US9062048, 21

ID: ALA3704040

PubChem CID: 54770389

Max Phase: Preclinical

Molecular Formula: C23H30F3N5O3S

Molecular Weight: 513.59

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H30F3N5O3S/c1-35(34)12-20(32)14-2-5-17(6-3-14)31-10-16(11-31)30-21(33)9-27-22-18-8-15(23(24,25)26)4-7-19(18)28-13-29-22/h4,7-8,13-14,16-17,20,32H,2-3,5-6,9-12H2,1H3,(H,30,33)(H,27,28,29)/t14-,17+,20?,35?

Standard InChI Key:  YTGGTNHFYFYRQH-RIIUPOOCSA-N

Molfile:  

     RDKit          2D

 35 38  0  0  1  0  0  0  0  0999 V2000
   10.3892   -8.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7904   -8.6386    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.7883   -7.9486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0446   -9.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0472   -9.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6459  -10.2789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013  -10.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3026  -11.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5563  -11.6653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8148  -11.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8072  -10.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5536   -9.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0011  -11.5257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6295  -12.3041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8791  -11.9225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2227  -11.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0648  -12.2086    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4096  -11.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5368  -10.9687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5953  -11.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9400  -11.3713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1258  -11.6574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9682  -12.5055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1550  -12.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5006  -12.2326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3431  -11.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9988  -10.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8413   -9.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0280   -9.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6276  -10.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4701  -11.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1296   -8.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3947   -8.3911    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.7802   -8.6099    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.2559   -8.1614    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  7  5  1  6
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  7  1  0
 10 13  1  6
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 13  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  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 30  1  0
 30 31  2  0
 31 22  1  0
 31 26  1  0
 29 32  1  0
 32 33  1  0
 32 34  1  0
 32 35  1  0
M  CHG  2   2   1   3  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3704040

   N-[1-[4-(1-hydroxy-2-methylsulfinylethyl)cyclohexyl]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: 513.59

Molecular Weight (Monoisotopic): 513.2021

AlogP: 2.16

#Rotatable Bonds: 8

Polar Surface Area: 113.44

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.42

CX Basic pKa: 6.84

CX LogP: 0.53

CX LogD: 0.43

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.46

Np Likeness Score: -1.09

References

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

Source

Source(1):

• BindingDB Database