US9062048, 163::US9062048, 164

ID: ALA3659050

PubChem CID: 58562603

Max Phase: Preclinical

Molecular Formula: C25H25F3N6O2S

Molecular Weight: 530.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  [C-]#[N+]c1cc(NCC(=O)N[C@H]2C[C@H](N3CCC(O)(c4cncs4)CC3)C2)c2cc(C(F)(F)F)ccc2n1

Standard InChI:  InChI=1S/C25H25F3N6O2S/c1-29-22-11-20(18-8-15(25(26,27)28)2-3-19(18)33-22)31-13-23(35)32-16-9-17(10-16)34-6-4-24(36,5-7-34)21-12-30-14-37-21/h2-3,8,11-12,14,16-17,36H,4-7,9-10,13H2,(H,31,33)(H,32,35)/t16-,17-

Standard InChI Key:  VFEJIGVQRKISNQ-QAQDUYKDSA-N

Molfile:  

     RDKit          2D

 37 41  0  0  1  0  0  0  0  0999 V2000
   14.2805   -4.8046    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
   13.4346   -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 N   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 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
    7.8003   -1.4887    0.0000 C   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
    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 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 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
   -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
    0.0000    3.0008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.2008    0.0000 C   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   -8.7593    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
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  2  1  0
  8  5  1  6
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  8  1  0
 10 12  1  1
 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
 19 31  1  0
 31 32  3  0
  2 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 33  1  0
M  CHG  2  31   1  32  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3659050

   N-[3-[4-hydroxy-4-(1,3-thiazol-5-yl)piperidin-1-yl]cyclobutyl]-2-[[2-isocyano-6-(trifluoromethyl)quinolin-4-yl]amino]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: 530.58

Molecular Weight (Monoisotopic): 530.1712

AlogP: 4.30

#Rotatable Bonds: 6

Polar Surface Area: 94.74

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.16

CX Basic pKa: 7.58

CX LogP: -0.46

CX LogD: -0.66

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.41

Np Likeness Score: -0.95

References

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

Source

Source(1):

• BindingDB Database