(5aR,5bS,7aS,10aS,10bS)-8-(5-methoxypyridin-3-yl)-5a,7a-dimethyl-4,5,5a,5b,6,7,7a,8,9,10,10a,10b,11,12-tetradecahydrocyclopenta[5,6]naphtho[1,2-d]azepin-2(3H)-one

ID: ALA3982013

PubChem CID: 68086878

Max Phase: Preclinical

Molecular Formula: C25H34N2O2

Molecular Weight: 394.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cncc(C2CC[C@H]3[C@@H]4CCC5=CC(=O)NCC[C@]5(C)[C@H]4CC[C@]23C)c1

Standard InChI:  InChI=1S/C25H34N2O2/c1-24-10-11-27-23(28)13-17(24)4-5-19-21-7-6-20(25(21,2)9-8-22(19)24)16-12-18(29-3)15-26-14-16/h12-15,19-22H,4-11H2,1-3H3,(H,27,28)/t19-,20?,21-,22-,24-,25+/m0/s1

Standard InChI Key:  CFUADGMSZIMWFG-DRLDVTDQSA-N

Molfile:  

     RDKit          2D

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   15.2167  -11.4184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9922  -12.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2208  -12.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2489  -13.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5530  -13.7356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5802  -14.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8893  -14.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1712  -14.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1420  -13.7847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8329  -13.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8057  -12.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5017  -12.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8329  -14.1739    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4812  -13.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6957  -13.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3672  -14.2519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7453  -14.9637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5438  -15.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3378  -15.6715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1420  -12.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5530  -12.9165    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.0306  -13.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4903  -12.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2489  -14.1216    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.2793  -11.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6477  -10.8283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8753  -10.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6683   -9.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2350  -10.4334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0142  -11.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3092   -9.4565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5365   -8.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  6  5  1  0
  7  6  1  0
  8  7  1  0
  9  8  1  0
  9 10  1  0
 11 10  1  0
 12 11  1  0
  3 12  1  0
  5 10  1  0
 10 13  1  6
  9 14  1  0
 15 14  1  0
 16 15  1  0
 17 16  1  0
 18 17  1  0
  8 18  2  0
 17 19  2  0
  9 20  1  1
  5 21  1  1
  4 22  1  0
 23 22  1  0
  2 23  1  0
  4 24  1  6
  3 25  1  1
 26  1  2  0
 27 26  1  0
 28 27  2  0
 29 28  1  0
 30 29  2  0
  1 30  1  0
 27 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3982013

   (3aS,3bS,10aR,10bS,12aS)-1-(5-methoxypyridin-3-yl)-10a,12a-dimethyl-2,3,3a,3b,4,5,8,9,10,10b,11,12-dodecahydro-1H-indeno[4,5-i][3]benzazepin-7-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 394.56

Molecular Weight (Monoisotopic): 394.2620

AlogP: 4.86

#Rotatable Bonds: 2

Polar Surface Area: 51.22

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.15

CX LogP: 3.46

CX LogD: 3.46

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.78

Np Likeness Score: 1.54

References

1.  (2013)  C-17-heteroaryl steroidal compounds as inhibitors of CYP11B, CYP17, and/or CYP21, 

2. Blass, Benjamin E BE and 18 more authors.  2016-12-01  Design, synthesis, and evaluation of (2S,4R)-Ketoconazole sulfonamide analogs as potential treatments for Metabolic Syndrome.  [PMID:27789139]

3. Fehl, Charlie C and 5 more authors.  2018-06-14  Structure-Based Design of Inhibitors with Improved Selectivity for Steroidogenic Cytochrome P450 17A1 over Cytochrome P450 21A2.  [PMID:29792703]

Source

Source(1):

• Patent Bioactivity Data