(3S,10S,13S)-17-(5-chloropyridin-3-yl)-3,10,13-trimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

ID: ALA3948301

PubChem CID: 68087727

Max Phase: Preclinical

Molecular Formula: C25H34ClNO

Molecular Weight: 400.01

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]1(O)CC[C@@]2(C)C(CC[C@@H]3[C@@H]2CC[C@]2(C)C(c4cncc(Cl)c4)=CC[C@@H]32)C1

Standard InChI:  InChI=1S/C25H34ClNO/c1-23(28)10-11-24(2)17(13-23)4-5-19-21-7-6-20(16-12-18(26)15-27-14-16)25(21,3)9-8-22(19)24/h6,12,14-15,17,19,21-22,28H,4-5,7-11,13H2,1-3H3/t17?,19-,21-,22-,23-,24-,25+/m0/s1

Standard InChI Key:  GHXGGVKSLVDREB-ZHJXBGCCSA-N

Molfile:  

     RDKit          2D

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   14.4940  -26.2676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9107  -25.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0854  -25.5506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7428  -24.7056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6116  -24.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2407  -24.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5314  -21.4465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7502  -25.5324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0374  -25.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9047  -24.7379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0159  -25.1178    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.7366  -23.8763    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.9207  -21.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4482  -23.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6265  -25.9636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2303  -23.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4780  -22.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3215  -24.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1648  -21.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7213  -23.8593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0153  -23.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0226  -24.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9736  -20.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7280  -23.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3289  -25.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4478  -25.1053    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.2836  -22.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5268  -22.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3024  -23.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4555  -24.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6051  -20.4139    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
 14 28  1  1
 22 11  1  6
 25 18  1  0
  2 15  1  0
 18  5  1  0
  5 10  1  0
  6 20  1  0
  9  8  1  0
 24 21  1  0
 17 27  2  0
 30 14  1  0
 23 19  1  0
 22 18  1  0
  7 23  2  0
 25 15  1  0
 13 17  1  0
 20 16  2  0
  4 12  1  1
 30 26  1  6
 18 29  1  1
 16 14  1  0
 25  9  1  0
 27  7  1  0
 10  2  1  0
 16 17  1  0
 19 13  2  0
 21 22  1  0
  4 22  1  0
  4 30  1  0
 14 24  1  0
 30  6  1  0
  8  4  1  0
 19 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3948301

   (3S,8R,9S,10S,13S,14S)-17-(5-chloropyridin-3-yl)-3,10,13-trimethyl-1,2,4,5,6,7,8,9,11,12,14,15-dodecahydrocyclopenta[a]phenanthren-3-ol

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: 400.01

Molecular Weight (Monoisotopic): 399.2329

AlogP: 6.52

#Rotatable Bonds: 1

Polar Surface Area: 33.12

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 3.00

CX LogP: 5.26

CX LogD: 5.26

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.58

Np Likeness Score: 1.69

References

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

Source

Source(1):

• Patent Bioactivity Data