US9394289, 12

ID: ALA3985982

PubChem CID: 24874639

Max Phase: Preclinical

Molecular Formula: C24H28N4O4S

Molecular Weight: 468.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CC=C(c2cc(C3(O)CCS(=O)(=O)CC3)ccc2NC(=O)c2nc(C#N)c[nH]2)CC1

Standard InChI:  InChI=1S/C24H28N4O4S/c1-23(2)7-5-16(6-8-23)19-13-17(24(30)9-11-33(31,32)12-10-24)3-4-20(19)28-22(29)21-26-15-18(14-25)27-21/h3-5,13,15,30H,6-12H2,1-2H3,(H,26,27)(H,28,29)

Standard InChI Key:  CFBZXKHPVPVDBF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    2.3238   -0.1256    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
    1.2709   -1.9497    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 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
   -2.5987    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8967    0.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1969    1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1993    2.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6012    3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3042    3.7556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3088    5.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3501    5.8529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0118    6.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1236    7.4927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5903    7.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3424    6.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3406    5.3928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1975    9.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6837   10.2737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4956    0.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5345    1.3445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1962    0.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1955   -1.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4941   -2.2145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4408   -2.7893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5469   -2.7905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7935   -1.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7943    0.0349    0.0000 C   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
  6  7  2  0
  7  8  1  0
  8  2  1  0
  6  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 18  1  0
 20 23  1  0
 23 24  3  0
 11 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  2  0
 29 32  1  0
 32 33  1  0
 33 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3985982

   5-cyano-N-[2-(4,4-dimethylcyclohexen-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: 468.58

Molecular Weight (Monoisotopic): 468.1831

AlogP: 3.52

#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: 2.00

CX LogD: 1.73

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.63

Np Likeness Score: -0.39

References

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

Source

Source(1):

• BindingDB Database