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

ID: ALA3982662

PubChem CID: 134157539

Max Phase: Preclinical

Molecular Formula: C24H28N2O

Molecular Weight: 360.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@H]3[C@@H](CCC4=C/C(=N/O)CC[C@@]43C)C1=CC=C2c1cccnc1

Standard InChI:  InChI=1S/C24H28N2O/c1-23-11-9-18(26-27)14-17(23)5-6-19-21-8-7-20(16-4-3-13-25-15-16)24(21,2)12-10-22(19)23/h3-4,7-8,13-15,19,22,27H,5-6,9-12H2,1-2H3/b26-18+/t19-,22-,23-,24+/m0/s1

Standard InChI Key:  JRXWVDLJKMWYQS-DTUDTTHBSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    3.7290  -13.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0168  -14.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1536  -13.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5846  -13.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1589  -12.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4412  -14.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3461  -10.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3739  -12.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6374  -11.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3595  -14.1004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3077  -15.4719    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4377  -15.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1465  -14.6422    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7115  -11.0374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8549  -13.4170    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0168  -15.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0863  -11.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7290  -15.4632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8498  -13.4408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4480  -11.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8801  -12.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1466  -15.4682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8631  -14.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5850  -15.0629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1623  -10.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4338  -13.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8635  -15.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5896  -13.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3717  -12.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8 28  1  0
 28 29  1  1
 28 21  1  0
  7 17  2  0
 14 25  2  0
 19  8  2  0
 23 15  1  1
 27 23  1  0
 21  5  1  0
 10 19  1  0
 17  9  1  0
  6  1  1  0
 16 18  1  0
  6 12  1  0
 12 22  1  0
 23  4  1  0
  8  9  1  0
 16 11  2  0
 25  7  1  0
  4 10  2  0
  2  1  1  0
  9 20  2  0
  3 23  1  0
  3  5  1  0
  6 26  1  1
  3 13  1  6
  6  3  1  0
 22 27  1  0
  2 16  1  0
 11 24  1  0
 18 12  2  0
 20 14  1  0
 28  4  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3982662

   ---

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: 360.50

Molecular Weight (Monoisotopic): 360.2202

AlogP: 5.79

#Rotatable Bonds: 1

Polar Surface Area: 45.48

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.49

CX Basic pKa: 4.78

CX LogP: 4.14

CX LogD: 4.14

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.51

Np Likeness Score: 1.45

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