(R)3-(1-Cyclopropyl-ethyl)-7-(2,4-dichloro-phenyl)-2-ethyl-3H-imidazo[4,5-b]pyridine

ID: ALA3085294

PubChem CID: 76313469

Max Phase: Preclinical

Molecular Formula: C19H19Cl2N3

Molecular Weight: 360.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1nc2c(-c3ccc(Cl)cc3Cl)ccnc2n1[C@H](C)C1CC1

Standard InChI:  InChI=1S/C19H19Cl2N3/c1-3-17-23-18-15(14-7-6-13(20)10-16(14)21)8-9-22-19(18)24(17)11(2)12-4-5-12/h6-12H,3-5H2,1-2H3/t11-/m1/s1

Standard InChI Key:  AAARPHXZKXDSID-LLVKDONJSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    5.7285    0.6722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9394    0.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7285   -0.6681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9394   -0.4176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2171   -0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2254   -0.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2254   -1.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9415    1.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3528    2.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9394   -2.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2254    0.8225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1273    2.8434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5511    2.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9394   -2.8935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5115   -2.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2254   -3.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6534   -1.6576    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.0438   -0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5115   -2.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5115    0.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5115   -0.4176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2254   -4.1378    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.7306    1.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4571   -0.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  5  2  0
  4  2  1  0
  5  1  1  0
  6  4  2  0
  7  6  1  0
  8  1  1  0
  8  9  1  1
 10  7  1  0
 11  2  2  0
 12  9  1  0
 13  9  1  0
 14 10  2  0
 15  7  2  0
 16 19  2  0
 17 10  1  0
 18  5  1  0
 19 15  1  0
 20 11  1  0
 21 20  2  0
 22 16  1  0
 23  8  1  0
 24 18  1  0
  4  3  1  0
 13 12  1  0
  6 21  1  0
 14 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3085294

   3-[(1R)-1-cyclopropylethyl]-7-(2,4-dichlorophenyl)-2-ethylimidazo[4,5-b]pyridine

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: 360.29

Molecular Weight (Monoisotopic): 359.0956

AlogP: 5.94

#Rotatable Bonds: 4

Polar Surface Area: 30.71

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 2.46

CX LogP: 5.51

CX LogD: 5.51

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.58

Np Likeness Score: -1.19

References

1. Arvanitis AG, Rescinito JT, Arnold CR, Wilde RG, Cain GA, Sun JH, Yan JS, Teleha CA, Fitzgerald LW, McElroy J, Zaczek R, Hartig PR, Grossman S, Arneric SP, Gilligan PJ, Olson RE, Robertson DW..  (2003)  Imidazo[4,5-b]pyridines as corticotropin releasing factor receptor ligands.,  13  (1): [PMID:12467631] [10.1016/s0960-894x(02)00833-8]

Source

Source(1):

• Scientific Literature