-(4-ethyl-3,4-dihydronaphthalen-2-yl)pyridine
1.14.15.4 0.001729
-
 CYP11B1 IC50: 1729 nM Homo sapiens 3-(3,4-dihydronaphthalen-2-yl)pyridine
1.14.15.4 0.002117
-
 CYP11B1 IC50: 2117 nM Homo sapiens 3-(1-ethyl-3,4-dihydronaphthalen-2-yl)-pyridine
1.14.15.4 0.002529
-
 CYP11B1 IC50: 2529 nM Homo sapiens 4-(6-methoxy-3,4-dihydronaphthalen-2-yl)pyridine
1.14.15.4 0.002834
-
 CYP11B2 IC50: 2834 nM, recombinant enzymes Homo sapiens 4-(6-methoxy-3,4-dihydronaphthalen-2-yl)pyridine
1.14.15.4 0.005684
-
 competitive, CYP11B1 IC50: 5684 nM Homo sapiens 3-(6-methoxy-1H-inden-2-yl)pyridine