US9169205, 1.11

ID: ALA3983944

PubChem CID: 117885503

Max Phase: Preclinical

Molecular Formula: C24H30N2O3

Molecular Weight: 394.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@@H](C)c1ccc(O[C@@H]2CCN(c3cccc(OCC4CC4)c3)C2)cc1

Standard InChI:  InChI=1S/C24H30N2O3/c1-17(25-18(2)27)20-8-10-22(11-9-20)29-24-12-13-26(15-24)21-4-3-5-23(14-21)28-16-19-6-7-19/h3-5,8-11,14,17,19,24H,6-7,12-13,15-16H2,1-2H3,(H,25,27)/t17-,24+/m0/s1

Standard InChI Key:  KEWGTVMRROKCTQ-BXKMTCNYSA-N

Molfile:  

     RDKit          2D

 29 32  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
    6.2382   -0.9086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1958   -2.7065    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
   -2.6003    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
   -7.5736   -2.6979    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
   -7.0995   -5.2524    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
   -4.6473   -6.1176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1721   -5.8416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1947   -6.9806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8401   -7.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9805   -8.3860    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
   -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
  2  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 12 11  1  1
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 24  1  0
 21 27  2  0
 27 17  1  0
 10 28  1  0
 28 29  2  0
 29  7  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3983944

   N-[(1S)-1-[4-[(3R)-1-[3-(cyclopropylmethoxy)phenyl]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: 394.52

Molecular Weight (Monoisotopic): 394.2256

AlogP: 4.33

#Rotatable Bonds: 8

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: 1.72

CX LogP: 3.66

CX LogD: 3.66

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.72

Np Likeness Score: -1.17

References

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

Source

Source(1):

• BindingDB Database