(8S,9S,10R,13S,14S)-6-fluoro-10,13-dimethyl-17-(pyridin-3-yl)-6,7,8,9,10,11,12,13,14,15-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

ID: ALA3937430

PubChem CID: 68087248

Max Phase: Preclinical

Molecular Formula: C24H28FNO

Molecular Weight: 365.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CCC(=O)C=C1C(F)C[C@@H]1[C@@H]2CC[C@]2(C)C(c3cccnc3)=CC[C@@H]12

Standard InChI:  InChI=1S/C24H28FNO/c1-23-10-8-20-17(13-22(25)21-12-16(27)7-9-24(20,21)2)19(23)6-5-18(23)15-4-3-11-26-14-15/h3-5,11-12,14,17,19-20,22H,6-10,13H2,1-2H3/t17-,19-,20-,22?,23+,24+/m0/s1

Standard InChI Key:  KTOVARHSIHCDSW-WTFVVCFVSA-N

Molfile:  

     RDKit          2D

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   22.2718  -15.4322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5435  -15.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5191  -16.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2189  -17.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9431  -16.6942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6428  -17.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3711  -16.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3954  -15.9137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1237  -15.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8865  -15.8082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3918  -15.1492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9359  -14.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1523  -14.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4525  -14.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7242  -14.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6999  -15.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9716  -15.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0001  -15.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6999  -16.2582    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.2627  -13.8976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2184  -13.7170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6721  -13.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9683  -12.2991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.7702  -12.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3166  -12.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0204  -13.5690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1237  -16.3028    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.3640  -15.0251    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.6428  -17.9042    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.7908  -17.0335    0.0000 O   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  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  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
 16 19  1  6
 13 20  1  1
 12 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
  9 27  1  6
  8 28  1  1
  6 29  1  0
  3 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3937430

   (8R,9S,10R,13S,14S)-6-fluoro-10,13-dimethyl-17-pyridin-3-yl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[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: 365.49

Molecular Weight (Monoisotopic): 365.2155

AlogP: 5.55

#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: 4.81

CX LogP: 4.19

CX LogD: 4.19

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.65

Np Likeness Score: 1.60

References

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

Source

Source(1):

• Patent Bioactivity Data