3-((10S,13S)-10,13-dimethyl-1,2,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydrospiro[cyclopenta[a]phenanthrene-3,2'-oxiran]-17-yl)pyridine

ID: ALA3929321

PubChem CID: 89882807

Max Phase: Preclinical

Molecular Formula: C25H33NO

Molecular Weight: 363.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CCC3(CO3)CC1CCC1C2CC[C@]2(C)C(c3cccnc3)=CCC12

Standard InChI:  InChI=1S/C25H33NO/c1-23-11-12-25(16-27-25)14-18(23)5-6-19-21-8-7-20(17-4-3-13-26-15-17)24(21,2)10-9-22(19)23/h3-4,7,13,15,18-19,21-22H,5-6,8-12,14,16H2,1-2H3/t18?,19?,21?,22?,23-,24+,25?/m0/s1

Standard InChI Key:  FABONGUPFNAOSV-ZGQTYYRWSA-N

Molfile:  

     RDKit          2D

 27 32  0  0  0  0  0  0  0  0999 V2000
   12.9812  -10.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5207  -11.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3235  -10.9103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5847  -10.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0412   -9.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2415   -9.6802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2604  -11.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7339  -12.5157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2454  -13.1679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4689  -12.9076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7549  -13.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7480  -14.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0340  -14.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3340  -14.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6201  -14.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9160  -14.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9259  -13.2745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6399  -12.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3398  -13.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0549  -12.8909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0648  -12.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7747  -11.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4788  -12.0883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5757  -11.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3508  -12.4728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0967  -14.0839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4980  -14.7978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  2  0
  2  7  1  0
  8  7  2  0
  9  8  1  0
 10  9  1  0
 11 10  1  0
 12 11  1  0
 13 12  1  0
 14 13  1  0
 15 14  1  0
 16 15  1  0
 17 16  1  0
 18 17  1  0
 18 19  1  0
 20 19  1  0
 21 20  1  0
 22 21  1  0
 23 22  1  0
  7 23  1  0
 10 23  1  0
 23 24  1  1
 11 20  1  0
 14 19  1  0
 19 25  1  1
 16 26  1  0
 26 27  1  0
 16 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3929321

   3-[(10S,13S)-10,13-dimethylspiro[1,2,4,5,6,7,8,9,11,12,14,15-dodecahydrocyclopenta[a]phenanthrene-3,2'-oxirane]-17-yl]pyridine

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: 363.55

Molecular Weight (Monoisotopic): 363.2562

AlogP: 5.89

#Rotatable Bonds: 1

Polar Surface Area: 25.42

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: 4.77

CX LogD: 4.77

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.58

Np Likeness Score: 1.83

References

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

Source

Source(1):

• Patent Bioactivity Data