(Z)-6-hydroxy-2-[(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one

ID: ALA4084953

PubChem CID: 86681998

Max Phase: Preclinical

Molecular Formula: C22H22N4O3

Molecular Weight: 390.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc2c(/C=C3\Oc4c(ccc(O)c4CN4CCNCC4)C3=O)c[nH]c2n1

Standard InChI:  InChI=1S/C22H22N4O3/c1-13-2-3-15-14(11-24-22(15)25-13)10-19-20(28)16-4-5-18(27)17(21(16)29-19)12-26-8-6-23-7-9-26/h2-5,10-11,23,27H,6-9,12H2,1H3,(H,24,25)/b19-10-

Standard InChI Key:  MNPGLCAYZJWXPV-GRSHGNNSSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   24.4854  -10.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4843  -11.5998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1923  -12.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1905  -10.3714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1881   -9.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4792   -9.1478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4748   -8.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7700   -7.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0611   -8.3279    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0615   -9.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7709   -9.5570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8992  -10.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9040  -11.5998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6884  -11.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1684  -11.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6806  -10.5178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9454  -12.6254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9855  -11.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3900  -10.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1990  -10.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3642   -9.5765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0501   -9.7226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6526   -9.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4792   -8.3818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.7039   -8.1347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1018   -8.6870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2783   -9.4784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7776  -10.3719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5280   -7.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3 13  2  0
 12  4  2  0
  4  1  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6 11  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
 14 17  2  0
 15 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 23  1  0
 22 19  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
  1 28  1  0
 25 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4084953

   (2Z)-6-hydroxy-2-[(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)methylidene]-7-(piperazin-1-ylmethyl)-1-benzofuran-3-one

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: 390.44

Molecular Weight (Monoisotopic): 390.1692

AlogP: 2.60

#Rotatable Bonds: 3

Polar Surface Area: 90.48

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.86

CX Basic pKa: 9.12

CX LogP: 0.58

CX LogD: 0.52

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.60

Np Likeness Score: -0.58

References

1. Nakano H, Hasegawa T, Kojima H, Okabe T, Nagano T..  (2017)  Design and Synthesis of Potent and Selective PIM Kinase Inhibitors by Targeting Unique Structure of ATP-Binding Pocket.,  8  (5): [PMID:28523101] [10.1021/acsmedchemlett.6b00518]

Source

Source(1):

• Scientific Literature