(5aR,5bS,7aS,10aS,10bR)-5a,7a-dimethyl-8-(1H-1,2,4-triazol-1-yl)-4,5,5a,5b,6,7,7a,10,10a,10b,11,12-dodecahydrocyclopenta[5,6]naphtho[2,1-c]azepin-3(2H)-one

ID: ALA3970637

PubChem CID: 68086720

Max Phase: Preclinical

Molecular Formula: C21H28N4O

Molecular Weight: 352.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CCNC(=O)C=C1CC[C@@H]1[C@@H]2CC[C@]2(C)C(n3cncn3)=CC[C@@H]12

Standard InChI:  InChI=1S/C21H28N4O/c1-20-9-10-23-19(26)11-14(20)3-4-15-16-5-6-18(25-13-22-12-24-25)21(16,2)8-7-17(15)20/h6,11-13,15-17H,3-5,7-10H2,1-2H3,(H,23,26)/t15-,16-,17-,20-,21-/m0/s1

Standard InChI Key:  MLFQUNUPEZQAEP-RNEDXHKXSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   21.4454  -17.6654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2192  -18.4610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4464  -18.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4706  -19.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7696  -19.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7971  -20.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1053  -21.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3778  -20.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3485  -20.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0444  -19.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0170  -18.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7180  -18.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0444  -20.4366    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.6872  -19.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8959  -19.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5609  -20.5193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9417  -21.2320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7501  -21.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3485  -19.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7696  -19.1743    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.2621  -19.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7251  -19.1097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4706  -20.3881    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.5053  -17.9199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2170  -17.3796    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1862  -16.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3905  -16.3270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9298  -17.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4425  -21.8865    0.0000 O   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  2  0
  9 19  1  1
  5 20  1  1
  4 21  1  0
 22 21  1  0
  2 22  2  0
  4 23  1  6
  3 24  1  1
  1 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28  1  1  0
 17 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3970637

   (3aS,3bR,10aR,10bS,12aS)-10a,12a-dimethyl-1-(1,2,4-triazol-1-yl)-3a,3b,4,5,8,9,10,10b,11,12-decahydro-3H-indeno[4,5-i][3]benzazepin-7-one

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: 352.48

Molecular Weight (Monoisotopic): 352.2263

AlogP: 3.42

#Rotatable Bonds: 1

Polar Surface Area: 59.81

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.64

CX LogP: 2.09

CX LogD: 2.09

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.84

Np Likeness Score: 1.05

References

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

Source

Source(1):

• Patent Bioactivity Data