US9169205, 2.59

ID: ALA3984286

PubChem CID: 118473242

Max Phase: Preclinical

Molecular Formula: C25H29N3O3

Molecular Weight: 419.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(OC2CC2)ccc1N1CC[C@@H](Oc2ccc([C@H](C)NC(=O)CC#N)cc2)C1

Standard InChI:  InChI=1S/C25H29N3O3/c1-17-15-22(30-21-7-8-21)9-10-24(17)28-14-12-23(16-28)31-20-5-3-19(4-6-20)18(2)27-25(29)11-13-26/h3-6,9-10,15,18,21,23H,7-8,11-12,14,16H2,1-2H3,(H,27,29)/t18-,23+/m0/s1

Standard InChI Key:  KZGPGJZTTCGNQC-FDDCHVKYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  1  0  0  0  0  0999 V2000
    2.5958   -2.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5978   -1.5022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   -0.7543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1978   -1.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1958   -2.7065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4990   -0.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7977   -1.5108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8362   -2.1122    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
    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
   -1.2990    0.7500    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
   -3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2526    1.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2524    0.2436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4979   -1.0529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0317   -0.7359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1035   -2.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1243   -3.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6247   -4.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0995   -5.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6030   -6.6662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0790   -6.9380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1329   -7.8920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4014   -6.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0739   -4.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5736   -2.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3529   -1.7854    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
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  3  0
  2  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 14 13  1  1
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 24  1  0
 22 27  1  0
 27 28  2  0
 28 19  1  0
 28 29  1  0
 12 30  1  0
 30 31  2  0
 31  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3984286

   2-cyano-N-[(1S)-1-[4-[(3R)-1-(4-cyclopropyloxy-2-methylphenyl)pyrrolidin-3-yl]oxyphenyl]ethyl]acetamide

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: 419.53

Molecular Weight (Monoisotopic): 419.2209

AlogP: 4.28

#Rotatable Bonds: 8

Polar Surface Area: 74.59

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.17

CX Basic pKa: 3.51

CX LogP: 3.81

CX LogD: 3.80

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.69

Np Likeness Score: -1.14

References

1.  (2015)  Pyrrolidine derivatives, pharmaceutical compositions and uses thereof, 

Source

Source(1):

• BindingDB Database