(S)-6-(2,3-Difluoro-5-(2-(1-methylpyrrolidin-2-yl)ethyl)-phenethyl)-4-methylpyridin-2-amine

ID: ALA4532683

PubChem CID: 137530121

Max Phase: Preclinical

Molecular Formula: C21H27F2N3

Molecular Weight: 359.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(N)nc(CCc2cc(CC[C@H]3CCCN3C)cc(F)c2F)c1

Standard InChI:  InChI=1S/C21H27F2N3/c1-14-10-17(25-20(24)11-14)7-6-16-12-15(13-19(22)21(16)23)5-8-18-4-3-9-26(18)2/h10-13,18H,3-9H2,1-2H3,(H2,24,25)/t18-/m1/s1

Standard InChI Key:  DWIFPRVVASXUJK-GOSISDBHSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   23.9198  -27.3629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9187  -28.1903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6334  -28.6032    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.3499  -28.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3470  -27.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6316  -26.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2038  -28.6022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.6292  -26.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0650  -28.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7789  -28.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4940  -28.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4906  -29.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2049  -29.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9197  -29.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9157  -28.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2009  -28.1832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2058  -30.6587    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.6281  -28.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7756  -29.8339    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.3447  -28.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0571  -28.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8101  -28.4978    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.3590  -27.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9428  -27.1694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1368  -27.3452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9859  -29.3038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  6  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 13 17  1  0
 15 18  1  0
 12 19  1  0
 18 20  1  0
 21 20  1  1
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 21  1  0
 22 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4532683

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 359.46

Molecular Weight (Monoisotopic): 359.2173

AlogP: 4.06

#Rotatable Bonds: 6

Polar Surface Area: 42.15

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.59

CX LogP: 4.87

CX LogD: 1.92

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.85

Np Likeness Score: -0.52

References

1. Do HT, Li H, Chreifi G, Poulos TL, Silverman RB..  (2019)  Optimization of Blood-Brain Barrier Permeability with Potent and Selective Human Neuronal Nitric Oxide Synthase Inhibitors Having a 2-Aminopyridine Scaffold.,  62  (5): [PMID:30802056] [10.1021/acs.jmedchem.8b02032]

Source

Source(1):

• Scientific Literature