US9062048, 165::US9062048, 166

ID: ALA3659051

Max Phase: Preclinical

Molecular Formula: C24H26F3N5O2S

Molecular Weight: 505.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CNc1nccc2ccc(C(F)(F)F)cc12)NC1CN([C@H]2CC[C@](O)(c3cncs3)CC2)C1

Standard InChI:  InChI=1S/C24H26F3N5O2S/c25-24(26,27)16-2-1-15-5-8-29-22(19(15)9-16)30-11-21(33)31-17-12-32(13-17)18-3-6-23(34,7-4-18)20-10-28-14-35-20/h1-2,5,8-10,14,17-18,34H,3-4,6-7,11-13H2,(H,29,30)(H,31,33)/t18-,23+

Standard InChI Key:  NFRZZRGASVENJS-QRTMHTFLSA-N

Molfile:  

     RDKit          2D

 35 39  0  0  1  0  0  0  0  0999 V2000
   14.2805   -4.8047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1583   -5.2296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4345   -3.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2959   -2.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8923   -3.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6046   -4.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7433   -5.7275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5926   -2.5235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2044   -1.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8003   -1.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1437   -2.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4990   -0.7409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2003   -1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2024   -2.6932    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
    2.6003   -1.4977    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 N   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
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -3.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.0000    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   -5.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3379   -5.8515    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596   -5.8505    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2984   -6.4508    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.8515   -6.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8605   -7.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1114   -9.0702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6440   -8.7594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4861   -7.2677    0.0000 S   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  1  0
  5  6  1  0
  6  7  1  0
  7  2  1  0
  5  8  1  1
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  8  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 17  1  0
 26 21  1  0
 24 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
  2 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3659051

   ---

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: 505.57

Molecular Weight (Monoisotopic): 505.1759

AlogP: 3.75

#Rotatable Bonds: 6

Polar Surface Area: 90.38

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.03

CX Basic pKa: 7.02

CX LogP: 2.34

CX LogD: 2.18

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.47

Np Likeness Score: -0.99

References

1.  (2015)  Cyclohexyl-azetidinyl antagonists of CCR2, 

Source

Source(1):

• BindingDB Database