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

ID: ALA3978652

PubChem CID: 57384144

Max Phase: Preclinical

Molecular Formula: C26H32N2O2

Molecular Weight: 404.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cncc(C2=CC=C3[C@@H]4CCC5=CC(=O)N(C)CC[C@]5(C)[C@H]4CC[C@]23C)c1

Standard InChI:  InChI=1S/C26H32N2O2/c1-25-11-12-28(3)24(29)14-18(25)5-6-20-22-8-7-21(26(22,2)10-9-23(20)25)17-13-19(30-4)16-27-15-17/h7-8,13-16,20,23H,5-6,9-12H2,1-4H3/t20-,23-,25-,26+/m0/s1

Standard InChI Key:  XEZTXELRFLXOOO-IDCRYQTOSA-N

Molfile:  

     RDKit          2D

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   14.4368  -21.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6628  -22.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6870  -22.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9891  -23.2926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0165  -24.1188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3196  -24.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5952  -24.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5658  -23.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2628  -22.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2353  -22.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9332  -21.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2628  -23.7348    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8992  -22.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1067  -23.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7712  -23.8135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1568  -24.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9623  -24.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7415  -25.2454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9449  -23.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5658  -22.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9891  -22.4663    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4797  -23.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9434  -22.4016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7218  -21.2099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0934  -20.3598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3189  -19.5704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1230  -19.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6947  -19.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4719  -20.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4938  -19.7588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0688  -20.3494    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
 16 20  1  0
  9 21  1  1
  5 22  1  1
  4 23  2  0
 24 23  1  0
  2 24  2  0
  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
 29 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3978652

   (3bR,10aR,10bS,12aS)-1-(5-methoxypyridin-3-yl)-8,10a,12a-trimethyl-3b,4,5,9,10,10b,11,12-octahydroindeno[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: 404.55

Molecular Weight (Monoisotopic): 404.2464

AlogP: 5.03

#Rotatable Bonds: 2

Polar Surface Area: 42.43

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.46

CX LogP: 3.01

CX LogD: 3.01

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.69

Np Likeness Score: 1.35

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