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

ID: ALA3984284

PubChem CID: 68087469

Max Phase: Preclinical

Molecular Formula: C25H35NO

Molecular Weight: 365.56

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(c4cccnc4)=CC[C@@H]32)C1

Standard InChI:  InChI=1S/C25H35NO/c1-23(27)12-13-24(2)18(15-23)6-7-19-21-9-8-20(17-5-4-14-26-16-17)25(21,3)11-10-22(19)24/h4-5,8,14,16,18-19,21-22,27H,6-7,9-13,15H2,1-3H3/t18?,19-,21-,22-,23-,24-,25+/m0/s1

Standard InChI Key:  MFZFIPYAPCDNNJ-BZLQTJNUSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
   14.5815  -13.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9942  -12.6788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1767  -12.6743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7074  -11.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9981  -11.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1261  -11.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5512  -11.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1314  -10.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4166  -11.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3096   -8.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3373  -10.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5436  -12.2785    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.5997   -9.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3229  -11.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4131  -12.6815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1190  -12.2666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.6695   -8.6766    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8246  -11.0464    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.0509   -9.0064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7074  -13.0842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8112  -11.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4069   -9.4587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8497  -10.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1191  -13.0891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8328  -11.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1225   -8.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4093  -11.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8332  -12.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5563  -10.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3393   -9.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
 11 29  1  0
 29 30  1  1
 29 23  1  0
 10 19  2  0
 17 26  2  0
  7 12  1  6
 21 11  2  0
 25 18  1  1
 28 25  1  0
 23  8  1  0
 14 21  1  0
 19 13  1  0
  9  4  1  0
  2 20  1  0
  9 15  1  0
 15 24  1  0
 25  7  1  0
 11 13  1  0
 26 10  1  0
  7 14  1  0
  5  4  1  0
 13 22  2  0
  6 25  1  0
  6  8  1  0
  9 27  1  1
  6 16  1  6
  9  6  1  0
 24 28  1  0
  5  2  1  0
 20 15  1  0
 22 17  1  0
 29  7  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3984284

   (3S,8R,9S,10S,13S,14S)-3,10,13-trimethyl-17-pyridin-3-yl-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: 365.56

Molecular Weight (Monoisotopic): 365.2719

AlogP: 5.87

#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: 4.81

CX LogP: 4.65

CX LogD: 4.65

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.68

Np Likeness Score: 1.92

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