US8497376, 19

ID: ALA3968152

PubChem CID: 57666482

Max Phase: Preclinical

Molecular Formula: C25H29N5O4

Molecular Weight: 463.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CC(c3ccc(NC(=O)c4ncc(C#N)[nH]4)c(C4=CCCCC4)n3)C[C@](C)(O1)[C@H](O)[C@@H]2O

Standard InChI:  InChI=1S/C25H29N5O4/c1-24-10-15(11-25(2,34-24)21(32)20(24)31)17-8-9-18(19(29-17)14-6-4-3-5-7-14)30-23(33)22-27-13-16(12-26)28-22/h6,8-9,13,15,20-21,31-32H,3-5,7,10-11H2,1-2H3,(H,27,28)(H,30,33)/t15?,20-,21+,24+,25-

Standard InChI Key:  FFHAUJKTAWRKHY-QNELOFPJSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  1  0  0  0  0  0999 V2000
   -0.2943   -1.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8393    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9488    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8975   -0.8028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6421    0.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6393   -0.3587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0947    1.4779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6568   -0.6386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2223   -1.4554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8063   -1.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6902   -2.1435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6417   -2.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9949   -2.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1594   -4.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9505   -5.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1182   -6.5714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4933   -7.1728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4592   -6.4607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6610   -8.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9615   -9.3857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6573  -10.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1664  -11.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4240  -12.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8294  -13.3628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5491   -9.6520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5770   -4.4770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4125   -2.9861    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3675   -5.3655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5296   -6.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6807   -7.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0532   -7.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2154   -5.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0051   -4.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
  6  8  1  0
  8  2  1  0
  6  9  1  0
  9 10  1  6
  9 11  1  0
 11  2  1  0
 11 12  1  6
  4 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  3  0
 23 26  1  0
 26 20  1  0
 16 27  1  0
 27 28  2  0
 28 13  1  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3968152

   5-cyano-N-[2-(cyclohexen-1-yl)-6-[(1S,5R,6S,7R)-6,7-dihydroxy-1,5-dimethyl-8-oxabicyclo[3.2.1]octan-3-yl]pyridin-3-yl]-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: 463.54

Molecular Weight (Monoisotopic): 463.2220

AlogP: 3.03

#Rotatable Bonds: 4

Polar Surface Area: 144.15

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.81

CX Basic pKa: 4.19

CX LogP: 1.80

CX LogD: 1.08

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.55

Np Likeness Score: 0.13

References

1.  (2013)  4-Cyano-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(2,6-dioxo-piperidin-4-yl)-phenyl]-amide; tyrosine kinase inhibitor; autoimmune diseases, antiinflammatory, anticarcinogenic agent, 

Source

Source(1):

• BindingDB Database