US9346786, 56

ID: ALA3980572

PubChem CID: 53246744

Max Phase: Preclinical

Molecular Formula: C25H28ClF2N3O3

Molecular Weight: 491.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(C(=O)Oc1ccc(F)cc1)[C@@H]1CN(C(=O)C2CCNCC2)C[C@H]1c1ccc(Cl)c(F)c1

Standard InChI:  InChI=1S/C25H28ClF2N3O3/c1-2-31(25(33)34-19-6-4-18(27)5-7-19)23-15-30(24(32)16-9-11-29-12-10-16)14-20(23)17-3-8-21(26)22(28)13-17/h3-8,13,16,20,23,29H,2,9-12,14-15H2,1H3/t20-,23+/m0/s1

Standard InChI Key:  YYOPTZCYJYCYFR-NZQKXSOJSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  1  0  0  0  0  0999 V2000
    3.3851    2.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1391    1.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2567    0.5852    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9511   -0.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9531   -1.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2010   -3.2956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343   -2.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -1.5004    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
    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
   -2.3383    1.3500    0.0000 Cl  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
    4.8054   -4.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9984   -4.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9195   -5.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5226   -7.2516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6348   -8.4606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1438   -8.2963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5407   -6.9229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4285   -5.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6819    1.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5772    0.2566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9880    2.5249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4132    2.9954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7213    4.4634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1466    4.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2640    3.9300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4043    4.3038    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.9560    2.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5307    1.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  3  1  6
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  8  9  1  1
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16  9  1  0
  6 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 19  1  0
  3 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 31 33  1  0
 33 34  2  0
 34 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3980572

   [(3S,4R)-4-(4-Chloro-3-fluoro-phenyl)-1-(piperidine-4-carbonyl)-pyrrolidin-3-yl]-ethyl-carbamic acid 4-fluoro-phenyl ester

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: 491.97

Molecular Weight (Monoisotopic): 491.1787

AlogP: 4.43

#Rotatable Bonds: 5

Polar Surface Area: 61.88

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.17

CX LogP: 3.85

CX LogD: 1.21

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.67

Np Likeness Score: -1.27

References

1.  (2016)  Pyrrolidine compounds, 

Source

Source(1):

• BindingDB Database