US9388210, 17b

ID: ALA3971720

PubChem CID: 129012578

Max Phase: Preclinical

Molecular Formula: C22H33NO2

Molecular Weight: 343.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@H]1C[C@]2(C)/C(=C/C#N)CC[C@H]2[C@@H]2CC[C@H]3C[C@H](O)CC[C@]3(C)[C@H]21

Standard InChI:  InChI=1S/C22H33NO2/c1-21-10-8-16(24)12-15(21)4-6-17-18-7-5-14(9-11-23)22(18,2)13-19(25-3)20(17)21/h9,15-20,24H,4-8,10,12-13H2,1-3H3/b14-9+/t15-,16+,17-,18-,19-,20+,21-,22+/m0/s1

Standard InChI Key:  NDRWXFUZQPBELD-INGLSRJASA-N

Molfile:  

     RDKit          2D

 25 28  0  0  1  0  0  0  0  0999 V2000
    3.6387   -0.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -1.4977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9769    2.1968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3947    1.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7758    3.1329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2851    2.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7292    4.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2815    5.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0763    6.6471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -3.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -5.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -6.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -7.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991   -5.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991   -3.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0392   -2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  4  5  1  0
  5  6  1  6
  5  7  1  0
  7  8  1  6
  8  9  1  0
  9 10  1  0
 10  5  1  0
 10 11  2  0
 11 12  1  0
 12 13  3  0
  7 14  1  0
 14 15  1  1
 15 16  1  0
 17 16  1  6
 17 18  1  0
 18 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 17  1  0
 23 24  1  6
 25 23  1  6
 25  3  1  0
 25 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3971720

   ---

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: 343.51

Molecular Weight (Monoisotopic): 343.2511

AlogP: 4.46

#Rotatable Bonds: 1

Polar Surface Area: 53.25

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.36

CX LogD: 3.36

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.71

Np Likeness Score: 2.63

References

1.  (2016)  Neuroactive 17(20)-Z-vinylcyano-substituted steroids, prodrugs thereof, and methods of treatment using same, 

Source

Source(1):

• BindingDB Database