(8R,9S,10R,13S)-6,10,13-trimethyl-17-(pyridin-3-yl)-6,7,8,9,10,11,12,13-octahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

ID: ALA3979173

PubChem CID: 68087242

Max Phase: Preclinical

Molecular Formula: C25H29NO

Molecular Weight: 359.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1C[C@H]2C3=CC=C(c4cccnc4)[C@@]3(C)CC[C@@H]2[C@@]2(C)CCC(=O)C=C12

Standard InChI:  InChI=1S/C25H29NO/c1-16-13-19-21-7-6-20(17-5-4-12-26-15-17)24(21,2)11-9-22(19)25(3)10-8-18(27)14-23(16)25/h4-7,12,14-16,19,22H,8-11,13H2,1-3H3/t16?,19-,22-,24+,25+/m0/s1

Standard InChI Key:  KBNYKBIYBRZPFU-LWHOHZQWSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    8.9218  -23.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2096  -24.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3464  -23.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7774  -23.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3517  -22.8712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6339  -24.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5389  -20.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5667  -22.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8302  -21.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5523  -23.9762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6304  -24.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3392  -24.5180    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9044  -20.9133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0477  -23.2928    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2096  -24.9348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2790  -21.2444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9218  -25.3391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0426  -23.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6407  -21.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0730  -22.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3393  -25.3440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0559  -24.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3552  -20.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6266  -23.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0563  -24.9408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7825  -22.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5645  -22.0842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5005  -25.3477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3347  -26.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8 26  1  0
 26 27  1  1
 26 20  1  0
  7 16  2  0
 13 23  2  0
 18  8  2  0
 22 14  1  1
 25 22  1  0
 20  5  1  0
 10 18  1  0
 16  9  1  0
  6  1  1  0
 15 17  1  0
  6 11  1  0
 11 21  1  0
 22  4  1  0
  8  9  1  0
 23  7  1  0
  4 10  2  0
  2  1  1  0
  9 19  2  0
  3 22  1  0
  3  5  1  0
  6 24  1  1
  3 12  1  6
  6  3  1  0
 21 25  1  0
  2 15  1  0
 17 11  2  0
 19 13  1  0
 26  4  1  0
 15 28  2  0
 21 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3979173

   (8R,9S,10R,13S)-6,10,13-trimethyl-17-pyridin-3-yl-1,2,6,7,8,9,11,12-octahydrocyclopenta[a]phenanthren-3-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: 359.51

Molecular Weight (Monoisotopic): 359.2249

AlogP: 5.77

#Rotatable Bonds: 1

Polar Surface Area: 29.96

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.77

CX LogP: 4.41

CX LogD: 4.41

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.64

Np Likeness Score: 1.80

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