US9394289, 15

ID: ALA3986237

PubChem CID: 24874642

Max Phase: Preclinical

Molecular Formula: C22H24N4O4S

Molecular Weight: 440.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1c[nH]c(C(=O)Nc2ccc(C3(O)CCS(=O)(=O)CC3)cc2C2=CCCCC2)n1

Standard InChI:  InChI=1S/C22H24N4O4S/c23-13-17-14-24-20(25-17)21(27)26-19-7-6-16(12-18(19)15-4-2-1-3-5-15)22(28)8-10-31(29,30)11-9-22/h4,6-7,12,14,28H,1-3,5,8-11H2,(H,24,25)(H,26,27)

Standard InChI Key:  DICWNZSIZHEUPQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    2.3238   -0.1256    0.0000 O   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 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2707    1.9497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3239    0.1257    0.0000 O   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
    1.2643   -2.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5453   -3.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101   -4.5101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1938   -5.2294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1617   -6.7299    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4445   -7.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4966   -6.9315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4124   -9.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6054   -9.8973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1085  -11.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6089  -11.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1790   -9.8404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604  -12.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6428  -13.5322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0872   -4.4491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520   -2.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4042   -5.1687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4419   -6.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7593   -7.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0392   -6.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0016   -5.1037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6841   -4.3865    0.0000 C   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  2  0
  5  7  2  0
  5  8  1  0
  8  9  1  0
  9  2  1  0
  2 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 17  1  0
 19 22  1  0
 22 23  3  0
 13 24  1  0
 24 25  2  0
 25 10  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3986237

   5-cyano-N-[2-(cyclohexen-1-yl)-4-(4-hydroxy-1,1-dioxothian-4-yl)phenyl]-1H-imidazole-2-carboxamide

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: 440.53

Molecular Weight (Monoisotopic): 440.1518

AlogP: 2.89

#Rotatable Bonds: 4

Polar Surface Area: 135.94

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.44

CX Basic pKa: ┄

CX LogP: 1.41

CX LogD: 1.14

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.67

Np Likeness Score: -0.74

References

1.  (2016)  Inhibitors of c-fms kinase, 

Source

Source(1):

• BindingDB Database