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

ID: ALA3973178

PubChem CID: 134153248

Max Phase: Preclinical

Molecular Formula: C25H32N2O

Molecular Weight: 376.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccncc1C1=CC=C2[C@@H]3CC[C@H]4CC(=O)NCC[C@]4(C)[C@H]3CC[C@]12C

Standard InChI:  InChI=1S/C25H32N2O/c1-16-9-12-26-15-19(16)21-7-6-20-18-5-4-17-14-23(28)27-13-11-24(17,2)22(18)8-10-25(20,21)3/h6-7,9,12,15,17-18,22H,4-5,8,10-11,13-14H2,1-3H3,(H,27,28)/t17-,18-,22-,24-,25-/m0/s1

Standard InChI Key:  DGZYNWUPJUSUHK-NVGXVCEOSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
    8.2215   -6.3207    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5870   -5.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3919   -5.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0326   -5.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0206   -6.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3654   -7.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5696   -7.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0489   -7.7026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7298   -7.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4499   -6.7619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4607   -5.9395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1808   -5.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1886   -4.7124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4764   -4.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7605   -4.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7485   -5.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7485   -6.3457    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9769   -4.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4533   -5.1361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9622   -5.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2396   -3.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6978   -3.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9606   -2.2790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.7690   -2.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3160   -2.7370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0503   -3.5175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6002   -4.1397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2844   -3.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4607   -5.1179    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0206   -7.5769    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1020   -5.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  1  7  1  0
  7  8  2  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 11 16  1  0
  4 16  1  0
 16 17  1  6
 13 18  1  0
 18 19  2  0
 19 20  1  0
 12 20  2  0
 18 21  1  0
 22 21  1  0
 22 23  2  0
 24 23  1  0
 25 24  2  0
 26 25  1  0
 21 26  2  0
 26 27  1  0
 13 28  1  1
 11 29  1  1
  5 30  1  6
  4 31  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3973178

   ---

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: 376.54

Molecular Weight (Monoisotopic): 376.2515

AlogP: 5.07

#Rotatable Bonds: 1

Polar Surface Area: 41.99

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 5.58

CX LogP: 3.51

CX LogD: 3.50

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.74

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