US8497376, 9

ID: ALA3963729

PubChem CID: 57666466

Max Phase: Preclinical

Molecular Formula: C28H32N4O3

Molecular Weight: 472.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CC=C(c2cc([C@@]3(O)C[C@]4(C)C=C[C@](C)(C3)O4)ccc2NC(=O)c2ncc(C#N)[nH]2)CC1

Standard InChI:  InChI=1S/C28H32N4O3/c1-25(2)9-7-18(8-10-25)21-13-19(28(34)16-26(3)11-12-27(4,17-28)35-26)5-6-22(21)32-24(33)23-30-15-20(14-29)31-23/h5-7,11-13,15,34H,8-10,16-17H2,1-4H3,(H,30,31)(H,32,33)/t26-,27+,28+

Standard InChI Key:  XNSXNDURWCBTFS-KUMHGWDASA-N

Molfile:  

     RDKit          2D

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   -0.3063   -4.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0412   -6.0540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4185  -12.4223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6371   -8.7239    0.0000 N   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
    3.0972   -0.8313    0.0000 O   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
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   -1.0947    1.4779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6393   -0.3587    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
   -0.6568   -0.6386    0.0000 C   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
  1  2  1  0
  2  3  1  0
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  9 10  2  0
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 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  3  0
 21 24  1  0
 24 18  1  0
 11 25  1  0
 25 26  1  6
 25 27  1  0
 27 28  1  0
 28 29  1  1
 28 30  1  0
 30 31  1  0
 31 32  1  6
 31 33  1  0
 33 25  1  0
 31 34  1  0
 34 35  2  0
 35 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3963729

   5-cyano-N-[2-(4,4-dimethylcyclohexen-1-yl)-4-[(1R,5S)-3-hydroxy-1,5-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-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: 472.59

Molecular Weight (Monoisotopic): 472.2474

AlogP: 5.21

#Rotatable Bonds: 4

Polar Surface Area: 111.03

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.80

CX Basic pKa: 0.62

CX LogP: 3.69

CX LogD: 2.85

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.53

Np Likeness Score: 0.40

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