US9169205, 1.62

ID: ALA3986816

PubChem CID: 118473390

Max Phase: Preclinical

Molecular Formula: C22H26F2N2O3

Molecular Weight: 404.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1ccc(N2CCC(Oc3ccc([C@H](C)NC(C)=O)cc3)C2)c(F)c1F

Standard InChI:  InChI=1S/C22H26F2N2O3/c1-4-28-20-10-9-19(21(23)22(20)24)26-12-11-18(13-26)29-17-7-5-16(6-8-17)14(2)25-15(3)27/h5-10,14,18H,4,11-13H2,1-3H3,(H,25,27)/t14-,18?/m0/s1

Standard InChI Key:  FNFUZFQCBDDGTP-PIVQAISJSA-N

Molfile:  

     RDKit          2D

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    3.8990   -0.7455    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
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987    1.5004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7390    2.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2067    3.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9546    1.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9492    0.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4441    1.8282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0504    0.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5414    0.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1445   -1.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2567   -2.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7657   -2.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1626   -0.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8583   -3.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1465   -4.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3498   -3.8339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9514   -5.2089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1439   -5.3427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2395   -6.1749    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
   -2.3383   -1.3500    0.0000 F   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
    0.0000   -2.7000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
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 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 17 20  1  0
 20 21  1  6
 20 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
  7 26  1  0
 26 27  1  0
 26 28  2  0
 28  4  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3986816

   N-[(1S)-1-[4-[1-(4-ethoxy-2,3-difluorophenyl)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: 404.46

Molecular Weight (Monoisotopic): 404.1911

AlogP: 4.22

#Rotatable Bonds: 7

Polar Surface Area: 50.80

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.52

CX LogD: 3.52

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.75

Np Likeness Score: -1.02

References

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

Source

Source(1):

• BindingDB Database