(8R,9S,10S,13S)-10,13-dimethyl-17-(4-methylpyridin-3-yl)-4,5,6,7,8,9,10,11,12,13-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

ID: ALA3976223

PubChem CID: 134152256

Max Phase: Preclinical

Molecular Formula: C25H31NO

Molecular Weight: 361.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccncc1C1=CC=C2[C@@H]3CCC4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C

Standard InChI:  InChI=1S/C25H31NO/c1-16-10-13-26-15-20(16)22-7-6-21-19-5-4-17-14-18(27)8-11-24(17,2)23(19)9-12-25(21,22)3/h6-7,10,13,15,17,19,23H,4-5,8-9,11-12,14H2,1-3H3/t17?,19-,23-,24-,25-/m0/s1

Standard InChI Key:  YSMWLKIEBIIILJ-ICPNLKIMSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   32.7894  -28.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0781  -29.2801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1323  -30.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8267  -30.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5380  -30.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2679  -30.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9792  -29.9930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9605  -29.1682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6717  -28.7279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4644  -28.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9283  -28.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4168  -27.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6175  -27.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9232  -27.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2119  -27.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2305  -28.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5193  -29.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5007  -28.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6920  -27.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6641  -26.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0680  -26.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2932  -25.4407    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.1010  -25.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6835  -25.8590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4363  -26.6516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9969  -27.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4211  -30.5231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.2305  -29.6088    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   34.9605  -28.3432    0.0000 H   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
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  8 16  1  0
 16 17  1  0
  5 17  1  0
  1 17  1  0
 17 18  1  1
 13 19  1  1
 12 20  1  0
 21 20  1  0
 21 22  2  0
 23 22  1  0
 24 23  2  0
 25 24  1  0
 20 25  2  0
 25 26  1  0
  3 27  2  0
 16 28  1  6
  8 29  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3976223

   ---

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: 361.53

Molecular Weight (Monoisotopic): 361.2406

AlogP: 5.92

#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: 5.58

CX LogP: 4.69

CX LogD: 4.68

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.62

Np Likeness Score: 1.85

References

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

Source

Source(1):

• Patent Bioactivity Data