2-(4-(5-(3-Acetamidophenyl)-2-(2-aminopyridin-3-yl)-3Himidazo[4,5-b]pyridin-3-yl)phenyl)-N-(3-fluorophenyl)-acetamide

ID: ALA2177828

PubChem CID: 58345232

Max Phase: Preclinical

Molecular Formula: C33H26FN7O2

Molecular Weight: 571.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1cccc(-c2ccc3nc(-c4cccnc4N)n(-c4ccc(CC(=O)Nc5cccc(F)c5)cc4)c3n2)c1

Standard InChI:  InChI=1S/C33H26FN7O2/c1-20(42)37-24-7-2-5-22(18-24)28-14-15-29-33(39-28)41(32(40-29)27-9-4-16-36-31(27)35)26-12-10-21(11-13-26)17-30(43)38-25-8-3-6-23(34)19-25/h2-16,18-19H,17H2,1H3,(H2,35,36)(H,37,42)(H,38,43)

Standard InChI Key:  XZDBUFJDOOKECF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 43 48  0  0  0  0  0  0  0  0999 V2000
    0.0275   -9.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0263  -10.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7344  -10.8243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7326   -9.1869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4412   -9.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4460  -10.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2260  -10.6592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7034   -9.9941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2183   -9.3347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6377  -11.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2322  -12.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6449  -12.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4629  -12.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8665  -12.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4515  -11.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5186   -9.9888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9307  -10.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7472  -10.6912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1524   -9.9806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7352   -9.2730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9202   -9.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5055   -8.5768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8772  -13.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6944  -13.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1087  -14.1719    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0973  -12.7565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7058  -14.8829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8876  -14.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4849  -15.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8992  -16.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7206  -16.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1197  -15.5815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6822  -10.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3943  -10.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0982  -10.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0972  -11.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3897  -12.0472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6829  -11.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8026  -10.4106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8036   -9.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5162   -9.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1003   -9.1857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1374  -16.9951    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  7 10  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  8 16  1  0
 21 22  1  0
 13 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 27  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 33  1  0
  2 33  1  0
 35 39  1  0
 39 40  1  0
 40 41  1  0
 40 42  2  0
 31 43  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2177828

   2-[4-[5-(3-acetamidophenyl)-2-(2-aminopyridin-3-yl)imidazo[4,5-b]pyridin-3-yl]phenyl]-N-(3-fluorophenyl)acetamide

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: 571.62

Molecular Weight (Monoisotopic): 571.2132

AlogP: 6.01

#Rotatable Bonds: 7

Polar Surface Area: 127.82

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.36

CX Basic pKa: 5.89

CX LogP: 5.35

CX LogD: 5.34

Aromatic Rings: 6

Heavy Atoms: 43

QED Weighted: 0.22

Np Likeness Score: -1.56

References

1. Ashwell MA, Lapierre JM, Brassard C, Bresciano K, Bull C, Cornell-Kennon S, Eathiraj S, France DS, Hall T, Hill J, Kelleher E, Khanapurkar S, Kizer D, Koerner S, Link J, Liu Y, Makhija S, Moussa M, Namdev N, Nguyen K, Nicewonger R, Palma R, Szwaya J, Tandon M, Uppalapati U, Vensel D, Volak LP, Volckova E, Westlund N, Wu H, Yang RY, Chan TC..  (2012)  Discovery and optimization of a series of 3-(3-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amines: orally bioavailable, selective, and potent ATP-independent Akt inhibitors.,  55  (11): [PMID:22533986] [10.1021/jm300276x]

Source

Source(1):

• Scientific Literature