3-((5aS,5bS,7aS,10aS,10bR,12aS)-5a,7a-dimethyl-2,4,5,5a,5b,6,7,7a,10,10a,10b,11,12,12a-tetradecahydro-1H-cyclopenta[5,6]naphtho[1,2-d]oxepin-8-yl)-5-methylpyridine

ID: ALA3931417

PubChem CID: 68086702

Max Phase: Preclinical

Molecular Formula: C25H35NO

Molecular Weight: 365.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cncc(C2=CC[C@H]3[C@@H]4CC[C@H]5CCOCC[C@]5(C)[C@H]4CC[C@]23C)c1

Standard InChI:  InChI=1S/C25H35NO/c1-17-14-18(16-26-15-17)21-6-7-22-20-5-4-19-9-12-27-13-11-24(19,2)23(20)8-10-25(21,22)3/h6,14-16,19-20,22-23H,4-5,7-13H2,1-3H3/t19-,20-,22-,23-,24-,25+/m0/s1

Standard InChI Key:  NWEHUYRHAUYHKV-ABVATSDPSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   22.1670  -24.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9425  -25.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1751  -25.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1992  -26.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5032  -27.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5304  -27.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8395  -28.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1214  -27.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0923  -27.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7832  -26.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7560  -25.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4520  -25.4026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7832  -27.4698    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.4356  -26.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6459  -26.8054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3175  -27.5519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6955  -28.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4941  -28.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0923  -26.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1214  -28.7147    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.5032  -26.2165    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.9850  -26.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4447  -26.1523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1992  -27.4174    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.2337  -24.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5980  -24.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8256  -23.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6185  -23.1452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1853  -23.7293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9644  -24.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2459  -22.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  6  5  1  0
  7  6  1  0
  8  7  1  0
  9  8  1  0
  9 10  1  0
 11 10  1  0
 12 11  1  0
  3 12  1  0
  5 10  1  0
 10 13  1  6
  9 14  1  0
 15 14  1  0
 16 15  1  0
 17 16  1  0
 18 17  1  0
  8 18  1  0
  9 19  1  1
  8 20  1  6
  5 21  1  1
  4 22  1  0
 23 22  1  0
  2 23  2  0
  4 24  1  6
  3 25  1  1
 26  1  2  0
 27 26  1  0
 28 27  2  0
 29 28  1  0
 30 29  2  0
  1 30  1  0
 27 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3931417

   3-[(1S,2S,8S,11R,12S,16S)-2,16-dimethyl-5-oxatetracyclo[9.7.0.02,8.012,16]octadec-14-en-15-yl]-5-methylpyridine

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: 6.05

#Rotatable Bonds: 1

Polar Surface Area: 22.12

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 5.32

CX LogP: 5.02

CX LogD: 5.02

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.60

Np Likeness Score: 1.39

References

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

Source

Source(1):

• Patent Bioactivity Data