US9062048, 41

ID: ALA3640029

PubChem CID: 54771067

Max Phase: Preclinical

Molecular Formula: C22H27F3N6O2

Molecular Weight: 464.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@H]1CC[C@@H](N2CC(NC(=O)CNc3ncnc4ccc(C(F)(F)F)cc34)C2)CC1

Standard InChI:  InChI=1S/C22H27F3N6O2/c1-13(32)29-15-3-5-17(6-4-15)31-10-16(11-31)30-20(33)9-26-21-18-8-14(22(23,24)25)2-7-19(18)27-12-28-21/h2,7-8,12,15-17H,3-6,9-11H2,1H3,(H,29,32)(H,30,33)(H,26,27,28)/t15-,17+

Standard InChI Key:  AZQQEUJRDLWUNT-WOVMCDHWSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  1  0  0  0  0  0999 V2000
   12.8844   -8.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0170   -7.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9264   -8.4667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2956   -6.2089    0.0000 N   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 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
  1  2  1  0
  2  3  2  0
  2  4  1  0
  5  4  1  1
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  5  1  0
  8 11  1  1
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 11  1  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 20  1  0
 29 24  1  0
 27 30  1  0
 30 31  1  0
 30 32  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3640029

   N-[1-(4-acetamidocyclohexyl)azetidin-3-yl]-2-[[6-(trifluoromethyl)quinazolin-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: 464.49

Molecular Weight (Monoisotopic): 464.2148

AlogP: 2.31

#Rotatable Bonds: 6

Polar Surface Area: 99.25

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.49

CX Basic pKa: 7.43

CX LogP: 1.30

CX LogD: 0.98

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.61

Np Likeness Score: -1.42

References

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

Source

Source(1):

• BindingDB Database